diff --git a/internal/cli/arguments.go b/internal/cli/arguments.go
index be5d59cb9..072d4fe4f 100644
--- a/internal/cli/arguments.go
+++ b/internal/cli/arguments.go
@@ -66,7 +66,7 @@ func selectArgument(cmd *cobra.Command, a *Argument, value interface{}, options
 
 func askArgument(cmd *cobra.Command, i commandInput, value interface{}) error {
 	if canPrompt(cmd) {
-		return ask(cmd, i, value, nil, true)
+		return ask(cmd, i, value, nil, false)
 	}
 
 	return fmt.Errorf("Missing a required argument: %s", i.GetName())
diff --git a/internal/cli/cli.go b/internal/cli/cli.go
index 9cf7221ea..b258b9e2b 100644
--- a/internal/cli/cli.go
+++ b/internal/cli/cli.go
@@ -40,10 +40,15 @@ type config struct {
 // tenant is the cli's concept of an auth0 tenant. The fields are tailor fit
 // specifically for interacting with the management API.
 type tenant struct {
-	Name        string    `json:"name"`
-	Domain      string    `json:"domain"`
-	AccessToken string    `json:"access_token,omitempty"`
-	ExpiresAt   time.Time `json:"expires_at"`
+	Name        string         `json:"name"`
+	Domain      string         `json:"domain"`
+	AccessToken string         `json:"access_token,omitempty"`
+	ExpiresAt   time.Time      `json:"expires_at"`
+	Apps        map[string]app `json:"apps,omitempty"`
+}
+
+type app struct {
+	FirstRuns map[string]bool `json:"first_runs"`
 }
 
 var errUnauthenticated = errors.New("Not yet configured. Try `auth0 login`.")
@@ -224,7 +229,7 @@ func (c *cli) addTenant(ten tenant) error {
 	c.config.Tenants[ten.Name] = ten
 
 	if err := c.persistConfig(); err != nil {
-		return fmt.Errorf("persisting config: %w", err)
+		return fmt.Errorf("unexpected error persisting config: %w", err)
 	}
 
 	return nil
@@ -271,6 +276,52 @@ func (c *cli) removeTenant(ten string) error {
 	return nil
 }
 
+func (c *cli) isFirstCommandRun(clientID string, command string) (bool, error) {
+	tenant, err := c.getTenant()
+
+	if err != nil {
+		return false, err
+	}
+
+	if a, found := tenant.Apps[clientID]; found {
+		if a.FirstRuns[command] {
+			return false, nil
+		}
+	}
+
+	return true, nil
+}
+
+func (c *cli) setFirstCommandRun(clientID string, command string) error {
+	tenant, err := c.getTenant()
+
+	if err != nil {
+		return err
+	}
+
+	if a, found := tenant.Apps[clientID]; found {
+		if a.FirstRuns == nil {
+			a.FirstRuns = map[string]bool{}
+		}
+		a.FirstRuns[command] = true
+		tenant.Apps[clientID] = a
+	} else {
+		tenant.Apps[clientID] = app{
+			FirstRuns: map[string]bool{
+				command: true,
+			},
+		}
+	}
+
+	c.config.Tenants[tenant.Name] = tenant
+
+	if err := c.persistConfig(); err != nil {
+		return fmt.Errorf("Unexpected error persisting config: %w", err)
+	}
+
+	return nil
+}
+
 func (c *cli) persistConfig() error {
 	dir := filepath.Dir(c.path)
 	if _, err := os.Stat(dir); os.IsNotExist(err) {
diff --git a/internal/cli/test.go b/internal/cli/test.go
index 5f9e8cee9..1a1676b94 100644
--- a/internal/cli/test.go
+++ b/internal/cli/test.go
@@ -65,7 +65,9 @@ If --client-id is not provided, the default client "CLI Login Testing" will be u
 auth0 test login --client-id <id>
 auth0 test login -c <id> --connection <connection>`,
 		RunE: func(cmd *cobra.Command, args []string) error {
+			const commandKey = "test_login"
 			var userInfo *authutil.UserInfo
+
 			tenant, err := cli.getTenant()
 			if err != nil {
 				return err
@@ -116,6 +118,21 @@ auth0 test login -c <id> --connection <connection>`,
 
 			fmt.Fprint(cli.renderer.MessageWriter, "\n")
 			cli.renderer.TryLogin(userInfo, tokenResponse)
+
+			isFirstRun, err := cli.isFirstCommandRun(inputs.ClientID, commandKey)
+			if err != nil {
+				return err
+			}
+
+			if isFirstRun {
+				cli.renderer.Infof("%s Login flow is working! Next, try downloading and running a Quickstart: 'auth0 quickstarts download %s'", 
+				ansi.Faint("Hint:"), inputs.ClientID)
+
+				if err := cli.setFirstCommandRun(inputs.ClientID, commandKey); err != nil {
+					return err
+				}
+			}
+
 			return nil
 		},
 	}