diff --git a/orbit/changes/39252-manual-migration-if-not-dep-capable b/orbit/changes/39252-manual-migration-if-not-dep-capable
new file mode 100644
index 0000000000..b2d8fc9193
--- /dev/null
+++ b/orbit/changes/39252-manual-migration-if-not-dep-capable
@@ -0,0 +1 @@
+* Fixed an issue where the automatic migration preview would show when the device was not MDM-enrolled and not enrolled via DEP.
\ No newline at end of file
diff --git a/orbit/pkg/profiles/profiles_darwin.go b/orbit/pkg/profiles/profiles_darwin.go
index 8cdd08d823..4832dbdd61 100644
--- a/orbit/pkg/profiles/profiles_darwin.go
+++ b/orbit/pkg/profiles/profiles_darwin.go
@@ -127,7 +127,10 @@ func IsEnrolledInMDM() (bool, string, error) {
 	return true, enrollmentURL, nil
 }
 
-func IsManuallyEnrolledInMDM() (bool, error) {
+// ParseMDMEnrollmentStatus runs the `profiles` command to get the current MDM
+// enrollment information and reports if the host is enrolled via DEP or not.
+// Which is used to check for manual enrollment or not.
+func ParseMDMEnrollmentStatus() (enrolledViaDEP bool, err error) {
 	out, err := getMDMInfoFromProfilesCmd()
 	if err != nil {
 		return false, fmt.Errorf("calling /usr/bin/profiles: %w", err)
@@ -141,21 +144,21 @@ func IsManuallyEnrolledInMDM() (bool, error) {
 	// MDM server: https://test.example.com/mdm/apple/mdm
 	// ```
 	//
-	// If the host is not enrolled into an MDM, the last line is ommitted,
+	// If the host is not enrolled into an MDM, the last line is omitted,
 	// so we need to check that:
 	//
-	// 1. We've got three rows
-	// 2. Whether the first line contains "Yes" or "No"
+	// 1. We've got two rows
+	// 2. The first row contains "Yes" or "No"
 	lines := bytes.Split(bytes.TrimSpace(out), []byte("\n"))
-	if len(lines) < 3 {
-		return false, nil
+	if len(lines) < 2 {
+		return false, fmt.Errorf("Got %d lines of output, when expected at least 2 or more", len(lines))
 	}
 
 	if strings.Contains(string(lines[0]), "Yes") {
-		return false, nil
+		return true, nil
 	}
 
-	return true, nil
+	return false, nil
 }
 
 // getMDMInfoFromProfilesCmd is declared as a variable so it can be overwritten by tests.
diff --git a/orbit/pkg/profiles/profiles_darwin_test.go b/orbit/pkg/profiles/profiles_darwin_test.go
index 1f4cf91a55..81192ea4f8 100644
--- a/orbit/pkg/profiles/profiles_darwin_test.go
+++ b/orbit/pkg/profiles/profiles_darwin_test.go
@@ -327,6 +327,45 @@ MDM server: https://valid.com/mdm/apple/mdm
 	}
 }
 
+func TestParseMDMEnrollmentStatus(t *testing.T) {
+	cases := []struct {
+		cmdOut  *string
+		cmdErr  error
+		want    bool
+		wantErr bool
+	}{
+		{nil, errors.New("test error"), false, true},
+		{ptr.String(""), nil, false, true},
+		{ptr.String("Enrolled via DEP: No\nMDM Enrollment: No"), nil, false, false},
+		{ptr.String("Enrolled via DEP: Yes\nMDM Enrollment: No"), nil, true, false},
+		{ptr.String("Enrolled via DEP: No\nMDM Enrollment: Yes (User Approved)"), nil, false, false},
+		{ptr.String("Enrolled via DEP: No\nMDM Enrollment: Yes (User Approved)\nMDM Server: https://mdm.example.com"), nil, false, false},
+		{ptr.String("Enrolled via DEP: Yes\nMDM Enrollment: Yes\nMDM Server: https://mdm.example.com"), nil, true, false},
+	}
+
+	origCmd := getMDMInfoFromProfilesCmd
+	t.Cleanup(func() { getMDMInfoFromProfilesCmd = origCmd })
+	for _, c := range cases {
+		getMDMInfoFromProfilesCmd = func() ([]byte, error) {
+			if c.cmdOut == nil {
+				return nil, c.cmdErr
+			}
+
+			var buf bytes.Buffer
+			buf.WriteString(*c.cmdOut)
+			return buf.Bytes(), nil
+		}
+
+		got, err := ParseMDMEnrollmentStatus()
+		if c.wantErr {
+			require.Error(t, err)
+		} else {
+			require.NoError(t, err)
+		}
+		require.Equal(t, c.want, got)
+	}
+}
+
 func TestCheckAssignedEnrollmentProfile(t *testing.T) {
 	fleetURL := "https://valid.com"
 	cases := []struct {
diff --git a/orbit/pkg/useraction/mdm_migration_darwin.go b/orbit/pkg/useraction/mdm_migration_darwin.go
index ad2fd40fe8..c4e487419d 100644
--- a/orbit/pkg/useraction/mdm_migration_darwin.go
+++ b/orbit/pkg/useraction/mdm_migration_darwin.go
@@ -406,7 +406,7 @@ func (m *swiftDialogMDMMigrator) waitForUnenrollment(isADEMigration bool) error
 
 func (m *swiftDialogMDMMigrator) renderMigration() error {
 	log.Debug().Msg("checking current enrollment status")
-	isCurrentlyManuallyEnrolled, err := profiles.IsManuallyEnrolledInMDM()
+	enrolledViaDEP, err := profiles.ParseMDMEnrollmentStatus()
 	if err != nil {
 		return err
 	}
@@ -418,10 +418,10 @@ func (m *swiftDialogMDMMigrator) renderMigration() error {
 		return fmt.Errorf("getting migration type: %w", err)
 	}
 
-	isManualMigration := isCurrentlyManuallyEnrolled || previousMigrationType == constant.MDMMigrationTypeManual
+	isManualMigration := !enrolledViaDEP || previousMigrationType == constant.MDMMigrationTypeManual
 	isADEMigration := previousMigrationType == constant.MDMMigrationTypeADE
 
-	log.Debug().Bool("isManualMigration", isManualMigration).Bool("isADEMigration", isADEMigration).Bool("isCurrentlyManuallyEnrolled", isCurrentlyManuallyEnrolled).Str("previousMigrationType", previousMigrationType).Msg("props after assigning")
+	log.Debug().Bool("isManualMigration", isManualMigration).Bool("isADEMigration", isADEMigration).Bool("enrolledViaDEP", enrolledViaDEP).Str("previousMigrationType", previousMigrationType).Msg("props after assigning")
 
 	vers, err := m.getMacOSMajorVersion()
 	if err != nil {
@@ -465,7 +465,7 @@ func (m *swiftDialogMDMMigrator) renderMigration() error {
 
 		if !m.props.IsUnmanaged {
 			// show the loading spinner
-			m.renderLoadingSpinner(isPreSonoma, isCurrentlyManuallyEnrolled)
+			m.renderLoadingSpinner(isPreSonoma, isManualMigration)
 
 			// send the API call
 			if notifyErr := m.handler.NotifyRemote(); notifyErr != nil {
@@ -498,7 +498,7 @@ func (m *swiftDialogMDMMigrator) renderMigration() error {
 			switch {
 			case isPreSonoma:
 				if err := m.mrw.SetMigrationFile(constant.MDMMigrationTypePreSonoma); err != nil {
-					log.Error().Str("migration_type", constant.MDMMigrationTypeADE).Err(err).Msg("set migration file")
+					log.Error().Str("migration_type", constant.MDMMigrationTypePreSonoma).Err(err).Msg("set migration file")
 				}
 
 				log.Info().Msg("showing instructions after pre-sonoma unenrollment")