diff --git a/cli/packages/cmd/dynamic_secrets.go b/cli/packages/cmd/dynamic_secrets.go
index 60f356185..665bfaa54 100644
--- a/cli/packages/cmd/dynamic_secrets.go
+++ b/cli/packages/cmd/dynamic_secrets.go
@@ -80,8 +80,9 @@ func getDynamicSecretList(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
+
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
 
@@ -197,7 +198,7 @@ func createDynamicSecretLeaseByName(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
@@ -328,8 +329,9 @@ func renewDynamicSecretLeaseByName(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
+
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
 
@@ -435,8 +437,9 @@ func revokeDynamicSecretLeaseByName(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
+
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
 
@@ -541,7 +544,7 @@ func listDynamicSecretLeaseByName(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
diff --git a/cli/packages/cmd/init.go b/cli/packages/cmd/init.go
index e10a11c06..2ef555a82 100644
--- a/cli/packages/cmd/init.go
+++ b/cli/packages/cmd/init.go
@@ -46,7 +46,7 @@ var initCmd = &cobra.Command{
 		}
 
 		if userCreds.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			userCreds = util.EstablishUserLoginSession()
 		}
 
 		httpClient, err := util.GetRestyClientWithCustomHeaders()
diff --git a/cli/packages/cmd/secrets.go b/cli/packages/cmd/secrets.go
index fdee3e7c0..4b3465d8f 100644
--- a/cli/packages/cmd/secrets.go
+++ b/cli/packages/cmd/secrets.go
@@ -237,7 +237,7 @@ var secretsSetCmd = &cobra.Command{
 			}
 
 			if loggedInUserDetails.LoginExpired {
-				util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+				loggedInUserDetails = util.EstablishUserLoginSession()
 			}
 
 			secretOperations, err = util.SetRawSecrets(processedArgs, secretType, environmentName, secretsPath, projectId, &models.TokenDetails{
@@ -325,7 +325,7 @@ var secretsDeleteCmd = &cobra.Command{
 			}
 
 			if loggedInUserDetails.LoginExpired {
-				util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+				loggedInUserDetails = util.EstablishUserLoginSession()
 			}
 
 			httpClient.SetAuthToken(loggedInUserDetails.UserCredentials.JTWToken)
diff --git a/cli/packages/cmd/ssh.go b/cli/packages/cmd/ssh.go
index 7f74d8ee6..4315989bd 100644
--- a/cli/packages/cmd/ssh.go
+++ b/cli/packages/cmd/ssh.go
@@ -184,7 +184,7 @@ func issueCredentials(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
@@ -417,7 +417,7 @@ func signKey(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
@@ -612,7 +612,7 @@ func sshConnect(cmd *cobra.Command, args []string) {
 	if err != nil {
 		util.HandleError(err, "Unable to parse flag")
 	}
-	
+
 	var infisicalToken string
 
 	if token != nil && (token.Type == util.SERVICE_TOKEN_IDENTIFIER || token.Type == util.UNIVERSAL_AUTH_TOKEN_IDENTIFIER) {
@@ -626,7 +626,7 @@ func sshConnect(cmd *cobra.Command, args []string) {
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
@@ -640,7 +640,7 @@ func sshConnect(cmd *cobra.Command, args []string) {
 	if err != nil {
 		util.HandleError(err, "Unable to parse flag")
 	}
-	
+
 	hostname, _ := cmd.Flags().GetString("hostname")
 	loginUser, _ := cmd.Flags().GetString("login-user")
 
@@ -858,7 +858,7 @@ func sshConnect(cmd *cobra.Command, args []string) {
 	err = sshCmd.Run()
 	if err != nil {
 		util.HandleError(err, "SSH connection failed")
-	}	
+	}
 }
 
 func sshAddHost(cmd *cobra.Command, args []string) {
@@ -879,7 +879,7 @@ func sshAddHost(cmd *cobra.Command, args []string) {
 			util.HandleError(err, "Unable to authenticate")
 		}
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login]")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 		infisicalToken = loggedInUserDetails.UserCredentials.JTWToken
 	}
@@ -904,7 +904,7 @@ func sshAddHost(cmd *cobra.Command, args []string) {
 	if err != nil {
 		util.HandleError(err, "Unable to parse --alias flag")
 	}
-	
+
 	// if alias == "" {
 	// 	util.PrintErrorMessageAndExit("You must provide --alias")
 	// }
@@ -937,7 +937,7 @@ func sshAddHost(cmd *cobra.Command, args []string) {
 	if configureSshd && (!writeUserCaToFile || !writeHostCertToFile) {
 		util.PrintErrorMessageAndExit("--configure-sshd requires both --write-user-ca-to-file and --write-host-cert-to-file to also be set")
 	}
-	
+
 	// Pre-check for file overwrites before proceeding
 	if writeUserCaToFile {
 		if strings.HasPrefix(userCaOutFilePath, "~") {
diff --git a/cli/packages/cmd/tokens.go b/cli/packages/cmd/tokens.go
index 386a7eda5..a2e445239 100644
--- a/cli/packages/cmd/tokens.go
+++ b/cli/packages/cmd/tokens.go
@@ -47,7 +47,7 @@ var tokensCreateCmd = &cobra.Command{
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
 
 		tokenOnly, err := cmd.Flags().GetBool("token-only")
diff --git a/cli/packages/cmd/user.go b/cli/packages/cmd/user.go
index 2879e4ccb..6c7d54d46 100644
--- a/cli/packages/cmd/user.go
+++ b/cli/packages/cmd/user.go
@@ -111,8 +111,9 @@ var userGetTokenCmd = &cobra.Command{
 	Run: func(cmd *cobra.Command, args []string) {
 		loggedInUserDetails, err := util.GetCurrentLoggedInUserDetails(true)
 		if loggedInUserDetails.LoginExpired {
-			util.PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = util.EstablishUserLoginSession()
 		}
+
 		if err != nil {
 			util.HandleError(err, "[infisical user get token]: Unable to get logged in user token")
 		}
diff --git a/cli/packages/util/auth.go b/cli/packages/util/auth.go
index cdcd7b50a..b54bde45b 100644
--- a/cli/packages/util/auth.go
+++ b/cli/packages/util/auth.go
@@ -1,5 +1,13 @@
 package util
 
+import (
+	"fmt"
+	"os"
+	"os/exec"
+
+	"github.com/rs/zerolog/log"
+)
+
 type AuthStrategyType string
 
 var AuthStrategy = struct {
@@ -43,3 +51,36 @@ func IsAuthMethodValid(authMethod string, allowUserAuth bool) (isValid bool, str
 	}
 	return false, ""
 }
+
+// EstablishUserLoginSession handles the login flow to either create a new session or restore an expired one.
+// It returns fresh user details if login is successful.
+func EstablishUserLoginSession() LoggedInUserDetails {
+	log.Info().Msg("No valid login session found, triggering login flow")
+
+	exePath, err := os.Executable()
+	if err != nil {
+		PrintErrorMessageAndExit(fmt.Sprintf("Failed to determine executable path: %v", err))
+	}
+
+	// Spawn infisical login command
+	loginCmd := exec.Command(exePath, "login", "--silent")
+	loginCmd.Stdin = os.Stdin
+	loginCmd.Stdout = os.Stdout
+	loginCmd.Stderr = os.Stderr
+
+	err = loginCmd.Run()
+	if err != nil {
+		PrintErrorMessageAndExit(fmt.Sprintf("Failed to automatically trigger login flow. Please run [infisical login] manually to login."))
+	}
+
+	loggedInUserDetails, err := GetCurrentLoggedInUserDetails(true)
+	if err != nil {
+		PrintErrorMessageAndExit("You must be logged in to run this command. To login, run [infisical login]")
+	}
+
+	if loggedInUserDetails.LoginExpired {
+		PrintErrorMessageAndExit("Your login session has expired. Please run [infisical login]")
+	}
+
+	return loggedInUserDetails
+}
diff --git a/cli/packages/util/folders.go b/cli/packages/util/folders.go
index 6bba05842..412f29ac3 100644
--- a/cli/packages/util/folders.go
+++ b/cli/packages/util/folders.go
@@ -25,7 +25,7 @@ func GetAllFolders(params models.GetAllFoldersParameters) ([]models.SingleFolder
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = EstablishUserLoginSession()
 		}
 
 		workspaceFile, err := GetWorkSpaceFromFile()
@@ -194,7 +194,7 @@ func CreateFolder(params models.CreateFolderParameters) (models.SingleFolder, er
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = EstablishUserLoginSession()
 		}
 
 		params.InfisicalToken = loggedInUserDetails.UserCredentials.JTWToken
@@ -244,7 +244,7 @@ func DeleteFolder(params models.DeleteFolderParameters) ([]models.SingleFolder,
 		}
 
 		if loggedInUserDetails.LoginExpired {
-			PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = EstablishUserLoginSession()
 		}
 
 		params.InfisicalToken = loggedInUserDetails.UserCredentials.JTWToken
diff --git a/cli/packages/util/helper.go b/cli/packages/util/helper.go
index 346122a64..153a5a281 100644
--- a/cli/packages/util/helper.go
+++ b/cli/packages/util/helper.go
@@ -174,7 +174,7 @@ func RequireLogin() {
 	configFile, _ := GetConfigFile()
 
 	if configFile.LoggedInUserEmail == "" {
-		PrintErrorMessageAndExit("You must be logged in to run this command. To login, run [infisical login]")
+		EstablishUserLoginSession()
 	}
 }
 
diff --git a/cli/packages/util/secrets.go b/cli/packages/util/secrets.go
index 0693db509..0ee3eaa72 100644
--- a/cli/packages/util/secrets.go
+++ b/cli/packages/util/secrets.go
@@ -273,7 +273,7 @@ func GetAllEnvironmentVariables(params models.GetAllSecretsParameters, projectCo
 		}
 
 		if isConnected && loggedInUserDetails.LoginExpired {
-			PrintErrorMessageAndExit("Your login session has expired, please run [infisical login] and try again")
+			loggedInUserDetails = EstablishUserLoginSession()
 		}
 
 		var infisicalDotJson models.WorkspaceConfigFile