diff --git a/changes/18085-fix-repeated-install-commands-of-fleetd-on-windows-mdm b/changes/18085-fix-repeated-install-commands-of-fleetd-on-windows-mdm
new file mode 100644
index 0000000000..ee04c643b4
--- /dev/null
+++ b/changes/18085-fix-repeated-install-commands-of-fleetd-on-windows-mdm
@@ -0,0 +1 @@
+* Fixed an issue on Windows hosts enrolled in MDM via Azure AD where the command to install Fleetd on the device was sent repeatedly, even though `fleetd` had been properly installed.
diff --git a/server/datastore/mysql/hosts.go b/server/datastore/mysql/hosts.go
index 9c799edf59..ce86ef3f4e 100644
--- a/server/datastore/mysql/hosts.go
+++ b/server/datastore/mysql/hosts.go
@@ -2680,13 +2680,13 @@ func (ds *Datastore) HostByIdentifier(ctx context.Context, identifier string) (*
       COALESCE(hd.percent_disk_space_available, 0) as percent_disk_space_available,
       COALESCE(hd.gigs_total_disk_space, 0) as gigs_total_disk_space,
       COALESCE(hst.seen_time, h.created_at) AS seen_time,
-	  COALESCE(hu.software_updated_at, h.created_at) AS software_updated_at
-	  ` + hostMDMSelect + `
+      COALESCE(hu.software_updated_at, h.created_at) AS software_updated_at
+    ` + hostMDMSelect + `
     FROM hosts h
     LEFT JOIN host_seen_times hst ON (h.id = hst.host_id)
-	LEFT JOIN host_updates hu ON (h.id = hu.host_id)
+    LEFT JOIN host_updates hu ON (h.id = hu.host_id)
     LEFT JOIN host_disks hd ON hd.host_id = h.id
-	` + hostMDMJoin + `
+    ` + hostMDMJoin + `
     WHERE ? IN (h.hostname, h.osquery_host_id, h.node_key, h.uuid, h.hardware_serial)
     LIMIT 1
 	`
@@ -3715,9 +3715,11 @@ func (ds *Datastore) GetHostOrbitInfo(ctx context.Context, hostID uint) (*fleet.
 	err := sqlx.GetContext(
 		ctx, ds.reader(ctx), &orbit, `
 	SELECT
-	  scripts_enabled
+		version,
+		desktop_version,
+		scripts_enabled
 	FROM
-	  host_orbit_info
+		host_orbit_info
 	WHERE host_id = ?`, hostID,
 	)
 	if err != nil {
@@ -5037,7 +5039,7 @@ func (ds *Datastore) loadHostLite(ctx context.Context, id *uint, identifier *str
 	stmt := `
     SELECT
       h.id,
-	  h.team_id,
+      h.team_id,
       h.osquery_host_id,
       h.node_key,
       h.hostname,
@@ -5048,7 +5050,7 @@ func (ds *Datastore) loadHostLite(ctx context.Context, id *uint, identifier *str
       COALESCE(hst.seen_time, h.created_at) AS seen_time
     FROM hosts h
     LEFT JOIN host_seen_times hst ON (h.id = hst.host_id)
-	%s
+    %s
     LIMIT 1
 	`
 	var (
diff --git a/server/fleet/hosts.go b/server/fleet/hosts.go
index ae0124c0d8..0ed16f60c3 100644
--- a/server/fleet/hosts.go
+++ b/server/fleet/hosts.go
@@ -361,7 +361,9 @@ type Host struct {
 
 // HostOrbitInfo maps to the host_orbit_info table in the database, which maps to the orbit_info agent table.
 type HostOrbitInfo struct {
-	ScriptsEnabled *bool `json:"scripts_enabled" db:"scripts_enabled"`
+	Version        string  `json:"version" db:"version"`
+	DesktopVersion *string `json:"desktop_version" db:"desktop_version"`
+	ScriptsEnabled *bool   `json:"scripts_enabled" db:"scripts_enabled"`
 }
 
 // HostHealth contains a subset of Host data that indicates how healthy a Host is. For fields with
diff --git a/server/service/integration_mdm_test.go b/server/service/integration_mdm_test.go
index 4510cfc2e6..dedd92f3e0 100644
--- a/server/service/integration_mdm_test.go
+++ b/server/service/integration_mdm_test.go
@@ -6069,22 +6069,79 @@ func (s *integrationMDMTestSuite) TestWindowsAutomaticEnrollmentCommands() {
 	d := mdmtest.NewTestMDMClientWindowsAutomatic(s.server.URL, azureMail)
 	require.NoError(t, d.Enroll())
 
-	cmds, err := d.StartManagementSession()
+	checkinAndAck := func(expectFleetdCmds bool) {
+		cmds, err := d.StartManagementSession()
+		require.NoError(t, err)
+
+		if !expectFleetdCmds {
+			// receives only the 2 status commands
+			require.Len(t, cmds, 2)
+			for _, c := range cmds {
+				require.Equal(t, "Status", c.Verb, c)
+			}
+			return
+		}
+
+		// 2 status + 2 commands to install fleetd
+		require.Len(t, cmds, 4)
+		var fleetdAddCmd, fleetdExecCmd fleet.ProtoCmdOperation
+		for _, c := range cmds {
+			switch c.Verb {
+			case "Add":
+				fleetdAddCmd = c
+			case "Exec":
+				fleetdExecCmd = c
+			}
+		}
+		require.Equal(t, syncml.FleetdWindowsInstallerGUID, fleetdAddCmd.Cmd.GetTargetURI())
+		require.Equal(t, syncml.FleetdWindowsInstallerGUID, fleetdExecCmd.Cmd.GetTargetURI())
+
+		// reply with success for both commands
+		msgID, err := d.GetCurrentMsgID()
+		require.NoError(t, err)
+
+		d.AppendResponse(fleet.SyncMLCmd{
+			XMLName: xml.Name{Local: fleet.CmdStatus},
+			MsgRef:  &msgID,
+			CmdRef:  &fleetdAddCmd.Cmd.CmdID.Value,
+			Cmd:     &fleetdAddCmd.Verb,
+			Data:    ptr.String("200"),
+			Items:   nil,
+			CmdID:   fleet.CmdID{Value: uuid.NewString()},
+		})
+		d.AppendResponse(fleet.SyncMLCmd{
+			XMLName: xml.Name{Local: fleet.CmdStatus},
+			MsgRef:  &msgID,
+			CmdRef:  &fleetdExecCmd.Cmd.CmdID.Value,
+			Cmd:     &fleetdExecCmd.Verb,
+			Data:    ptr.String("200"),
+			Items:   nil,
+			CmdID:   fleet.CmdID{Value: uuid.NewString()},
+		})
+		cmds, err = d.SendResponse()
+		require.NoError(t, err)
+
+		// the ack of the message should be the only returned command
+		require.Len(t, cmds, 1)
+	}
+
+	// start a management session, will receive the install fleetd commands
+	checkinAndAck(true)
+
+	// start a new management session again, Fleetd is not reported as installed
+	// so it receives the commands again
+	checkinAndAck(true)
+
+	// simulate fleetd installed and enrolled
+	host := createOrbitEnrolledHost(t, "windows", "h1", s.ds)
+	err = s.ds.UpdateMDMWindowsEnrollmentsHostUUID(ctx, host.UUID, d.DeviceID)
+	require.NoError(t, err)
+	err = s.ds.SetOrUpdateHostOrbitInfo(ctx, host.ID, "1.23", sql.NullString{}, sql.NullBool{})
 	require.NoError(t, err)
 
-	// 2 status + 2 commands to install fleetd
-	require.Len(t, cmds, 4)
-	var fleetdAddCmd, fleetdExecCmd fleet.ProtoCmdOperation
-	for _, c := range cmds {
-		switch c.Verb {
-		case "Add":
-			fleetdAddCmd = c
-		case "Exec":
-			fleetdExecCmd = c
-		}
-	}
-	require.Equal(t, syncml.FleetdWindowsInstallerGUID, fleetdAddCmd.Cmd.GetTargetURI())
-	require.Equal(t, syncml.FleetdWindowsInstallerGUID, fleetdExecCmd.Cmd.GetTargetURI())
+	// start a new management session again, Fleetd is reported as installed so
+	// it does not receive the commands
+	checkinAndAck(false)
 }
 
 func (s *integrationMDMTestSuite) TestValidManagementUnenrollRequest() {
diff --git a/server/service/microsoft_mdm.go b/server/service/microsoft_mdm.go
index 1a6e113f50..4ceab6d20b 100644
--- a/server/service/microsoft_mdm.go
+++ b/server/service/microsoft_mdm.go
@@ -1274,7 +1274,23 @@ func (svc *Service) isFleetdPresentOnDevice(ctx context.Context, deviceID string
 	// If user identity is a MS-MDM UPN it means that the device was enrolled through user-driven flow
 	// This means that fleetd might not be installed
 	if isValidUPN(enrolledDevice.MDMEnrollUserID) {
-		return false, nil
+		var isPresent bool
+		if enrolledDevice.HostUUID != "" {
+			host, err := svc.ds.HostLiteByIdentifier(ctx, enrolledDevice.HostUUID)
+			if err != nil && !fleet.IsNotFound(err) {
+				return false, ctxerr.Wrap(ctx, err, "get host lite by identifier")
+			}
+			if host != nil {
+				orbitInfo, err := svc.ds.GetHostOrbitInfo(ctx, host.ID)
+				if err != nil && !fleet.IsNotFound(err) {
+					return false, ctxerr.Wrap(ctx, err, "get host orbit info")
+				}
+				if orbitInfo != nil {
+					isPresent = orbitInfo.Version != ""
+				}
+			}
+		}
+		return isPresent, nil
 	}
 
 	// TODO: Add check here to determine if MDM DeviceID is connected with Smbios UUID present on