diff --git a/cli/packages/api/api.go b/cli/packages/api/api.go
index a414b03d3..7417a2594 100644
--- a/cli/packages/api/api.go
+++ b/cli/packages/api/api.go
@@ -5,6 +5,7 @@ import (
 
 	"github.com/Infisical/infisical-merge/packages/config"
 	"github.com/go-resty/resty/v2"
+	log "github.com/sirupsen/logrus"
 )
 
 const USER_AGENT = "cli"
@@ -144,3 +145,24 @@ func CallGetAllWorkSpacesUserBelongsTo(httpClient *resty.Client) (GetWorkSpacesR
 
 	return workSpacesResponse, nil
 }
+
+func CallIsAuthenticated(httpClient *resty.Client) bool {
+	var workSpacesResponse GetWorkSpacesResponse
+	response, err := httpClient.
+		R().
+		SetResult(&workSpacesResponse).
+		SetHeader("User-Agent", USER_AGENT).
+		Post(fmt.Sprintf("%v/v1/auth/checkAuth", config.INFISICAL_URL))
+
+	log.Debugln(fmt.Errorf("CallIsAuthenticated: Unsuccessful response:  [response=%v]", response))
+
+	if err != nil {
+		return false
+	}
+
+	if response.IsError() {
+		return false
+	}
+
+	return true
+}
diff --git a/cli/packages/cmd/login.go b/cli/packages/cmd/login.go
index c10f38fc4..74573c226 100644
--- a/cli/packages/cmd/login.go
+++ b/cli/packages/cmd/login.go
@@ -33,13 +33,13 @@ var loginCmd = &cobra.Command{
 	PreRun:                toggleDebug,
 	Run: func(cmd *cobra.Command, args []string) {
 		currentLoggedInUserDetails, err := util.GetCurrentLoggedInUserDetails()
-		if err != nil && strings.Contains(err.Error(), "The specified item could not be found in the keyring") { // if the key can't be found allow them to override
+		if err != nil && (strings.Contains(err.Error(), "The specified item could not be found in the keyring") || strings.Contains(err.Error(), "unable to get key from Keyring")) { // if the key can't be found allow them to override
 			log.Debug(err)
 		} else if err != nil {
 			util.HandleError(err)
 		}
 
-		if currentLoggedInUserDetails.IsUserLoggedIn {
+		if currentLoggedInUserDetails.IsUserLoggedIn && !currentLoggedInUserDetails.LoginExpired { // if you are logged in but not expired
 			shouldOverride, err := shouldOverrideLoginPrompt(currentLoggedInUserDetails.UserCredentials.Email)
 			if err != nil {
 				util.HandleError(err)
diff --git a/cli/packages/util/constants.go b/cli/packages/util/constants.go
index 6c21dd787..95b6ca228 100644
--- a/cli/packages/util/constants.go
+++ b/cli/packages/util/constants.go
@@ -11,5 +11,8 @@ const (
 	KEYRING_SERVICE_NAME                 = "infisical"
 	PERSONAL_SECRET_TYPE_NAME            = "personal"
 	SHARED_SECRET_TYPE_NAME              = "shared"
-	CLI_VERSION                          = "v0.2.9" //
+)
+
+var (
+	CLI_VERSION = "v0.2.9"
 )
diff --git a/cli/packages/util/credentials.go b/cli/packages/util/credentials.go
index 6410002c0..1766f04c7 100644
--- a/cli/packages/util/credentials.go
+++ b/cli/packages/util/credentials.go
@@ -5,7 +5,7 @@ import (
 	"fmt"
 
 	"github.com/99designs/keyring"
-	"github.com/Infisical/infisical-merge/packages/config"
+	"github.com/Infisical/infisical-merge/packages/api"
 	"github.com/Infisical/infisical-merge/packages/models"
 	"github.com/go-resty/resty/v2"
 )
@@ -87,17 +87,10 @@ func GetCurrentLoggedInUserDetails() (LoggedInUserDetails, error) {
 			SetAuthToken(userCreds.JTWToken).
 			SetHeader("Accept", "application/json")
 
-		response, err := httpClient.
-			R().
-			Post(fmt.Sprintf("%v/v1/auth/checkAuth", config.INFISICAL_URL))
-
-		if err != nil {
-			return LoggedInUserDetails{}, err
-		}
-
-		if response.StatusCode() > 299 {
+		isAuthenticated := api.CallIsAuthenticated(httpClient)
+		if !isAuthenticated {
 			return LoggedInUserDetails{
-				IsUserLoggedIn:  true,
+				IsUserLoggedIn:  true, // was logged in
 				LoginExpired:    true,
 				UserCredentials: userCreds,
 			}, nil