diff --git a/cli/login.go b/cli/login.go
index 2c6498a63f..03332a0f8f 100644
--- a/cli/login.go
+++ b/cli/login.go
@@ -49,9 +49,18 @@ func login() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "login <url>",
 		Short: "Authenticate with Coder deployment",
-		Args:  cobra.ExactArgs(1),
+		Args:  cobra.MaximumNArgs(1),
 		RunE: func(cmd *cobra.Command, args []string) error {
-			rawURL := args[0]
+			rawURL := ""
+			if len(args) == 0 {
+				var err error
+				rawURL, err = cmd.Flags().GetString(varURL)
+				if err != nil {
+					return xerrors.Errorf("get global url flag")
+				}
+			} else {
+				rawURL = args[0]
+			}
 
 			if !strings.HasPrefix(rawURL, "http://") && !strings.HasPrefix(rawURL, "https://") {
 				scheme := "https"
diff --git a/cli/login_test.go b/cli/login_test.go
index 540adc13c2..bf4507b61b 100644
--- a/cli/login_test.go
+++ b/cli/login_test.go
@@ -68,13 +68,45 @@ func TestLogin(t *testing.T) {
 		<-doneChan
 	})
 
-	t.Run("InitialUserFlags", func(t *testing.T) {
+	t.Run("InitialUserTTYFlag", func(t *testing.T) {
 		t.Parallel()
 		client := coderdtest.New(t, nil)
 		// The --force-tty flag is required on Windows, because the `isatty` library does not
 		// accurately detect Windows ptys when they are not attached to a process:
 		// https://github.com/mattn/go-isatty/issues/59
 		doneChan := make(chan struct{})
+		root, _ := clitest.New(t, "--url", client.URL.String(), "login", "--force-tty")
+		pty := ptytest.New(t)
+		root.SetIn(pty.Input())
+		root.SetOut(pty.Output())
+		go func() {
+			defer close(doneChan)
+			err := root.Execute()
+			assert.NoError(t, err)
+		}()
+
+		matches := []string{
+			"first user?", "yes",
+			"username", "testuser",
+			"email", "user@coder.com",
+			"password", "password",
+			"password", "password", // Confirm.
+			"trial", "yes",
+		}
+		for i := 0; i < len(matches); i += 2 {
+			match := matches[i]
+			value := matches[i+1]
+			pty.ExpectMatch(match)
+			pty.WriteLine(value)
+		}
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+	})
+
+	t.Run("InitialUserFlags", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, nil)
+		doneChan := make(chan struct{})
 		root, _ := clitest.New(t, "login", client.URL.String(), "--first-user-username", "testuser", "--first-user-email", "user@coder.com", "--first-user-password", "password", "--first-user-trial")
 		pty := ptytest.New(t)
 		root.SetIn(pty.Input())
diff --git a/cli/root.go b/cli/root.go
index cc9cae9488..eb1bc98cf1 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -97,8 +97,8 @@ func Core() []*cobra.Command {
 		update(),
 		users(),
 		versionCmd(),
-		workspaceAgent(),
 		vscodeipcCmd(),
+		workspaceAgent(),
 	}
 }