diff --git a/server/fleet/hosts.go b/server/fleet/hosts.go
index 5e1a792aee..58119cb43b 100644
--- a/server/fleet/hosts.go
+++ b/server/fleet/hosts.go
@@ -690,9 +690,17 @@ func (h *Host) IsDEPAssignedToFleet() bool {
 func (h *Host) IsEligibleForDEPMigration(isConnectedToFleetMDM bool) bool {
 	return h.IsOsqueryEnrolled() &&
 		h.IsDEPAssignedToFleet() &&
+		h.MDMInfo != nil &&
 		h.MDMInfo.HasJSONProfileAssigned() &&
 		h.MDMInfo.Enrolled &&
-		!isConnectedToFleetMDM
+		// as a special case for migration with user interaction, we
+		// also check the information stored in host_mdm, and assume
+		// the host needs migration if it's not Fleet
+		//
+		// this is because we can't always rely on nano setting
+		// `nano_enrollment.active = 1` since sometimes Fleet won't get
+		// the checkout message from the host.
+		(!isConnectedToFleetMDM || h.MDMInfo.Name != WellKnownMDMFleet)
 }
 
 // NeedsDEPEnrollment returns true if the host should be DEP enrolled into
diff --git a/server/service/integration_mdm_test.go b/server/service/integration_mdm_test.go
index 1e310addaf..720397a494 100644
--- a/server/service/integration_mdm_test.go
+++ b/server/service/integration_mdm_test.go
@@ -5063,7 +5063,6 @@ func (s *integrationMDMTestSuite) TestMDMMigration() {
 		s.DoJSON("POST", "/api/fleet/orbit/config", json.RawMessage(fmt.Sprintf(`{"orbit_node_key": %q}`, *host.OrbitNodeKey)), http.StatusOK, &orbitConfigResp)
 		require.True(t, orbitConfigResp.Notifications.NeedsMDMMigration)
 		require.False(t, orbitConfigResp.Notifications.RenewEnrollmentProfile)
-		cleanAssignmentStatus()
 
 		// simulate that the device needs to be enrolled in fleet, DEP capable
 		err = s.ds.SetOrUpdateMDMData(
@@ -5109,6 +5108,16 @@ func (s *integrationMDMTestSuite) TestMDMMigration() {
 			"",
 		)
 		require.NoError(t, err)
+		mdmDevice := mdmtest.NewTestMDMClientAppleDirect(mdmtest.AppleEnrollInfo{
+			SCEPChallenge: s.scepChallenge,
+			SCEPURL:       s.server.URL + apple_mdm.SCEPPath,
+			MDMURL:        s.server.URL + apple_mdm.MDMPath,
+		}, "MacBookPro16,1")
+		mdmDevice.SerialNumber = host.HardwareSerial
+		mdmDevice.UUID = host.UUID
+		err = mdmDevice.Enroll()
+		require.NoError(t, err)
+		require.NoError(t, err)
 		getDesktopResp = fleetDesktopResponse{}
 		res = s.DoRawNoAuth("GET", "/api/latest/fleet/device/"+token+"/desktop", nil, http.StatusOK)
 		require.NoError(t, json.NewDecoder(res.Body).Decode(&getDesktopResp))
@@ -5127,6 +5136,51 @@ func (s *integrationMDMTestSuite) TestMDMMigration() {
 		s.DoJSON("POST", "/api/fleet/orbit/config", json.RawMessage(fmt.Sprintf(`{"orbit_node_key": %q}`, *host.OrbitNodeKey)), http.StatusOK, &orbitConfigResp)
 		require.False(t, orbitConfigResp.Notifications.NeedsMDMMigration)
 		require.False(t, orbitConfigResp.Notifications.RenewEnrollmentProfile)
+
+		// simulate a host that was reset to factory, but fleet still has an mdm record active
+		err = s.ds.SetOrUpdateMDMData(
+			ctx,
+			host.ID,
+			false,
+			true,
+			s.server.URL,
+			false,
+			fleet.WellKnownMDMSimpleMDM,
+			"",
+		)
+		require.NoError(t, err)
+		getDesktopResp = fleetDesktopResponse{}
+		res = s.DoRawNoAuth("GET", "/api/latest/fleet/device/"+token+"/desktop", nil, http.StatusOK)
+		require.NoError(t, json.NewDecoder(res.Body).Decode(&getDesktopResp))
+		require.NoError(t, res.Body.Close())
+		require.NoError(t, getDesktopResp.Err)
+		require.Zero(t, *getDesktopResp.FailingPolicies)
+		require.True(t, getDesktopResp.Notifications.NeedsMDMMigration)
+		require.False(t, getDesktopResp.Notifications.RenewEnrollmentProfile)
+		require.Equal(t, acResp.OrgInfo.OrgLogoURL, getDesktopResp.Config.OrgInfo.OrgLogoURL)
+		require.Equal(t, acResp.OrgInfo.OrgLogoURLLightBackground, getDesktopResp.Config.OrgInfo.OrgLogoURLLightBackground)
+		require.Equal(t, acResp.OrgInfo.ContactURL, getDesktopResp.Config.OrgInfo.ContactURL)
+		require.Equal(t, acResp.OrgInfo.OrgName, getDesktopResp.Config.OrgInfo.OrgName)
+		require.Equal(t, acResp.MDM.MacOSMigration.Mode, getDesktopResp.Config.MDM.MacOSMigration.Mode)
+
+		orbitConfigResp = orbitGetConfigResponse{}
+		s.DoJSON("POST", "/api/fleet/orbit/config", json.RawMessage(fmt.Sprintf(`{"orbit_node_key": %q}`, *host.OrbitNodeKey)), http.StatusOK, &orbitConfigResp)
+		require.True(t, orbitConfigResp.Notifications.NeedsMDMMigration)
+		require.False(t, orbitConfigResp.Notifications.RenewEnrollmentProfile)
+
+		// clean up nano tables
+		mysql.ExecAdhocSQL(t, s.ds, func(q sqlx.ExtContext) error {
+			_, err := q.ExecContext(context.Background(), `
+			DELETE FROM nano_enrollments WHERE id = ?
+			`, host.UUID)
+			return err
+		})
+		mysql.ExecAdhocSQL(t, s.ds, func(q sqlx.ExtContext) error {
+			_, err := q.ExecContext(context.Background(), `
+			DELETE FROM nano_devices WHERE id = ?
+			`, host.UUID)
+			return err
+		})
 	}
 
 	token := "token_test_migration"