diff --git a/cli/root.go b/cli/root.go
index b0e9ec715ddb9..34d9cb1473c91 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -417,6 +417,17 @@ func isTTY(cmd *cobra.Command) bool {
 // This accepts a reader to work with Cobra's "OutOrStdout"
 // function for simple testing.
 func isTTYOut(cmd *cobra.Command) bool {
+	return isTTYWriter(cmd, cmd.OutOrStdout)
+}
+
+// isTTYErr returns whether the passed reader is a TTY or not.
+// This accepts a reader to work with Cobra's "ErrOrStderr"
+// function for simple testing.
+func isTTYErr(cmd *cobra.Command) bool {
+	return isTTYWriter(cmd, cmd.ErrOrStderr)
+}
+
+func isTTYWriter(cmd *cobra.Command, writer func() io.Writer) bool {
 	// If the `--force-tty` command is available, and set,
 	// assume we're in a tty. This is primarily for cases on Windows
 	// where we may not be able to reliably detect this automatically (ie, tests)
@@ -424,7 +435,7 @@ func isTTYOut(cmd *cobra.Command) bool {
 	if forceTty && err == nil {
 		return true
 	}
-	file, ok := cmd.OutOrStdout().(*os.File)
+	file, ok := writer().(*os.File)
 	if !ok {
 		return false
 	}
diff --git a/cli/ssh.go b/cli/ssh.go
index 7d5b25337b3fb..f4dcce3180395 100644
--- a/cli/ssh.go
+++ b/cli/ssh.go
@@ -5,6 +5,7 @@ import (
 	"errors"
 	"fmt"
 	"io"
+	"net/url"
 	"os"
 	"path/filepath"
 	"strings"
@@ -72,6 +73,11 @@ func ssh() *cobra.Command {
 				return err
 			}
 
+			updateWorkspaceBanner, outdated := verifyWorkspaceOutdated(client, workspace)
+			if outdated && isTTYErr(cmd) {
+				_, _ = fmt.Fprintln(cmd.ErrOrStderr(), updateWorkspaceBanner)
+			}
+
 			// OpenSSH passes stderr directly to the calling TTY.
 			// This is required in "stdio" mode so a connecting indicator can be displayed.
 			err = cliui.Agent(ctx, cmd.ErrOrStderr(), cliui.AgentOptions{
@@ -343,3 +349,18 @@ func notifyCondition(ctx context.Context, client *codersdk.Client, workspaceID u
 		return deadline.Truncate(time.Minute), callback
 	}
 }
+
+// Verify if the user workspace is outdated and prepare an actionable message for user.
+func verifyWorkspaceOutdated(client *codersdk.Client, workspace codersdk.Workspace) (string, bool) {
+	if !workspace.Outdated {
+		return "", false // workspace is up-to-date
+	}
+
+	workspaceLink := buildWorkspaceLink(client.URL, workspace)
+	return fmt.Sprintf("👋 Your workspace is outdated! Update it here: %s\n", workspaceLink), true
+}
+
+// Build the user workspace link which navigates to the Coder web UI.
+func buildWorkspaceLink(serverURL *url.URL, workspace codersdk.Workspace) *url.URL {
+	return serverURL.ResolveReference(&url.URL{Path: fmt.Sprintf("@%s/%s", workspace.OwnerName, workspace.Name)})
+}
diff --git a/cli/ssh_internal_test.go b/cli/ssh_internal_test.go
new file mode 100644
index 0000000000000..d9624f393dfa6
--- /dev/null
+++ b/cli/ssh_internal_test.go
@@ -0,0 +1,58 @@
+package cli
+
+import (
+	"net/url"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+
+	"github.com/coder/coder/codersdk"
+)
+
+const (
+	fakeOwnerName     = "fake-owner-name"
+	fakeServerURL     = "https://fake-foo-url"
+	fakeWorkspaceName = "fake-workspace-name"
+)
+
+func TestVerifyWorkspaceOutdated(t *testing.T) {
+	t.Parallel()
+
+	serverURL, err := url.Parse(fakeServerURL)
+	require.NoError(t, err)
+
+	client := codersdk.Client{URL: serverURL}
+
+	t.Run("Up-to-date", func(t *testing.T) {
+		t.Parallel()
+
+		workspace := codersdk.Workspace{Name: fakeWorkspaceName, OwnerName: fakeOwnerName}
+
+		_, outdated := verifyWorkspaceOutdated(&client, workspace)
+
+		assert.False(t, outdated, "workspace should be up-to-date")
+	})
+	t.Run("Outdated", func(t *testing.T) {
+		t.Parallel()
+
+		workspace := codersdk.Workspace{Name: fakeWorkspaceName, OwnerName: fakeOwnerName, Outdated: true}
+
+		updateWorkspaceBanner, outdated := verifyWorkspaceOutdated(&client, workspace)
+
+		assert.True(t, outdated, "workspace should be outdated")
+		assert.NotEmpty(t, updateWorkspaceBanner, "workspace banner should be present")
+	})
+}
+
+func TestBuildWorkspaceLink(t *testing.T) {
+	t.Parallel()
+
+	serverURL, err := url.Parse(fakeServerURL)
+	require.NoError(t, err)
+
+	workspace := codersdk.Workspace{Name: fakeWorkspaceName, OwnerName: fakeOwnerName}
+	workspaceLink := buildWorkspaceLink(serverURL, workspace)
+
+	assert.Equal(t, workspaceLink.String(), fakeServerURL+"/@"+fakeOwnerName+"/"+fakeWorkspaceName)
+}