diff --git a/CODEOWNERS b/CODEOWNERS
index 524ca884048f..6209b3092a80 100644
--- a/CODEOWNERS
+++ b/CODEOWNERS
@@ -49,7 +49,7 @@ go.mod @fleetdm/go
 /ee/fleetd-chrome @lucasmrod @getvictor
 /ee/vulnerability-dashboard @eashaw
 /ee/cis @sharon-fdm @lucasmrod
-/ee/server/calender @lucasmrod @getvictor
+/ee/server/calendar @lucasmrod @getvictor
 /ee/server/service @roperzh @gillespi314 @lucasmrod @getvictor
 /scripts/mdm @roperzh @gillespi314
 
diff --git a/changes/20059-fix-last_enrolled_at b/changes/20059-fix-last_enrolled_at
new file mode 100644
index 000000000000..da8b3bfabc73
--- /dev/null
+++ b/changes/20059-fix-last_enrolled_at
@@ -0,0 +1 @@
+* Fixed bug that set `Added to Fleet` to `Never` after macOS hosts re-enrolled to Fleet via MDM. 
diff --git a/server/datastore/mysql/apple_mdm.go b/server/datastore/mysql/apple_mdm.go
index 0845814eb3e7..8cf2944e9db4 100644
--- a/server/datastore/mysql/apple_mdm.go
+++ b/server/datastore/mysql/apple_mdm.go
@@ -784,30 +784,37 @@ func updateMDMAppleHostDB(
 ) error {
 	refetchRequested, lastEnrolledAt := mdmHostEnrollFields(mdmHost)
 
-	updateStmt := `
-		UPDATE hosts SET
-			hardware_serial = ?,
-			uuid = ?,
-			hardware_model = ?,
-			platform =  ?,
-			refetch_requested = ?,
-			last_enrolled_at = ?,
-			osquery_host_id = COALESCE(NULLIF(osquery_host_id, ''), ?)
-		WHERE id = ?`
-
-	if _, err := tx.ExecContext(
-		ctx,
-		updateStmt,
+	args := []interface{}{
 		mdmHost.HardwareSerial,
 		mdmHost.UUID,
 		mdmHost.HardwareModel,
 		mdmHost.Platform,
 		refetchRequested,
-		lastEnrolledAt,
 		// Set osquery_host_id to the device UUID only if it is not already set.
 		mdmHost.UUID,
 		hostID,
-	); err != nil {
+	}
+
+	// Only update last_enrolled_at if this is a iOS/iPadOS device.
+	// macOS should not update last_enrolled_at as it is set when osquery enrolls.
+	lastEnrolledAtColumn := ""
+	if mdmHost.Platform == "ios" || mdmHost.Platform == "ipados" {
+		lastEnrolledAtColumn = "last_enrolled_at = ?,"
+		args = append([]interface{}{lastEnrolledAt}, args...)
+	}
+
+	updateStmt := fmt.Sprintf(`
+		UPDATE hosts SET
+			%s
+			hardware_serial = ?,
+			uuid = ?,
+			hardware_model = ?,
+			platform =  ?,
+			refetch_requested = ?,
+			osquery_host_id = COALESCE(NULLIF(osquery_host_id, ''), ?)
+		WHERE id = ?`, lastEnrolledAtColumn)
+
+	if _, err := tx.ExecContext(ctx, updateStmt, args...); err != nil {
 		return ctxerr.Wrap(ctx, err, "update mdm apple host")
 	}
 
diff --git a/server/datastore/mysql/migrations/tables/20240710155623_FixResetLastEnrolledAt.go b/server/datastore/mysql/migrations/tables/20240710155623_FixResetLastEnrolledAt.go
new file mode 100644
index 000000000000..5f494e637926
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20240710155623_FixResetLastEnrolledAt.go
@@ -0,0 +1,36 @@
+package tables
+
+import (
+	"database/sql"
+	"fmt"
+)
+
+func init() {
+	MigrationClient.AddMigration(Up_20240710155623, Down_20240710155623)
+}
+
+func Up_20240710155623(tx *sql.Tx) error {
+	// `hosts.last_enrolled_at` contains the date the osquery agent enrolled.
+	//
+	// A bug in v4.51.0 caused the `last_enrolled_at` column to be set to
+	// '2000-01-01 00:00:00' (aka the "Never" date) when macOS hosts perform a
+	// MDM re-enrollment (see https://github.com/fleetdm/fleet/issues/20059
+	// for more details).
+	//
+	// We cannot restore the exact date of the osquery enrollment but
+	// `host_disks.created_at` is a good approximation.
+	if _, err := tx.Exec(`
+		UPDATE hosts h
+		JOIN host_disks hd ON h.id=hd.host_id
+		SET h.last_enrolled_at = hd.created_at, h.updated_at = h.updated_at
+		WHERE h.platform = 'darwin' AND h.last_enrolled_at = '2000-01-01 00:00:00';`,
+	); err != nil {
+		return fmt.Errorf("failed to update hosts.last_enrolled_at: %w", err)
+	}
+
+	return nil
+}
+
+func Down_20240710155623(tx *sql.Tx) error {
+	return nil
+}
diff --git a/server/datastore/mysql/migrations/tables/20240710155623_FixResetLastEnrolledAt_test.go b/server/datastore/mysql/migrations/tables/20240710155623_FixResetLastEnrolledAt_test.go
new file mode 100644
index 000000000000..275933b033c4
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20240710155623_FixResetLastEnrolledAt_test.go
@@ -0,0 +1,94 @@
+package tables
+
+import (
+	"fmt"
+	"testing"
+	"time"
+
+	"github.com/stretchr/testify/require"
+)
+
+func TestUp_20240710155623(t *testing.T) {
+	db := applyUpToPrev(t)
+
+	i := uint(1)
+	newHost := func(platform, lastEnrolledAt string, hostDisk bool) uint {
+		id := fmt.Sprintf("%d", i)
+		i++
+		hostID := uint(execNoErrLastID(t, db,
+			`INSERT INTO hosts (osquery_host_id, node_key, uuid, platform, last_enrolled_at) VALUES (?, ?, ?, ?, ?);`,
+			id, id, id, platform, lastEnrolledAt,
+		))
+		if hostDisk {
+			execNoErr(t, db,
+				`INSERT INTO host_disks (host_id) VALUES (?);`,
+				hostID,
+			)
+		}
+		return hostID
+	}
+	neverDate := "2000-01-01 00:00:00"
+	ubuntuHostID := newHost("ubuntu", neverDate, true)                 // non-darwin hosts should not be updated.
+	validMacOSHostID := newHost("darwin", "2024-07-08 18:00:53", true) // host without the issue, should not be updated.
+	pendingMacOSDEPHostID := newHost("darwin", neverDate, false)       // host without the issue (e.g. DEP pending, not enrolled), should not be updated.
+	invalidMacOSHostID := newHost("darwin", neverDate, true)           // host with the issue, should be updated.
+
+	const getColumnsQuery = `
+		SELECT h.last_enrolled_at, h.updated_at, hd.created_at AS host_disks_created_at
+		FROM hosts h LEFT JOIN host_disks hd ON h.id=hd.host_id WHERE h.id = ?;`
+	type hostTimestamps struct {
+		LastEnrolledAt     time.Time  `db:"last_enrolled_at"`
+		UpdatedAt          time.Time  `db:"updated_at"`
+		HostDisksCreatedAt *time.Time `db:"host_disks_created_at"`
+	}
+	var ubuntuTimestampsBefore hostTimestamps
+	err := db.Get(&ubuntuTimestampsBefore, getColumnsQuery, ubuntuHostID)
+	require.NoError(t, err)
+	require.NotZero(t, ubuntuTimestampsBefore.UpdatedAt)
+	require.Equal(t, ubuntuTimestampsBefore.LastEnrolledAt.Format("2006-01-02 15:04:05"), neverDate)
+	require.NotNil(t, ubuntuTimestampsBefore.HostDisksCreatedAt)
+	require.NotZero(t, *ubuntuTimestampsBefore.HostDisksCreatedAt)
+	var validMacOSTimestampsBefore hostTimestamps
+	err = db.Get(&validMacOSTimestampsBefore, getColumnsQuery, validMacOSHostID)
+	require.NoError(t, err)
+	require.NotZero(t, validMacOSTimestampsBefore.UpdatedAt)
+	require.Equal(t, validMacOSTimestampsBefore.LastEnrolledAt.Format("2006-01-02 15:04:05"), "2024-07-08 18:00:53")
+	require.NotNil(t, validMacOSTimestampsBefore.HostDisksCreatedAt)
+	require.NotZero(t, *validMacOSTimestampsBefore.HostDisksCreatedAt)
+	var pendingMacOSDEPTimestampsBefore hostTimestamps
+	err = db.Get(&pendingMacOSDEPTimestampsBefore, getColumnsQuery, pendingMacOSDEPHostID)
+	require.NoError(t, err)
+	require.NotZero(t, pendingMacOSDEPTimestampsBefore.UpdatedAt)
+	require.Equal(t, pendingMacOSDEPTimestampsBefore.LastEnrolledAt.Format("2006-01-02 15:04:05"), neverDate)
+	require.Nil(t, pendingMacOSDEPTimestampsBefore.HostDisksCreatedAt)
+	var invalidMacOSTimestampsBefore hostTimestamps
+	err = db.Get(&invalidMacOSTimestampsBefore, getColumnsQuery, invalidMacOSHostID)
+	require.NoError(t, err)
+	require.NotZero(t, invalidMacOSTimestampsBefore.UpdatedAt)
+	require.Equal(t, invalidMacOSTimestampsBefore.LastEnrolledAt.Format("2006-01-02 15:04:05"), neverDate)
+	require.NotNil(t, invalidMacOSTimestampsBefore.HostDisksCreatedAt)
+	require.NotZero(t, *invalidMacOSTimestampsBefore.HostDisksCreatedAt)
+
+	// Apply current migration.
+	applyNext(t, db)
+
+	var ubuntuTimestampsAfter hostTimestamps
+	err = db.Get(&ubuntuTimestampsAfter, getColumnsQuery, ubuntuHostID)
+	require.NoError(t, err)
+	require.Equal(t, ubuntuTimestampsBefore, ubuntuTimestampsAfter)
+	var validMacOSTimestampsAfter hostTimestamps
+	err = db.Get(&validMacOSTimestampsAfter, getColumnsQuery, validMacOSHostID)
+	require.NoError(t, err)
+	require.Equal(t, validMacOSTimestampsBefore, validMacOSTimestampsAfter)
+	var pendingMacOSDEPTimestampsAfter hostTimestamps
+	err = db.Get(&pendingMacOSDEPTimestampsAfter, getColumnsQuery, pendingMacOSDEPHostID)
+	require.NoError(t, err)
+	require.Equal(t, pendingMacOSDEPTimestampsBefore.UpdatedAt, pendingMacOSDEPTimestampsAfter.UpdatedAt)    // updated_at is unmodified
+	require.Equal(t, neverDate, pendingMacOSDEPTimestampsAfter.LastEnrolledAt.Format("2006-01-02 15:04:05")) // last_enrolled_at was not modified
+	var invalidMacOSTimestampsAfter hostTimestamps
+	err = db.Get(&invalidMacOSTimestampsAfter, getColumnsQuery, invalidMacOSHostID)
+	require.NoError(t, err)
+	require.Equal(t, invalidMacOSTimestampsBefore.UpdatedAt, invalidMacOSTimestampsAfter.UpdatedAt) // updated_at is unmodified
+	require.NotNil(t, invalidMacOSTimestampsAfter.HostDisksCreatedAt)
+	require.Equal(t, *invalidMacOSTimestampsAfter.HostDisksCreatedAt, invalidMacOSTimestampsAfter.LastEnrolledAt) // last_enrolled_at was updated to host_disks date
+}
diff --git a/server/datastore/mysql/schema.sql b/server/datastore/mysql/schema.sql
index 04d18194efc8..409ff2924ae1 100644
--- a/server/datastore/mysql/schema.sql
+++ b/server/datastore/mysql/schema.sql
@@ -950,9 +950,9 @@ CREATE TABLE `migration_status_tables` (
   `tstamp` timestamp NULL DEFAULT CURRENT_TIMESTAMP,
   PRIMARY KEY (`id`),
   UNIQUE KEY `id` (`id`)
-) ENGINE=InnoDB AUTO_INCREMENT=285 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
+) ENGINE=InnoDB AUTO_INCREMENT=286 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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 /*!40101 SET @saved_cs_client     = @@character_set_client */;
 /*!40101 SET character_set_client = utf8 */;
 CREATE TABLE `mobile_device_management_solutions` (
diff --git a/server/service/integration_mdm_test.go b/server/service/integration_mdm_test.go
index 27b9b0b2f5f6..90a45e183793 100644
--- a/server/service/integration_mdm_test.go
+++ b/server/service/integration_mdm_test.go
@@ -2222,8 +2222,7 @@ func (s *integrationMDMTestSuite) TestEnrollOrbitAfterDEPSync() {
 	ctx := context.Background()
 
 	// create a host with minimal information and the serial, no uuid/osquery id
-	// (as when created via DEP sync). Platform must be "darwin" as this is the
-	// only supported OS with DEP.
+	// (as when created via DEP sync).
 	dbZeroTime := time.Date(2000, 1, 1, 0, 0, 0, 0, time.UTC)
 	h, err := s.ds.NewHost(ctx, &fleet.Host{
 		HardwareSerial:   uuid.New().String(),
@@ -2233,6 +2232,7 @@ func (s *integrationMDMTestSuite) TestEnrollOrbitAfterDEPSync() {
 		RefetchRequested: true,
 	})
 	require.NoError(t, err)
+	require.Equal(t, dbZeroTime, h.LastEnrolledAt)
 
 	// create an enroll secret
 	secret := uuid.New().String()
@@ -2258,6 +2258,7 @@ func (s *integrationMDMTestSuite) TestEnrollOrbitAfterDEPSync() {
 	var hostResp getHostResponse
 	s.DoJSON("GET", fmt.Sprintf("/api/latest/fleet/hosts/%d", h.ID), nil, http.StatusOK, &hostResp)
 	require.Equal(t, h.ID, hostResp.Host.ID)
+	require.NotEqual(t, dbZeroTime, hostResp.Host.LastEnrolledAt)
 
 	got, err := s.ds.LoadHostByOrbitNodeKey(ctx, resp.OrbitNodeKey)
 	require.NoError(t, err)
@@ -9174,6 +9175,41 @@ func (s *integrationMDMTestSuite) TestMDMRequestWithoutCerts() {
 	require.NoError(t, res.Body.Close())
 }
 
+func (s *integrationMDMTestSuite) TestMDMEnrollDoesntClearLastEnrolledAtForMacOS() {
+	t := s.T()
+
+	// Enroll to Fleet with fleetd first.
+	desktopToken := uuid.New().String()
+	lastEnrolledAt := time.Now().UTC()
+	mdmDevice := mdmtest.NewTestMDMClientAppleDesktopManual(s.server.URL, desktopToken)
+	fleetHost, err := s.ds.NewHost(context.Background(), &fleet.Host{
+		DetailUpdatedAt: time.Now(),
+		LabelUpdatedAt:  time.Now(),
+		PolicyUpdatedAt: time.Now(),
+		LastEnrolledAt:  lastEnrolledAt,
+		SeenTime:        time.Now().Add(-1 * time.Minute),
+		OsqueryHostID:   ptr.String(t.Name() + uuid.New().String()),
+		NodeKey:         ptr.String(t.Name() + uuid.New().String()),
+		Hostname:        fmt.Sprintf("%sfoo.local", t.Name()),
+		Platform:        "darwin",
+
+		UUID:           mdmDevice.UUID,
+		HardwareSerial: mdmDevice.SerialNumber,
+	})
+	require.NoError(t, err)
+	err = s.ds.SetOrUpdateDeviceAuthToken(context.Background(), fleetHost.ID, desktopToken)
+	require.NoError(t, err)
+
+	// Enroll with MDM manually after.
+	err = mdmDevice.Enroll()
+	require.NoError(t, err)
+
+	hostResp := getHostResponse{}
+	s.DoJSON("GET", fmt.Sprintf("/api/latest/fleet/hosts/%d", fleetHost.ID), nil, http.StatusOK, &hostResp)
+	require.NotNil(t, hostResp.Host)
+	require.Equal(t, lastEnrolledAt.Truncate(1*time.Second).UTC(), hostResp.Host.LastEnrolledAt.Truncate(1*time.Second).UTC())
+}
+
 func (s *integrationMDMTestSuite) TestConnectedToFleetWithoutCheckout() {
 	t := s.T()
 	ctx := context.Background()
@@ -9213,3 +9249,40 @@ func (s *integrationMDMTestSuite) TestConnectedToFleetWithoutCheckout() {
 	require.NotNil(t, hostResp.Host.MDM.ConnectedToFleet)
 	require.False(t, *hostResp.Host.MDM.ConnectedToFleet)
 }
+
+func (s *integrationMDMTestSuite) TestEnrollAfterDEPSyncIOSIPadOS() {
+	t := s.T()
+	ctx := context.Background()
+
+	// create a host with minimal information and the serial, no uuid/osquery id
+	// (as when created via DEP sync).
+	dbZeroTime := time.Date(2000, 1, 1, 0, 0, 0, 0, time.UTC)
+	serialNumber := mdmtest.RandSerialNumber()
+	h, err := s.ds.NewHost(ctx, &fleet.Host{
+		HardwareSerial:   serialNumber,
+		Platform:         "ios",
+		LastEnrolledAt:   dbZeroTime,
+		DetailUpdatedAt:  dbZeroTime,
+		RefetchRequested: true,
+	})
+	require.NoError(t, err)
+	require.Equal(t, dbZeroTime, h.LastEnrolledAt)
+
+	// Perform the MDM enrollment.
+	mdmEnrollInfo := mdmtest.AppleEnrollInfo{
+		SCEPChallenge: s.scepChallenge,
+		SCEPURL:       s.server.URL + apple_mdm.SCEPPath,
+		MDMURL:        s.server.URL + apple_mdm.MDMPath,
+	}
+	mdmDevice := mdmtest.NewTestMDMClientAppleDirect(mdmEnrollInfo, "iPhone14,6")
+	mdmDevice.SerialNumber = serialNumber
+	err = mdmDevice.Enroll()
+	require.NoError(t, err)
+
+	// fetch the host, it will match the one created above
+	// (NOTE: cannot check the returned OrbitNodeKey, this field is not part of the response)
+	var hostResp getHostResponse
+	s.DoJSON("GET", fmt.Sprintf("/api/latest/fleet/hosts/%d", h.ID), nil, http.StatusOK, &hostResp)
+	require.Equal(t, h.ID, hostResp.Host.ID)
+	require.NotEqual(t, dbZeroTime, hostResp.Host.LastEnrolledAt)
+}