diff --git a/api/datastore/init.go b/api/datastore/init.go
index 32c4e7aab..ceffd29cb 100644
--- a/api/datastore/init.go
+++ b/api/datastore/init.go
@@ -1,6 +1,8 @@
 package datastore
 
 import (
+	"os"
+
 	portainer "github.com/portainer/portainer/api"
 )
 
@@ -20,6 +22,12 @@ func (store *Store) Init() error {
 }
 
 func (store *Store) checkOrCreateDefaultSettings() error {
+
+	isDDExtention := false
+	if _, ok := os.LookupEnv("DOCKER_EXTENSION"); ok {
+		isDDExtention = true
+	}
+
 	// TODO: these need to also be applied when importing
 	settings, err := store.SettingsService.Settings()
 	if store.IsErrObjectNotFound(err) {
@@ -51,6 +59,8 @@ func (store *Store) checkOrCreateDefaultSettings() error {
 			UserSessionTimeout:       portainer.DefaultUserSessionTimeout,
 			KubeconfigExpiry:         portainer.DefaultKubeconfigExpiry,
 			KubectlShellImage:        portainer.DefaultKubectlShellImage,
+
+			IsDockerDesktopExtention: isDDExtention,
 		}
 
 		return store.SettingsService.UpdateSettings(defaultSettings)
diff --git a/api/datastore/migrator/migrate_dbversion100.go b/api/datastore/migrator/migrate_dbversion100.go
new file mode 100644
index 000000000..d47947d3f
--- /dev/null
+++ b/api/datastore/migrator/migrate_dbversion100.go
@@ -0,0 +1,29 @@
+package migrator
+
+import (
+	"os"
+
+	"github.com/rs/zerolog/log"
+)
+
+func (m *Migrator) migrateDockerDesktopExtentionSetting() error {
+	log.Info().Msg("updating docker desktop extention flag in settings")
+
+	isDDExtention := false
+	if _, ok := os.LookupEnv("DOCKER_EXTENSION"); ok {
+		isDDExtention = true
+	}
+
+	settings, err := m.settingsService.Settings()
+	if err != nil {
+		return err
+	}
+
+	settings.IsDockerDesktopExtention = isDDExtention
+	err = m.settingsService.UpdateSettings(settings)
+	if err != nil {
+		return err
+	}
+
+	return nil
+}
diff --git a/api/datastore/migrator/migrator.go b/api/datastore/migrator/migrator.go
index 75645c42c..74b224a6a 100644
--- a/api/datastore/migrator/migrator.go
+++ b/api/datastore/migrator/migrator.go
@@ -211,6 +211,8 @@ func (m *Migrator) initMigrations() {
 	m.addMigrations("2.17", m.migrateDBVersionToDB80)
 	m.addMigrations("2.18", m.migrateDBVersionToDB90)
 
+	m.addMigrations("2.19", m.migrateDockerDesktopExtentionSetting)
+
 	// Add new migrations below...
 	// One function per migration, each versions migration funcs in the same file.
 }
diff --git a/api/datastore/test_data/output_24_to_latest.json b/api/datastore/test_data/output_24_to_latest.json
index 256fd1aae..a4a0e17e3 100644
--- a/api/datastore/test_data/output_24_to_latest.json
+++ b/api/datastore/test_data/output_24_to_latest.json
@@ -606,6 +606,7 @@
     "InternalAuthSettings": {
       "RequiredPasswordLength": 12
     },
+    "IsDockerDesktopExtention": false,
     "KubeconfigExpiry": "0",
     "KubectlShellImage": "portainer/kubectl-shell",
     "LDAPSettings": {
@@ -945,6 +946,6 @@
     }
   ],
   "version": {
-    "VERSION": "{\"SchemaVersion\":\"2.19.0\",\"MigratorCount\":0,\"Edition\":1,\"InstanceID\":\"463d5c47-0ea5-4aca-85b1-405ceefee254\"}"
+    "VERSION": "{\"SchemaVersion\":\"2.19.0\",\"MigratorCount\":1,\"Edition\":1,\"InstanceID\":\"463d5c47-0ea5-4aca-85b1-405ceefee254\"}"
   }
 }
\ No newline at end of file
diff --git a/api/http/handler/settings/settings_public.go b/api/http/handler/settings/settings_public.go
index aad2b1023..4aea4a9a6 100644
--- a/api/http/handler/settings/settings_public.go
+++ b/api/http/handler/settings/settings_public.go
@@ -49,6 +49,8 @@ type publicSettingsResponse struct {
 		// The check in interval for edge agent (in seconds) - used in non async mode [seconds]
 		CheckinInterval int `example:"60"`
 	}
+
+	IsDockerDesktopExtention bool `json:"IsDockerDesktopExtention" example:"false"`
 }
 
 // @id SettingsPublic
@@ -89,6 +91,8 @@ func generatePublicSettings(appSettings *portainer.Settings) *publicSettingsResp
 	publicSettings.Edge.CommandInterval = appSettings.Edge.CommandInterval
 	publicSettings.Edge.CheckinInterval = appSettings.EdgeAgentCheckinInterval
 
+	publicSettings.IsDockerDesktopExtention = appSettings.IsDockerDesktopExtention
+
 	//if OAuth authentication is on, compose the related fields from application settings
 	if publicSettings.AuthenticationMethod == portainer.AuthenticationOAuth {
 		publicSettings.OAuthLogoutURI = appSettings.OAuthSettings.LogoutURI
diff --git a/api/jwt/jwt.go b/api/jwt/jwt.go
index 905cbfeee..4eddf58c2 100644
--- a/api/jwt/jwt.go
+++ b/api/jwt/jwt.go
@@ -3,7 +3,6 @@ package jwt
 import (
 	"errors"
 	"fmt"
-	"os"
 	"time"
 
 	portainer "github.com/portainer/portainer/api"
@@ -169,7 +168,12 @@ func (service *Service) generateSignedToken(data *portainer.TokenData, expiresAt
 		return "", fmt.Errorf("invalid scope: %v", scope)
 	}
 
-	if _, ok := os.LookupEnv("DOCKER_EXTENSION"); ok {
+	settings, err := service.dataStore.Settings().Settings()
+	if err != nil {
+		return "", fmt.Errorf("failed fetching settings from db: %w", err)
+	}
+
+	if settings.IsDockerDesktopExtention {
 		// Set expiration to 99 years for docker desktop extension.
 		log.Info().Msg("detected docker desktop extension mode")
 		expiresAt = time.Now().Add(time.Hour * 8760 * 99).Unix()
diff --git a/api/portainer.go b/api/portainer.go
index 21c8a6d67..9bb4329d2 100644
--- a/api/portainer.go
+++ b/api/portainer.go
@@ -967,6 +967,8 @@ type (
 		AllowStackManagementForRegularUsers       bool `json:"AllowStackManagementForRegularUsers"`
 		AllowDeviceMappingForRegularUsers         bool `json:"AllowDeviceMappingForRegularUsers"`
 		AllowContainerCapabilitiesForRegularUsers bool `json:"AllowContainerCapabilitiesForRegularUsers"`
+
+		IsDockerDesktopExtention bool `json:"IsDockerDesktopExtention"`
 	}
 
 	// SnapshotJob represents a scheduled job that can create environment(endpoint) snapshots