diff --git a/CosmosDBShell.Tests/CommandTests/ConnectCommandTests.cs b/CosmosDBShell.Tests/CommandTests/ConnectCommandTests.cs
index db40cef..5a113ca 100644
--- a/CosmosDBShell.Tests/CommandTests/ConnectCommandTests.cs
+++ b/CosmosDBShell.Tests/CommandTests/ConnectCommandTests.cs
@@ -8,6 +8,7 @@ namespace CosmosShell.Tests.CommandTests;
 using Azure.Data.Cosmos.Shell.Core;
 using Azure.Data.Cosmos.Shell.Lsp.Semantics;
 using Azure.Data.Cosmos.Shell.Parser;
+using Azure.Data.Cosmos.Shell.Util;
 using Microsoft.Azure.Cosmos;
 
 public class ConnectCommandTests
@@ -78,4 +79,41 @@ private static async Task<ConnectCommand> BindConnectCommandAsync(string command
         var command = await statement.CreateCommandAsync(factory, shell, new CommandState(), CancellationToken.None);
         return Assert.IsType<ConnectCommand>(command);
     }
+
+    [Fact]
+    public void ConnectCommand_NotConnectedUsageHint_LocalizationKeysAreDefined()
+    {
+        // Issue #81: running `connect` while disconnected used to print only
+        // "Not connected" with no hint about how to authenticate. The hint
+        // strings must resolve to non-empty values.
+        Assert.False(string.IsNullOrWhiteSpace(MessageService.GetString("command-connect-not_connected-usage-header")));
+        Assert.False(string.IsNullOrWhiteSpace(MessageService.GetString("command-connect-not_connected-usage-footer")));
+        Assert.False(string.IsNullOrWhiteSpace(MessageService.GetString("shell-not_connected_hint")));
+    }
+
+    [Fact]
+    public void ConnectCommand_PrintConnectUsageHint_HasExamplesToPrint()
+    {
+        // The hint helper iterates the connect command's CosmosExample metadata and
+        // skips the bare `connect` no-arg form. Confirm there is at least one other
+        // example to display so the helper output is meaningful.
+        Assert.True(CommandFactory.TryCreateFactory(typeof(ConnectCommand), out var factory));
+
+        var examples = factory.ExamplesWithDescriptions
+            .Where(e => !string.IsNullOrWhiteSpace(e.Example) && e.Example != "connect")
+            .ToList();
+
+        Assert.NotEmpty(examples);
+    }
+
+    [Fact]
+    public void ConnectCommand_PrintConnectUsageHint_RunsWithoutThrowing()
+    {
+        using var shell = ShellInterpreter.CreateInstance();
+
+        // Smoke test: must not throw even when the shell's command map exposes the
+        // factory through ShellInterpreter.App.Commands.
+        var ex = Record.Exception(() => ConnectCommand.PrintConnectUsageHint(shell));
+        Assert.Null(ex);
+    }
 }
diff --git a/CosmosDBShell/Azure.Data.Cosmos.Shell.Commands/ConnectCommand.cs b/CosmosDBShell/Azure.Data.Cosmos.Shell.Commands/ConnectCommand.cs
index 692eb62..2839034 100644
--- a/CosmosDBShell/Azure.Data.Cosmos.Shell.Commands/ConnectCommand.cs
+++ b/CosmosDBShell/Azure.Data.Cosmos.Shell.Commands/ConnectCommand.cs
@@ -135,11 +135,53 @@ internal static void AskForRBacPermissions(string principalId, string permission
         ShellInterpreter.WriteLine(MessageService.GetArgsString("command-connect-rbac-error", "id", principalId, "permission", permission));
     }
 
+    /// <summary>
+    /// Prints a short usage block with examples taken from the <see cref="CosmosExampleAttribute"/>
+    /// metadata on this command. Shown when the user runs <c>connect</c> without arguments while
+    /// disconnected so the available authentication options are discoverable without having to know
+    /// about <c>help connect</c> (see issue #81).
+    /// </summary>
+    internal static void PrintConnectUsageHint(ShellInterpreter shell)
+    {
+        AnsiConsole.MarkupLine(Markup.Escape(MessageService.GetString("command-connect-not_connected-usage-header")));
+
+        if (shell.App.Commands.TryGetValue("connect", out var factory))
+        {
+            const int MaxExamples = 2;
+            var shown = 0;
+            foreach (var (example, description) in factory.ExamplesWithDescriptions)
+            {
+                if (shown >= MaxExamples)
+                {
+                    break;
+                }
+
+                if (string.IsNullOrWhiteSpace(example) || example == "connect")
+                {
+                    // Skip the no-arg example — that's the one the user just ran.
+                    continue;
+                }
+
+                var highlighted = shell.BuildHighlightedMarkup(example);
+                AnsiConsole.MarkupLine($"  {highlighted}");
+                if (!string.IsNullOrWhiteSpace(description))
+                {
+                    AnsiConsole.MarkupLine($"    [silver]{Markup.Escape(description)}[/]");
+                }
+
+                shown++;
+            }
+        }
+
+        AnsiConsole.MarkupLine(Markup.Escape(MessageService.GetString("command-connect-not_connected-usage-footer")));
+    }
+
     private static async Task<CommandState> PrintConnectionInfoAsync(ShellInterpreter shell, CommandState commandState, CancellationToken token)
     {
         if (shell.State is not ConnectedState connectedState)
         {
             AnsiConsole.MarkupLine(MessageService.GetString("command-connect-not_connected"));
+            PrintConnectUsageHint(shell);
             commandState.IsPrinted = true;
             var notConnectedJson = new Dictionary<string, object?>
             {
diff --git a/CosmosDBShell/Azure.Data.Cosmos.Shell.Core/ShellInterpreter.cs b/CosmosDBShell/Azure.Data.Cosmos.Shell.Core/ShellInterpreter.cs
index 7460313..cb480e9 100644
--- a/CosmosDBShell/Azure.Data.Cosmos.Shell.Core/ShellInterpreter.cs
+++ b/CosmosDBShell/Azure.Data.Cosmos.Shell.Core/ShellInterpreter.cs
@@ -464,6 +464,15 @@ internal async Task<int> RunAsync()
         var result = 0;
         this.PrintVersion(null);
         WriteLine(MessageService.GetString("shell-ready"));
+
+        // First-run hint: if the shell starts without a connection, point users at
+        // the `connect` command. Otherwise users can land at the prompt with no
+        // obvious next step (see issue #81).
+        if (this.State is DisconnectedState)
+        {
+            AnsiConsole.MarkupLine("[yellow]" + Markup.Escape(MessageService.GetString("shell-not_connected_hint")) + "[/]");
+        }
+
         while (this.IsRunning)
         {
             this.StdOutRedirect = null;
diff --git a/CosmosDBShell/lang/en.ftl b/CosmosDBShell/lang/en.ftl
index 50c60b8..9b40837 100644
--- a/CosmosDBShell/lang/en.ftl
+++ b/CosmosDBShell/lang/en.ftl
@@ -1,4 +1,5 @@
 shell-ready = Cosmos DB shell ready.
+shell-not_connected_hint = Not connected. Run 'connect <endpoint>' to authenticate, or 'help connect' for more options.
 shell-hisory_file_deleted = History deleted.
 shell-connect-browser-auth = Authenticating via browser. Please complete the login in the browser window that opens.
 shell-connect-devicecode-auth = Browser authentication failed. Falling back to device code authentication.
@@ -324,6 +325,8 @@ command-connect-connected = Connected to account '{ $account }'
 command-connect-emulator-detected = Emulator endpoint detected, using well-known account key and gateway mode.
 command-connect-switching = Disconnecting from '{ $endpoint }'...
 command-connect-not_connected = Not connected to any Cosmos DB account.
+command-connect-not_connected-usage-header = Use 'connect <endpoint>' to authenticate. Common forms:
+command-connect-not_connected-usage-footer = Run 'help connect' for the full list of options.
 command-connect-info-title = Connection Information
 command-connect-info-account = Account
 command-connect-info-endpoint = Endpoint