diff --git a/.github/workflows/test-packaging.yml b/.github/workflows/test-packaging.yml
index 7190314cb9..b4f0a33cac 100644
--- a/.github/workflows/test-packaging.yml
+++ b/.github/workflows/test-packaging.yml
@@ -70,7 +70,7 @@ jobs:
       # - colima is pre-installed in macos-12 runners, but not in macos-13 or
       #   macos-14 runners
       run: |
-        brew install docker colima
+        brew install --no-binaries docker colima
         colima start --mount $TMPDIR:w
 
     - name: Install Go
diff --git a/ee/server/service/devices.go b/ee/server/service/devices.go
index 2721676e1d..7c3b580e92 100644
--- a/ee/server/service/devices.go
+++ b/ee/server/service/devices.go
@@ -62,7 +62,12 @@ func (svc *Service) TriggerMigrateMDMDevice(ctx context.Context, host *fleet.Hos
 		return ctxerr.Wrap(ctx, err, "fetching host mdm info")
 	}
 
-	if !fleet.IsEligibleForDEPMigration(host, mdmInfo, connected) && !fleet.IsEligibleForManualMigration(host, mdmInfo, connected) {
+	manualMigrationEligible, err := fleet.IsEligibleForManualMigration(host, mdmInfo, connected)
+	if err != nil {
+		return ctxerr.Wrap(ctx, err, "checking manual migration eligibility")
+	}
+
+	if !fleet.IsEligibleForDEPMigration(host, mdmInfo, connected) && !manualMigrationEligible {
 		bre.InternalErr = ctxerr.New(ctx, "host not eligible for macOS migration")
 	}
 
@@ -139,7 +144,12 @@ func (svc *Service) GetFleetDesktopSummary(ctx context.Context) (fleet.DesktopSu
 			sum.Notifications.RenewEnrollmentProfile = true
 		}
 
-		if fleet.IsEligibleForDEPMigration(host, mdmInfo, connected) || fleet.IsEligibleForManualMigration(host, mdmInfo, connected) {
+		manualMigrationEligible, err := fleet.IsEligibleForManualMigration(host, mdmInfo, connected)
+		if err != nil {
+			return sum, ctxerr.Wrap(ctx, err, "checking manual migration eligibility")
+		}
+
+		if fleet.IsEligibleForDEPMigration(host, mdmInfo, connected) || manualMigrationEligible {
 			sum.Notifications.NeedsMDMMigration = true
 		}
 
diff --git a/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx b/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx
index 25ff5b8f89..b7aad232de 100644
--- a/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx
+++ b/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx
@@ -2,28 +2,16 @@ import React from "react";
 
 import Button from "components/buttons/Button";
 import Modal from "components/Modal";
-import { IDeviceUserResponse } from "interfaces/host";
 
 interface IAutoEnrollMdmModalProps {
-  host: IDeviceUserResponse["host"];
   onCancel: () => void;
 }
 
 const baseClass = "auto-enroll-mdm-modal";
 
 const AutoEnrollMdmModal = ({
-  host: { platform, os_version },
   onCancel,
 }: IAutoEnrollMdmModalProps): JSX.Element => {
-  let isMacOsSonomaOrLater = false;
-  if (platform === "darwin" && os_version.startsWith("macOS ")) {
-    const [major] = os_version
-      .replace("macOS ", "")
-      .split(".")
-      .map((s) => parseInt(s, 10));
-    isMacOsSonomaOrLater = major >= 14;
-  }
-
   return (
     <Modal
       title="Turn on MDM"
@@ -41,18 +29,12 @@ const AutoEnrollMdmModal = ({
             <b>System Settings</b>.
           </li>
           <li>
-            {isMacOsSonomaOrLater ? (
-              <>
-                In the sidebar menu, select <b>Enroll in Remote Management</b>,
-                and select <b>Enroll</b>.
-              </>
-            ) : (
-              <>
-                In the search bar, type “Profiles.” Select <b>Profiles</b>, find
-                and double-click the <b>[Organization name] enrollment</b>{" "}
-                profile.
-              </>
-            )}
+            In the search bar, type “Profiles.” Select <b>Profiles</b>, find and
+            double-click the{" "}
+            <b>
+              [Organization name] <br /> enrollment
+            </b>{" "}
+            profile.
           </li>
           <li>
             Enter your password, and select <b>Enroll</b>.
diff --git a/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx b/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx
index 1a03eeeecf..1362b697d9 100644
--- a/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx
+++ b/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx
@@ -306,7 +306,7 @@ const DeviceUserPage = ({
 
   const renderEnrollMdmModal = () => {
     return host?.dep_assigned_to_fleet ? (
-      <AutoEnrollMdmModal host={host} onCancel={toggleEnrollMdmModal} />
+      <AutoEnrollMdmModal onCancel={toggleEnrollMdmModal} />
     ) : (
       <ManualEnrollMdmModal
         onCancel={toggleEnrollMdmModal}
diff --git a/orbit/pkg/constant/constant.go b/orbit/pkg/constant/constant.go
index 36bbba483f..5ce8fae24d 100644
--- a/orbit/pkg/constant/constant.go
+++ b/orbit/pkg/constant/constant.go
@@ -62,6 +62,8 @@ const (
 	MDMMigrationTypeManual = "manual"
 	// MDMMigrationTypeADE indicates that the MDM migration is for an ADE enrolled host.
 	MDMMigrationTypeADE = "ade"
+	// MDMMigrationTypePreSonoma indicates that the MDM migration is for a host on a macOS version < 14.
+	MDMMigrationTypePreSonoma = "pre-sonoma"
 	// MDMMigrationOfflineWatcherInterval is the interval at which the offline watcher checks for
 	// the presence of the migration file.
 	MDMMigrationOfflineWatcherInterval = 3 * time.Minute
diff --git a/orbit/pkg/useraction/mdm_migration_darwin.go b/orbit/pkg/useraction/mdm_migration_darwin.go
index 96bed0d9d4..44273f0b59 100644
--- a/orbit/pkg/useraction/mdm_migration_darwin.go
+++ b/orbit/pkg/useraction/mdm_migration_darwin.go
@@ -61,15 +61,7 @@ var mdmMigrationTemplatePreSonoma = template.Must(template.New("mdmMigrationTemp
 
 Select **Start** and look for this notification in your notification center:` +
 	"\n\n![Image showing MDM migration notification](https://fleetdm.com/images/permanent/mdm-migration-screenshot-notification-2048x480.png)\n\n" +
-	"After you start, this window will popup every 15-20 minutes until you finish.",
-))
-
-var mdmMigrationTemplate = template.Must(template.New("mdmMigrationTemplate").Parse(`
-## Migrate to Fleet
-
-Select **Start** and Remote Management window will appear soon:` +
-	"\n\n![Image showing MDM migration notification](https://fleetdm.com/images/permanent/mdm-migration-sonoma-1500x938.png)\n\n" +
-	"After you start, this window will popup every 15-20 minutes until you finish.",
+	"After you start, this window will popup every 15 minutes until you finish.",
 ))
 
 var mdmManualMigrationTemplate = template.Must(template.New("").Parse(`
@@ -94,6 +86,8 @@ var errorTemplate = template.Must(template.New("").Parse(`
 Please contact your IT admin [here]({{ .ContactURL }}).
 `))
 
+var unenrollPreSonoma = "## Migrate to Fleet\nUnenrolling you from your old MDM. This could take 90 seconds...\n\n![Image showing MDM migration notification](https://fleetdm.com/images/permanent/mdm-migration-pre-sonoma-unenroll-1024x500.png)"
+
 var mdmMigrationTemplateOffline = template.Must(template.New("").Parse(`
 ## Migrate to Fleet
 
@@ -280,12 +274,19 @@ func (m *swiftDialogMDMMigrator) render(message string, flags ...string) (chan s
 	return m.baseDialog.render(flags...)
 }
 
-func (m *swiftDialogMDMMigrator) renderLoadingSpinner() (chan swiftDialogExitCode, chan error) {
-	return m.render("## Migrate to Fleet\nUnenrolling you from your old MDM. This could take 90 seconds...",
+func (m *swiftDialogMDMMigrator) renderLoadingSpinner(preSonoma bool) (chan swiftDialogExitCode, chan error) {
+	body := "## Migrate to Fleet\nUnenrolling you from your old MDM. This could take 90 seconds..."
+	height := "200"
+	if preSonoma {
+		body = unenrollPreSonoma
+		height = "669"
+	}
+
+	return m.render(body,
 		"--button1text", "Start",
 		"--button1disabled",
 		"--quitkey", "x",
-		"--height", "220",
+		"--height", height,
 	)
 }
 
@@ -377,7 +378,13 @@ func (m *swiftDialogMDMMigrator) renderMigration() error {
 
 	log.Debug().Bool("isManualMigration", isManualMigration).Bool("isADEMigration", isADEMigration).Bool("isCurrentlyManuallyEnrolled", isCurrentlyManuallyEnrolled).Str("previousMigrationType", previousMigrationType).Msg("props after assigning")
 
-	message, flags, err := m.getMessageAndFlags(isManualMigration)
+	vers, err := m.getMacOSMajorVersion()
+	if err != nil {
+		// log error for debugging and continue with default template
+		log.Error().Err(err).Msg("getting macOS major version failed: using default migration template")
+	}
+
+	message, flags, err := m.getMessageAndFlags(vers, isManualMigration)
 	if err != nil {
 		return fmt.Errorf("getting mdm migrator message: %w", err)
 	}
@@ -410,7 +417,7 @@ func (m *swiftDialogMDMMigrator) renderMigration() error {
 
 		if !m.props.IsUnmanaged {
 			// show the loading spinner
-			m.renderLoadingSpinner()
+			m.renderLoadingSpinner(vers < 14)
 
 			// send the API call
 			if notifyErr := m.handler.NotifyRemote(); notifyErr != nil {
@@ -440,19 +447,32 @@ func (m *swiftDialogMDMMigrator) renderMigration() error {
 				}
 			}
 
-			if isManualMigration {
+			switch true {
+			case vers < 14:
+				if err := m.mrw.SetMigrationFile(constant.MDMMigrationTypePreSonoma); err != nil {
+					log.Error().Str("migration_type", constant.MDMMigrationTypeADE).Err(err).Msg("set migration file")
+				}
+
+				log.Info().Msg("showing instructions after pre-sonoma unenrollment")
+				if err := m.handler.ShowInstructions(); err != nil {
+					return err
+				}
+
+			case isManualMigration:
 				if err := m.mrw.SetMigrationFile(constant.MDMMigrationTypeManual); err != nil {
 					log.Error().Str("migration_type", constant.MDMMigrationTypeManual).Err(err).Msg("set migration file")
 				}
 
-				log.Info().Msg("showing instructions after unenrollment")
+				log.Info().Msg("showing instructions after manual unenrollment")
 				if err := m.handler.ShowInstructions(); err != nil {
 					return err
 				}
-			} else {
+
+			default:
 				if err := m.mrw.SetMigrationFile(constant.MDMMigrationTypeADE); err != nil {
 					log.Error().Str("migration_type", constant.MDMMigrationTypeADE).Err(err).Msg("set migration file")
 				}
+
 			}
 
 			// close the spinner
@@ -512,20 +532,14 @@ func (m *swiftDialogMDMMigrator) SetProps(props MDMMigratorProps) {
 	m.props = props
 }
 
-func (m *swiftDialogMDMMigrator) getMessageAndFlags(isManualMigration bool) (*bytes.Buffer, []string, error) {
-	vers, err := m.getMacOSMajorVersion()
-	if err != nil {
-		// log error for debugging and continue with default template
-		log.Error().Err(err).Msg("getting macOS major version failed: using default migration template")
-	}
-
+func (m *swiftDialogMDMMigrator) getMessageAndFlags(version int, isManualMigration bool) (*bytes.Buffer, []string, error) {
 	tmpl := mdmADEMigrationTemplate
 	if isManualMigration {
 		tmpl = mdmManualMigrationTemplate
 	}
 
 	height := "669"
-	if vers != 0 && vers < 14 {
+	if version != 0 && version < 15 {
 		height = "440"
 		tmpl = mdmMigrationTemplatePreSonoma
 	}
diff --git a/server/fleet/hosts.go b/server/fleet/hosts.go
index 4221356d2c..2f07240b16 100644
--- a/server/fleet/hosts.go
+++ b/server/fleet/hosts.go
@@ -7,6 +7,8 @@ import (
 	"fmt"
 	"strings"
 	"time"
+
+	"github.com/Masterminds/semver"
 )
 
 type HostStatus string
@@ -1223,14 +1225,45 @@ func IsEligibleForDEPMigration(host *Host, mdmInfo *HostMDM, isConnectedToFleetM
 		(!isConnectedToFleetMDM || mdmInfo.Name != WellKnownMDMFleet)
 }
 
+var macOSADEMigrationOnlyLastVersion = semver.MustParse("14")
+
 // IsEligibleForManualMigration returns true if the host is manually enrolled into a 3rd party MDM
 // and is able to migrate to Fleet.
-func IsEligibleForManualMigration(host *Host, mdmInfo *HostMDM, isConnectedToFleetMDM bool) bool {
-	return host.IsOsqueryEnrolled() &&
+func IsEligibleForManualMigration(host *Host, mdmInfo *HostMDM, isConnectedToFleetMDM bool) (bool, error) {
+	goodVersion, err := IsMacOSMajorVersionOK(host)
+	if err != nil {
+		return false, fmt.Errorf("checking macOS version for manual migration eligibility: %w", err)
+	}
+
+	return goodVersion &&
+		host.IsOsqueryEnrolled() &&
 		!host.IsDEPAssignedToFleet() &&
 		mdmInfo != nil &&
 		!mdmInfo.InstalledFromDep &&
 		!mdmInfo.HasJSONProfileAssigned() &&
 		mdmInfo.Enrolled &&
-		(!isConnectedToFleetMDM || mdmInfo.Name != WellKnownMDMFleet)
+		(!isConnectedToFleetMDM || mdmInfo.Name != WellKnownMDMFleet), nil
+}
+
+func IsMacOSMajorVersionOK(host *Host) (bool, error) {
+	if host == nil {
+		return false, nil
+	}
+
+	parts := strings.Split(host.OSVersion, " ")
+
+	if len(parts) < 2 || parts[0] != "macOS" {
+		return false, nil
+	}
+
+	version, err := semver.NewVersion(parts[1])
+	if err != nil {
+		return false, fmt.Errorf("parsing macOS version \"%s\": %w", parts[1], err)
+	}
+
+	if version.GreaterThan(macOSADEMigrationOnlyLastVersion) {
+		return true, nil
+	}
+
+	return false, nil
 }
diff --git a/server/fleet/hosts_test.go b/server/fleet/hosts_test.go
index e6deb677c7..49c781e81f 100644
--- a/server/fleet/hosts_test.go
+++ b/server/fleet/hosts_test.go
@@ -223,6 +223,7 @@ func TestIsEligibleForDEPMigration(t *testing.T) {
 		enrolledInThirdPartyMDM bool
 		expected                bool
 		expectedManual          bool
+		hostOS                  string
 	}{
 		{
 			name:                    "Eligible for DEP migration",
@@ -268,6 +269,7 @@ func TestIsEligibleForDEPMigration(t *testing.T) {
 			enrolledInThirdPartyMDM: true,
 			expected:                false,
 			expectedManual:          true,
+			hostOS:                  "macOS 14.5",
 		},
 		{
 			name:                    "Not eligible - DEP assigned and DEP profile failed",
@@ -304,6 +306,17 @@ func TestIsEligibleForDEPMigration(t *testing.T) {
 			enrolledInThirdPartyMDM: true,
 			expected:                false,
 			expectedManual:          true,
+			hostOS:                  "macOS 14.5",
+		},
+		{
+			name:                    "Manual migration ineligible - enrolled in 3rd party, not DEP, but OS version too low",
+			osqueryHostID:           ptr.String("some-id"),
+			depAssignedToFleet:      ptr.Bool(false),
+			depProfileResponse:      "",
+			enrolledInThirdPartyMDM: true,
+			expected:                false,
+			expectedManual:          false,
+			hostOS:                  "macOS 13.9",
 		},
 	}
 
@@ -312,6 +325,7 @@ func TestIsEligibleForDEPMigration(t *testing.T) {
 			host := &Host{
 				OsqueryHostID:      tc.osqueryHostID,
 				DEPAssignedToFleet: tc.depAssignedToFleet,
+				OSVersion:          tc.hostOS,
 			}
 
 			mdmInfo := &HostMDM{
@@ -321,7 +335,9 @@ func TestIsEligibleForDEPMigration(t *testing.T) {
 			}
 
 			require.Equal(t, tc.expected, IsEligibleForDEPMigration(host, mdmInfo, false))
-			require.Equal(t, tc.expectedManual, IsEligibleForManualMigration(host, mdmInfo, false))
+			manual, err := IsEligibleForManualMigration(host, mdmInfo, false)
+			require.NoError(t, err)
+			require.Equal(t, tc.expectedManual, manual)
 		})
 	}
 }
diff --git a/server/service/orbit.go b/server/service/orbit.go
index 30d8b628ff..394230c602 100644
--- a/server/service/orbit.go
+++ b/server/service/orbit.go
@@ -203,8 +203,13 @@ func (svc *Service) GetOrbitConfig(ctx context.Context) (fleet.OrbitConfig, erro
 			notifs.RenewEnrollmentProfile = true
 		}
 
+		manualMigrationEligible, err := fleet.IsEligibleForManualMigration(host, mdmInfo, isConnectedToFleetMDM)
+		if err != nil {
+			return fleet.OrbitConfig{}, ctxerr.Wrap(ctx, err, "checking manual migration eligibility")
+		}
+
 		if appConfig.MDM.MacOSMigration.Enable &&
-			(fleet.IsEligibleForDEPMigration(host, mdmInfo, isConnectedToFleetMDM) || fleet.IsEligibleForManualMigration(host, mdmInfo, isConnectedToFleetMDM)) {
+			(fleet.IsEligibleForDEPMigration(host, mdmInfo, isConnectedToFleetMDM) || manualMigrationEligible) {
 			notifs.NeedsMDMMigration = true
 		}
 
diff --git a/website/assets/images/permanent/mdm-migration-pre-sonoma-unenroll-1024x500.png b/website/assets/images/permanent/mdm-migration-pre-sonoma-unenroll-1024x500.png
new file mode 100644
index 0000000000..993bcbd72e
Binary files /dev/null and b/website/assets/images/permanent/mdm-migration-pre-sonoma-unenroll-1024x500.png differ