diff --git a/cli/cmd/configure_cmd.go b/cli/cmd/configure_cmd.go
index 0ad4db749b..d757a24c6a 100644
--- a/cli/cmd/configure_cmd.go
+++ b/cli/cmd/configure_cmd.go
@@ -36,7 +36,7 @@ var configureCmd = &cobra.Command{
 			flags.ServerURL = configParams.ServerURL
 		}
 
-		if flagProvided(cmd, "token") {
+		if configParams.Token != "" {
 			flags.Token = configParams.Token
 		}
 
@@ -62,13 +62,13 @@ var deprecatedEndpoint string
 func init() {
 	configureCmd.PersistentFlags().BoolVarP(&configParams.Global, "global", "g", false, "configuration will be saved in your home dir")
 
-	configureCmd.PersistentFlags().StringVarP(&configParams.Token, "token", "t", "", "set authetication with token, so the CLI won't ask you for authentication")
+	configureCmd.PersistentFlags().StringVarP(&configParams.Token, "token", "t", defaultToken, "set authetication with token, so the CLI won't ask you for authentication")
 	configureCmd.PersistentFlags().StringVarP(&configParams.EnvironmentID, "environment", "", "", "set environmentID, so the CLI won't ask you for it")
 	configureCmd.PersistentFlags().StringVarP(&configParams.OrganizationID, "organization", "", "", "set organizationID, so the CLI won't ask you for it")
 
 	configureCmd.PersistentFlags().BoolVarP(&configParams.CI, "ci", "", false, "if cloud is used, don't ask for authentication")
 
-	configureCmd.PersistentFlags().StringVarP(&deprecatedEndpoint, "endpoint", "e", "", "set the value for the endpoint, so the CLI won't ask for this value")
+	configureCmd.PersistentFlags().StringVarP(&deprecatedEndpoint, "endpoint", "e", defaultEndpoint, "set the value for the endpoint, so the CLI won't ask for this value")
 	configureCmd.PersistentFlags().MarkDeprecated("endpoint", "use --server-url instead")
 	configureCmd.PersistentFlags().MarkShorthandDeprecated("e", "use --server-url instead")
 
diff --git a/cli/config/config.go b/cli/config/config.go
index 0aaf045d9b..57ae20e15c 100644
--- a/cli/config/config.go
+++ b/cli/config/config.go
@@ -29,6 +29,7 @@ type Config struct {
 	OrganizationID    string `yaml:"organizationID,omitempty"`
 	EnvironmentID     string `yaml:"environmentID,omitempty"`
 	Token             string `yaml:"token,omitempty"`
+	IsOrgToken        bool   `yaml:"isOrgToken,omitempty"`
 	Jwt               string `yaml:"jwt,omitempty"`
 	AgentApiKey       string `yaml:"-"`
 	EndpointOverriden bool   `yaml:"-"`
diff --git a/cli/config/configurator.go b/cli/config/configurator.go
index e7c583e635..99ca05bb53 100644
--- a/cli/config/configurator.go
+++ b/cli/config/configurator.go
@@ -329,6 +329,9 @@ func (c Configurator) exchangeToken(cfg Config, token string) (Config, error) {
 	if environmentId != "" {
 		c.logger.Debug("Using environment ID from token", zap.String("environmentID", environmentId))
 		c.flags.EnvironmentID = environmentId
+	} else {
+		c.logger.Debug("Environment ID not found in token, using default")
+		cfg.IsOrgToken = true
 	}
 
 	return cfg, nil
@@ -374,7 +377,7 @@ func (c Configurator) showOrganizationSelector(ctx context.Context, prev *Config
 	}
 
 	cfg.EnvironmentID = c.flags.EnvironmentID
-	if cfg.EnvironmentID == "" && c.flags.AgentApiKey == "" {
+	if cfg.EnvironmentID == "" && c.flags.AgentApiKey == "" && !cfg.IsOrgToken {
 		c.logger.Debug("Environment ID not found, prompting for environment")
 		envID, err := c.environmentSelector(ctx, cfg, prev)
 		if err != nil {