diff --git a/changes/issue-12260-trigger-windows-mdm-enrollment b/changes/issue-12260-trigger-windows-mdm-enrollment
new file mode 100644
index 0000000000..771bed72e6
--- /dev/null
+++ b/changes/issue-12260-trigger-windows-mdm-enrollment
@@ -0,0 +1 @@
+* Added execution of programmatic Windows MDM enrollment on eligible devices when Windows MDM is enabled.
diff --git a/orbit/cmd/orbit/orbit.go b/orbit/cmd/orbit/orbit.go
index 55fa3f1982..1474e76137 100644
--- a/orbit/cmd/orbit/orbit.go
+++ b/orbit/cmd/orbit/orbit.go
@@ -614,10 +614,14 @@ func main() {
 
 		// create the notifications middleware that wraps the orbit client
 		// (must be shared by all runners that use a ConfigFetcher).
-		const renewEnrollmentProfileCommandFrequency = time.Hour
+		const (
+			renewEnrollmentProfileCommandFrequency = time.Hour
+			microsoftMDMEnrollmentCommandFrequency = time.Hour
+		)
 		configFetcher := update.ApplyRenewEnrollmentProfileConfigFetcherMiddleware(orbitClient, renewEnrollmentProfileCommandFrequency)
 
-		if runtime.GOOS == "darwin" {
+		switch runtime.GOOS {
+		case "darwin":
 			// add middleware to handle nudge installation and updates
 			const nudgeLaunchInterval = 30 * time.Minute
 			configFetcher = update.ApplyNudgeConfigFetcherMiddleware(configFetcher, update.NudgeConfigFetcherOptions{
@@ -626,6 +630,8 @@ func main() {
 
 			configFetcher = update.ApplyDiskEncryptionRunnerMiddleware(configFetcher)
 			configFetcher = update.ApplySwiftDialogDownloaderMiddleware(configFetcher, updateRunner)
+		case "windows":
+			configFetcher = update.ApplyMicrosoftMDMEnrollmentFetcherMiddleware(configFetcher, microsoftMDMEnrollmentCommandFrequency, orbitHostInfo.HardwareUUID)
 		}
 
 		const orbitFlagsUpdateInterval = 30 * time.Second
diff --git a/orbit/pkg/update/execwinapi.go b/orbit/pkg/update/execwinapi.go
new file mode 100644
index 0000000000..78107ddbff
--- /dev/null
+++ b/orbit/pkg/update/execwinapi.go
@@ -0,0 +1,9 @@
+package update
+
+// Exported so that it can be used in tools/ (so that it can be built for
+// Windows and tested on a Windows machine). Otherwise not meant to be used
+// from outside this package.
+type MicrosoftMDMEnrollmentArgs struct {
+	DiscoveryURL string
+	HostUUID     string
+}
diff --git a/orbit/pkg/update/execwinapi_stub.go b/orbit/pkg/update/execwinapi_stub.go
new file mode 100644
index 0000000000..a40713a815
--- /dev/null
+++ b/orbit/pkg/update/execwinapi_stub.go
@@ -0,0 +1,7 @@
+//go:build !windows
+
+package update
+
+func RunMicrosoftMDMEnrollment(args MicrosoftMDMEnrollmentArgs) error {
+	return nil
+}
diff --git a/orbit/pkg/update/execwinapi_windows.go b/orbit/pkg/update/execwinapi_windows.go
new file mode 100644
index 0000000000..a1a9bc4970
--- /dev/null
+++ b/orbit/pkg/update/execwinapi_windows.go
@@ -0,0 +1,125 @@
+//go:build windows
+
+package update
+
+import (
+	"encoding/json"
+	"fmt"
+	"net/http"
+	"strings"
+	"syscall"
+	"unsafe"
+
+	"github.com/fleetdm/fleet/v4/server/fleet"
+	"github.com/rs/zerolog/log"
+	"golang.org/x/sys/windows"
+	"golang.org/x/sys/windows/registry"
+)
+
+var (
+	dllMDMRegistration *windows.LazyDLL = windows.NewLazySystemDLL("mdmregistration.dll")
+
+	// RegisterDeviceWithManagement registers a device with a MDM service:
+	// https://learn.microsoft.com/en-us/windows/win32/api/mdmregistration/nf-mdmregistration-registerdevicewithmanagement
+	procRegisterDeviceWithManagement *windows.LazyProc = dllMDMRegistration.NewProc("RegisterDeviceWithManagement")
+)
+
+// Exported so that it can be used in tools/ (so that it can be built for
+// Windows and tested on a Windows machine). Otherwise not meant to be called
+// from outside this package.
+func RunMicrosoftMDMEnrollment(args MicrosoftMDMEnrollmentArgs) error {
+	installType, err := readInstallationType()
+	if err != nil {
+		return err
+	}
+	if strings.ToLower(installType) == "server" {
+		// do not enroll, it is a server
+		return errIsWindowsServer
+	}
+	return enrollHostToMDM(args)
+}
+
+func readInstallationType() (string, error) {
+	k, err := registry.OpenKey(registry.LOCAL_MACHINE, `SOFTWARE\Microsoft\Windows NT\CurrentVersion`, registry.QUERY_VALUE)
+	if err != nil {
+		return "", err
+	}
+	defer k.Close()
+
+	s, _, err := k.GetStringValue("InstallationType")
+	if err != nil {
+		return "", err
+	}
+	return s, nil
+}
+
+// TODO(mna): refactor to a Windows-specific package to constrain usage of
+// unsafe to that package, once https://github.com/fleetdm/fleet/pull/12387
+// lands.
+
+// Perform the host MDM enrollment process using MS-MDE protocol:
+// https://learn.microsoft.com/en-us/openspecs/windows_protocols/ms-mde/5c841535-042e-489e-913c-9d783d741267
+func enrollHostToMDM(args MicrosoftMDMEnrollmentArgs) error {
+	discoveryURLPtr, err := syscall.UTF16PtrFromString(args.DiscoveryURL)
+	if err != nil {
+		return fmt.Errorf("discovery URL to UTF16 pointer: %w", err)
+	}
+
+	// we use an empty user UPN, it is not a required argument
+	userPtr, err := syscall.UTF16PtrFromString("")
+	if err != nil {
+		return fmt.Errorf("user UPN to UTF16 pointer: %w", err)
+	}
+
+	accessTok, err := generateWindowsMDMAccessTokenPayload(args)
+	if err != nil {
+		return fmt.Errorf("generate access token payload: %w", err)
+	}
+	accessTokPtr, err := syscall.UTF16PtrFromString(string(accessTok))
+	if err != nil {
+		return fmt.Errorf("access token to UTF16 pointer: %w", err)
+	}
+
+	// pre-load the DLL and pre-find the procedure, to return a more meaningful
+	// message if those steps fail and avoid a panic.
+	if err := dllMDMRegistration.Load(); err != nil {
+		return fmt.Errorf("load MDM dll: %w", err)
+	}
+	if err := procRegisterDeviceWithManagement.Find(); err != nil {
+		return fmt.Errorf("find MDM RegisterDeviceWithManagement procedure: %w", err)
+	}
+
+	code, _, err := procRegisterDeviceWithManagement.Call(
+		uintptr(unsafe.Pointer(userPtr)),
+		uintptr(unsafe.Pointer(discoveryURLPtr)),
+		uintptr(unsafe.Pointer(accessTokPtr)),
+	)
+	log.Debug().Msgf("RegisterDeviceWithManagement returned code: %#x ; message: %v", code, err)
+	if code != uintptr(windows.ERROR_SUCCESS) {
+		// hexadecimal error code can help identify error here:
+		//   https://learn.microsoft.com/en-us/windows/win32/mdmreg/mdm-registration-constants
+		// decimal error code can help identify error here (look for the ERROR_xxx constants):
+		//   https://pkg.go.dev/golang.org/x/sys/windows#pkg-constants
+		//
+		// Note that the error message may be "The operation completed
+		// successfully." even though there is an error (e.g. if the discovery URL
+		// results in a 404 not found, the error code will be 0x80190194 which
+		// means windows.HTTP_E_STATUS_NOT_FOUND). In this case, translate the
+		// message to something more useful.
+		if httpCode := code - uintptr(windows.HTTP_E_STATUS_BAD_REQUEST); httpCode >= 0 && httpCode < 200 {
+			// status bad request is 400, so if error code is between 400 and < 600.
+			err = fmt.Errorf("using discovery URL %q: HTTP error code %d", args.DiscoveryURL, http.StatusBadRequest+httpCode)
+		}
+		return fmt.Errorf("RegisterDeviceWithManagement failed: %s (%#x - %[2]d)", err, code)
+	}
+
+	return nil
+}
+
+func generateWindowsMDMAccessTokenPayload(args MicrosoftMDMEnrollmentArgs) ([]byte, error) {
+	var pld fleet.MicrosoftMDMAccessTokenPayload
+
+	pld.Type = fleet.MicrosoftMDMProgrammaticEnrollmentType // always programmatic for now
+	pld.Payload.HostUUID = args.HostUUID
+	return json.Marshal(pld)
+}
diff --git a/orbit/pkg/update/notifications.go b/orbit/pkg/update/notifications.go
index 9d15c76c05..edfe908b83 100644
--- a/orbit/pkg/update/notifications.go
+++ b/orbit/pkg/update/notifications.go
@@ -1,6 +1,7 @@
 package update
 
 import (
+	"errors"
 	"sync"
 	"time"
 
@@ -10,7 +11,7 @@ import (
 
 type runCmdFunc func() error
 
-// RenewEnrollmentProfileConfigFetcher is a kind of middleware that wraps an
+// renewEnrollmentProfileConfigFetcher is a kind of middleware that wraps an
 // OrbitConfigFetcher and detects if the fleet server sent a notification to
 // renew the enrollment profile. If so, it runs the command (as root) to
 // bootstrap the renewal of the profile on the device (the user still needs to
@@ -18,7 +19,7 @@ type runCmdFunc func() error
 //
 // It ensures only one renewal command is executed at any given time, and that
 // it doesn't re-execute the command until a certain amount of time has passed.
-type RenewEnrollmentProfileConfigFetcher struct {
+type renewEnrollmentProfileConfigFetcher struct {
 	// Fetcher is the OrbitConfigFetcher that will be wrapped. It is responsible
 	// for actually returning the orbit configuration or an error.
 	Fetcher OrbitConfigFetcher
@@ -36,13 +37,13 @@ type RenewEnrollmentProfileConfigFetcher struct {
 }
 
 func ApplyRenewEnrollmentProfileConfigFetcherMiddleware(fetcher OrbitConfigFetcher, frequency time.Duration) OrbitConfigFetcher {
-	return &RenewEnrollmentProfileConfigFetcher{Fetcher: fetcher, Frequency: frequency}
+	return &renewEnrollmentProfileConfigFetcher{Fetcher: fetcher, Frequency: frequency}
 }
 
 // GetConfig calls the wrapped Fetcher's GetConfig method, and if the fleet
 // server set the renew enrollment profile flag to true, executes the command
 // to renew the enrollment profile.
-func (h *RenewEnrollmentProfileConfigFetcher) GetConfig() (*fleet.OrbitConfig, error) {
+func (h *renewEnrollmentProfileConfigFetcher) GetConfig() (*fleet.OrbitConfig, error) {
 	cfg, err := h.Fetcher.GetConfig()
 
 	// TODO: download and use swiftDialog following the same patterns we
@@ -83,3 +84,84 @@ func (h *RenewEnrollmentProfileConfigFetcher) GetConfig() (*fleet.OrbitConfig, e
 	}
 	return cfg, err
 }
+
+type execWinAPIFunc func(MicrosoftMDMEnrollmentArgs) error
+
+type microsoftMDMEnrollmentConfigFetcher struct {
+	// Fetcher is the OrbitConfigFetcher that will be wrapped. It is responsible
+	// for actually returning the orbit configuration or an error.
+	Fetcher OrbitConfigFetcher
+	// Frequency is the minimum amount of time that must pass between two
+	// executions of the windows MDM enrollment attempt.
+	Frequency time.Duration
+	// HostUUID is the current host's UUID.
+	HostUUID string
+
+	// for tests, to be able to mock command execution. If nil, will use
+	// RunMicrosoftMDMEnrollment.
+	execWinAPIFn execWinAPIFunc
+
+	// ensures only one command runs at a time, protects access to lastRun and
+	// isWindowsServer.
+	mu              sync.Mutex
+	lastRun         time.Time
+	isWindowsServer bool
+}
+
+func ApplyMicrosoftMDMEnrollmentFetcherMiddleware(
+	fetcher OrbitConfigFetcher,
+	frequency time.Duration,
+	hostUUID string,
+) OrbitConfigFetcher {
+	return &microsoftMDMEnrollmentConfigFetcher{
+		Fetcher:   fetcher,
+		Frequency: frequency,
+		HostUUID:  hostUUID,
+	}
+}
+
+var errIsWindowsServer = errors.New("device is a Windows Server")
+
+// GetConfig calls the wrapped Fetcher's GetConfig method, and if the fleet
+// server set the "needs windows enrollment" flag to true, executes the command
+// to enroll into Windows MDM (or not, if the device is a Windows Server).
+func (w *microsoftMDMEnrollmentConfigFetcher) GetConfig() (*fleet.OrbitConfig, error) {
+	cfg, err := w.Fetcher.GetConfig()
+
+	if err == nil && cfg.Notifications.NeedsProgrammaticMicrosoftMDMEnrollment {
+		if cfg.Notifications.MicrosoftMDMDiscoveryEndpoint == "" {
+			log.Info().Err(errors.New("discovery endpoint is missing")).Msg("skipping enrollment, discovery endpoint is empty")
+		} else if w.mu.TryLock() {
+			defer w.mu.Unlock()
+
+			// do not enroll Windows Servers, and do not attempt enrollment if the
+			// last run is not at least Frequency ago.
+			if !w.isWindowsServer && time.Since(w.lastRun) > w.Frequency {
+				fn := w.execWinAPIFn
+				if fn == nil {
+					fn = RunMicrosoftMDMEnrollment
+				}
+				args := MicrosoftMDMEnrollmentArgs{
+					DiscoveryURL: cfg.Notifications.MicrosoftMDMDiscoveryEndpoint,
+					HostUUID:     w.HostUUID,
+				}
+				if err := fn(args); err != nil {
+					if errors.Is(err, errIsWindowsServer) {
+						w.isWindowsServer = true
+						log.Info().Msg("device is a Windows Server, skipping enrollment")
+					} else {
+						log.Info().Err(err).Msg("calling RegisterDeviceWithManagement to enroll Windows device failed")
+					}
+				} else {
+					w.lastRun = time.Now()
+					log.Info().Msg("successfully called RegisterDeviceWithManagement to enroll Windows device")
+				}
+			} else if w.isWindowsServer {
+				log.Debug().Msg("skipped calling RegisterDeviceWithManagement to enroll Windows device, device is a server")
+			} else {
+				log.Debug().Msg("skipped calling RegisterDeviceWithManagement to enroll Windows device, last run was too recent")
+			}
+		}
+	}
+	return cfg, err
+}
diff --git a/orbit/pkg/update/notifications_test.go b/orbit/pkg/update/notifications_test.go
index a065b6d9c1..d0ad149247 100644
--- a/orbit/pkg/update/notifications_test.go
+++ b/orbit/pkg/update/notifications_test.go
@@ -39,7 +39,7 @@ func TestRenewEnrollmentProfile(t *testing.T) {
 			}
 
 			var cmdGotCalled bool
-			renewFetcher := &RenewEnrollmentProfileConfigFetcher{
+			renewFetcher := &renewEnrollmentProfileConfigFetcher{
 				Fetcher:   fetcher,
 				Frequency: time.Hour, // doesn't matter for this test
 				runCmdFn: func() error {
@@ -71,7 +71,7 @@ func TestRenewEnrollmentProfilePrevented(t *testing.T) {
 
 	var cmdCallCount int
 	chProceed := make(chan struct{})
-	renewFetcher := &RenewEnrollmentProfileConfigFetcher{
+	renewFetcher := &renewEnrollmentProfileConfigFetcher{
 		Fetcher:   fetcher,
 		Frequency: 2 * time.Second, // just to be safe with slow environments (CI)
 		runCmdFn: func() error {
@@ -120,3 +120,140 @@ func TestRenewEnrollmentProfilePrevented(t *testing.T) {
 
 	require.Equal(t, 2, cmdCallCount) // the initial call and the one after sleep
 }
+
+func TestWindowsMDMEnrollment(t *testing.T) {
+	var logBuf bytes.Buffer
+
+	oldLog := log.Logger
+	log.Logger = log.Output(&logBuf)
+	t.Cleanup(func() { log.Logger = oldLog })
+
+	cases := []struct {
+		desc          string
+		enrollFlag    bool
+		discoveryURL  string
+		apiErr        error
+		wantAPICalled bool
+		wantLog       string
+	}{
+		{"enroll=false", false, "", nil, false, ""},
+		{"enroll=true,discovery=''", true, "", nil, false, "discovery endpoint is empty"},
+		{"enroll=true,discovery!='',success", true, "http://example.com", nil, true, "successfully called RegisterDeviceWithManagement"},
+		{"enroll=true,discovery!='',fail", true, "http://example.com", io.ErrUnexpectedEOF, true, "enroll Windows device failed"},
+		{"enroll=true,discovery!='',server", true, "http://example.com", errIsWindowsServer, true, "device is a Windows Server, skipping enrollment"},
+	}
+
+	for _, c := range cases {
+		t.Run(c.desc, func(t *testing.T) {
+			logBuf.Reset()
+
+			fetcher := &dummyConfigFetcher{
+				cfg: &fleet.OrbitConfig{Notifications: fleet.OrbitConfigNotifications{
+					NeedsProgrammaticMicrosoftMDMEnrollment: c.enrollFlag,
+					MicrosoftMDMDiscoveryEndpoint:           c.discoveryURL,
+				}},
+			}
+
+			var apiGotCalled bool
+			enrollFetcher := &microsoftMDMEnrollmentConfigFetcher{
+				Fetcher:   fetcher,
+				Frequency: time.Hour, // doesn't matter for this test
+				execWinAPIFn: func(args MicrosoftMDMEnrollmentArgs) error {
+					apiGotCalled = true
+					return c.apiErr
+				},
+			}
+
+			cfg, err := enrollFetcher.GetConfig()
+			require.NoError(t, err)            // the dummy fetcher never returns an error
+			require.Equal(t, fetcher.cfg, cfg) // the enrollment wrapper properly returns the expected config
+
+			require.Equal(t, c.wantAPICalled, apiGotCalled)
+			require.Contains(t, logBuf.String(), c.wantLog)
+		})
+	}
+}
+
+func TestWindowsMDMEnrollmentPrevented(t *testing.T) {
+	var logBuf bytes.Buffer
+
+	oldLog := log.Logger
+	log.Logger = log.Output(&logBuf)
+	t.Cleanup(func() { log.Logger = oldLog })
+
+	fetcher := &dummyConfigFetcher{
+		cfg: &fleet.OrbitConfig{Notifications: fleet.OrbitConfigNotifications{
+			NeedsProgrammaticMicrosoftMDMEnrollment: true,
+			MicrosoftMDMDiscoveryEndpoint:           "http://example.com",
+		}},
+	}
+
+	var (
+		apiCallCount int
+		apiErr       error
+	)
+	chProceed := make(chan struct{})
+	enrollFetcher := &microsoftMDMEnrollmentConfigFetcher{
+		Fetcher:   fetcher,
+		Frequency: 2 * time.Second, // just to be safe with slow environments (CI)
+		execWinAPIFn: func(args MicrosoftMDMEnrollmentArgs) error {
+			<-chProceed    // will be unblocked only when allowed
+			apiCallCount++ // no need for sync, single-threaded call of this func is guaranteed by the fetcher's mutex
+			return apiErr
+		},
+	}
+
+	assertResult := func(cfg *fleet.OrbitConfig, err error) {
+		require.NoError(t, err)
+		require.Equal(t, fetcher.cfg, cfg)
+	}
+
+	started := make(chan struct{})
+	go func() {
+		close(started)
+
+		// the first call will block in execWinAPIFn
+		cfg, err := enrollFetcher.GetConfig()
+		assertResult(cfg, err)
+	}()
+
+	<-started
+	// this call will happen while the first call is blocked in execWinAPIFn, so it
+	// won't call the API (won't be able to lock the mutex). However it will
+	// still complete successfully without being blocked by the other call in
+	// progress.
+	cfg, err := enrollFetcher.GetConfig()
+	assertResult(cfg, err)
+
+	// unblock the first call and wait for it to complete
+	close(chProceed)
+	time.Sleep(100 * time.Millisecond)
+
+	// this next call won't execute the command because of the frequency
+	// restriction (it got called less than N seconds ago)
+	cfg, err = enrollFetcher.GetConfig()
+	assertResult(cfg, err)
+
+	// wait for the fetcher's frequency to pass
+	time.Sleep(enrollFetcher.Frequency)
+
+	// this call executes the command, and it returns the Is Windows Server error
+	apiErr = errIsWindowsServer
+	cfg, err = enrollFetcher.GetConfig()
+	assertResult(cfg, err)
+
+	// this next call won't execute the command (both due to frequency and the
+	// detection of windows server)
+	cfg, err = enrollFetcher.GetConfig()
+	assertResult(cfg, err)
+
+	// wait for the fetcher's frequency to pass
+	time.Sleep(enrollFetcher.Frequency)
+
+	// this next call still won't execute the command (due to the detection of
+	// windows server)
+	cfg, err = enrollFetcher.GetConfig()
+	assertResult(cfg, err)
+
+	require.Equal(t, 2, apiCallCount) // the initial call and the one that returned errIsWindowsServer after first sleep
+}
diff --git a/server/fleet/microsoft_mdm.go b/server/fleet/microsoft_mdm.go
index d878ac8ec8..c765ac55bf 100644
--- a/server/fleet/microsoft_mdm.go
+++ b/server/fleet/microsoft_mdm.go
@@ -341,3 +341,20 @@ type SoapFault struct {
 	Reason              Reason   `xml:"s:reason"`
 	OriginalMessageType int      `xml:"-"`
 }
+
+// MicrosoftMDMAccessTokenPayload is the payload that gets encoded as JSON and
+// provided as opaque access token to the RegisterDeviceWithManagement API.
+type MicrosoftMDMAccessTokenPayload struct {
+	// Type is the enrollment type, such as "programmatic".
+	Type    MicrosoftMDMEnrollmentType `json:"type"`
+	Payload struct {
+		HostUUID string `json:"host_uuid"`
+	} `json:"payload"`
+}
+
+type MicrosoftMDMEnrollmentType int
+
+// List of supported Microsoft MDM enrollment types.
+const (
+	MicrosoftMDMProgrammaticEnrollmentType MicrosoftMDMEnrollmentType = 1
+)
diff --git a/tools/windows-mdm-enroll/main.go b/tools/windows-mdm-enroll/main.go
new file mode 100644
index 0000000000..b2a05adc75
--- /dev/null
+++ b/tools/windows-mdm-enroll/main.go
@@ -0,0 +1,22 @@
+package main
+
+import (
+	"flag"
+	"fmt"
+
+	"github.com/fleetdm/fleet/v4/orbit/pkg/update"
+)
+
+func main() {
+	var (
+		discoveryURL = flag.String("discovery-url", "", "The Windows MDM discovery URL")
+		hostUUID     = flag.String("host-uuid", "", "The Host UUID")
+	)
+	flag.Parse()
+
+	err := update.RunMicrosoftMDMEnrollment(update.MicrosoftMDMEnrollmentArgs{
+		DiscoveryURL: *discoveryURL,
+		HostUUID:     *hostUUID,
+	})
+	fmt.Println(err)
+}