diff --git a/changes/19352-calendar-real-time b/changes/19352-calendar-real-time
new file mode 100644
index 0000000000..dc72e98899
--- /dev/null
+++ b/changes/19352-calendar-real-time
@@ -0,0 +1 @@
+- In maintenance windows using Google Calendar, calendar event is now recreated within 30 seconds if deleted or moved to the past.
diff --git a/ee/server/calendar/google_calendar.go b/ee/server/calendar/google_calendar.go
index 938f7d65a6..db7f98cc79 100644
--- a/ee/server/calendar/google_calendar.go
+++ b/ee/server/calendar/google_calendar.go
@@ -8,6 +8,7 @@ import (
 	"net/http"
 	"os"
 	"regexp"
+	"strconv"
 	"strings"
 	"time"
 
@@ -16,6 +17,7 @@ import (
 	"github.com/fleetdm/fleet/v4/server/fleet"
 	kitlog "github.com/go-kit/log"
 	"github.com/go-kit/log/level"
+	"github.com/google/uuid"
 	"golang.org/x/oauth2/google"
 	"golang.org/x/oauth2/jwt"
 	"google.golang.org/api/calendar/v3"
@@ -35,7 +37,7 @@ const (
 	endHour     = 17
 	eventLength = 30 * time.Minute
 	calendarID  = "primary"
-	mockEmail   = "calendar-mock@example.com"
+	MockEmail   = "calendar-mock@example.com"
 	loadEmail   = "calendar-load@example.com"
 )
 
@@ -52,6 +54,7 @@ type GoogleCalendarConfig struct {
 	Context           context.Context
 	IntegrationConfig *fleet.GoogleCalendarIntegration
 	Logger            kitlog.Logger
+	ServerURL         string
 	// Should be nil for production
 	API GoogleCalendarAPI
 }
@@ -71,7 +74,7 @@ func NewGoogleCalendar(config *GoogleCalendarConfig) *GoogleCalendar {
 		// Use the provided API.
 	case config.IntegrationConfig.ApiKey[fleet.GoogleCalendarEmail] == loadEmail:
 		config.API = &GoogleCalendarLoadAPI{Logger: config.Logger}
-	case config.IntegrationConfig.ApiKey[fleet.GoogleCalendarEmail] == mockEmail:
+	case config.IntegrationConfig.ApiKey[fleet.GoogleCalendarEmail] == MockEmail:
 		config.API = &GoogleCalendarMockAPI{config.Logger}
 	default:
 		config.API = &GoogleCalendarLowLevelAPI{logger: config.Logger}
@@ -82,27 +85,33 @@ func NewGoogleCalendar(config *GoogleCalendarConfig) *GoogleCalendar {
 }
 
 type GoogleCalendarAPI interface {
-	Configure(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string) error
+	Configure(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string) error
 	GetSetting(name string) (*calendar.Setting, error)
 	ListEvents(timeMin, timeMax string) (*calendar.Events, error)
 	CreateEvent(event *calendar.Event) (*calendar.Event, error)
 	GetEvent(id, eTag string) (*calendar.Event, error)
 	DeleteEvent(id string) error
+	Watch(eventUUID string, channelID string, ttl uint64) (resourceID string, err error)
+	Stop(channelID string, resourceID string) error
 }
 
 type eventDetails struct {
 	ID   string `json:"id"`
 	ETag string `json:"etag"`
+	// ChannelID and ResourceID are for watching event changes
+	ChannelID  string `json:"channel_id"`
+	ResourceID string `json:"resource_id"`
 }
 
 type GoogleCalendarLowLevelAPI struct {
-	service *calendar.Service
-	logger  kitlog.Logger
+	service   *calendar.Service
+	logger    kitlog.Logger
+	serverURL string
 }
 
 // Configure creates a new Google Calendar service using the provided credentials.
 func (lowLevelAPI *GoogleCalendarLowLevelAPI) Configure(
-	ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string,
+	ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string,
 ) error {
 	// Create a new calendar service
 	conf := &jwt.Config{
@@ -118,6 +127,7 @@ func (lowLevelAPI *GoogleCalendarLowLevelAPI) Configure(
 		return err
 	}
 	lowLevelAPI.service = service
+	lowLevelAPI.serverURL = serverURL
 	return nil
 }
 
@@ -181,6 +191,38 @@ func (lowLevelAPI *GoogleCalendarLowLevelAPI) DeleteEvent(id string) error {
 	return err
 }
 
+func (lowLevelAPI *GoogleCalendarLowLevelAPI) Watch(eventUUID string, channelID string, ttl uint64) (resourceID string, err error) {
+	resp, err := lowLevelAPI.withRetry(
+		func() (any, error) {
+			return lowLevelAPI.service.Events.Watch(calendarID, &calendar.Channel{
+				Id:   channelID, // channelID is also used for authentication -- it should be a random value
+				Type: "web_hook",
+				Address: fmt.Sprintf("%s/api/v1/fleet/calendar/webhook/%s",
+					lowLevelAPI.serverURL, eventUUID),
+				Params: map[string]string{
+					"ttl": strconv.FormatUint(ttl, 10),
+				},
+			}).EventTypes("default").Do()
+		},
+	)
+	if err != nil {
+		return "", err
+	}
+	return resp.(*calendar.Channel).ResourceId, nil
+}
+
+func (lowLevelAPI *GoogleCalendarLowLevelAPI) Stop(channelID string, resourceID string) error {
+	_, err := lowLevelAPI.withRetry(
+		func() (any, error) {
+			return nil, lowLevelAPI.service.Channels.Stop(&calendar.Channel{
+				Id:         channelID,
+				ResourceId: resourceID,
+			}).Do()
+		},
+	)
+	return err
+}
+
 func (lowLevelAPI *GoogleCalendarLowLevelAPI) withRetry(fn func() (any, error)) (any, error) {
 	retryStrategy := backoff.NewExponentialBackOff()
 	retryStrategy.MaxElapsedTime = 10 * time.Minute
@@ -207,6 +249,7 @@ func (c *GoogleCalendar) Configure(userEmail string) error {
 	err := c.config.API.Configure(
 		c.config.Context, c.config.IntegrationConfig.ApiKey[fleet.GoogleCalendarEmail],
 		c.config.IntegrationConfig.ApiKey[fleet.GoogleCalendarPrivateKey], adjustedUserEmail,
+		c.config.ServerURL,
 	)
 	if err != nil {
 		return ctxerr.Wrap(c.config.Context, err, "creating Google calendar service")
@@ -218,7 +261,7 @@ func (c *GoogleCalendar) Configure(userEmail string) error {
 	return nil
 }
 
-func (c *GoogleCalendar) GetAndUpdateEvent(event *fleet.CalendarEvent, genBodyFn func(conflict bool) string) (
+func (c *GoogleCalendar) GetAndUpdateEvent(event *fleet.CalendarEvent, genBodyFn func(conflict bool) (body string, ok bool, err error)) (
 	*fleet.CalendarEvent, bool, error,
 ) {
 	// We assume that the Fleet event has not already ended. We will simply return it if it has not been modified.
@@ -235,6 +278,11 @@ func (c *GoogleCalendar) GetAndUpdateEvent(event *fleet.CalendarEvent, genBodyFn
 	// http.StatusNotFound should be very rare -- Google keeps events for a while after they are deleted
 	case isNotFound(err):
 		deleted = true
+		// If event was deleted, we need to stop watching it
+		err = c.config.API.Stop(details.ChannelID, details.ResourceID)
+		if err != nil {
+			level.Warn(c.config.Logger).Log("msg", "stopping Google calendar event watch", "err", err)
+		}
 	case err != nil:
 		return nil, false, ctxerr.Wrap(c.config.Context, err, "retrieving Google calendar event")
 	}
@@ -294,7 +342,7 @@ func (c *GoogleCalendar) GetAndUpdateEvent(event *fleet.CalendarEvent, genBodyFn
 			if err != nil {
 				return nil, false, err
 			}
-			fleetEvent, err := c.googleEventToFleetEvent(*startTime, *endTime, gEvent)
+			fleetEvent, err := c.googleEventToFleetEvent(*startTime, *endTime, gEvent, event.UUID, details.ChannelID, details.ResourceID)
 			if err != nil {
 				return nil, false, err
 			}
@@ -381,14 +429,15 @@ func (c *GoogleCalendar) unmarshalDetails(event *fleet.CalendarEvent) (*eventDet
 	return &details, nil
 }
 
-func (c *GoogleCalendar) CreateEvent(dayOfEvent time.Time, genBodyFn func(conflict bool) string) (*fleet.CalendarEvent, error) {
+func (c *GoogleCalendar) CreateEvent(dayOfEvent time.Time,
+	genBodyFn func(conflict bool) (body string, ok bool, err error)) (*fleet.CalendarEvent, error) {
 	return c.createEvent(dayOfEvent, genBodyFn, time.Now)
 }
 
 // createEvent creates a new event on the calendar on the given date. timeNow is a function that returns the current time.
 // timeNow can be overwritten for testing
 func (c *GoogleCalendar) createEvent(
-	dayOfEvent time.Time, genBodyFn func(conflict bool) string, timeNow func() time.Time,
+	dayOfEvent time.Time, genBodyFn func(conflict bool) (body string, ok bool, err error), timeNow func() time.Time,
 ) (*fleet.CalendarEvent, error) {
 	var err error
 	if c.location == nil {
@@ -482,14 +531,31 @@ func (c *GoogleCalendar) createEvent(
 	event.Start = &calendar.EventDateTime{DateTime: eventStart.Format(time.RFC3339)}
 	event.End = &calendar.EventDateTime{DateTime: eventEnd.Format(time.RFC3339)}
 	event.Summary = eventTitle
-	event.Description = genBodyFn(conflict)
+	body, ok, err := genBodyFn(conflict)
+	if err != nil {
+		return nil, ctxerr.Wrap(c.config.Context, err, "generating Google calendar event body")
+	}
+	if !ok {
+		// We don't need to create this event
+		return nil, nil
+	}
+	event.Description = body
 	event, err = c.config.API.CreateEvent(event)
 	if err != nil {
 		return nil, ctxerr.Wrap(c.config.Context, err, "creating Google calendar event")
 	}
 
+	// Watch for event changes
+	secondsToEventEnd := eventEnd.Sub(now).Milliseconds() / 1000
+	eventUUID := uuid.New().String()
+	channelUUID := uuid.New().String()
+	resourceID, err := c.config.API.Watch(eventUUID, channelUUID, uint64(secondsToEventEnd))
+	if err != nil {
+		return nil, ctxerr.Wrap(c.config.Context, err, "watching Google calendar event")
+	}
+
 	// Convert Google event to Fleet event
-	fleetEvent, err := c.googleEventToFleetEvent(eventStart, eventEnd, event)
+	fleetEvent, err := c.googleEventToFleetEvent(eventStart, eventEnd, event, eventUUID, channelUUID, resourceID)
 	if err != nil {
 		return nil, err
 	}
@@ -539,7 +605,9 @@ func getLocation(tz string, config *GoogleCalendarConfig) *time.Location {
 	return loc
 }
 
-func (c *GoogleCalendar) googleEventToFleetEvent(startTime time.Time, endTime time.Time, event *calendar.Event) (
+func (c *GoogleCalendar) googleEventToFleetEvent(startTime time.Time, endTime time.Time, event *calendar.Event, eventUUID string,
+	channelID string,
+	resourceID string) (
 	*fleet.CalendarEvent, error,
 ) {
 	fleetEvent := &fleet.CalendarEvent{}
@@ -547,9 +615,12 @@ func (c *GoogleCalendar) googleEventToFleetEvent(startTime time.Time, endTime ti
 	fleetEvent.EndTime = endTime
 	fleetEvent.Email = c.currentUserEmail
 	fleetEvent.TimeZone = c.location.String()
+	fleetEvent.UUID = eventUUID
 	details := &eventDetails{
-		ID:   event.Id,
-		ETag: event.Etag,
+		ID:         event.Id,
+		ETag:       event.Etag,
+		ChannelID:  channelID,
+		ResourceID: resourceID,
 	}
 	detailsJson, err := json.Marshal(details)
 	if err != nil {
@@ -564,6 +635,14 @@ func (c *GoogleCalendar) DeleteEvent(event *fleet.CalendarEvent) error {
 	if err != nil {
 		return err
 	}
+	// Stop watching the event before deleting the event so that we don't get a callback for the deletion
+	if details.ChannelID != "" && details.ResourceID != "" {
+		stopErr := c.config.API.Stop(details.ChannelID, details.ResourceID)
+		if stopErr != nil {
+			level.Warn(c.config.Logger).Log("msg", "stopping Google calendar event watch", "err", stopErr)
+		}
+	}
+	// Delete the event
 	err = c.config.API.DeleteEvent(details.ID)
 	switch {
 	case isAlreadyDeleted(err):
@@ -573,3 +652,28 @@ func (c *GoogleCalendar) DeleteEvent(event *fleet.CalendarEvent) error {
 	}
 	return nil
 }
+
+func (c *GoogleCalendar) StopEventChannel(event *fleet.CalendarEvent) error {
+	details, err := c.unmarshalDetails(event)
+	if err != nil {
+		return err
+	}
+	if details.ChannelID != "" && details.ResourceID != "" {
+		stopErr := c.config.API.Stop(details.ChannelID, details.ResourceID)
+		if stopErr != nil {
+			level.Warn(c.config.Logger).Log("msg", "stopping Google calendar event watch", "err", stopErr)
+		}
+	}
+	return nil
+}
+
+func (c *GoogleCalendar) Get(event *fleet.CalendarEvent, key string) (interface{}, error) {
+	if key == "channelID" {
+		details, err := c.unmarshalDetails(event)
+		if err != nil {
+			return nil, err
+		}
+		return details.ChannelID, nil
+	}
+	return nil, ctxerr.Errorf(c.config.Context, "unknown key: %s", key)
+}
diff --git a/ee/server/calendar/google_calendar_integration_test.go b/ee/server/calendar/google_calendar_integration_test.go
index 7f42b23b22..6e2bce57a2 100644
--- a/ee/server/calendar/google_calendar_integration_test.go
+++ b/ee/server/calendar/google_calendar_integration_test.go
@@ -66,8 +66,8 @@ func (s *googleCalendarIntegrationTestSuite) TestCreateGetDeleteEvent() {
 	gCal := NewGoogleCalendar(config)
 	err := gCal.Configure(userEmail)
 	require.NoError(t, err)
-	genBodyFn := func(bool) string {
-		return "Test event"
+	genBodyFn := func(bool) (string, bool, error) {
+		return "Test event", true, nil
 	}
 	eventDate := time.Now().Add(48 * time.Hour)
 	event, err := gCal.CreateEvent(eventDate, genBodyFn)
@@ -110,8 +110,8 @@ func (s *googleCalendarIntegrationTestSuite) TestFillUpCalendar() {
 	gCal := NewGoogleCalendar(config)
 	err := gCal.Configure(userEmail)
 	require.NoError(t, err)
-	genBodyFn := func(bool) string {
-		return "Test event"
+	genBodyFn := func(bool) (string, bool, error) {
+		return "Test event", true, nil
 	}
 	eventDate := time.Now().Add(48 * time.Hour)
 	event, err := gCal.CreateEvent(eventDate, genBodyFn)
diff --git a/ee/server/calendar/google_calendar_load.go b/ee/server/calendar/google_calendar_load.go
index 8446af20c5..cb9c1bf917 100644
--- a/ee/server/calendar/google_calendar_load.go
+++ b/ee/server/calendar/google_calendar_load.go
@@ -22,10 +22,12 @@ type GoogleCalendarLoadAPI struct {
 	userToImpersonate string
 	ctx               context.Context
 	client            *http.Client
+	serverURL         string
 }
 
 // Configure creates a new Google Calendar service using the provided credentials.
-func (lowLevelAPI *GoogleCalendarLoadAPI) Configure(ctx context.Context, _ string, privateKey string, userToImpersonate string) error {
+func (lowLevelAPI *GoogleCalendarLoadAPI) Configure(ctx context.Context, _ string, privateKey string, userToImpersonate string,
+	serverURL string) error {
 	if lowLevelAPI.Logger == nil {
 		lowLevelAPI.Logger = kitlog.With(kitlog.NewLogfmtLogger(os.Stderr), "mock", "GoogleCalendarLoadAPI", "user", userToImpersonate)
 	}
@@ -35,6 +37,7 @@ func (lowLevelAPI *GoogleCalendarLoadAPI) Configure(ctx context.Context, _ strin
 	if lowLevelAPI.client == nil {
 		lowLevelAPI.client = fleethttp.NewClient()
 	}
+	lowLevelAPI.serverURL = serverURL
 	return nil
 }
 
@@ -232,3 +235,11 @@ func (lowLevelAPI *GoogleCalendarLoadAPI) DeleteEvent(id string) error {
 	}
 	return nil
 }
+
+func (lowLevelAPI *GoogleCalendarLoadAPI) Watch(eventUUID string, channelID string, ttl uint64) (resourceID string, err error) {
+	return "resourceID", nil
+}
+
+func (lowLevelAPI *GoogleCalendarLoadAPI) Stop(channelID string, resourceID string) error {
+	return nil
+}
diff --git a/ee/server/calendar/google_calendar_mock.go b/ee/server/calendar/google_calendar_mock.go
index 1dd6f16bb4..cc6ab94c35 100644
--- a/ee/server/calendar/google_calendar_mock.go
+++ b/ee/server/calendar/google_calendar_mock.go
@@ -3,6 +3,7 @@ package calendar
 import (
 	"context"
 	"errors"
+	"github.com/google/uuid"
 	"net/http"
 	"os"
 	"strconv"
@@ -18,16 +19,22 @@ type GoogleCalendarMockAPI struct {
 	logger kitlog.Logger
 }
 
+type channel struct {
+	channelID  string
+	resourceID string
+}
+
 var (
-	mockEvents = make(map[string]*calendar.Event)
-	mu         sync.Mutex
-	id         uint64
+	mockEvents   = make(map[string]*calendar.Event)
+	mockChannels = make([]channel, 0)
+	mu           sync.Mutex
+	id           uint64
 )
 
-const latency = 500 * time.Millisecond
+const latency = 200 * time.Millisecond
 
 // Configure creates a new Google Calendar service using the provided credentials.
-func (lowLevelAPI *GoogleCalendarMockAPI) Configure(_ context.Context, _ string, _ string, userToImpersonate string) error {
+func (lowLevelAPI *GoogleCalendarMockAPI) Configure(_ context.Context, _ string, _ string, userToImpersonate string, _ string) error {
 	if lowLevelAPI.logger == nil {
 		lowLevelAPI.logger = kitlog.With(kitlog.NewLogfmtLogger(os.Stderr), "mock", "GoogleCalendarMockAPI", "user", userToImpersonate)
 	}
@@ -84,6 +91,31 @@ func (lowLevelAPI *GoogleCalendarMockAPI) DeleteEvent(id string) error {
 	return nil
 }
 
+func (lowLevelAPI *GoogleCalendarMockAPI) Watch(eventUUID string, channelID string, ttl uint64) (resourceID string, err error) {
+	time.Sleep(latency)
+	mu.Lock()
+	defer mu.Unlock()
+	resourceID = uuid.New().String()
+	mockChannels = append(mockChannels, channel{
+		channelID:  channelID,
+		resourceID: resourceID,
+	})
+	return resourceID, nil
+}
+
+func (lowLevelAPI *GoogleCalendarMockAPI) Stop(channelID string, resourceID string) error {
+	time.Sleep(latency)
+	mu.Lock()
+	defer mu.Unlock()
+	for i, ch := range mockChannels {
+		if ch.channelID == channelID && ch.resourceID == resourceID {
+			mockChannels = append(mockChannels[:i], mockChannels[i+1:]...)
+			return nil
+		}
+	}
+	return errors.New("channel not found")
+}
+
 func ListGoogleMockEvents() map[string]*calendar.Event {
 	return mockEvents
 }
@@ -94,6 +126,16 @@ func ClearMockEvents() {
 	mockEvents = make(map[string]*calendar.Event)
 }
 
+func MockChannelsCount() int {
+	return len(mockChannels)
+}
+
+func ClearMockChannels() {
+	mu.Lock()
+	defer mu.Unlock()
+	mockChannels = make([]channel, 0)
+}
+
 func SetMockEventsToNow() {
 	mu.Lock()
 	defer mu.Unlock()
diff --git a/ee/server/calendar/google_calendar_test.go b/ee/server/calendar/google_calendar_test.go
index 8d35cba69e..848be3693b 100644
--- a/ee/server/calendar/google_calendar_test.go
+++ b/ee/server/calendar/google_calendar_test.go
@@ -18,6 +18,7 @@ const (
 	baseServiceEmail = "service@example.com"
 	basePrivateKey   = "private-key"
 	baseUserEmail    = "user@example.com"
+	baseServerURL    = "https://example.com"
 )
 
 var (
@@ -26,18 +27,28 @@ var (
 )
 
 type MockGoogleCalendarLowLevelAPI struct {
-	ConfigureFunc   func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string) error
+	ConfigureFunc   func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string) error
 	GetSettingFunc  func(name string) (*calendar.Setting, error)
 	ListEventsFunc  func(timeMin, timeMax string) (*calendar.Events, error)
 	CreateEventFunc func(event *calendar.Event) (*calendar.Event, error)
 	GetEventFunc    func(id, eTag string) (*calendar.Event, error)
 	DeleteEventFunc func(id string) error
+	WatchFunc       func(eventUUID string, channelID string, ttl uint64) (resourceID string, err error)
+	StopFunc        func(channelID string, resourceID string) error
+}
+
+func (m *MockGoogleCalendarLowLevelAPI) Watch(eventUUID string, channelID string, ttl uint64) (resourceID string, err error) {
+	return m.WatchFunc(eventUUID, channelID, ttl)
+}
+
+func (m *MockGoogleCalendarLowLevelAPI) Stop(channelID string, resourceID string) error {
+	return m.StopFunc(channelID, resourceID)
 }
 
 func (m *MockGoogleCalendarLowLevelAPI) Configure(
-	ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string,
+	ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string,
 ) error {
-	return m.ConfigureFunc(ctx, serviceAccountEmail, privateKey, userToImpersonateEmail)
+	return m.ConfigureFunc(ctx, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL)
 }
 
 func (m *MockGoogleCalendarLowLevelAPI) GetSetting(name string) (*calendar.Setting, error) {
@@ -63,11 +74,12 @@ func (m *MockGoogleCalendarLowLevelAPI) DeleteEvent(id string) error {
 func TestGoogleCalendar_Configure(t *testing.T) {
 	t.Parallel()
 	mockAPI := &MockGoogleCalendarLowLevelAPI{}
-	mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string) error {
+	mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string) error {
 		assert.Equal(t, baseCtx, ctx)
 		assert.Equal(t, baseServiceEmail, serviceAccountEmail)
 		assert.Equal(t, basePrivateKey, privateKey)
 		assert.Equal(t, baseUserEmail, userToImpersonateEmail)
+		assert.Equal(t, baseServerURL, serverURL)
 		return nil
 	}
 
@@ -77,7 +89,7 @@ func TestGoogleCalendar_Configure(t *testing.T) {
 	assert.NoError(t, err)
 
 	// Configure error test
-	mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string) error {
+	mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string) error {
 		return assert.AnError
 	}
 	err = cal.Configure(baseUserEmail)
@@ -94,10 +106,11 @@ func TestGoogleCalendar_ConfigurePlusAddressing(t *testing.T) {
 	)
 	email := "user+my_test+email@example.com"
 	mockAPI := &MockGoogleCalendarLowLevelAPI{}
-	mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string) error {
+	mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string) error {
 		assert.Equal(t, baseCtx, ctx)
 		assert.Equal(t, baseServiceEmail, serviceAccountEmail)
 		assert.Equal(t, basePrivateKey, privateKey)
+		assert.Equal(t, baseServerURL, serverURL)
 		assert.Equal(t, "user@example.com", userToImpersonateEmail)
 		return nil
 	}
@@ -109,7 +122,7 @@ func TestGoogleCalendar_ConfigurePlusAddressing(t *testing.T) {
 
 func makeConfig(mockAPI *MockGoogleCalendarLowLevelAPI) *GoogleCalendarConfig {
 	if mockAPI != nil && mockAPI.ConfigureFunc == nil {
-		mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail string) error {
+		mockAPI.ConfigureFunc = func(ctx context.Context, serviceAccountEmail, privateKey, userToImpersonateEmail, serverURL string) error {
 			return nil
 		}
 	}
@@ -121,8 +134,9 @@ func makeConfig(mockAPI *MockGoogleCalendarLowLevelAPI) *GoogleCalendarConfig {
 				fleet.GoogleCalendarPrivateKey: basePrivateKey,
 			},
 		},
-		Logger: logger,
-		API:    mockAPI,
+		Logger:    logger,
+		API:       mockAPI,
+		ServerURL: baseServerURL,
 	}
 	return config
 }
@@ -187,6 +201,7 @@ func TestGoogleCalendar_GetAndUpdateEvent(t *testing.T) {
 	mockAPI := &MockGoogleCalendarLowLevelAPI{}
 	const baseETag = "event-eTag"
 	const baseEventID = "event-id"
+	const baseResourceID = "resource-id"
 	mockAPI.GetEventFunc = func(id, eTag string) (*calendar.Event, error) {
 		assert.Equal(t, baseEventID, id)
 		assert.Equal(t, baseETag, eTag)
@@ -194,9 +209,9 @@ func TestGoogleCalendar_GetAndUpdateEvent(t *testing.T) {
 			Etag: baseETag, // ETag matches -- no modifications to event
 		}, nil
 	}
-	genBodyFn := func(bool) string {
+	genBodyFn := func(bool) (string, bool, error) {
 		t.Error("genBodyFn should not be called")
-		return "event-body"
+		return "event-body", false, nil
 	}
 	var cal fleet.UserCalendar = NewGoogleCalendar(makeConfig(mockAPI))
 	err := cal.Configure(baseUserEmail)
@@ -332,14 +347,29 @@ func TestGoogleCalendar_GetAndUpdateEvent(t *testing.T) {
 	mockAPI.ListEventsFunc = func(timeMin, timeMax string) (*calendar.Events, error) {
 		return &calendar.Events{}, nil
 	}
-	genBodyFn = func(conflict bool) string {
+	mockAPI.StopFunc = func(channelID string, resourceID string) error {
+		details, err := gCal.unmarshalDetails(event)
+		require.NoError(t, err)
+		assert.Equal(t, details.ChannelID, channelID)
+		assert.Equal(t, details.ResourceID, resourceID)
+		return nil
+	}
+	var uuid, channelUUID string
+	mockAPI.WatchFunc = func(eventUUID string, channelID string, ttl uint64) (resourceID string, err error) {
+		uuid = eventUUID
+		channelUUID = channelID
+		assert.Greater(t, ttl, uint64(60*30-1))
+		return baseResourceID, nil
+	}
+	genBodyFn = func(conflict bool) (string, bool, error) {
 		assert.False(t, conflict)
-		return "event-body"
+		return "event-body", true, nil
 	}
 	eventCreated := false
 	mockAPI.CreateEventFunc = func(event *calendar.Event) (*calendar.Event, error) {
 		assert.Equal(t, eventTitle, event.Summary)
-		assert.Equal(t, genBodyFn(false), event.Description)
+		body, _, _ := genBodyFn(false)
+		assert.Equal(t, body, event.Description)
 		event.Id = baseEventID
 		event.Etag = baseETag
 		eventCreated = true
@@ -350,12 +380,17 @@ func TestGoogleCalendar_GetAndUpdateEvent(t *testing.T) {
 	assert.True(t, updated)
 	assert.NotEqual(t, event, retrievedEvent)
 	require.NotNil(t, retrievedEvent)
+	assert.Equal(t, uuid, retrievedEvent.UUID)
 	assert.Equal(t, baseUserEmail, retrievedEvent.Email)
 	newEventDate := calculateNewEventDate(eventStartTime)
 	expectedStartTime := time.Date(newEventDate.Year(), newEventDate.Month(), newEventDate.Day(), startHour, 0, 0, 0, time.UTC)
 	assert.Equal(t, expectedStartTime.UTC(), retrievedEvent.StartTime.UTC())
 	assert.Equal(t, expectedStartTime.Add(eventLength).UTC(), retrievedEvent.EndTime.UTC())
 	assert.True(t, eventCreated)
+	details, err = gCal.unmarshalDetails(retrievedEvent)
+	require.NoError(t, err)
+	assert.Equal(t, channelUUID, details.ChannelID)
+	assert.Equal(t, baseResourceID, details.ResourceID)
 
 	// cancelled (deleted)
 	mockAPI.GetEventFunc = func(id, eTag string) (*calendar.Event, error) {
@@ -426,6 +461,7 @@ func TestGoogleCalendar_CreateEvent(t *testing.T) {
 	const baseEventID = "event-id"
 	const baseETag = "event-eTag"
 	const eventBody = "event-body"
+	const baseResourceID = "resource-id"
 	var cal fleet.UserCalendar = NewGoogleCalendar(makeConfig(mockAPI))
 	err := cal.Configure(baseUserEmail)
 	assert.NoError(t, err)
@@ -444,13 +480,13 @@ func TestGoogleCalendar_CreateEvent(t *testing.T) {
 		event.Etag = baseETag
 		return event, nil
 	}
-	genBodyFn := func(conflict bool) string {
+	genBodyFn := func(conflict bool) (string, bool, error) {
 		assert.False(t, conflict)
-		return eventBody
+		return eventBody, true, nil
 	}
-	genBodyConflictFn := func(conflict bool) string {
+	genBodyConflictFn := func(conflict bool) (string, bool, error) {
 		assert.True(t, conflict)
-		return eventBody
+		return eventBody, true, nil
 	}
 
 	// Happy path test -- empty calendar
@@ -458,8 +494,16 @@ func TestGoogleCalendar_CreateEvent(t *testing.T) {
 	location, _ := time.LoadLocation(tzId)
 	expectedStartTime := time.Date(date.Year(), date.Month(), date.Day(), startHour, 0, 0, 0, location)
 	_, expectedOffset := expectedStartTime.Zone()
+	var uuid, channelUUID string
+	mockAPI.WatchFunc = func(eventUUID string, channelID string, ttl uint64) (resourceID string, err error) {
+		uuid = eventUUID
+		channelUUID = channelID
+		assert.Greater(t, ttl, uint64(60*30-1))
+		return baseResourceID, nil
+	}
 	event, err := cal.CreateEvent(date, genBodyFn)
 	require.NoError(t, err)
+	assert.Equal(t, uuid, event.UUID)
 	assert.Equal(t, baseUserEmail, event.Email)
 	assert.Equal(t, expectedStartTime.UTC(), event.StartTime.UTC())
 	assert.Equal(t, expectedStartTime.Add(eventLength).UTC(), event.EndTime.UTC())
@@ -472,6 +516,9 @@ func TestGoogleCalendar_CreateEvent(t *testing.T) {
 	require.NoError(t, err)
 	assert.Equal(t, baseETag, details.ETag)
 	assert.Equal(t, baseEventID, details.ID)
+	assert.Equal(t, channelUUID, details.ChannelID)
+	assert.Equal(t, baseResourceID, details.ResourceID)
+	assert.Equal(t, tzId, event.TimeZone)
 
 	// Workday already ended
 	date = time.Now().Add(-48 * time.Hour)
diff --git a/ee/server/service/calendar.go b/ee/server/service/calendar.go
new file mode 100644
index 0000000000..eee0e84fa4
--- /dev/null
+++ b/ee/server/service/calendar.go
@@ -0,0 +1,133 @@
+package service
+
+import (
+	"context"
+	"fmt"
+	"github.com/fleetdm/fleet/v4/server/authz"
+	"github.com/fleetdm/fleet/v4/server/contexts/ctxerr"
+	"github.com/fleetdm/fleet/v4/server/fleet"
+	"github.com/fleetdm/fleet/v4/server/service/calendar"
+	"github.com/go-kit/log/level"
+	"sync"
+)
+
+func (svc *Service) CalendarWebhook(ctx context.Context, eventUUID string, channelID string, resourceState string) error {
+
+	appConfig, err := svc.ds.AppConfig(ctx)
+	if err != nil {
+		return fmt.Errorf("load app config: %w", err)
+	}
+
+	if len(appConfig.Integrations.GoogleCalendar) == 0 {
+		svc.authz.SkipAuthorization(ctx)
+		level.Warn(svc.logger).Log("msg", "Received calendar callback, but Google Calendar integration is not configured")
+		return nil
+	}
+	googleCalendarIntegrationConfig := appConfig.Integrations.GoogleCalendar[0]
+
+	if resourceState == "sync" {
+		// This is a sync notification, not a real event
+		svc.authz.SkipAuthorization(ctx)
+		return nil
+	}
+
+	eventDetails, err := svc.ds.GetCalendarEventDetailsByUUID(ctx, eventUUID)
+	if err != nil {
+		svc.authz.SkipAuthorization(ctx)
+		if fleet.IsNotFound(err) {
+			// We could try to stop the channel callbacks here, but that may not be secure since we don't know if the request is legitimate
+			level.Warn(svc.logger).Log("msg", "Received calendar callback, but did not find corresponding event in database", "event_uuid",
+				eventUUID, "channel_id", channelID)
+			return err
+		}
+		return err
+	}
+	if eventDetails.TeamID == nil {
+		// Should not happen
+		return fmt.Errorf("calendar event %s has no team ID", eventUUID)
+	}
+
+	localConfig := &calendar.CalendarConfig{
+		GoogleCalendarIntegration: *googleCalendarIntegrationConfig,
+		ServerURL:                 appConfig.ServerSettings.ServerURL,
+	}
+	userCalendar := calendar.CreateUserCalendarFromConfig(ctx, localConfig, svc.logger)
+
+	// Authenticate request. We will use the channel ID for authentication.
+	svc.authz.SkipAuthorization(ctx)
+	savedChannelID, err := userCalendar.Get(&eventDetails.CalendarEvent, "channelID")
+	if err != nil {
+		return ctxerr.Wrap(ctx, err, "get channel ID")
+	}
+	if savedChannelID != channelID {
+		return authz.ForbiddenWithInternal(fmt.Sprintf("calendar channel ID mismatch: %s != %s", savedChannelID, channelID), nil, nil, nil)
+	}
+
+	genBodyFn := func(conflict bool) (body string, ok bool, err error) {
+
+		// This function is called when a new event is being created.
+		var team *fleet.Team
+		team, err = svc.ds.TeamWithoutExtras(ctx, *eventDetails.TeamID)
+		if err != nil {
+			return "", false, err
+		}
+
+		if team.Config.Integrations.GoogleCalendar == nil ||
+			!team.Config.Integrations.GoogleCalendar.Enable {
+			return "", false, nil
+		}
+
+		var policies []fleet.PolicyCalendarData
+		policies, err = svc.ds.GetCalendarPolicies(ctx, team.ID)
+		if err != nil {
+			return "", false, err
+		}
+
+		if len(policies) == 0 {
+			return "", false, nil
+		}
+
+		policyIDs := make([]uint, 0, len(policies))
+		for _, policy := range policies {
+			policyIDs = append(policyIDs, policy.ID)
+		}
+
+		var hosts []fleet.HostPolicyMembershipData
+		hosts, err = svc.ds.GetTeamHostsPolicyMemberships(ctx, googleCalendarIntegrationConfig.Domain, team.ID, policyIDs,
+			&eventDetails.HostID)
+		if err != nil {
+			return "", false, err
+		}
+		if len(hosts) != 1 {
+			return "", false, nil
+		}
+		host := hosts[0]
+		if host.Passing { // host is passing all configured policies
+			return "", false, nil
+		}
+		if host.Email == "" {
+			err = fmt.Errorf("host %d has no associated email", host.HostID)
+			return "", false, err
+		}
+
+		return calendar.GenerateCalendarEventBody(ctx, svc.ds, team.Name, host, &sync.Map{}, conflict, svc.logger), true, nil
+	}
+
+	err = userCalendar.Configure(eventDetails.Email)
+	if err != nil {
+		return ctxerr.Wrap(ctx, err, "configure calendar")
+	}
+	event, updated, err := userCalendar.GetAndUpdateEvent(&eventDetails.CalendarEvent, genBodyFn)
+	if err != nil {
+		return ctxerr.Wrap(ctx, err, "get and update event")
+	}
+	if updated && event != nil {
+		// Event was updated, so we need to save it
+		_, err = svc.ds.CreateOrUpdateCalendarEvent(ctx, event.UUID, event.Email, event.StartTime, event.EndTime, event.Data,
+			event.TimeZone, eventDetails.ID, fleet.CalendarWebhookStatusNone)
+		if err != nil {
+			return ctxerr.Wrap(ctx, err, "create or update calendar event")
+		}
+	}
+	return nil
+}
diff --git a/server/cron/calendar_cron.go b/server/cron/calendar_cron.go
index 874de3dfbc..c1aaab2217 100644
--- a/server/cron/calendar_cron.go
+++ b/server/cron/calendar_cron.go
@@ -5,15 +5,13 @@ import (
 	"errors"
 	"fmt"
 	"slices"
-	"strconv"
-	"strings"
 	"sync"
 	"time"
 
-	"github.com/fleetdm/fleet/v4/ee/server/calendar"
 	"github.com/fleetdm/fleet/v4/server/config"
 	"github.com/fleetdm/fleet/v4/server/fleet"
 	"github.com/fleetdm/fleet/v4/server/ptr"
+	"github.com/fleetdm/fleet/v4/server/service/calendar"
 	"github.com/fleetdm/fleet/v4/server/service/schedule"
 	"github.com/go-kit/log"
 	kitlog "github.com/go-kit/log"
@@ -21,16 +19,10 @@ import (
 )
 
 const (
-	calendarConsumers  = 18
-	defaultDescription = "needs to make sure your device meets the organization's requirements."
-	defaultResolution  = "During this maintenance window, you can expect updates to be applied automatically. Your device may be unavailable during this time."
+	calendarConsumers = 18
+	reloadFrequency   = 12 * time.Hour
 )
 
-type calendarConfig struct {
-	config.CalendarConfig
-	fleet.GoogleCalendarIntegration
-}
-
 func NewCalendarSchedule(
 	ctx context.Context,
 	instanceID string,
@@ -86,9 +78,10 @@ func cronCalendarEvents(ctx context.Context, ds fleet.Datastore, serverConfig co
 		return fmt.Errorf("list teams: %w", err)
 	}
 
-	localConfig := calendarConfig{
+	localConfig := &calendar.CalendarConfig{
 		CalendarConfig:            serverConfig,
 		GoogleCalendarIntegration: *googleCalendarIntegrationConfig,
+		ServerURL:                 appConfig.ServerSettings.ServerURL,
 	}
 	for _, team := range teams {
 		if err := cronCalendarEventsForTeam(
@@ -101,19 +94,10 @@ func cronCalendarEvents(ctx context.Context, ds fleet.Datastore, serverConfig co
 	return nil
 }
 
-func createUserCalendarFromConfig(ctx context.Context, config *fleet.GoogleCalendarIntegration, logger kitlog.Logger) fleet.UserCalendar {
-	googleCalendarConfig := calendar.GoogleCalendarConfig{
-		Context:           ctx,
-		IntegrationConfig: config,
-		Logger:            log.With(logger, "component", "google_calendar"),
-	}
-	return calendar.NewGoogleCalendar(&googleCalendarConfig)
-}
-
 func cronCalendarEventsForTeam(
 	ctx context.Context,
 	ds fleet.Datastore,
-	calendarConfig calendarConfig,
+	calendarConfig *calendar.CalendarConfig,
 	team fleet.Team,
 	orgName string,
 	domain string,
@@ -151,7 +135,7 @@ func cronCalendarEventsForTeam(
 	for _, policy := range policies {
 		policyIDs = append(policyIDs, policy.ID)
 	}
-	hosts, err := ds.GetTeamHostsPolicyMemberships(ctx, domain, team.ID, policyIDs)
+	hosts, err := ds.GetTeamHostsPolicyMemberships(ctx, domain, team.ID, policyIDs, nil)
 	if err != nil {
 		return fmt.Errorf("get team hosts failing policies: %w", err)
 	}
@@ -188,7 +172,7 @@ func cronCalendarEventsForTeam(
 	// policies on one of its hosts, and possibly create a new calendar event if they have
 	// another failing host on the same team.
 	start := time.Now()
-	removeCalendarEventsFromPassingHosts(ctx, ds, &calendarConfig.GoogleCalendarIntegration, passingHosts, logger)
+	removeCalendarEventsFromPassingHosts(ctx, ds, calendarConfig, passingHosts, logger)
 	level.Debug(logger).Log(
 		"msg", "passing_hosts", "took", time.Since(start),
 	)
@@ -213,7 +197,7 @@ func cronCalendarEventsForTeam(
 func processCalendarFailingHosts(
 	ctx context.Context,
 	ds fleet.Datastore,
-	calendarConfig calendarConfig,
+	calendarConfig *calendar.CalendarConfig,
 	orgName string,
 	hosts []fleet.HostPolicyMembershipData,
 	logger kitlog.Logger,
@@ -260,7 +244,7 @@ func processCalendarFailingHosts(
 					}
 				}
 
-				userCalendar := createUserCalendarFromConfig(ctx, &calendarConfig.GoogleCalendarIntegration, logger)
+				userCalendar := calendar.CreateUserCalendarFromConfig(ctx, calendarConfig, logger)
 				if err := userCalendar.Configure(host.Email); err != nil {
 					level.Error(logger).Log("msg", "configure user calendar", "err", err)
 					continue // continue with next host
@@ -319,13 +303,13 @@ func filterHostsWithSameEmail(hosts []fleet.HostPolicyMembershipData) []fleet.Ho
 func processFailingHostExistingCalendarEvent(
 	ctx context.Context,
 	ds fleet.Datastore,
-	calendar fleet.UserCalendar,
+	userCalendar fleet.UserCalendar,
 	orgName string,
 	hostCalendarEvent *fleet.HostCalendarEvent,
 	calendarEvent *fleet.CalendarEvent,
 	host fleet.HostPolicyMembershipData,
 	policyIDtoPolicy *sync.Map,
-	calendarConfig calendarConfig,
+	calendarConfig *calendar.CalendarConfig,
 	logger kitlog.Logger,
 ) error {
 	updatedEvent := calendarEvent
@@ -334,9 +318,9 @@ func processFailingHostExistingCalendarEvent(
 
 	if calendarConfig.AlwaysReloadEvent() || shouldReloadCalendarEvent(now, calendarEvent, hostCalendarEvent) {
 		var err error
-		updatedEvent, _, err = calendar.GetAndUpdateEvent(
-			calendarEvent, func(conflict bool) string {
-				return generateCalendarEventBody(ctx, ds, orgName, host, policyIDtoPolicy, conflict, logger)
+		updatedEvent, _, err = userCalendar.GetAndUpdateEvent(
+			calendarEvent, func(conflict bool) (string, bool, error) {
+				return calendar.GenerateCalendarEventBody(ctx, ds, orgName, host, policyIDtoPolicy, conflict, logger), true, nil
 			},
 		)
 		if err != nil {
@@ -350,6 +334,7 @@ func processFailingHostExistingCalendarEvent(
 		if err := ds.UpdateCalendarEvent(
 			ctx,
 			calendarEvent.ID,
+			updatedEvent.UUID,
 			updatedEvent.StartTime,
 			updatedEvent.EndTime,
 			updatedEvent.Data,
@@ -395,13 +380,18 @@ func processFailingHostExistingCalendarEvent(
 	if err := ds.UpdateHostRefetchRequested(ctx, host.HostID, true); err != nil {
 		return fmt.Errorf("refetch host: %w", err)
 	}
+
+	// We no longer need to watch the event for changes
+	if err = userCalendar.StopEventChannel(calendarEvent); err != nil {
+		return fmt.Errorf("delete event channel: %w", err)
+	}
 	return nil
 }
 
 func shouldReloadCalendarEvent(now time.Time, calendarEvent *fleet.CalendarEvent, hostCalendarEvent *fleet.HostCalendarEvent) bool {
-	// Check the user calendar every 30 minutes (and not every cron run)
+	// Check the user calendar regularly (but not every cron run)
 	// to reduce load on both Fleet and the calendar service.
-	if time.Since(calendarEvent.UpdatedAt) > 30*time.Minute {
+	if time.Since(calendarEvent.UpdatedAt) > reloadFrequency {
 		return true
 	}
 	// If the event is supposed to be happening now, we want to check if the user moved/deleted the
@@ -436,7 +426,8 @@ func processFailingHostCreateCalendarEvent(
 		return fmt.Errorf("create event on user calendar: %w", err)
 	}
 	if _, err := ds.CreateOrUpdateCalendarEvent(
-		ctx, host.Email, calendarEvent.StartTime, calendarEvent.EndTime, calendarEvent.Data, calendarEvent.TimeZone, host.HostID, fleet.CalendarWebhookStatusNone,
+		ctx, calendarEvent.UUID, host.Email, calendarEvent.StartTime, calendarEvent.EndTime, calendarEvent.Data, calendarEvent.TimeZone,
+		host.HostID, fleet.CalendarWebhookStatusNone,
 	); err != nil {
 		return fmt.Errorf("create calendar event on db: %w", err)
 	}
@@ -456,8 +447,8 @@ func attemptCreatingEventOnUserCalendar(
 	preferredDate := getPreferredCalendarEventDate(year, month, today)
 	for {
 		calendarEvent, err := userCalendar.CreateEvent(
-			preferredDate, func(conflict bool) string {
-				return generateCalendarEventBody(ctx, ds, orgName, host, policyIDtoPolicy, conflict, logger)
+			preferredDate, func(conflict bool) (string, bool, error) {
+				return calendar.GenerateCalendarEventBody(ctx, ds, orgName, host, policyIDtoPolicy, conflict, logger), true, nil
 			},
 		)
 		var dee fleet.DayEndedError
@@ -501,7 +492,7 @@ func addBusinessDay(date time.Time) time.Time {
 func removeCalendarEventsFromPassingHosts(
 	ctx context.Context,
 	ds fleet.Datastore,
-	calendarConfig *fleet.GoogleCalendarIntegration,
+	calendarConfig *calendar.CalendarConfig,
 	hosts []fleet.HostPolicyMembershipData,
 	logger kitlog.Logger,
 ) {
@@ -546,7 +537,7 @@ func removeCalendarEventsFromPassingHosts(
 					level.Error(logger).Log("msg", "get calendar event from DB", "err", err)
 					continue
 				}
-				userCalendar := createUserCalendarFromConfig(ctx, calendarConfig, logger)
+				userCalendar := calendar.CreateUserCalendarFromConfig(ctx, calendarConfig, logger)
 				if err := deleteCalendarEvent(ctx, ds, userCalendar, calendarEvent); err != nil {
 					level.Error(logger).Log("msg", "delete user calendar event", "err", err)
 					continue
@@ -582,74 +573,6 @@ func logHostsWithoutAssociatedEmail(
 	)
 }
 
-func generateCalendarEventBody(
-	ctx context.Context, ds fleet.Datastore, orgName string, host fleet.HostPolicyMembershipData, policyIDtoPolicy *sync.Map, conflict bool,
-	logger kitlog.Logger,
-) string {
-	description, resolution := getCalendarEventDescriptionAndResolution(ctx, ds, orgName, host, policyIDtoPolicy, logger)
-
-	conflictStr := ""
-	if conflict {
-		conflictStr = " because there was no remaining availability"
-	}
-	return fmt.Sprintf(
-		`%s reserved this time to make some changes to your work computer%s.
-
-Please leave your device on and connected to power.
-
-<b>Why it matters</b>
-%s
-
-<b>What we'll do</b>
-%s
-`,
-		orgName, conflictStr, description, resolution,
-	)
-}
-
-func getCalendarEventDescriptionAndResolution(
-	ctx context.Context, ds fleet.Datastore, orgName string, host fleet.HostPolicyMembershipData, policyIDtoPolicy *sync.Map,
-	logger kitlog.Logger,
-) (string, string) {
-	getDefaultDescription := func() string {
-		return fmt.Sprintf(`%s %s`, orgName, defaultDescription)
-	}
-
-	var description, resolution string
-	policyIDs := strings.Split(host.FailingPolicyIDs, ",")
-	if len(policyIDs) == 1 && policyIDs[0] != "" {
-		var policy *fleet.PolicyLite
-		policyAny, ok := policyIDtoPolicy.Load(policyIDs[0])
-		if !ok {
-			id, err := strconv.ParseUint(policyIDs[0], 10, 64)
-			if err != nil {
-				level.Error(logger).Log("msg", "parse policy id", "err", err)
-				return getDefaultDescription(), defaultResolution
-			}
-			policy, err = ds.PolicyLite(ctx, uint(id))
-			if err != nil {
-				level.Error(logger).Log("msg", "get policy", "err", err)
-				return getDefaultDescription(), defaultResolution
-			}
-			policyIDtoPolicy.Store(policyIDs[0], policy)
-		} else {
-			policy = policyAny.(*fleet.PolicyLite)
-		}
-		policyDescription := strings.TrimSpace(policy.Description)
-		if policyDescription == "" || policy.Resolution == nil || strings.TrimSpace(*policy.Resolution) == "" {
-			description = getDefaultDescription()
-			resolution = defaultResolution
-		} else {
-			description = policyDescription
-			resolution = strings.TrimSpace(*policy.Resolution)
-		}
-	} else {
-		description = getDefaultDescription()
-		resolution = defaultResolution
-	}
-	return description, resolution
-}
-
 func isHostOnline(ctx context.Context, ds fleet.Datastore, hostID uint) (bool, error) {
 	hostLite, err := ds.HostLiteByID(ctx, hostID)
 	if err != nil {
@@ -678,10 +601,13 @@ func cronCalendarEventsCleanup(ctx context.Context, ds fleet.Datastore, logger k
 	}
 
 	var userCalendar fleet.UserCalendar
-	var calendarConfig *fleet.GoogleCalendarIntegration
+	var calConfig *calendar.CalendarConfig
 	if len(appConfig.Integrations.GoogleCalendar) > 0 {
-		calendarConfig = appConfig.Integrations.GoogleCalendar[0]
-		userCalendar = createUserCalendarFromConfig(ctx, calendarConfig, logger)
+		calConfig = &calendar.CalendarConfig{
+			GoogleCalendarIntegration: *appConfig.Integrations.GoogleCalendar[0],
+			ServerURL:                 appConfig.ServerSettings.ServerURL,
+		}
+		userCalendar = calendar.CreateUserCalendarFromConfig(ctx, calConfig, logger)
 	}
 
 	// If global setting is disabled, we remove all calendar events from the DB
@@ -710,7 +636,7 @@ func cronCalendarEventsCleanup(ctx context.Context, ds fleet.Datastore, logger k
 	}
 
 	for _, team := range teams {
-		if err := cleanupTeamCalendarEvents(ctx, ds, calendarConfig, *team, logger); err != nil {
+		if err := cleanupTeamCalendarEvents(ctx, ds, calConfig, *team, logger); err != nil {
 			level.Info(logger).Log("msg", "delete team calendar events", "team_id", team.ID, "err", err)
 		}
 	}
@@ -724,14 +650,14 @@ func cronCalendarEventsCleanup(ctx context.Context, ds fleet.Datastore, logger k
 	if err != nil {
 		return fmt.Errorf("list out of date calendar events: %w", err)
 	}
-	deleteCalendarEventsInParallel(ctx, ds, calendarConfig, outOfDateCalendarEvents, logger)
+	deleteCalendarEventsInParallel(ctx, ds, calConfig, outOfDateCalendarEvents, logger)
 	return nil
 }
 
 func deleteAllCalendarEvents(
 	ctx context.Context,
 	ds fleet.Datastore,
-	calendarConfig *fleet.GoogleCalendarIntegration,
+	calendarConfig *calendar.CalendarConfig,
 	teamID *uint,
 	logger kitlog.Logger,
 ) error {
@@ -744,7 +670,7 @@ func deleteAllCalendarEvents(
 }
 
 func deleteCalendarEventsInParallel(
-	ctx context.Context, ds fleet.Datastore, calendarConfig *fleet.GoogleCalendarIntegration, calendarEvents []*fleet.CalendarEvent,
+	ctx context.Context, ds fleet.Datastore, calendarConfig *calendar.CalendarConfig, calendarEvents []*fleet.CalendarEvent,
 	logger kitlog.Logger,
 ) {
 	if len(calendarEvents) > 0 {
@@ -757,7 +683,7 @@ func deleteCalendarEventsInParallel(
 				for calEvent := range calendarEventCh {
 					var userCalendar fleet.UserCalendar
 					if calendarConfig != nil {
-						userCalendar = createUserCalendarFromConfig(ctx, calendarConfig, logger)
+						userCalendar = calendar.CreateUserCalendarFromConfig(ctx, calendarConfig, logger)
 					}
 					if err := deleteCalendarEvent(ctx, ds, userCalendar, calEvent); err != nil {
 						level.Error(logger).Log("msg", "delete user calendar event", "err", err)
@@ -777,7 +703,7 @@ func deleteCalendarEventsInParallel(
 func cleanupTeamCalendarEvents(
 	ctx context.Context,
 	ds fleet.Datastore,
-	calendarConfig *fleet.GoogleCalendarIntegration,
+	calendarConfig *calendar.CalendarConfig,
 	team fleet.Team,
 	logger kitlog.Logger,
 ) error {
diff --git a/server/cron/calendar_cron_test.go b/server/cron/calendar_cron_test.go
index e03d633569..85c4761e84 100644
--- a/server/cron/calendar_cron_test.go
+++ b/server/cron/calendar_cron_test.go
@@ -167,7 +167,7 @@ func TestEventForDifferentHost(t *testing.T) {
 	hostID2 := uint(101)
 	userEmail1 := "user@example.com"
 	ds.GetTeamHostsPolicyMembershipsFunc = func(
-		ctx context.Context, domain string, teamID uint, policyIDs []uint,
+		ctx context.Context, domain string, teamID uint, policyIDs []uint, _ *uint,
 	) ([]fleet.HostPolicyMembershipData, error) {
 		require.Equal(t, teamID1, teamID)
 		require.Equal(t, []uint{policyID1}, policyIDs)
@@ -209,6 +209,7 @@ func TestCalendarEventsMultipleHosts(t *testing.T) {
 	logger := kitlog.With(kitlog.NewLogfmtLogger(os.Stdout))
 	t.Cleanup(func() {
 		calendar.ClearMockEvents()
+		calendar.ClearMockChannels()
 	})
 
 	//
@@ -279,7 +280,7 @@ func TestCalendarEventsMultipleHosts(t *testing.T) {
 	hostID4 := uint(103)
 
 	ds.GetTeamHostsPolicyMembershipsFunc = func(
-		ctx context.Context, domain string, teamID uint, policyIDs []uint,
+		ctx context.Context, domain string, teamID uint, policyIDs []uint, _ *uint,
 	) ([]fleet.HostPolicyMembershipData, error) {
 		require.Equal(t, "example.com", domain)
 		require.Equal(t, teamID1, teamID)
@@ -336,6 +337,7 @@ func TestCalendarEventsMultipleHosts(t *testing.T) {
 	hostCalendarEvents := make(map[uint]*fleet.HostCalendarEvent)
 
 	ds.CreateOrUpdateCalendarEventFunc = func(ctx context.Context,
+		uuid string,
 		email string,
 		startTime, endTime time.Time,
 		data []byte,
@@ -343,6 +345,7 @@ func TestCalendarEventsMultipleHosts(t *testing.T) {
 		hostID uint,
 		webhookStatus fleet.CalendarWebhookStatus,
 	) (*fleet.CalendarEvent, error) {
+		assert.NotEmpty(t, uuid)
 		require.Equal(t, hostID1, hostID)
 		require.Equal(t, userEmail1, email)
 		require.Equal(t, fleet.CalendarWebhookStatusNone, webhookStatus)
@@ -380,8 +383,8 @@ func TestCalendarEventsMultipleHosts(t *testing.T) {
 
 	createdCalendarEvents := calendar.ListGoogleMockEvents()
 	require.Len(t, createdCalendarEvents, 1)
-	strings.Contains(createdCalendarEvents["1"].Description, defaultDescription)
-	strings.Contains(createdCalendarEvents["1"].Description, defaultResolution)
+	strings.Contains(createdCalendarEvents["1"].Description, fleet.CalendarDefaultDescription)
+	strings.Contains(createdCalendarEvents["1"].Description, fleet.CalendarDefaultResolution)
 }
 
 type notFoundErr struct{}
@@ -405,6 +408,7 @@ func TestCalendarEvents1KHosts(t *testing.T) {
 	}
 	t.Cleanup(func() {
 		calendar.ClearMockEvents()
+		calendar.ClearMockChannels()
 	})
 
 	ds.AppConfigFunc = func(ctx context.Context) (*fleet.AppConfig, error) {
@@ -594,7 +598,7 @@ func TestCalendarEvents1KHosts(t *testing.T) {
 	}
 
 	ds.GetTeamHostsPolicyMembershipsFunc = func(
-		ctx context.Context, domain string, teamID uint, policyIDs []uint,
+		ctx context.Context, domain string, teamID uint, policyIDs []uint, _ *uint,
 	) ([]fleet.HostPolicyMembershipData, error) {
 		var start, end int
 		switch teamID {
@@ -622,6 +626,7 @@ func TestCalendarEvents1KHosts(t *testing.T) {
 	eventPerHost := make(map[uint]*fleet.CalendarEvent)
 
 	ds.CreateOrUpdateCalendarEventFunc = func(ctx context.Context,
+		uuid string,
 		email string,
 		startTime, endTime time.Time,
 		data []byte,
@@ -629,6 +634,7 @@ func TestCalendarEvents1KHosts(t *testing.T) {
 		hostID uint,
 		webhookStatus fleet.CalendarWebhookStatus,
 	) (*fleet.CalendarEvent, error) {
+		assert.NotEmpty(t, uuid)
 		require.Equal(t, fmt.Sprintf("user%d@example.com", hostID), email)
 		eventsCreatedMu.Lock()
 		eventsCreated += 1
@@ -708,6 +714,7 @@ func TestEventDescription(t *testing.T) {
 	t.Cleanup(
 		func() {
 			calendar.ClearMockEvents()
+			calendar.ClearMockChannels()
 		},
 	)
 
@@ -807,7 +814,7 @@ func TestEventDescription(t *testing.T) {
 	hostID7, userEmail7 := uint(106), "user7@example.com"
 
 	ds.GetTeamHostsPolicyMembershipsFunc = func(
-		ctx context.Context, domain string, teamID uint, policyIDs []uint,
+		ctx context.Context, domain string, teamID uint, policyIDs []uint, _ *uint,
 	) ([]fleet.HostPolicyMembershipData, error) {
 		require.Equal(t, "example.com", domain)
 		require.Equal(t, teamID1, teamID)
@@ -900,6 +907,7 @@ func TestEventDescription(t *testing.T) {
 
 	ds.CreateOrUpdateCalendarEventFunc = func(
 		ctx context.Context,
+		uuid string,
 		email string,
 		startTime, endTime time.Time,
 		data []byte,
@@ -907,6 +915,7 @@ func TestEventDescription(t *testing.T) {
 		hostID uint,
 		webhookStatus fleet.CalendarWebhookStatus,
 	) (*fleet.CalendarEvent, error) {
+		assert.NotEmpty(t, uuid)
 		require.Equal(t, fleet.CalendarWebhookStatusNone, webhookStatus)
 		require.NotEmpty(t, data)
 		require.NotZero(t, startTime)
@@ -948,14 +957,14 @@ func TestEventDescription(t *testing.T) {
 		err = json.Unmarshal(calendarEvents[hostCalEvent.HostID].Data, &details)
 		require.NoError(t, err)
 		description := createdCalendarEvents[details["id"]].Description
-		defaultDescriptionWithOrg := fmt.Sprintf("%s %s", orgName, defaultDescription)
+		defaultDescriptionWithOrg := fmt.Sprintf("%s %s", orgName, fleet.CalendarDefaultDescription)
 		switch hostCalEvent.HostID {
 		case hostID1, hostID6:
 			assert.Contains(t, description, "Description for policy 1")
 			assert.Contains(t, description, "Resolution for policy 1")
 		default:
 			assert.Contains(t, description, defaultDescriptionWithOrg)
-			assert.Contains(t, description, defaultResolution)
+			assert.Contains(t, description, fleet.CalendarDefaultResolution)
 		}
 	}
 }
diff --git a/server/datastore/mysql/calendar_events.go b/server/datastore/mysql/calendar_events.go
index 29fb263ada..fa58b8f3af 100644
--- a/server/datastore/mysql/calendar_events.go
+++ b/server/datastore/mysql/calendar_events.go
@@ -3,6 +3,7 @@ package mysql
 import (
 	"context"
 	"database/sql"
+	"errors"
 	"fmt"
 	"time"
 
@@ -13,6 +14,7 @@ import (
 
 func (ds *Datastore) CreateOrUpdateCalendarEvent(
 	ctx context.Context,
+	uuid string,
 	email string,
 	startTime time.Time,
 	endTime time.Time,
@@ -25,13 +27,15 @@ func (ds *Datastore) CreateOrUpdateCalendarEvent(
 	if err := ds.withRetryTxx(ctx, func(tx sqlx.ExtContext) error {
 		const calendarEventsQuery = `
 			INSERT INTO calendar_events (
+				uuid,
 				email,
 				start_time,
 				end_time,
 				event,
 				timezone
-			) VALUES (?, ?, ?, ?, ?)
+			) VALUES (?, ?, ?, ?, ?, ?)
 			ON DUPLICATE KEY UPDATE
+				uuid = VALUES(uuid),
 				start_time = VALUES(start_time),
 				end_time = VALUES(end_time),
 				event = VALUES(event),
@@ -41,6 +45,7 @@ func (ds *Datastore) CreateOrUpdateCalendarEvent(
 		result, err := tx.ExecContext(
 			ctx,
 			calendarEventsQuery,
+			uuid,
 			email,
 			startTime,
 			endTime,
@@ -122,9 +127,29 @@ func (ds *Datastore) GetCalendarEvent(ctx context.Context, email string) (*fleet
 	return &calendarEvent, nil
 }
 
-func (ds *Datastore) UpdateCalendarEvent(ctx context.Context, calendarEventID uint, startTime time.Time, endTime time.Time, data []byte, timeZone string) error {
+func (ds *Datastore) GetCalendarEventDetailsByUUID(ctx context.Context, uuid string) (*fleet.CalendarEventDetails, error) {
+	const calendarEventsByUUIDQuery = `
+		SELECT ce.*, h.team_id as team_id, h.id as host_id FROM calendar_events ce
+		LEFT JOIN host_calendar_events hce ON hce.calendar_event_id = ce.id
+		LEFT JOIN hosts h ON h.id = hce.host_id
+		WHERE ce.uuid = ?;
+	`
+	var calendarEvent fleet.CalendarEventDetails
+	err := sqlx.GetContext(ctx, ds.reader(ctx), &calendarEvent, calendarEventsByUUIDQuery, uuid)
+	if err != nil {
+		if errors.Is(err, sql.ErrNoRows) {
+			return nil, ctxerr.Wrap(ctx, notFound("CalendarEvent").WithMessage(fmt.Sprintf("uuid: %s", uuid)))
+		}
+		return nil, ctxerr.Wrap(ctx, err, "get calendar event")
+	}
+	return &calendarEvent, nil
+}
+
+func (ds *Datastore) UpdateCalendarEvent(ctx context.Context, calendarEventID uint, uuid string, startTime time.Time, endTime time.Time,
+	data []byte, timeZone string) error {
 	const calendarEventsQuery = `
 		UPDATE calendar_events SET
+			uuid = ?,
 			start_time = ?,
 			end_time = ?,
 			event = ?,
@@ -132,7 +157,8 @@ func (ds *Datastore) UpdateCalendarEvent(ctx context.Context, calendarEventID ui
 			updated_at = CURRENT_TIMESTAMP
 		WHERE id = ?;
 	`
-	if _, err := ds.writer(ctx).ExecContext(ctx, calendarEventsQuery, startTime, endTime, data, timeZone, calendarEventID); err != nil {
+	if _, err := ds.writer(ctx).ExecContext(ctx, calendarEventsQuery, uuid, startTime, endTime, data, timeZone,
+		calendarEventID); err != nil {
 		return ctxerr.Wrap(ctx, err, "update calendar event")
 	}
 	return nil
diff --git a/server/datastore/mysql/calendar_events_test.go b/server/datastore/mysql/calendar_events_test.go
index 2b37d7f826..b4ec9d510a 100644
--- a/server/datastore/mysql/calendar_events_test.go
+++ b/server/datastore/mysql/calendar_events_test.go
@@ -2,6 +2,8 @@ package mysql
 
 import (
 	"context"
+	"github.com/google/uuid"
+	"github.com/stretchr/testify/assert"
 	"testing"
 	"time"
 
@@ -56,20 +58,32 @@ func testUpdateCalendarEvent(t *testing.T, ds *Datastore) {
 	startTime1 := time.Now()
 	endTime1 := startTime1.Add(30 * time.Minute)
 	timeZone := "America/Argentina/Buenos_Aires"
-	calendarEvent, err := ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", startTime1, endTime1, []byte(`{}`), timeZone, host.ID, fleet.CalendarWebhookStatusNone)
+	eventUUID := uuid.New().String()
+	calendarEvent, err := ds.CreateOrUpdateCalendarEvent(ctx, eventUUID, "foo@example.com", startTime1, endTime1, []byte(`{}`), timeZone,
+		host.ID, fleet.CalendarWebhookStatusNone)
 	require.NoError(t, err)
 
 	time.Sleep(1 * time.Second)
 
-	err = ds.UpdateCalendarEvent(ctx, calendarEvent.ID, startTime1, endTime1, []byte(`{}`), timeZone)
+	eventUUIDNew := uuid.New().String()
+	err = ds.UpdateCalendarEvent(ctx, calendarEvent.ID, eventUUIDNew, startTime1, endTime1, []byte(`{}`), timeZone)
 	require.NoError(t, err)
 
 	calendarEvent2, err := ds.GetCalendarEvent(ctx, "foo@example.com")
 	require.NoError(t, err)
 	require.NotEqual(t, *calendarEvent, *calendarEvent2)
 	calendarEvent.UpdatedAt = calendarEvent2.UpdatedAt
+	assert.NotEqual(t, calendarEvent.UUID, calendarEvent2.UUID)
+	calendarEvent.UUID = calendarEvent2.UUID
 	require.Equal(t, *calendarEvent, *calendarEvent2)
 
+	eventDetails, err := ds.GetCalendarEventDetailsByUUID(ctx, eventUUIDNew)
+	require.NoError(t, err)
+	assert.Equal(t, eventUUIDNew, eventDetails.UUID)
+	assert.Equal(t, *calendarEvent, eventDetails.CalendarEvent)
+	assert.Equal(t, host.ID, eventDetails.HostID)
+	assert.Nil(t, eventDetails.TeamID)
+
 	// TODO(lucas): Add more tests here.
 }
 
@@ -101,23 +115,30 @@ func testCreateOrUpdateCalendarEvent(t *testing.T, ds *Datastore) {
 
 	startTime1 := time.Now()
 	endTime1 := startTime1.Add(30 * time.Minute)
-	calendarEvent, err := ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", startTime1, endTime1, []byte(`{}`), timeZone, host.ID, fleet.CalendarWebhookStatusNone)
+	eventUUID := uuid.New().String()
+	calendarEvent, err := ds.CreateOrUpdateCalendarEvent(ctx, eventUUID, "foo@example.com", startTime1, endTime1, []byte(`{}`), timeZone,
+		host.ID, fleet.CalendarWebhookStatusNone)
 	require.NoError(t, err)
 	require.Equal(t, calendarEvent.TimeZone, timeZone)
 
 	time.Sleep(1 * time.Second)
 
-	calendarEvent2, err := ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", startTime1, endTime1, []byte(`{}`), timeZone, host.ID, fleet.CalendarWebhookStatusNone)
+	eventUUID2 := uuid.New().String()
+	calendarEvent2, err := ds.CreateOrUpdateCalendarEvent(ctx, eventUUID2, "foo@example.com", startTime1, endTime1, []byte(`{}`), timeZone,
+		host.ID, fleet.CalendarWebhookStatusNone)
 	require.NoError(t, err)
 	require.Greater(t, calendarEvent2.UpdatedAt, calendarEvent.UpdatedAt)
 	calendarEvent.UpdatedAt = calendarEvent2.UpdatedAt
+	assert.NotEqual(t, calendarEvent.UUID, calendarEvent2.UUID)
+	calendarEvent.UUID = calendarEvent2.UUID
 	require.Equal(t, *calendarEvent, *calendarEvent2)
 
 	time.Sleep(1 * time.Second)
 
 	startTime2 := startTime1.Add(1 * time.Hour)
 	endTime2 := startTime1.Add(30 * time.Minute)
-	calendarEvent3, err := ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", startTime2, endTime2, []byte(`{"foo": "bar"}`), timeZone, host.ID, fleet.CalendarWebhookStatusPending)
+	calendarEvent3, err := ds.CreateOrUpdateCalendarEvent(ctx, eventUUID2, "foo@example.com", startTime2, endTime2,
+		[]byte(`{"foo": "bar"}`), timeZone, host.ID, fleet.CalendarWebhookStatusPending)
 	require.NoError(t, err)
 	require.Greater(t, calendarEvent3.UpdatedAt, calendarEvent2.UpdatedAt)
 	require.WithinDuration(t, startTime2, calendarEvent3.StartTime, 1*time.Second)
diff --git a/server/datastore/mysql/hosts_test.go b/server/datastore/mysql/hosts_test.go
index 02ce272c8e..8c552448f7 100644
--- a/server/datastore/mysql/hosts_test.go
+++ b/server/datastore/mysql/hosts_test.go
@@ -9520,7 +9520,8 @@ func testListUpcomingHostMaintenanceWindows(t *testing.T, ds *Datastore) {
 
 	startTime := time.Now().UTC().Add(30 * time.Minute)
 	endTime := startTime.Add(30 * time.Minute)
-	calendarEvent, err := ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", startTime, endTime, []byte(`{}`), timeZone, host.ID, fleet.CalendarWebhookStatusNone)
+	calendarEvent, err := ds.CreateOrUpdateCalendarEvent(ctx, uuid.New().String(), "foo@example.com", startTime, endTime, []byte(`{}`),
+		timeZone, host.ID, fleet.CalendarWebhookStatusNone)
 	require.NoError(t, err)
 	require.Equal(t, calendarEvent.TimeZone, timeZone)
 
diff --git a/server/datastore/mysql/migrations/tables/20240626195531_AddTimezoneToCalendarEvents.go b/server/datastore/mysql/migrations/tables/20240626195531_AddTimezoneToCalendarEvents.go
index 34b88fc724..0e289a8c7c 100644
--- a/server/datastore/mysql/migrations/tables/20240626195531_AddTimezoneToCalendarEvents.go
+++ b/server/datastore/mysql/migrations/tables/20240626195531_AddTimezoneToCalendarEvents.go
@@ -10,7 +10,7 @@ func init() {
 }
 
 func Up_20240626195531(tx *sql.Tx) error {
-	if _, err := tx.Exec(`ALTER TABLE calendar_events ADD COLUMN timezone VARCHAR(64) NULL`); err != nil {
+	if _, err := tx.Exec(`ALTER TABLE calendar_events ADD COLUMN timezone VARCHAR(64) COLLATE utf8mb4_unicode_ci NULL`); err != nil {
 		return fmt.Errorf("failed to add `timezone` column to `calendar_events` table: %w", err)
 	}
 	return nil
diff --git a/server/datastore/mysql/migrations/tables/20240707134035_AddUUIDToCalendarEvents.go b/server/datastore/mysql/migrations/tables/20240707134035_AddUUIDToCalendarEvents.go
new file mode 100644
index 0000000000..11e58a0596
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20240707134035_AddUUIDToCalendarEvents.go
@@ -0,0 +1,34 @@
+package tables
+
+import (
+	"database/sql"
+	"fmt"
+)
+
+func init() {
+	MigrationClient.AddMigration(Up_20240707134035, Down_20240707134035)
+}
+
+func Up_20240707134035(tx *sql.Tx) error {
+	// UUID is a 36-character string with the most common 8-4-4-4-12 format, xxxxxxxx-xxxx-xxxx-xxxx-xxxxxxxxxxxx
+	// Reference: https://en.wikipedia.org/wiki/Universally_unique_identifier#Textual_representation
+	if _, err := tx.Exec(`ALTER TABLE calendar_events ADD COLUMN uuid VARCHAR(36) COLLATE utf8mb4_unicode_ci NOT NULL`); err != nil {
+		return fmt.Errorf("failed to add `uuid` column to `calendar_events` table: %w", err)
+	}
+
+	// Generate UUIDs for existing calendar events, without changing the updated_at timestamp
+	if _, err := tx.Exec(`UPDATE calendar_events SET uuid = UUID(), updated_at = updated_at`); err != nil {
+		return fmt.Errorf("failed to generate UUIDs for existing calendar events: %w", err)
+	}
+
+	// Add unique constraint to uuid column
+	if _, err := tx.Exec(`ALTER TABLE calendar_events ADD CONSTRAINT idx_calendar_events_uuid_unique UNIQUE (uuid)`); err != nil {
+		return fmt.Errorf("failed to add unique constraint to `uuid` column in `calendar_events` table: %w", err)
+	}
+
+	return nil
+}
+
+func Down_20240707134035(_ *sql.Tx) error {
+	return nil
+}
diff --git a/server/datastore/mysql/migrations/tables/20240707134035_AddUUIDToCalendarEvents_test.go b/server/datastore/mysql/migrations/tables/20240707134035_AddUUIDToCalendarEvents_test.go
new file mode 100644
index 0000000000..851997f251
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20240707134035_AddUUIDToCalendarEvents_test.go
@@ -0,0 +1,42 @@
+package tables
+
+import (
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+func TestUp_20240707134035(t *testing.T) {
+	db := applyUpToPrev(t)
+
+	startTime := time.Now().UTC()
+	endTime := time.Now().UTC().Add(30 * time.Minute)
+	data := []byte("{\"foo\": \"bar\"}")
+	const insertStmt = `INSERT INTO calendar_events (email, start_time, end_time, event) VALUES (?, ?, ?, ?)`
+	event1ID := uint(execNoErrLastID(t, db, insertStmt, "foo@example.com", startTime, endTime, data))
+	event2ID := uint(execNoErrLastID(t, db, insertStmt, "bar@example.com", startTime, endTime, data))
+
+	// Apply current migration.
+	applyNext(t, db)
+
+	// check that it's NULL
+	const selectUUIDStmt = `SELECT uuid FROM calendar_events WHERE id = ?`
+	var uuid1, uuid2 string
+	err := db.Get(&uuid1, selectUUIDStmt, event1ID)
+	require.NoError(t, err)
+	assert.NotEmpty(t, uuid1)
+	err = db.Get(&uuid2, selectUUIDStmt, event2ID)
+	require.NoError(t, err)
+	assert.NotEmpty(t, uuid2)
+	assert.NotEqual(t, uuid1, uuid2)
+
+	const testUUID = "test-uuid"
+	const insertStmtUUID = `INSERT INTO calendar_events (email, start_time, end_time, event, uuid) VALUES (?, ?, ?, ?, ?)`
+	_ = execNoErrLastID(t, db, insertStmtUUID, "bob@example.com", startTime, endTime, data, testUUID)
+	// Try to use the same uuid again
+	_, err = db.Exec(insertStmt, "alice@example.com", startTime, endTime, data, testUUID)
+	assert.Error(t, err)
+
+}
diff --git a/server/datastore/mysql/policies.go b/server/datastore/mysql/policies.go
index 52dc8303b4..4df1f9324a 100644
--- a/server/datastore/mysql/policies.go
+++ b/server/datastore/mysql/policies.go
@@ -1434,6 +1434,7 @@ func (ds *Datastore) GetTeamHostsPolicyMemberships(
 	domain string,
 	teamID uint,
 	policyIDs []uint,
+	hostID *uint,
 ) ([]fleet.HostPolicyMembershipData, error) {
 	query := `
 	SELECT 
@@ -1459,13 +1460,17 @@ func (ds *Datastore) GetTeamHostsPolicyMemberships(
 	) sh ON h.id = sh.host_id
 	LEFT JOIN host_display_names hdn ON h.id = hdn.host_id
 	LEFT JOIN host_calendar_events hce ON h.id = hce.host_id
-	WHERE h.team_id = ? AND ((pm.passing IS NOT NULL AND NOT pm.passing) OR (COALESCE(pm.passing, 1) AND hce.host_id IS NOT NULL));
+	WHERE h.team_id = ? AND ((pm.passing IS NOT NULL AND NOT pm.passing) OR (COALESCE(pm.passing, 1) AND hce.host_id IS NOT NULL))
 `
 
 	query, args, err := sqlx.In(query, policyIDs, domain, teamID, teamID)
 	if err != nil {
 		return nil, ctxerr.Wrapf(ctx, err, "build select get team hosts policy memberships query")
 	}
+	if hostID != nil {
+		query += ` AND h.id = ?`
+		args = append(args, *hostID)
+	}
 	var hosts []fleet.HostPolicyMembershipData
 	if err := sqlx.SelectContext(ctx, ds.reader(ctx), &hosts, query, args...); err != nil {
 		return nil, ctxerr.Wrap(ctx, err, "listing policies")
diff --git a/server/datastore/mysql/policies_test.go b/server/datastore/mysql/policies_test.go
index e5437e352c..f505ebc3bb 100644
--- a/server/datastore/mysql/policies_test.go
+++ b/server/datastore/mysql/policies_test.go
@@ -3485,7 +3485,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	require.NoError(t, err)
 
 	// Empty teams.
-	hostsTeam1, err := ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policy1.ID, team1Policy2.ID})
+	hostsTeam1, err := ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policy1.ID, team1Policy2.ID}, nil)
 	require.NoError(t, err)
 	require.Empty(t, hostsTeam1)
 
@@ -3538,12 +3538,12 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	require.NoError(t, err)
 
 	// Some domain that doesn't exist on any of the hosts
-	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "not-exists.com", team1.ID, []uint{team1Policy1.ID, team1Policy2.ID})
+	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "not-exists.com", team1.ID, []uint{team1Policy1.ID, team1Policy2.ID}, nil)
 	require.NoError(t, err)
 	require.Empty(t, hostsTeam1)
 
 	// No policy results yet (and no calendar events).
-	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policy1.ID, team1Policy2.ID})
+	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policy1.ID, team1Policy2.ID}, nil)
 	require.NoError(t, err)
 	require.Empty(t, hostsTeam1)
 
@@ -3633,7 +3633,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	require.Len(t, team2Policies, 2)
 
 	// Only returns the failing host, because the passing hosts do not have a calendar event.
-	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policies[0].ID})
+	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policies[0].ID}, nil)
 	require.NoError(t, err)
 	sort.Slice(hostsTeam1, func(i, j int) bool {
 		return hostsTeam1[i].HostID < hostsTeam1[j].HostID
@@ -3650,12 +3650,16 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	//
 	tZ := "America/Argentina/Buenos_Aires"
 	now := time.Now()
-	_, err = ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ, host1.ID, fleet.CalendarWebhookStatusPending)
+	eventUUID1 := "event-uuid"
+	_, err = ds.CreateOrUpdateCalendarEvent(ctx, eventUUID1, "foo@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ,
+		host1.ID, fleet.CalendarWebhookStatusPending)
 	require.NoError(t, err)
-	_, err = ds.CreateOrUpdateCalendarEvent(ctx, "bar@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ, host6.ID, fleet.CalendarWebhookStatusPending)
+	eventUUID2 := "event-uuid2"
+	_, err = ds.CreateOrUpdateCalendarEvent(ctx, eventUUID2, "bar@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ,
+		host6.ID, fleet.CalendarWebhookStatusPending)
 	require.NoError(t, err)
 
-	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policies[0].ID})
+	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policies[0].ID}, nil)
 	require.NoError(t, err)
 	sort.Slice(hostsTeam1, func(i, j int) bool {
 		return hostsTeam1[i].HostID < hostsTeam1[j].HostID
@@ -3689,7 +3693,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	}, time.Now(), false)
 	require.NoError(t, err)
 
-	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policies[0].ID})
+	hostsTeam1, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team1.ID, []uint{team1Policies[0].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam1, 4)
 	sort.Slice(hostsTeam1, func(i, j int) bool {
@@ -3720,7 +3724,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	// host3 doesn't have a calendar event so it's not returned by GetTeamHostsPolicyMemberships.
 	//
 
-	hostsTeam2, err := ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID})
+	hostsTeam2, err := ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam2, 1)
 	require.Equal(t, host2.ID, hostsTeam2[0].HostID)
@@ -3733,16 +3737,19 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	// Create a calendar event on host2 and host3.
 	//
 	now = time.Now()
-	_, err = ds.CreateOrUpdateCalendarEvent(ctx, "foo@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ, host2.ID, fleet.CalendarWebhookStatusPending)
+	_, err = ds.CreateOrUpdateCalendarEvent(ctx, eventUUID1, "foo@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ,
+		host2.ID, fleet.CalendarWebhookStatusPending)
 	require.NoError(t, err)
-	calendarEventHost3, err := ds.CreateOrUpdateCalendarEvent(ctx, "zoo@example.com", now, now.Add(30*time.Minute), []byte(`{"foo": "bar"}`), tZ, host3.ID, fleet.CalendarWebhookStatusPending)
+	eventUUID3 := "event-uuid3"
+	calendarEventHost3, err := ds.CreateOrUpdateCalendarEvent(ctx, eventUUID3, "zoo@example.com", now, now.Add(30*time.Minute),
+		[]byte(`{"foo": "bar"}`), tZ, host3.ID, fleet.CalendarWebhookStatusPending)
 	require.NoError(t, err)
 
 	//
 	// Now it should return host3 because it's passing and has a calendar event.
 	//
 
-	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID})
+	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam2, 2)
 	sort.Slice(hostsTeam2, func(i, j int) bool {
@@ -3771,7 +3778,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	)
 	require.NoError(t, err)
 
-	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID})
+	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam2, 2)
 	sort.Slice(
@@ -3800,7 +3807,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	}, time.Now(), false)
 	require.NoError(t, err)
 
-	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID})
+	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam2, 2)
 	sort.Slice(hostsTeam2, func(i, j int) bool {
@@ -3817,6 +3824,17 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	require.Equal(t, "serial3", hostsTeam2[1].HostHardwareSerial)
 	require.Equal(t, "display_name3", hostsTeam2[1].HostDisplayName)
 
+	// Retrieve the data only for host2.
+	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID},
+		&host2.ID)
+	require.NoError(t, err)
+	require.Len(t, hostsTeam2, 1)
+	require.Equal(t, host2.ID, hostsTeam2[0].HostID)
+	require.Equal(t, "foo@example.com", hostsTeam2[0].Email)
+	require.True(t, hostsTeam2[0].Passing)
+	require.Equal(t, "serial2", hostsTeam2[0].HostHardwareSerial)
+	require.Equal(t, "display_name2", hostsTeam2[0].HostDisplayName)
+
 	//
 	// Delete host3 calendar event
 	//
@@ -3824,7 +3842,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	err = ds.DeleteCalendarEvent(ctx, calendarEventHost3.ID)
 	require.NoError(t, err)
 
-	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID})
+	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam2, 1)
 	require.Equal(t, host2.ID, hostsTeam2[0].HostID)
@@ -3848,7 +3866,7 @@ func testGetTeamHostsPolicyMemberships(t *testing.T, ds *Datastore) {
 	// We should still get host2 as passing because it has an associated calendar event.
 	//
 
-	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID})
+	hostsTeam2, err = ds.GetTeamHostsPolicyMemberships(ctx, "example.com", team2.ID, []uint{team2Policies[0].ID, team2Policies[1].ID}, nil)
 	require.NoError(t, err)
 	require.Len(t, hostsTeam2, 1)
 	require.Equal(t, host2.ID, hostsTeam2[0].HostID)
diff --git a/server/datastore/mysql/schema.sql b/server/datastore/mysql/schema.sql
index 2b5d5bd1b8..391b8ed54b 100644
--- a/server/datastore/mysql/schema.sql
+++ b/server/datastore/mysql/schema.sql
@@ -53,8 +53,10 @@ CREATE TABLE `calendar_events` (
   `created_at` timestamp NOT NULL DEFAULT CURRENT_TIMESTAMP,
   `updated_at` timestamp NULL DEFAULT CURRENT_TIMESTAMP ON UPDATE CURRENT_TIMESTAMP,
   `timezone` varchar(64) COLLATE utf8mb4_unicode_ci DEFAULT NULL,
+  `uuid` varchar(36) COLLATE utf8mb4_unicode_ci NOT NULL,
   PRIMARY KEY (`id`),
-  UNIQUE KEY `idx_one_calendar_event_per_email` (`email`)
+  UNIQUE KEY `idx_one_calendar_event_per_email` (`email`),
+  UNIQUE KEY `idx_calendar_events_uuid_unique` (`uuid`)
 ) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
 /*!40101 SET @saved_cs_client     = @@character_set_client */;
@@ -943,9 +945,9 @@ CREATE TABLE `migration_status_tables` (
   `tstamp` timestamp NULL DEFAULT CURRENT_TIMESTAMP,
   PRIMARY KEY (`id`),
   UNIQUE KEY `id` (`id`)
-) ENGINE=InnoDB AUTO_INCREMENT=278 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
+) ENGINE=InnoDB AUTO_INCREMENT=279 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
-INSERT INTO `migration_status_tables` VALUES (1,0,1,'2020-01-01 01:01:01'),(2,20161118193812,1,'2020-01-01 01:01:01'),(3,20161118211713,1,'2020-01-01 01:01:01'),(4,20161118212436,1,'2020-01-01 01:01:01'),(5,20161118212515,1,'2020-01-01 01:01:01'),(6,20161118212528,1,'2020-01-01 01:01:01'),(7,20161118212538,1,'2020-01-01 01:01:01'),(8,20161118212549,1,'2020-01-01 01:01:01'),(9,20161118212557,1,'2020-01-01 01:01:01'),(10,20161118212604,1,'2020-01-01 01:01:01'),(11,20161118212613,1,'2020-01-01 01:01:01'),(12,20161118212621,1,'2020-01-01 01:01:01'),(13,20161118212630,1,'2020-01-01 01:01:01'),(14,20161118212641,1,'2020-01-01 01:01:01'),(15,20161118212649,1,'2020-01-01 01:01:01'),(16,20161118212656,1,'2020-01-01 01:01:01'),(17,20161118212758,1,'2020-01-01 01:01:01'),(18,20161128234849,1,'2020-01-01 01:01:01'),(19,20161230162221,1,'2020-01-01 01:01:01'),(20,20170104113816,1,'2020-01-01 01:01:01'),(21,20170105151732,1,'2020-01-01 01:01:01'),(22,20170108191242,1,'2020-01-01 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01:01:01'),(265,20240515200020,1,'2020-01-01 01:01:01'),(266,20240521143023,1,'2020-01-01 01:01:01'),(267,20240521143024,1,'2020-01-01 01:01:01'),(268,20240601174138,1,'2020-01-01 01:01:01'),(269,20240607133721,1,'2020-01-01 01:01:01'),(270,20240612150059,1,'2020-01-01 01:01:01'),(271,20240613162201,1,'2020-01-01 01:01:01'),(272,20240613172616,1,'2020-01-01 01:01:01'),(273,20240618142419,1,'2020-01-01 01:01:01'),(274,20240625093543,1,'2020-01-01 01:01:01'),(275,20240626195531,1,'2020-01-01 01:01:01'),(276,20240702123921,1,'2020-01-01 01:01:01'),(277,20240703154849,1,'2020-01-01 01:01:01'),(278,20240707134035,1,'2020-01-01 01:01:01');
 /*!40101 SET @saved_cs_client     = @@character_set_client */;
 /*!40101 SET character_set_client = utf8 */;
 CREATE TABLE `mobile_device_management_solutions` (
diff --git a/server/datastore/mysql/teams.go b/server/datastore/mysql/teams.go
index 5711835d24..c25b4a791c 100644
--- a/server/datastore/mysql/teams.go
+++ b/server/datastore/mysql/teams.go
@@ -56,10 +56,14 @@ func (ds *Datastore) NewTeam(ctx context.Context, team *fleet.Team) (*fleet.Team
 }
 
 func (ds *Datastore) Team(ctx context.Context, tid uint) (*fleet.Team, error) {
-	return teamDB(ctx, ds.reader(ctx), tid)
+	return teamDB(ctx, ds.reader(ctx), tid, true)
 }
 
-func teamDB(ctx context.Context, q sqlx.QueryerContext, tid uint) (*fleet.Team, error) {
+func (ds *Datastore) TeamWithoutExtras(ctx context.Context, tid uint) (*fleet.Team, error) {
+	return teamDB(ctx, ds.reader(ctx), tid, false)
+}
+
+func teamDB(ctx context.Context, q sqlx.QueryerContext, tid uint, withExtras bool) (*fleet.Team, error) {
 	stmt := `
 		SELECT ` + teamColumns + ` FROM teams
 			WHERE id = ?
@@ -73,18 +77,20 @@ func teamDB(ctx context.Context, q sqlx.QueryerContext, tid uint) (*fleet.Team,
 		return nil, ctxerr.Wrap(ctx, err, "select team")
 	}
 
-	if err := loadSecretsForTeamsDB(ctx, q, []*fleet.Team{team}); err != nil {
-		return nil, ctxerr.Wrap(ctx, err, "getting secrets for teams")
-	}
+	if withExtras {
+		if err := loadSecretsForTeamsDB(ctx, q, []*fleet.Team{team}); err != nil {
+			return nil, ctxerr.Wrap(ctx, err, "getting secrets for teams")
+		}
 
-	if err := loadUsersForTeamDB(ctx, q, team); err != nil {
-		return nil, err
-	}
-	if err := loadHostCountForTeamDB(ctx, q, team); err != nil {
-		return nil, err
-	}
-	if err := loadFeaturesForTeamDB(ctx, q, team); err != nil {
-		return nil, err
+		if err := loadUsersForTeamDB(ctx, q, team); err != nil {
+			return nil, err
+		}
+		if err := loadHostCountForTeamDB(ctx, q, team); err != nil {
+			return nil, err
+		}
+		if err := loadFeaturesForTeamDB(ctx, q, team); err != nil {
+			return nil, err
+		}
 	}
 
 	return team, nil
diff --git a/server/fleet/calendar.go b/server/fleet/calendar.go
index 5eb4597f44..b9184f52eb 100644
--- a/server/fleet/calendar.go
+++ b/server/fleet/calendar.go
@@ -9,6 +9,11 @@ import (
 	"github.com/fleetdm/fleet/v4/server"
 )
 
+const (
+	CalendarDefaultDescription = "needs to make sure your device meets the organization's requirements."
+	CalendarDefaultResolution  = "During this maintenance window, you can expect updates to be applied automatically. Your device may be unavailable during this time."
+)
+
 type DayEndedError struct {
 	Msg string
 }
@@ -22,13 +27,18 @@ type UserCalendar interface {
 	// CreateEvent, GetAndUpdateEvent and DeleteEvent reference the user's calendar.
 	Configure(userEmail string) error
 	// CreateEvent creates a new event on the calendar on the given date. DayEndedError is returned if there is no time left on the given date to schedule event.
-	CreateEvent(dateOfEvent time.Time, genBodyFn func(conflict bool) string) (event *CalendarEvent, err error)
+	CreateEvent(dateOfEvent time.Time, genBodyFn func(conflict bool) (body string, ok bool, err error)) (event *CalendarEvent, err error)
 	// GetAndUpdateEvent retrieves the event from the calendar.
 	// If the event has been modified, it returns the updated event.
 	// If the event has been deleted, it schedules a new event with given body callback and returns the new event.
-	GetAndUpdateEvent(event *CalendarEvent, genBodyFn func(conflict bool) string) (updatedEvent *CalendarEvent, updated bool, err error)
+	GetAndUpdateEvent(event *CalendarEvent, genBodyFn func(conflict bool) (body string, ok bool, err error)) (updatedEvent *CalendarEvent,
+		updated bool, err error)
 	// DeleteEvent deletes the event with the given ID.
 	DeleteEvent(event *CalendarEvent) error
+	// StopEventChannel stops the event's callback channel.
+	StopEventChannel(event *CalendarEvent) error
+	// Get retrieves the value of the given key from the event.
+	Get(event *CalendarEvent, key string) (interface{}, error)
 }
 
 type CalendarWebhookPayload struct {
diff --git a/server/fleet/calendar_events.go b/server/fleet/calendar_events.go
index 30cfcd11c6..96d5a9a93f 100644
--- a/server/fleet/calendar_events.go
+++ b/server/fleet/calendar_events.go
@@ -4,6 +4,7 @@ import "time"
 
 type CalendarEvent struct {
 	ID        uint      `db:"id"`
+	UUID      string    `db:"uuid"`
 	Email     string    `db:"email"`
 	StartTime time.Time `db:"start_time"`
 	EndTime   time.Time `db:"end_time"`
@@ -13,6 +14,12 @@ type CalendarEvent struct {
 	UpdateCreateTimestamps
 }
 
+type CalendarEventDetails struct {
+	CalendarEvent
+	TeamID *uint `db:"team_id"` // Should not be nil, but is nullable in the database
+	HostID uint  `db:"host_id"`
+}
+
 type CalendarWebhookStatus int
 
 const (
diff --git a/server/fleet/datastore.go b/server/fleet/datastore.go
index b973317e22..da5d4df785 100644
--- a/server/fleet/datastore.go
+++ b/server/fleet/datastore.go
@@ -490,7 +490,9 @@ type Datastore interface {
 	SaveTeam(ctx context.Context, team *Team) (*Team, error)
 	// Team retrieves the Team by ID.
 	Team(ctx context.Context, tid uint) (*Team, error)
-	// Team deletes the Team by ID.
+	// TeamWithoutExtras retrieves the Team by ID without extra fields.
+	TeamWithoutExtras(ctx context.Context, tid uint) (*Team, error)
+	// DeleteTeam deletes the Team by ID.
 	DeleteTeam(ctx context.Context, tid uint) error
 	// TeamByName retrieves the Team by Name.
 	TeamByName(ctx context.Context, name string) (*Team, error)
@@ -656,12 +658,13 @@ type Datastore interface {
 
 	PolicyQueriesForHost(ctx context.Context, host *Host) (map[string]string, error)
 
-	// GetTeamHostsPolicyMembmerships returns the hosts that belong to the given team and their pass/fail statuses
+	// GetTeamHostsPolicyMemberships returns the hosts that belong to the given team and their pass/fail statuses
 	// around the provided policyIDs.
 	// 	- Returns hosts of the team that are failing one or more of the provided policies.
 	//	- Returns hosts of the team that are passing all the policies (or are not running any of the provided policies)
 	//	  and have a calendar event scheduled.
-	GetTeamHostsPolicyMemberships(ctx context.Context, domain string, teamID uint, policyIDs []uint) ([]HostPolicyMembershipData, error)
+	GetTeamHostsPolicyMemberships(ctx context.Context, domain string, teamID uint, policyIDs []uint,
+		hostID *uint) ([]HostPolicyMembershipData, error)
 	GetCalendarPolicies(ctx context.Context, teamID uint) ([]PolicyCalendarData, error)
 
 	// Methods used for async processing of host policy query results.
@@ -686,10 +689,13 @@ type Datastore interface {
 	///////////////////////////////////////////////////////////////////////////////
 	// Calendar events
 
-	CreateOrUpdateCalendarEvent(ctx context.Context, email string, startTime time.Time, endTime time.Time, data []byte, timeZone string, hostID uint, webhookStatus CalendarWebhookStatus) (*CalendarEvent, error)
+	CreateOrUpdateCalendarEvent(ctx context.Context, uuid string, email string, startTime time.Time, endTime time.Time, data []byte,
+		timeZone string, hostID uint, webhookStatus CalendarWebhookStatus) (*CalendarEvent, error)
 	GetCalendarEvent(ctx context.Context, email string) (*CalendarEvent, error)
+	GetCalendarEventDetailsByUUID(ctx context.Context, uuid string) (*CalendarEventDetails, error)
 	DeleteCalendarEvent(ctx context.Context, calendarEventID uint) error
-	UpdateCalendarEvent(ctx context.Context, calendarEventID uint, startTime time.Time, endTime time.Time, data []byte, timeZone string) error
+	UpdateCalendarEvent(ctx context.Context, calendarEventID uint, uuid string, startTime time.Time, endTime time.Time, data []byte,
+		timeZone string) error
 	GetHostCalendarEvent(ctx context.Context, hostID uint) (*HostCalendarEvent, *CalendarEvent, error)
 	GetHostCalendarEventByEmail(ctx context.Context, email string) (*HostCalendarEvent, *CalendarEvent, error)
 	UpdateHostCalendarWebhookStatus(ctx context.Context, hostID uint, status CalendarWebhookStatus) error
diff --git a/server/fleet/service.go b/server/fleet/service.go
index 4ef1619f0f..ac1bbffb9c 100644
--- a/server/fleet/service.go
+++ b/server/fleet/service.go
@@ -1058,4 +1058,10 @@ type Service interface {
 	GetSoftwareInstallerMetadata(ctx context.Context, titleID uint, teamID *uint) (*SoftwareInstaller, error)
 	DownloadSoftwareInstaller(ctx context.Context, titleID uint, teamID *uint) (*DownloadSoftwareInstallerPayload, error)
 	OrbitDownloadSoftwareInstaller(ctx context.Context, installerID uint) (*DownloadSoftwareInstallerPayload, error)
+
+	// /////////////////////////////////////////////////////////////////////////////
+	// Maintenance windows
+
+	// CalendarWebhook handles incoming calendar callback requests.
+	CalendarWebhook(ctx context.Context, eventUUID string, channelID string, resourceState string) error
 }
diff --git a/server/mock/datastore_mock.go b/server/mock/datastore_mock.go
index b230cf2405..d38323714a 100644
--- a/server/mock/datastore_mock.go
+++ b/server/mock/datastore_mock.go
@@ -361,6 +361,8 @@ type SaveTeamFunc func(ctx context.Context, team *fleet.Team) (*fleet.Team, erro
 
 type TeamFunc func(ctx context.Context, tid uint) (*fleet.Team, error)
 
+type TeamWithoutExtrasFunc func(ctx context.Context, tid uint) (*fleet.Team, error)
+
 type DeleteTeamFunc func(ctx context.Context, tid uint) error
 
 type TeamByNameFunc func(ctx context.Context, name string) (*fleet.Team, error)
@@ -477,7 +479,7 @@ type UpdateHostPolicyCountsFunc func(ctx context.Context) error
 
 type PolicyQueriesForHostFunc func(ctx context.Context, host *fleet.Host) (map[string]string, error)
 
-type GetTeamHostsPolicyMembershipsFunc func(ctx context.Context, domain string, teamID uint, policyIDs []uint) ([]fleet.HostPolicyMembershipData, error)
+type GetTeamHostsPolicyMembershipsFunc func(ctx context.Context, domain string, teamID uint, policyIDs []uint, hostID *uint) ([]fleet.HostPolicyMembershipData, error)
 
 type GetCalendarPoliciesFunc func(ctx context.Context, teamID uint) ([]fleet.PolicyCalendarData, error)
 
@@ -499,13 +501,15 @@ type DeleteSoftwareVulnerabilitiesFunc func(ctx context.Context, vulnerabilities
 
 type DeleteOutOfDateVulnerabilitiesFunc func(ctx context.Context, source fleet.VulnerabilitySource, duration time.Duration) error
 
-type CreateOrUpdateCalendarEventFunc func(ctx context.Context, email string, startTime time.Time, endTime time.Time, data []byte, timeZone string, hostID uint, webhookStatus fleet.CalendarWebhookStatus) (*fleet.CalendarEvent, error)
+type CreateOrUpdateCalendarEventFunc func(ctx context.Context, uuid string, email string, startTime time.Time, endTime time.Time, data []byte, timeZone string, hostID uint, webhookStatus fleet.CalendarWebhookStatus) (*fleet.CalendarEvent, error)
 
 type GetCalendarEventFunc func(ctx context.Context, email string) (*fleet.CalendarEvent, error)
 
+type GetCalendarEventDetailsByUUIDFunc func(ctx context.Context, uuid string) (*fleet.CalendarEventDetails, error)
+
 type DeleteCalendarEventFunc func(ctx context.Context, calendarEventID uint) error
 
-type UpdateCalendarEventFunc func(ctx context.Context, calendarEventID uint, startTime time.Time, endTime time.Time, data []byte, timeZone string) error
+type UpdateCalendarEventFunc func(ctx context.Context, calendarEventID uint, uuid string, startTime time.Time, endTime time.Time, data []byte, timeZone string) error
 
 type GetHostCalendarEventFunc func(ctx context.Context, hostID uint) (*fleet.HostCalendarEvent, *fleet.CalendarEvent, error)
 
@@ -1495,6 +1499,9 @@ type DataStore struct {
 	TeamFunc        TeamFunc
 	TeamFuncInvoked bool
 
+	TeamWithoutExtrasFunc        TeamWithoutExtrasFunc
+	TeamWithoutExtrasFuncInvoked bool
+
 	DeleteTeamFunc        DeleteTeamFunc
 	DeleteTeamFuncInvoked bool
 
@@ -1708,6 +1715,9 @@ type DataStore struct {
 	GetCalendarEventFunc        GetCalendarEventFunc
 	GetCalendarEventFuncInvoked bool
 
+	GetCalendarEventDetailsByUUIDFunc        GetCalendarEventDetailsByUUIDFunc
+	GetCalendarEventDetailsByUUIDFuncInvoked bool
+
 	DeleteCalendarEventFunc        DeleteCalendarEventFunc
 	DeleteCalendarEventFuncInvoked bool
 
@@ -3625,6 +3635,13 @@ func (s *DataStore) Team(ctx context.Context, tid uint) (*fleet.Team, error) {
 	return s.TeamFunc(ctx, tid)
 }
 
+func (s *DataStore) TeamWithoutExtras(ctx context.Context, tid uint) (*fleet.Team, error) {
+	s.mu.Lock()
+	s.TeamWithoutExtrasFuncInvoked = true
+	s.mu.Unlock()
+	return s.TeamWithoutExtrasFunc(ctx, tid)
+}
+
 func (s *DataStore) DeleteTeam(ctx context.Context, tid uint) error {
 	s.mu.Lock()
 	s.DeleteTeamFuncInvoked = true
@@ -4031,11 +4048,11 @@ func (s *DataStore) PolicyQueriesForHost(ctx context.Context, host *fleet.Host)
 	return s.PolicyQueriesForHostFunc(ctx, host)
 }
 
-func (s *DataStore) GetTeamHostsPolicyMemberships(ctx context.Context, domain string, teamID uint, policyIDs []uint) ([]fleet.HostPolicyMembershipData, error) {
+func (s *DataStore) GetTeamHostsPolicyMemberships(ctx context.Context, domain string, teamID uint, policyIDs []uint, hostID *uint) ([]fleet.HostPolicyMembershipData, error) {
 	s.mu.Lock()
 	s.GetTeamHostsPolicyMembershipsFuncInvoked = true
 	s.mu.Unlock()
-	return s.GetTeamHostsPolicyMembershipsFunc(ctx, domain, teamID, policyIDs)
+	return s.GetTeamHostsPolicyMembershipsFunc(ctx, domain, teamID, policyIDs, hostID)
 }
 
 func (s *DataStore) GetCalendarPolicies(ctx context.Context, teamID uint) ([]fleet.PolicyCalendarData, error) {
@@ -4108,11 +4125,11 @@ func (s *DataStore) DeleteOutOfDateVulnerabilities(ctx context.Context, source f
 	return s.DeleteOutOfDateVulnerabilitiesFunc(ctx, source, duration)
 }
 
-func (s *DataStore) CreateOrUpdateCalendarEvent(ctx context.Context, email string, startTime time.Time, endTime time.Time, data []byte, timeZone string, hostID uint, webhookStatus fleet.CalendarWebhookStatus) (*fleet.CalendarEvent, error) {
+func (s *DataStore) CreateOrUpdateCalendarEvent(ctx context.Context, uuid string, email string, startTime time.Time, endTime time.Time, data []byte, timeZone string, hostID uint, webhookStatus fleet.CalendarWebhookStatus) (*fleet.CalendarEvent, error) {
 	s.mu.Lock()
 	s.CreateOrUpdateCalendarEventFuncInvoked = true
 	s.mu.Unlock()
-	return s.CreateOrUpdateCalendarEventFunc(ctx, email, startTime, endTime, data, timeZone, hostID, webhookStatus)
+	return s.CreateOrUpdateCalendarEventFunc(ctx, uuid, email, startTime, endTime, data, timeZone, hostID, webhookStatus)
 }
 
 func (s *DataStore) GetCalendarEvent(ctx context.Context, email string) (*fleet.CalendarEvent, error) {
@@ -4122,6 +4139,13 @@ func (s *DataStore) GetCalendarEvent(ctx context.Context, email string) (*fleet.
 	return s.GetCalendarEventFunc(ctx, email)
 }
 
+func (s *DataStore) GetCalendarEventDetailsByUUID(ctx context.Context, uuid string) (*fleet.CalendarEventDetails, error) {
+	s.mu.Lock()
+	s.GetCalendarEventDetailsByUUIDFuncInvoked = true
+	s.mu.Unlock()
+	return s.GetCalendarEventDetailsByUUIDFunc(ctx, uuid)
+}
+
 func (s *DataStore) DeleteCalendarEvent(ctx context.Context, calendarEventID uint) error {
 	s.mu.Lock()
 	s.DeleteCalendarEventFuncInvoked = true
@@ -4129,11 +4153,11 @@ func (s *DataStore) DeleteCalendarEvent(ctx context.Context, calendarEventID uin
 	return s.DeleteCalendarEventFunc(ctx, calendarEventID)
 }
 
-func (s *DataStore) UpdateCalendarEvent(ctx context.Context, calendarEventID uint, startTime time.Time, endTime time.Time, data []byte, timeZone string) error {
+func (s *DataStore) UpdateCalendarEvent(ctx context.Context, calendarEventID uint, uuid string, startTime time.Time, endTime time.Time, data []byte, timeZone string) error {
 	s.mu.Lock()
 	s.UpdateCalendarEventFuncInvoked = true
 	s.mu.Unlock()
-	return s.UpdateCalendarEventFunc(ctx, calendarEventID, startTime, endTime, data, timeZone)
+	return s.UpdateCalendarEventFunc(ctx, calendarEventID, uuid, startTime, endTime, data, timeZone)
 }
 
 func (s *DataStore) GetHostCalendarEvent(ctx context.Context, hostID uint) (*fleet.HostCalendarEvent, *fleet.CalendarEvent, error) {
diff --git a/server/service/calendar.go b/server/service/calendar.go
new file mode 100644
index 0000000000..6f7ff6b26e
--- /dev/null
+++ b/server/service/calendar.go
@@ -0,0 +1,59 @@
+package service
+
+import (
+	"context"
+	"net/http"
+	"net/url"
+
+	"github.com/fleetdm/fleet/v4/server/contexts/ctxerr"
+	"github.com/fleetdm/fleet/v4/server/fleet"
+	"github.com/gorilla/mux"
+)
+
+type calendarWebhookRequest struct {
+	eventUUID           string
+	googleChannelID     string
+	googleResourceState string
+}
+
+// DecodeRequest implement requestDecoder interface to take full control of decoding the request
+func (calendarWebhookRequest) DecodeRequest(_ context.Context, r *http.Request) (interface{}, error) {
+	var req calendarWebhookRequest
+	eventUUID, ok := mux.Vars(r)["event_uuid"]
+	if !ok {
+		return nil, errBadRoute
+	}
+	unescaped, err := url.PathUnescape(eventUUID)
+	if err != nil {
+		return "", ctxerr.Wrap(r.Context(), err, "unescape value in path")
+	}
+	req.eventUUID = unescaped
+
+	req.googleChannelID = r.Header.Get("X-Goog-Channel-Id")
+	req.googleResourceState = r.Header.Get("X-Goog-Resource-State")
+
+	return &req, nil
+}
+
+type calendarWebhookResponse struct {
+	Err error `json:"error,omitempty"`
+}
+
+func (r calendarWebhookResponse) error() error { return r.Err }
+
+func calendarWebhookEndpoint(ctx context.Context, request interface{}, svc fleet.Service) (errorer, error) {
+	req := request.(*calendarWebhookRequest)
+	err := svc.CalendarWebhook(ctx, req.eventUUID, req.googleChannelID, req.googleResourceState)
+	if err != nil {
+		return calendarWebhookResponse{Err: err}, err
+	}
+
+	resp := calendarWebhookResponse{}
+	return resp, nil
+}
+
+func (svc *Service) CalendarWebhook(ctx context.Context, eventUUID string, channelID string, resourceState string) error {
+	// skipauth: No authorization check needed due to implementation returning only license error.
+	svc.authz.SkipAuthorization(ctx)
+	return fleet.ErrMissingLicense
+}
diff --git a/server/service/calendar/calendar.go b/server/service/calendar/calendar.go
new file mode 100644
index 0000000000..1e7eff60d0
--- /dev/null
+++ b/server/service/calendar/calendar.go
@@ -0,0 +1,94 @@
+package calendar
+
+// This package contains common calendar code used by cron and service packages.
+
+import (
+	"context"
+	"fmt"
+	"strconv"
+	"strings"
+	"sync"
+
+	"github.com/fleetdm/fleet/v4/ee/server/calendar"
+	"github.com/fleetdm/fleet/v4/server/config"
+	"github.com/fleetdm/fleet/v4/server/fleet"
+	kitlog "github.com/go-kit/log"
+	"github.com/go-kit/log/level"
+)
+
+type CalendarConfig struct {
+	config.CalendarConfig
+	fleet.GoogleCalendarIntegration
+	ServerURL string
+}
+
+func CreateUserCalendarFromConfig(ctx context.Context, config *CalendarConfig, logger kitlog.Logger) fleet.UserCalendar {
+	googleCalendarConfig := calendar.GoogleCalendarConfig{
+		Context:           ctx,
+		IntegrationConfig: &config.GoogleCalendarIntegration,
+		ServerURL:         config.ServerURL,
+		Logger:            kitlog.With(logger, "component", "google_calendar"),
+	}
+	return calendar.NewGoogleCalendar(&googleCalendarConfig)
+}
+
+func GenerateCalendarEventBody(ctx context.Context, ds fleet.Datastore, orgName string, host fleet.HostPolicyMembershipData,
+	policyIDtoPolicy *sync.Map, conflict bool, logger kitlog.Logger) string {
+	description, resolution := getCalendarEventDescriptionAndResolution(ctx, ds, orgName, host, policyIDtoPolicy, logger)
+
+	conflictStr := ""
+	if conflict {
+		conflictStr = " because there was no remaining availability"
+	}
+	return fmt.Sprintf(`%s reserved this time to make some changes to your work computer%s.
+
+Please leave your device on and connected to power.
+
+<b>Why it matters</b>
+%s
+
+<b>What we'll do</b>
+%s
+`, orgName, conflictStr, description, resolution)
+}
+
+func getCalendarEventDescriptionAndResolution(ctx context.Context, ds fleet.Datastore, orgName string, host fleet.HostPolicyMembershipData,
+	policyIDtoPolicy *sync.Map, logger kitlog.Logger) (string, string) {
+	getDefaultDescription := func() string {
+		return fmt.Sprintf(`%s %s`, orgName, fleet.CalendarDefaultDescription)
+	}
+
+	var description, resolution string
+	policyIDs := strings.Split(host.FailingPolicyIDs, ",")
+	if len(policyIDs) == 1 && policyIDs[0] != "" {
+		var policy *fleet.PolicyLite
+		policyAny, ok := policyIDtoPolicy.Load(policyIDs[0])
+		if !ok {
+			id, err := strconv.ParseUint(policyIDs[0], 10, 64)
+			if err != nil {
+				level.Error(logger).Log("msg", "parse policy id", "err", err)
+				return getDefaultDescription(), fleet.CalendarDefaultResolution
+			}
+			policy, err = ds.PolicyLite(ctx, uint(id))
+			if err != nil {
+				level.Error(logger).Log("msg", "get policy", "err", err)
+				return getDefaultDescription(), fleet.CalendarDefaultResolution
+			}
+			policyIDtoPolicy.Store(policyIDs[0], policy)
+		} else {
+			policy = policyAny.(*fleet.PolicyLite)
+		}
+		policyDescription := strings.TrimSpace(policy.Description)
+		if policyDescription == "" || policy.Resolution == nil || strings.TrimSpace(*policy.Resolution) == "" {
+			description = getDefaultDescription()
+			resolution = fleet.CalendarDefaultResolution
+		} else {
+			description = policyDescription
+			resolution = strings.TrimSpace(*policy.Resolution)
+		}
+	} else {
+		description = getDefaultDescription()
+		resolution = fleet.CalendarDefaultResolution
+	}
+	return description, resolution
+}
diff --git a/server/service/handler.go b/server/service/handler.go
index 2d7ad4ded3..c7892d7306 100644
--- a/server/service/handler.go
+++ b/server/service/handler.go
@@ -938,6 +938,9 @@ func attachFleetAPIRoutes(r *mux.Router, svc fleet.Service, config config.FleetC
 
 	ne.HEAD("/api/fleet/orbit/ping", orbitPingEndpoint, orbitPingRequest{})
 
+	// This is a callback endpoint for calendar integration -- it is called to notify an event change in a user calendar
+	ne.POST("/api/_version_/fleet/calendar/webhook/{event_uuid}", calendarWebhookEndpoint, calendarWebhookRequest{})
+
 	neAppleMDM.WithCustomMiddleware(limiter.Limit("login", throttled.RateQuota{MaxRate: loginRateLimit, MaxBurst: 9})).
 		POST("/api/_version_/fleet/mdm/sso", initiateMDMAppleSSOEndpoint, initiateMDMAppleSSORequest{})
 
diff --git a/server/service/integration_core_test.go b/server/service/integration_core_test.go
index c6f29aea66..fd66f2227c 100644
--- a/server/service/integration_core_test.go
+++ b/server/service/integration_core_test.go
@@ -8293,9 +8293,11 @@ func (s *integrationTestSuite) TestGetHostMaintenanceWindow() {
 		Data:      []byte(`{}`),
 		// will replace with NULL - db method doesn't allow nil
 		TimeZone: "",
+		UUID:     uuid.New().String(),
 	}
 
-	dsEvent, err := s.ds.CreateOrUpdateCalendarEvent(ctx, testEvent.Email, testEvent.StartTime, testEvent.EndTime, testEvent.Data, testEvent.TimeZone, host.ID, fleet.CalendarWebhookStatusNone)
+	dsEvent, err := s.ds.CreateOrUpdateCalendarEvent(ctx, testEvent.UUID, testEvent.Email, testEvent.StartTime, testEvent.EndTime,
+		testEvent.Data, testEvent.TimeZone, host.ID, fleet.CalendarWebhookStatusNone)
 	require.NoError(t, err)
 
 	time.Sleep(1 * time.Second)
@@ -8325,7 +8327,8 @@ func (s *integrationTestSuite) TestGetHostMaintenanceWindow() {
 	zonedStartsAt := startTime.In(tZLoc).Round(time.Second)
 
 	// update the timezone
-	_, err = s.ds.CreateOrUpdateCalendarEvent(ctx, testEvent.Email, testEvent.StartTime, testEvent.EndTime, testEvent.Data, timeZone, host.ID, fleet.CalendarWebhookStatusNone)
+	_, err = s.ds.CreateOrUpdateCalendarEvent(ctx, testEvent.UUID, testEvent.Email, testEvent.StartTime, testEvent.EndTime, testEvent.Data,
+		timeZone, host.ID, fleet.CalendarWebhookStatusNone)
 	require.NoError(t, err)
 
 	time.Sleep(1 * time.Second)
diff --git a/server/service/integration_enterprise_test.go b/server/service/integration_enterprise_test.go
index 39e632d5b5..f8fa76a59b 100644
--- a/server/service/integration_enterprise_test.go
+++ b/server/service/integration_enterprise_test.go
@@ -8346,6 +8346,7 @@ func (s *integrationEnterpriseTestSuite) TestCalendarEvents() {
 	t := s.T()
 	t.Cleanup(func() {
 		calendar.ClearMockEvents()
+		calendar.ClearMockChannels()
 	})
 	currentAppCfg, err := s.ds.AppConfig(ctx)
 	require.NoError(t, err)
@@ -8472,8 +8473,8 @@ func (s *integrationEnterpriseTestSuite) TestCalendarEvents() {
 	s.DoJSON("POST", "/api/osquery/distributed/write", genDistributedReqWithPolicyResults(
 		host2Team1,
 		map[uint]*bool{
-			team2Policy1Calendar.ID: ptr.Bool(true),
-			team2Policy2.ID:         ptr.Bool(false),
+			team1Policy1Calendar.ID: ptr.Bool(true),
+			team1Policy2.ID:         ptr.Bool(false),
 			globalPolicy.ID:         nil,
 		},
 	), http.StatusOK, &distributedResp)
@@ -8611,8 +8612,8 @@ func (s *integrationEnterpriseTestSuite) TestCalendarEvents() {
 	s.DoJSON("POST", "/api/osquery/distributed/write", genDistributedReqWithPolicyResults(
 		host2Team1,
 		map[uint]*bool{
-			team2Policy1Calendar.ID: ptr.Bool(true),
-			team2Policy2.ID:         ptr.Bool(false),
+			team1Policy1Calendar.ID: ptr.Bool(true),
+			team1Policy2.ID:         ptr.Bool(false),
 			globalPolicy.ID:         nil,
 		},
 	), http.StatusOK, &distributedResp)
@@ -8698,9 +8699,9 @@ func (s *integrationEnterpriseTestSuite) TestCalendarEvents() {
 	calendar.SetMockEventsToNow()
 
 	mysql.ExecAdhocSQL(t, s.ds, func(db sqlx.ExtContext) error {
-		// Update updated_at so the event gets updated (the event is updated every 30 minutes)
+		// Update updated_at so the event gets updated (the event is updated regularly)
 		_, err := db.ExecContext(ctx,
-			`UPDATE calendar_events SET updated_at = DATE_SUB(CURRENT_TIMESTAMP, INTERVAL 1 HOUR) WHERE id = ?`, team1CalendarEvents[0].ID)
+			`UPDATE calendar_events SET updated_at = DATE_SUB(CURRENT_TIMESTAMP, INTERVAL 25 HOUR) WHERE id = ?`, team1CalendarEvents[0].ID)
 		if err != nil {
 			return err
 		}
@@ -8735,8 +8736,8 @@ func (s *integrationEnterpriseTestSuite) TestCalendarEvents() {
 	s.DoJSON("POST", "/api/osquery/distributed/write", genDistributedReqWithPolicyResults(
 		host2Team1,
 		map[uint]*bool{
-			team2Policy1Calendar.ID: ptr.Bool(true),
-			team2Policy2.ID:         ptr.Bool(false),
+			team1Policy1Calendar.ID: ptr.Bool(true),
+			team1Policy2.ID:         ptr.Bool(false),
 			globalPolicy.ID:         nil,
 		},
 	), http.StatusOK, &distributedResp)
@@ -8785,6 +8786,7 @@ func (s *integrationEnterpriseTestSuite) TestCalendarEventsTransferringHosts() {
 	t := s.T()
 	t.Cleanup(func() {
 		calendar.ClearMockEvents()
+		calendar.ClearMockChannels()
 	})
 	currentAppCfg, err := s.ds.AppConfig(ctx)
 	require.NoError(t, err)
@@ -10570,3 +10572,300 @@ func (s *integrationEnterpriseTestSuite) TestAutofillPoliciesAuthTeamUser() {
 		)
 	}
 }
+
+func (s *integrationEnterpriseTestSuite) TestCalendarCallback() {
+	ctx := context.Background()
+	t := s.T()
+	t.Cleanup(func() {
+		calendar.ClearMockEvents()
+		calendar.ClearMockChannels()
+	})
+	currentAppCfg, err := s.ds.AppConfig(ctx)
+	require.NoError(t, err)
+	t.Cleanup(func() {
+		err = s.ds.SaveAppConfig(ctx, currentAppCfg)
+		require.NoError(t, err)
+	})
+
+	team1, err := s.ds.NewTeam(ctx, &fleet.Team{
+		Name: "team1",
+	})
+	require.NoError(t, err)
+
+	newHost := func(name string, teamID *uint) *fleet.Host {
+		h, err := s.ds.NewHost(ctx, &fleet.Host{
+			DetailUpdatedAt: time.Now(),
+			LabelUpdatedAt:  time.Now(),
+			PolicyUpdatedAt: time.Now(),
+			SeenTime:        time.Now().Add(-1 * time.Minute),
+			OsqueryHostID:   ptr.String(t.Name() + name),
+			NodeKey:         ptr.String(t.Name() + name),
+			UUID:            uuid.New().String(),
+			Hostname:        fmt.Sprintf("%s.%s.local", name, t.Name()),
+			Platform:        "darwin",
+			TeamID:          teamID,
+		})
+		require.NoError(t, err)
+		return h
+	}
+
+	host1Team1 := newHost("host1", &team1.ID)
+	host2Team1 := newHost("host2", &team1.ID)
+	_ = newHost("host5", nil) // global host
+
+	team1Policy1Calendar, err := s.ds.NewTeamPolicy(
+		ctx, team1.ID, nil, fleet.PolicyPayload{
+			Name:                  "team1Policy1Calendar",
+			Query:                 "SELECT 1;",
+			CalendarEventsEnabled: true,
+		},
+	)
+	require.NoError(t, err)
+	team1Policy2, err := s.ds.NewTeamPolicy(
+		ctx, team1.ID, nil, fleet.PolicyPayload{
+			Name:                  "team1Policy2",
+			Query:                 "SELECT 2;",
+			CalendarEventsEnabled: true,
+		},
+	)
+	require.NoError(t, err)
+	globalPolicy, err := s.ds.NewGlobalPolicy(
+		ctx, nil, fleet.PolicyPayload{
+			Name:                  "globalPolicy",
+			Query:                 "SELECT 5;",
+			CalendarEventsEnabled: false,
+		},
+	)
+	require.NoError(t, err)
+
+	genDistributedReqWithPolicyResults := func(host *fleet.Host, policyResults map[uint]*bool) submitDistributedQueryResultsRequestShim {
+		var (
+			results  = make(map[string]json.RawMessage)
+			statuses = make(map[string]interface{})
+			messages = make(map[string]string)
+		)
+		for policyID, policyResult := range policyResults {
+			distributedQueryName := hostPolicyQueryPrefix + fmt.Sprint(policyID)
+			switch {
+			case policyResult == nil:
+				results[distributedQueryName] = json.RawMessage(`[]`)
+				statuses[distributedQueryName] = 1
+				messages[distributedQueryName] = "policy failed execution"
+			case *policyResult:
+				results[distributedQueryName] = json.RawMessage(`[{"1": "1"}]`)
+				statuses[distributedQueryName] = 0
+			case !*policyResult:
+				results[distributedQueryName] = json.RawMessage(`[]`)
+				statuses[distributedQueryName] = 0
+			}
+		}
+		return submitDistributedQueryResultsRequestShim{
+			NodeKey:  *host.NodeKey,
+			Results:  results,
+			Statuses: statuses,
+			Messages: messages,
+			Stats:    map[string]*fleet.Stats{},
+		}
+	}
+
+	// host1Team1 is failing a calendar policy and not a non-calendar policy (no results for global).
+	distributedResp := submitDistributedQueryResultsResponse{}
+	s.DoJSON("POST", "/api/osquery/distributed/write", genDistributedReqWithPolicyResults(
+		host1Team1,
+		map[uint]*bool{
+			team1Policy1Calendar.ID: ptr.Bool(false),
+			team1Policy2.ID:         ptr.Bool(true),
+			globalPolicy.ID:         nil,
+		},
+	), http.StatusOK, &distributedResp)
+
+	// host2Team1 is passing the calendar policy but not the non-calendar policy (no results for global).
+	s.DoJSON("POST", "/api/osquery/distributed/write", genDistributedReqWithPolicyResults(
+		host2Team1,
+		map[uint]*bool{
+			team1Policy1Calendar.ID: ptr.Bool(true),
+			team1Policy2.ID:         ptr.Bool(false),
+			globalPolicy.ID:         nil,
+		},
+	), http.StatusOK, &distributedResp)
+
+	// Set global configuration for the calendar feature.
+	appCfg, err := s.ds.AppConfig(ctx)
+	require.NoError(t, err)
+	appCfg.Integrations.GoogleCalendar = []*fleet.GoogleCalendarIntegration{
+		{
+			Domain: "example.com",
+			ApiKey: map[string]string{
+				fleet.GoogleCalendarEmail: calendar.MockEmail,
+			},
+		},
+	}
+	err = s.ds.SaveAppConfig(ctx, appCfg)
+	require.NoError(t, err)
+	time.Sleep(2 * time.Second) // Wait 2 seconds for the app config cache to clear.
+
+	team1.Config.Integrations.GoogleCalendar = &fleet.TeamGoogleCalendarIntegration{
+		Enable:     true,
+		WebhookURL: "https://example.com",
+	}
+	team1, err = s.ds.SaveTeam(ctx, team1)
+	require.NoError(t, err)
+
+	// Add email mapping for host1Team1
+	const user1Email = "user1@example.com"
+	err = s.ds.ReplaceHostDeviceMapping(ctx, host1Team1.ID, []*fleet.HostDeviceMapping{
+		{
+			HostID: host1Team1.ID,
+			Email:  user1Email,
+			Source: "google_chrome_profiles",
+		},
+	}, "google_chrome_profiles")
+	require.NoError(t, err)
+	assert.Equal(t, 0, calendar.MockChannelsCount())
+
+	// Trigger the calendar cron, global feature enabled, team1 enabled
+	// and host1Team1 has a domain email associated.
+	triggerAndWait(ctx, t, s.ds, s.calendarSchedule, 5*time.Second)
+
+	// An event should be generated for host1Team1
+	team1CalendarEvents, err := s.ds.ListCalendarEvents(ctx, &team1.ID)
+	require.NoError(t, err)
+	require.Len(t, team1CalendarEvents, 1)
+	event := team1CalendarEvents[0]
+	require.NotZero(t, event.ID)
+	require.Equal(t, user1Email, event.Email)
+	require.NotZero(t, event.StartTime)
+	require.NotZero(t, event.EndTime)
+	require.NotEmpty(t, event.UUID)
+	assert.Equal(t, 1, calendar.MockChannelsCount())
+
+	// Get channel ID
+	type eventDetails struct {
+		ChannelID string `json:"channel_id"`
+	}
+	var details eventDetails
+	err = json.Unmarshal(event.Data, &details)
+	require.NoError(t, err)
+
+	// Send a sync command
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+event.UUID, []byte(""), http.StatusOK, map[string]string{
+		"X-Goog-Channel-Id":     details.ChannelID,
+		"X-Goog-Resource-State": "sync",
+	})
+
+	// Send a regular callback with bad channel ID
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+event.UUID, []byte(""), http.StatusForbidden, map[string]string{
+		"X-Goog-Channel-Id":     "bad",
+		"X-Goog-Resource-State": "exists",
+	})
+
+	// Send a regular callback
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+event.UUID, []byte(""), http.StatusOK, map[string]string{
+		"X-Goog-Channel-Id":     details.ChannelID,
+		"X-Goog-Resource-State": "exists",
+	})
+
+	// Delete the event on the calendar
+	calendar.ClearMockEvents()
+
+	// This callback should recreate the event
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+event.UUID, []byte(""), http.StatusOK, map[string]string{
+		"X-Goog-Channel-Id":     details.ChannelID,
+		"X-Goog-Resource-State": "exists",
+	})
+
+	team1CalendarEvents, err = s.ds.ListCalendarEvents(ctx, &team1.ID)
+	require.NoError(t, err)
+	require.Len(t, team1CalendarEvents, 1)
+	eventRecreated := team1CalendarEvents[0]
+	assert.NotZero(t, eventRecreated.ID)
+	assert.Equal(t, user1Email, eventRecreated.Email)
+	assert.NotZero(t, eventRecreated.StartTime)
+	assert.NotZero(t, eventRecreated.EndTime)
+	assert.NotEmpty(t, eventRecreated.UUID)
+	assert.NotEqual(t, event.UUID, eventRecreated.UUID)
+	assert.NotEqual(t, event.StartTime, eventRecreated.StartTime)
+	assert.NotEqual(t, event.EndTime, eventRecreated.EndTime)
+	assert.Equal(t, 1, calendar.MockChannelsCount())
+
+	// The previous event UUID should not work anymore
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+event.UUID, []byte(""), http.StatusNotFound, map[string]string{
+		"X-Goog-Channel-Id":     details.ChannelID,
+		"X-Goog-Resource-State": "exists",
+	})
+
+	err = json.Unmarshal(eventRecreated.Data, &details)
+	require.NoError(t, err)
+
+	// New event callback should work
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+eventRecreated.UUID, []byte(""), http.StatusOK,
+		map[string]string{
+			"X-Goog-Channel-Id":     details.ChannelID,
+			"X-Goog-Resource-State": "exists",
+		})
+
+	// Update the time of the event
+	events := calendar.ListGoogleMockEvents()
+	require.Len(t, events, 1)
+	for _, e := range events {
+		st, err := time.Parse(time.RFC3339, e.Start.DateTime)
+		require.NoError(t, err)
+		newStartTime := st.Add(5 * time.Minute).Format(time.RFC3339)
+		e.Start.DateTime = newStartTime
+	}
+
+	// New event callback should cause the time to be updated in the DB
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+eventRecreated.UUID, []byte(""), http.StatusOK,
+		map[string]string{
+			"X-Goog-Channel-Id":     details.ChannelID,
+			"X-Goog-Resource-State": "exists",
+		})
+
+	// Check that the time was updated in the DB
+	team1CalendarEvents, err = s.ds.ListCalendarEvents(ctx, &team1.ID)
+	require.NoError(t, err)
+	require.Len(t, team1CalendarEvents, 1)
+	eventUpdated := team1CalendarEvents[0]
+	assert.NotZero(t, eventUpdated.ID)
+	assert.Equal(t, user1Email, eventUpdated.Email)
+	assert.Equal(t, eventRecreated.UUID, eventUpdated.UUID)
+	assert.Greater(t, eventUpdated.StartTime, eventRecreated.StartTime)
+	assert.Equal(t, eventRecreated.EndTime, eventUpdated.EndTime)
+	assert.Equal(t, 1, calendar.MockChannelsCount())
+
+	// Delete the event on the calendar
+	calendar.ClearMockEvents()
+
+	// Make host1Team1 pass all policies.
+	s.DoJSON("POST", "/api/osquery/distributed/write", genDistributedReqWithPolicyResults(
+		host1Team1,
+		map[uint]*bool{
+			team1Policy1Calendar.ID: ptr.Bool(true),
+			team1Policy2.ID:         ptr.Bool(true),
+			globalPolicy.ID:         nil,
+		},
+	), http.StatusOK, &distributedResp)
+
+	// Callback should still work, but only clear the callback channel. Event in DB will be deleted on the next cron run.
+	_ = s.DoRawWithHeaders("POST", "/api/v1/fleet/calendar/webhook/"+eventRecreated.UUID, []byte(""), http.StatusOK,
+		map[string]string{
+			"X-Goog-Channel-Id":     details.ChannelID,
+			"X-Goog-Resource-State": "exists",
+		})
+	assert.Equal(t, 0, calendar.MockChannelsCount())
+
+	team1CalendarEvents, err = s.ds.ListCalendarEvents(ctx, &team1.ID)
+	require.NoError(t, err)
+	require.Len(t, team1CalendarEvents, 1)
+	assert.Equal(t, eventUpdated, team1CalendarEvents[0])
+
+	// Trigger calendar should cleanup the events
+	triggerAndWait(ctx, t, s.ds, s.calendarSchedule, 5*time.Second)
+	assert.Equal(t, 0, calendar.MockChannelsCount())
+
+	// Event should be cleaned up from our database.
+	team1CalendarEvents, err = s.ds.ListCalendarEvents(ctx, &team1.ID)
+	require.NoError(t, err)
+	assert.Empty(t, team1CalendarEvents)
+
+}
diff --git a/tools/calendar/README.md b/tools/calendar/README.md
index bab2f481b4..b6bb88a4f5 100644
--- a/tools/calendar/README.md
+++ b/tools/calendar/README.md
@@ -4,6 +4,8 @@ To delete all downtime events from a Google Calendar, use `delete-events/delete-
 
 To move all downtime events from multiple Google Calendars to a specific time, use `move-events/move-events.go`
 
+To use the helper scripts, you must set `FLEET_TEST_GOOGLE_CALENDAR_SERVICE_EMAIL` and `FLEET_TEST_GOOGLE_CALENDAR_PRIVATE_KEY` environment variables. The email is the `client_email` from JSON key file. The private key also comes from JSON key file for the service account, and starts with `-----BEGIN PRIVATE KEY-----`.
+
 # Calendar server for load testing
 
 Test calendar server that provides a REST API for managing events.
diff --git a/tools/calendar/delete-events/delete-events.go b/tools/calendar/delete-events/delete-events.go
index dea8197dfa..676da9d88f 100644
--- a/tools/calendar/delete-events/delete-events.go
+++ b/tools/calendar/delete-events/delete-events.go
@@ -34,6 +34,8 @@ func main() {
 	if serviceEmail == "" || privateKey == "" {
 		log.Fatal("FLEET_TEST_GOOGLE_CALENDAR_SERVICE_EMAIL and FLEET_TEST_GOOGLE_CALENDAR_PRIVATE_KEY must be set")
 	}
+	// Strip newlines from private key
+	privateKey = strings.Replace(privateKey, "\\n", "\n", -1)
 	userEmails := flag.String("users", "", "Comma-separated list of user emails to impersonate")
 	flag.Parse()
 	if *userEmails == "" {
diff --git a/tools/calendar/move-events/move-events.go b/tools/calendar/move-events/move-events.go
index 7e413abaf7..3e22032c99 100644
--- a/tools/calendar/move-events/move-events.go
+++ b/tools/calendar/move-events/move-events.go
@@ -35,6 +35,8 @@ func main() {
 	if serviceEmail == "" || privateKey == "" {
 		log.Fatal("FLEET_TEST_GOOGLE_CALENDAR_SERVICE_EMAIL and FLEET_TEST_GOOGLE_CALENDAR_PRIVATE_KEY must be set")
 	}
+	// Strip newlines from private key
+	privateKey = strings.Replace(privateKey, "\\n", "\n", -1)
 	userEmails := flag.String("users", "", "Comma-separated list of user emails to impersonate")
 	dateTimeStr := flag.String("datetime", "", "Event time in "+time.RFC3339+" format")
 	flag.Parse()
diff --git a/tools/calendar/stop-channel/stop-channel.go b/tools/calendar/stop-channel/stop-channel.go
new file mode 100644
index 0000000000..15e61a27e2
--- /dev/null
+++ b/tools/calendar/stop-channel/stop-channel.go
@@ -0,0 +1,123 @@
+package main
+
+import (
+	"context"
+	"errors"
+	"flag"
+	"github.com/cenkalti/backoff/v4"
+	"golang.org/x/oauth2/google"
+	"golang.org/x/oauth2/jwt"
+	"google.golang.org/api/calendar/v3"
+	"google.golang.org/api/googleapi"
+	"google.golang.org/api/option"
+	"log"
+	"net/http"
+	"os"
+	"strings"
+	"time"
+)
+
+// Stop watching the channel with the given ID. This command only accepts one user.
+// Reference: https://developers.google.com/calendar/api/v3/reference/channels/stop
+
+// Example: go run stop-channel.go --users john@example.com --channel-id 55ebefd7-4271-4295-a80a-97f4dcb01d93 --resource-id Io5ygBoEZ-FmQus7ziNrS_Jjcz4
+
+var (
+	serviceEmail = os.Getenv("FLEET_TEST_GOOGLE_CALENDAR_SERVICE_EMAIL")
+	privateKey   = os.Getenv("FLEET_TEST_GOOGLE_CALENDAR_PRIVATE_KEY")
+)
+
+func main() {
+	if serviceEmail == "" || privateKey == "" {
+		log.Fatal("FLEET_TEST_GOOGLE_CALENDAR_SERVICE_EMAIL and FLEET_TEST_GOOGLE_CALENDAR_PRIVATE_KEY must be set")
+	}
+	// Strip newlines from private key
+	privateKey = strings.Replace(privateKey, "\\n", "\n", -1)
+	userEmails := flag.String("users", "", "Comma-separated list of user emails to impersonate")
+	channelIDStr := flag.String("channel-id", "", "Channel ID")
+	resourceIDStr := flag.String("resource-id", "", "Resource ID")
+	flag.Parse()
+	if *userEmails == "" {
+		log.Fatal("--users are required")
+	}
+	if *channelIDStr == "" {
+		log.Fatal("--channel-id is required")
+	}
+	if *resourceIDStr == "" {
+		log.Fatal("--resource-id is required")
+	}
+	userEmailList := strings.Split(*userEmails, ",")
+	if len(userEmailList) == 0 {
+		log.Fatal("No user emails provided")
+	}
+	if len(userEmailList) > 1 {
+		log.Fatal("Only one user email is allowed")
+	}
+
+	ctx := context.Background()
+
+	userEmail := userEmailList[0]
+	conf := &jwt.Config{
+		Email: serviceEmail,
+		Scopes: []string{
+			"https://www.googleapis.com/auth/calendar.events", "https://www.googleapis.com/auth/calendar.settings.readonly",
+		},
+		PrivateKey: []byte(privateKey),
+		TokenURL:   google.JWTTokenURL,
+		Subject:    userEmail,
+	}
+	client := conf.Client(ctx)
+	// Create a new calendar service
+	service, err := calendar.NewService(ctx, option.WithHTTPClient(client))
+	if err != nil {
+		log.Fatalf("Unable to create Calendar service: %v", err)
+	}
+
+	_, err = withRetry(
+		func() (any, error) {
+			return nil, service.Channels.Stop(&calendar.Channel{
+				Id:         *channelIDStr,
+				ResourceId: *resourceIDStr,
+			}).Do()
+		},
+	)
+
+	if err != nil {
+		log.Fatalf("Unable to stop watching channel: %v", err)
+	}
+	log.Printf("DONE. Stopped watching channel resource for %s", userEmail)
+
+}
+
+func withRetry(fn func() (any, error)) (any, error) {
+	retryStrategy := backoff.NewExponentialBackOff()
+	retryStrategy.MaxElapsedTime = 60 * time.Minute
+	var result any
+	err := backoff.Retry(
+		func() error {
+			var err error
+			result, err = fn()
+			if err != nil {
+				if isRateLimited(err) {
+					return err
+				}
+				return backoff.Permanent(err)
+			}
+			return nil
+		}, retryStrategy,
+	)
+	return result, err
+}
+
+func isRateLimited(err error) bool {
+	if err == nil {
+		return false
+	}
+	var ae *googleapi.Error
+	ok := errors.As(err, &ae)
+	return ok && (ae.Code == http.StatusTooManyRequests ||
+		(ae.Code == http.StatusForbidden &&
+			(ae.Message == "Rate Limit Exceeded" || ae.Message == "User Rate Limit Exceeded" || ae.Message == "Calendar usage limits exceeded." || strings.HasPrefix(
+				ae.Message, "Quota exceeded",
+			))))
+}