diff --git a/internal/cli/cli.go b/internal/cli/cli.go
index 6c82ef0a0..8ef80e8ec 100644
--- a/internal/cli/cli.go
+++ b/internal/cli/cli.go
@@ -111,6 +111,13 @@ func (c *cli) setupWithAuthentication(ctx context.Context) error {
 		}
 	}
 
+	if errors.Is(err, config.ErrMalformedToken) {
+		return fmt.Errorf("authentication token is corrupted, please run: %s\n\n%s",
+			ansi.Cyan("auth0 logout && auth0 login"),
+			ansi.Yellow("Note: Token handling was enhanced in v1.18.0+ to prevent malformed tokens."),
+		)
+	}
+
 	api, err := initializeManagementClient(tenant.Domain, tenant.GetAccessToken())
 	if err != nil {
 		return err
diff --git a/internal/config/tenant.go b/internal/config/tenant.go
index 91e3ecafb..de216a0c9 100644
--- a/internal/config/tenant.go
+++ b/internal/config/tenant.go
@@ -8,6 +8,8 @@ import (
 	"slices"
 	"time"
 
+	"github.com/lestrrat-go/jwx/v2/jwt"
+
 	"github.com/auth0/auth0-cli/internal/auth"
 	"github.com/auth0/auth0-cli/internal/keyring"
 )
@@ -17,6 +19,8 @@ const accessTokenExpThreshold = 5 * time.Minute
 var (
 	// ErrInvalidToken is thrown when the token is invalid.
 	ErrInvalidToken = errors.New("token is invalid")
+	// ErrMalformedToken indicates a corrupted JWT token was found in keyring.
+	ErrMalformedToken = errors.New("corrupted authentication token detected")
 )
 
 type ErrTokenMissingRequiredScopes struct {
@@ -115,11 +119,16 @@ func (t *Tenant) CheckAuthenticationStatus() error {
 	}
 
 	accessToken := t.GetAccessToken()
-	if accessToken != "" && !t.HasExpiredToken() {
-		return nil
+	if accessToken == "" || t.HasExpiredToken() {
+		return ErrInvalidToken
+	}
+
+	// Validate that the access token is a well-formed JWT token.
+	if _, err := jwt.ParseInsecure([]byte(accessToken)); err != nil {
+		return ErrMalformedToken
 	}
 
-	return ErrInvalidToken
+	return nil
 }
 
 // RegenerateAccessToken regenerates the access token for the tenant.
diff --git a/internal/keyring/keyring.go b/internal/keyring/keyring.go
index 6a946eca4..bdb64a097 100644
--- a/internal/keyring/keyring.go
+++ b/internal/keyring/keyring.go
@@ -71,6 +71,16 @@ func DeleteSecretsForTenant(tenant string) error {
 }
 
 func StoreAccessToken(tenant, value string) error {
+	// First, clear any existing chunks to prevent concatenation issues.
+	for i := 0; i < secretAccessTokenMaxChunks; i++ {
+		if err := keyring.Delete(secretClientSecret, tenant); err != nil {
+			if !errors.Is(err, keyring.ErrNotFound) {
+				return fmt.Errorf("failed to delete client secret from keyring: %s", err)
+			}
+		}
+	}
+
+	// Now store the new token in chunks.
 	chunks := chunk(value, secretAccessTokenChunkSizeInBytes)
 
 	for i := 0; i < len(chunks); i++ {