diff --git a/cli/login.go b/cli/login.go
index 834ba73ce38a0..dd11d4e22b883 100644
--- a/cli/login.go
+++ b/cli/login.go
@@ -151,9 +151,12 @@ func (r *RootCmd) login() *serpent.Command {
 		useTokenForSession bool
 	)
 	cmd := &serpent.Command{
-		Use:        "login [<url>]",
-		Short:      "Authenticate with Coder deployment",
-		Middleware: serpent.RequireRangeArgs(0, 1),
+		Use:   "login [<url>]",
+		Short: "Authenticate with Coder deployment",
+		Middleware: serpent.Chain(
+			serpent.RequireRangeArgs(0, 1),
+			r.CheckExistingUserSession(),
+		),
 		Handler: func(inv *serpent.Invocation) error {
 			ctx := inv.Context()
 			rawURL := ""
diff --git a/cli/login_test.go b/cli/login_test.go
index 0428c332d02b0..ba6d56232f0c5 100644
--- a/cli/login_test.go
+++ b/cli/login_test.go
@@ -442,4 +442,48 @@ func TestLogin(t *testing.T) {
 		require.NoError(t, err)
 		require.Equal(t, selected, first.OrganizationID.String())
 	})
+
+	t.Run("ExistingUserValidTokenTTYWarnReloggin", func(t *testing.T) {
+		t.Parallel()
+		client := coderdtest.New(t, nil)
+		coderdtest.CreateFirstUser(t, client)
+
+		doneChan := make(chan struct{})
+		root, _ := clitest.New(t, "login", "--force-tty", client.URL.String(), "--no-open")
+		pty := ptytest.New(t).Attach(root)
+		go func() {
+			defer close(doneChan)
+			err := root.Run()
+			assert.NoError(t, err)
+		}()
+
+		pty.ExpectMatch(fmt.Sprintf("Attempting to authenticate with argument URL: '%s'", client.URL.String()))
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		if runtime.GOOS != "windows" {
+			// For some reason, the match does not show up on Windows.
+			pty.ExpectMatch(client.SessionToken())
+		}
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+
+		doneChan = make(chan struct{})
+		root, _ = clitest.New(t, "login", "--force-tty", client.URL.String(), "--no-open")
+		pty = ptytest.New(t).Attach(root)
+		go func() {
+			defer close(doneChan)
+			err := root.Run()
+			assert.NoError(t, err)
+		}()
+		pty.ExpectMatch(fmt.Sprintf("You are already logged in to '%s'!", client.URL.String()))
+		pty.ExpectMatch(fmt.Sprintf("Attempting to authenticate with argument URL: '%s'", client.URL.String()))
+		pty.ExpectMatch("Paste your token here:")
+		pty.WriteLine(client.SessionToken())
+		if runtime.GOOS != "windows" {
+			// For some reason, the match does not show up on Windows.
+			pty.ExpectMatch(client.SessionToken())
+		}
+		pty.ExpectMatch("Welcome to Coder")
+		<-doneChan
+	})
 }
diff --git a/cli/root.go b/cli/root.go
index 22d153c00f7f1..02f5715a2251d 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -546,6 +546,50 @@ func (r *RootCmd) InitClient(client *codersdk.Client) serpent.MiddlewareFunc {
 	}
 }
 
+func (r *RootCmd) CheckExistingUserSession() serpent.MiddlewareFunc {
+	return func(next serpent.HandlerFunc) serpent.HandlerFunc {
+		return func(inv *serpent.Invocation) error {
+			conf := r.createConfig()
+			var err error
+			// Read the client URL stored on disk.
+			if r.clientURL == nil || r.clientURL.String() == "" {
+				rawURL, err := conf.URL().Read()
+				// If the configuration files are absent, the user is logged out
+				if os.IsNotExist(err) {
+					return next(inv)
+				}
+				if err != nil {
+					return err
+				}
+
+				r.clientURL, err = url.Parse(strings.TrimSpace(rawURL))
+				if err != nil {
+					return err
+				}
+			}
+			// Read the token stored on disk.
+			if r.token == "" {
+				r.token, err = conf.Session().Read()
+				// Even if there isn't a token, we don't care.
+				if err != nil && !os.IsNotExist(err) {
+					return next(inv)
+				}
+			}
+
+			// IF r.token and r.clientUR, exists then print warning "You are already logged in to $"
+			if r.token != "" && r.clientURL.String() != "" {
+				_, _ = fmt.Fprintf(inv.Stderr, Caret+"%s!\n", pretty.Sprint(cliui.DefaultStyles.Warn, "You are already logged in to "+r.clientURL.String()+"!"))
+			}
+
+			// We remove the token and clientURL from the RootCmd, so the user can still go ahead and login
+			r.clientURL = nil
+			r.token = ""
+
+			return next(inv)
+		}
+	}
+}
+
 // HeaderTransport creates a new transport that executes `--header-command`
 // if it is set to add headers for all outbound requests.
 func (r *RootCmd) HeaderTransport(ctx context.Context, serverURL *url.URL) (*codersdk.HeaderTransport, error) {

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