diff --git a/src/BuslyCLI.Console/Commands/NsbTimeout/SendTimeout.cs b/src/BuslyCLI.Console/Commands/NsbTimeout/SendTimeout.cs
new file mode 100644
index 00000000..6c46ea18
--- /dev/null
+++ b/src/BuslyCLI.Console/Commands/NsbTimeout/SendTimeout.cs
@@ -0,0 +1,78 @@
+using System.Text;
+using BuslyCLI.Config;
+using BuslyCLI.Config.Transports;
+using BuslyCLI.Infrastructure.Factories;
+using NServiceBus.DelayedDelivery;
+using NServiceBus.Routing;
+using NServiceBus.Transport;
+using Spectre.Console;
+using Spectre.Console.Cli;
+
+namespace BuslyCLI.Commands.NsbTimeout;
+
+public class SendTimeout(IAnsiConsole console, IRawEndpointFactory rawEndpointFactory, INServiceBusConfiguration nServiceBusConfiguration) : AsyncCommand<SendTimeoutCommandSettings>
+{
+    private static readonly HashSet<Type> UnsupportedTransportTypes =
+    [
+        typeof(SqlServerTransportConfig),
+        typeof(PostgreSqlTransportConfig),
+        typeof(AzureStorageQueuesTransportConfig)
+    ];
+
+    protected override async Task<int> ExecuteAsync(CommandContext context, SendTimeoutCommandSettings settings, CancellationToken cancellationToken)
+    {
+        var config = await nServiceBusConfiguration.GetValidatedConfigurationAsync(settings.Config.Path);
+
+        if (UnsupportedTransportTypes.Contains(config.CurrentTransportConfig.Config.GetType()))
+        {
+            console.MarkupLine($"[red]Error:[/] The [bold]{config.CurrentTransportConfig.Config.GetType().Name.Replace("Config", "")}[/] transport does not support sending timeouts.");
+            console.MarkupLine("This transport relies on an in-process poller to forward deferred messages, which is incompatible with the CLI's fire-and-forget execution model.");
+            console.MarkupLine("For details see: [link]https://tragiccode.com/busly-cli/docs/cli-reference/timeout/send[/]");
+            return 1;
+        }
+
+        var rawEndpoint = await rawEndpointFactory.CreateRawSendOnlyEndpoint(Constants.DefaultOriginatingEndpoint, config.CurrentTransportConfig);
+        // TODO: Validate body is valid json/xml
+        var headers = new Dictionary<string, string>
+        {
+            ["NServiceBus.OriginatingEndpoint"] = Constants.DefaultOriginatingEndpoint,
+            ["NServiceBus.OriginatingMachine"] = Environment.MachineName,
+            ["NServiceBus.ConversationId"] = Guid.NewGuid().ToString(),
+            ["NServiceBus.CorrelationId"] = Guid.NewGuid().ToString(),
+            ["NServiceBus.MessageIntent"] = Constants.NServiceBus.CommandMessageIntent,
+            ["NServiceBus.ContentType"] = settings.ContentType,
+            ["NServiceBus.EnclosedMessageTypes"] = settings.EnclosedMessageType
+        };
+        var message = new OutgoingMessage(
+            Guid.NewGuid().ToString(),
+            headers,
+            Encoding.ASCII.GetBytes(settings.MessageBody)
+        );
+
+        var dispatchProperties = new DispatchProperties();
+
+        if (settings.DoNotDeliverBefore is not null)
+        {
+            dispatchProperties.DoNotDeliverBefore = new DoNotDeliverBefore(settings.DoNotDeliverBefore.Value);
+        }
+        else if (settings.DelayDeliveryWith is not null)
+        {
+            dispatchProperties.DelayDeliveryWith = new DelayDeliveryWith(settings.DelayDeliveryWith.Value);
+        }
+
+        var transportOperation = new TransportOperation(
+            message,
+            new UnicastAddressTag(settings.DestinationEndpoint),
+            dispatchProperties
+        );
+
+        await rawEndpoint.Dispatch(
+            new TransportOperations(transportOperation),
+            new TransportTransaction(),
+            cancellationToken);
+
+        await rawEndpoint.ShutDownAndCleanUp();
+
+        return 0;
+    }
+}
\ No newline at end of file
diff --git a/src/BuslyCLI.Console/Commands/NsbTimeout/SendTimeoutCommandSettings.cs b/src/BuslyCLI.Console/Commands/NsbTimeout/SendTimeoutCommandSettings.cs
new file mode 100644
index 00000000..6b144326
--- /dev/null
+++ b/src/BuslyCLI.Console/Commands/NsbTimeout/SendTimeoutCommandSettings.cs
@@ -0,0 +1,38 @@
+using System.ComponentModel;
+using Spectre.Console;
+using Spectre.Console.Cli;
+
+namespace BuslyCLI.Commands.NsbTimeout;
+
+public class SendTimeoutCommandSettings : CommonCommandSettings
+{
+    [CommandOption("--do-not-deliver-before <do-not-deliver-before>")]
+    [Description("Allows specifying a date before which the delivery should not occur, using ISO-8601 format (YYYY-MM-DDTHH:mm:ssZ)")]
+    public DateTime? DoNotDeliverBefore { get; init; }
+
+    [CommandOption("--delay-delivery-with <delay-delivery-with>")]
+    //  ([days.]hh:mm:ss[.fffffff])
+    [Description("Specifies the delay before the timeout is delivered, using a TimeSpan format")]
+    public TimeSpan? DelayDeliveryWith { get; init; }
+
+    public override ValidationResult Validate()
+    {
+        var baseResult = base.Validate();
+        if (baseResult.Successful == false) return baseResult;
+        // Neither provided
+        if (DelayDeliveryWith is null && DoNotDeliverBefore is null)
+        {
+            return ValidationResult.Error(
+                "You must specify either --do-not-deliver-before or --delay-delivery-with.");
+        }
+
+        // Both provided
+        if (DelayDeliveryWith is not null && DoNotDeliverBefore is not null)
+        {
+            return ValidationResult.Error(
+                "--do-not-deliver-before and --delay-delivery-with cannot be used together.");
+        }
+
+        return ValidationResult.Success();
+    }
+}
\ No newline at end of file
diff --git a/src/BuslyCLI.Console/Infrastructure/AppConfiguration.cs b/src/BuslyCLI.Console/Infrastructure/AppConfiguration.cs
index 0fdcca0a..e2f0a9c8 100644
--- a/src/BuslyCLI.Console/Infrastructure/AppConfiguration.cs
+++ b/src/BuslyCLI.Console/Infrastructure/AppConfiguration.cs
@@ -2,6 +2,7 @@
 using BuslyCLI.Commands.Demo;
 using BuslyCLI.Commands.NsbCommand;
 using BuslyCLI.Commands.NsbEvent;
+using BuslyCLI.Commands.NsbTimeout;
 using BuslyCLI.Commands.Transport;
 using Spectre.Console;
 using Spectre.Console.Cli;
@@ -48,6 +49,13 @@ public static Action<IConfigurator> GetSpectreCommandConfiguration()
                     .WithAlias("p")
                     .WithDescription("Publish an event to subscribing endpoints.");
             });
+            config.AddBranch("timeout", timeout =>
+            {
+                timeout.SetDescription("Operations related to NServiceBus timeouts.");
+                timeout.AddCommand<SendTimeout>("send")
+                    .WithAlias("s")
+                    .WithDescription("Send a timeout message to an endpoint.");
+            });
             config.AddBranch("demo", demo =>
             {
                 demo.SetDescription("Demo mode for the busly quick start guide.");
diff --git a/src/BuslyCLI.Console/Infrastructure/Endpoints/RawEndpoint.cs b/src/BuslyCLI.Console/Infrastructure/Endpoints/RawEndpoint.cs
index 8fb15dba..021b45cb 100644
--- a/src/BuslyCLI.Console/Infrastructure/Endpoints/RawEndpoint.cs
+++ b/src/BuslyCLI.Console/Infrastructure/Endpoints/RawEndpoint.cs
@@ -76,12 +76,6 @@ public Task<ErrorHandleResult> OnError(ErrorContext errorContext, CancellationTo
         return Task.FromResult(ErrorHandleResult.Handled);
     }
 
-    public IncomingMessage TryReceiveMessageWithTimeout()
-    {
-        if (_receivedMessages.TryTake(out var incomingMessage, IncomingMessageTimeout)) return incomingMessage;
-        throw new TimeoutException($"The message did not arrive within {IncomingMessageTimeout.TotalSeconds} seconds.");
-    }
-
     public IncomingMessage TryReceiveMessage()
     {
         if (_receivedMessages.TryTake(out var incomingMessage, IncomingMessageTimeout)) return incomingMessage;
diff --git a/tests/BuslyCLI.Console.Tests/BuslyCLI.Console.Tests.csproj b/tests/BuslyCLI.Console.Tests/BuslyCLI.Console.Tests.csproj
index ceb87ecc..afb6e04f 100644
--- a/tests/BuslyCLI.Console.Tests/BuslyCLI.Console.Tests.csproj
+++ b/tests/BuslyCLI.Console.Tests/BuslyCLI.Console.Tests.csproj
@@ -48,10 +48,6 @@
     <ProjectReference Include="..\..\src\BuslyCLI.Console\BuslyCLI.Console.csproj" />
   </ItemGroup>
 
-  <ItemGroup>
-    <Folder Include="Commands\Event\" />
-  </ItemGroup>
-
   <ItemGroup>
     <Reference Include="Microsoft.Extensions.DependencyInjection.Abstractions" />
   </ItemGroup>
diff --git a/tests/BuslyCLI.Console.Tests/Commands/NsbTimeout/SendTimeoutTests.cs b/tests/BuslyCLI.Console.Tests/Commands/NsbTimeout/SendTimeoutTests.cs
new file mode 100644
index 00000000..ee1bdf3d
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/Commands/NsbTimeout/SendTimeoutTests.cs
@@ -0,0 +1,99 @@
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.Commands.NsbTimeout;
+
+public class SendTimeoutTests : CommandTestBase
+{
+    [Test]
+    public void ShouldOutputAnErrorWhenTransportIsSqlServer()
+    {
+        // Arrange
+        var yamlFile = """
+                       ---
+                       current-transport: local-sql-server
+                       transports:
+                         - name: local-sql-server
+                           sql-server-transport-config:
+                             connection-string: Server=localhost;Database=test;
+                       """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout", "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", "Sales",
+            "--message-body", "{}",
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(result.Output, Does.Contain("SqlServerTransport"));
+        Assert.That(result.Output, Does.Contain("does not support sending timeouts"));
+        Assert.That(result.Output, Does.Contain("https://tragiccode.com/busly-cli/docs/cli-reference/timeout/send"));
+    }
+
+    [Test]
+    public void ShouldOutputAnErrorWhenTransportIsPostgreSql()
+    {
+        // Arrange
+        var yamlFile = """
+                       ---
+                       current-transport: local-postgresql
+                       transports:
+                         - name: local-postgresql
+                           postgre-sql-transport-config:
+                             connection-string: Host=localhost;Database=test;
+                       """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout", "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", "Sales",
+            "--message-body", "{}",
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(result.Output, Does.Contain("PostgreSqlTransport"));
+        Assert.That(result.Output, Does.Contain("does not support sending timeouts"));
+        Assert.That(result.Output, Does.Contain("https://tragiccode.com/busly-cli/docs/cli-reference/timeout/send"));
+    }
+
+    [Test]
+    public void ShouldOutputAnErrorWhenTransportIsAzureStorageQueues()
+    {
+        // Arrange
+        var yamlFile = """
+                       ---
+                       current-transport: local-azure-storage-queues
+                       transports:
+                         - name: local-azure-storage-queues
+                           azure-storage-queues-transport-config:
+                             connection-string: UseDevelopmentStorage=true
+                       """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout", "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", "Sales",
+            "--message-body", "{}",
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(result.Output, Does.Contain("AzureStorageQueuesTransport"));
+        Assert.That(result.Output, Does.Contain("does not support sending timeouts"));
+        Assert.That(result.Output, Does.Contain("https://tragiccode.com/busly-cli/docs/cli-reference/timeout/send"));
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/PublishEventCommandAmazonSqsEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/PublishEventCommandAmazonSqsEndToEndTests.cs
new file mode 100644
index 00000000..5551a1cf
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/PublishEventCommandAmazonSqsEndToEndTests.cs
@@ -0,0 +1,41 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.AmazonSQS;
+
+[TestFixture]
+public class PublishEventCommandAmazonSqsEndToEndTests : AmazonSqsEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-amazonsqs
+                        transports:
+                          - name: local-amazonsqs
+                            amazonsqs-transport-config:
+                              service-url: {Container.GetConnectionString()}
+                              region-name: us-east-1
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendCommandAmazonSqsEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendCommandAmazonSqsEndToEndTests.cs
index 24682e3b..13ffca86 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendCommandAmazonSqsEndToEndTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendCommandAmazonSqsEndToEndTests.cs
@@ -39,36 +39,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-amazonsqs
-                        transports:
-                          - name: local-amazonsqs
-                            amazonsqs-transport-config:
-                              service-url: {Container.GetConnectionString()}
-                              region-name: us-east-1
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendTimeoutCommandAmazonSqsEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendTimeoutCommandAmazonSqsEndToEndTests.cs
new file mode 100644
index 00000000..e3115946
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AmazonSQS/SendTimeoutCommandAmazonSqsEndToEndTests.cs
@@ -0,0 +1,76 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.AmazonSQS;
+
+[TestFixture]
+public class SendTimeoutCommandAmazonSqsEndToEndTests : AmazonSqsEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldSendTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-amazonsqs
+                        transports:
+                          - name: local-amazonsqs
+                            amazonsqs-transport-config:
+                              service-url: {Container.GetConnectionString()}
+                              region-name: us-east-1
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+
+    [Test]
+    public async Task ShouldSendTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-amazonsqs
+                        transports:
+                          - name: local-amazonsqs
+                            amazonsqs-transport-config:
+                              service-url: {Container.GetConnectionString()}
+                              region-name: us-east-1
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/PublishEventCommandAzureServiceBusEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/PublishEventCommandAzureServiceBusEndToEndTests.cs
new file mode 100644
index 00000000..cfc10018
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/PublishEventCommandAzureServiceBusEndToEndTests.cs
@@ -0,0 +1,41 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.AzureServiceBus;
+
+[TestFixture]
+public class PublishEventCommandAzureServiceBusEndToEndTests : AzureServiceBusEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-azure-service-bus
+                        transports:
+                          - name: local-azure-service-bus
+                            azure-service-bus-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendCommandAzureServiceBusEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendCommandAzureServiceBusEndToEndTests.cs
index fe8b5f88..5cbbf836 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendCommandAzureServiceBusEndToEndTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendCommandAzureServiceBusEndToEndTests.cs
@@ -38,36 +38,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-azure-service-bus
-                        transports:
-                          - name: local-azure-service-bus
-                            azure-service-bus-transport-config:
-                              connection-string: {Container.GetConnectionString()}
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendTimeoutCommandAzureServiceBusEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendTimeoutCommandAzureServiceBusEndToEndTests.cs
new file mode 100644
index 00000000..73ab61e3
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureServiceBus/SendTimeoutCommandAzureServiceBusEndToEndTests.cs
@@ -0,0 +1,74 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.AzureServiceBus;
+
+[TestFixture]
+public class SendTimeoutCommandAzureServiceBusEndToEndTests : AzureServiceBusEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldSendTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-azure-service-bus
+                        transports:
+                          - name: local-azure-service-bus
+                            azure-service-bus-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+
+    [Test]
+    public async Task ShouldSendTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-azure-service-bus
+                        transports:
+                          - name: local-azure-service-bus
+                            azure-service-bus-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/PublishEventCommandAzureStorageQueuesEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/PublishEventCommandAzureStorageQueuesEndToEndTests.cs
new file mode 100644
index 00000000..5d0367cf
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/PublishEventCommandAzureStorageQueuesEndToEndTests.cs
@@ -0,0 +1,39 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.AzureStorageQueues;
+
+[TestFixture]
+public class PublishEventCommandAzureStorageQueuesEndToEndTests : AzureStorageQueuesEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-azure-storage-queues
+                        transports:
+                          - name: local-azure-storage-queues
+                            azure-storage-queues-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendCommandAzureStorageQueuesEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendCommandAzureStorageQueuesEndToEndTests.cs
index 2129fd27..2de88fd1 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendCommandAzureStorageQueuesEndToEndTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendCommandAzureStorageQueuesEndToEndTests.cs
@@ -37,34 +37,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-azure-storage-queues
-                        transports:
-                          - name: local-azure-storage-queues
-                            azure-storage-queues-transport-config:
-                              connection-string: {Container.GetConnectionString()}
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendTimeoutCommandAzureStorageQueuesEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendTimeoutCommandAzureStorageQueuesEndToEndTests.cs
new file mode 100644
index 00000000..e8efbbdb
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/AzureStorageQueues/SendTimeoutCommandAzureStorageQueuesEndToEndTests.cs
@@ -0,0 +1,72 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.AzureStorageQueues;
+
+[TestFixture]
+public class SendTimeoutCommandAzureStorageQueuesEndToEndTests : AzureStorageQueuesEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldReturnErrorWhenSendingTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-azure-storage-queues
+                        transports:
+                          - name: local-azure-storage-queues
+                            azure-storage-queues-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(TestEndpoint.TryReceiveMessage(), Is.Null);
+    }
+
+    [Test]
+    public async Task ShouldReturnErrorWhenSendingTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-azure-storage-queues
+                        transports:
+                          - name: local-azure-storage-queues
+                            azure-storage-queues-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(TestEndpoint.TryReceiveMessage(), Is.Null);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/PublishEventCommandLearningEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/PublishEventCommandLearningEndToEndTests.cs
new file mode 100644
index 00000000..59d2014e
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/PublishEventCommandLearningEndToEndTests.cs
@@ -0,0 +1,39 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.Learning;
+
+[TestFixture]
+public class PublishEventCommandLearningEndToEndTests : LearningEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-learning
+                        transports:
+                          - name: local-learning
+                            learning-transport-config:
+                              storage-directory: ./.learningtransport
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendCommandEndToEndLearningTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendCommandEndToEndLearningTests.cs
index 342bfd96..5f0e85da 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendCommandEndToEndLearningTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendCommandEndToEndLearningTests.cs
@@ -37,34 +37,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-learning
-                        transports:
-                          - name: local-learning
-                            learning-transport-config:
-                              storage-directory: ./.learningtransport
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendTimeoutCommandLearningEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendTimeoutCommandLearningEndToEndTests.cs
new file mode 100644
index 00000000..99e51068
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/Learning/SendTimeoutCommandLearningEndToEndTests.cs
@@ -0,0 +1,72 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.Learning;
+
+[TestFixture]
+public class SendTimeoutCommandLearningEndToEndTests : LearningEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldSendTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-learning
+                        transports:
+                          - name: local-learning
+                            learning-transport-config:
+                              storage-directory: ./.learningtransport
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+
+    [Test]
+    public async Task ShouldSendTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-learning
+                        transports:
+                          - name: local-learning
+                            learning-transport-config:
+                              storage-directory: ./.learningtransport
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/PublishEventCommandPostgreSqlEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/PublishEventCommandPostgreSqlEndToEndTests.cs
new file mode 100644
index 00000000..d7a51cad
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/PublishEventCommandPostgreSqlEndToEndTests.cs
@@ -0,0 +1,39 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.PostgreSql;
+
+[TestFixture]
+public class PublishEventCommandPostgreSqlEndToEndTests : PostgreSqlEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-postgre-sql
+                        transports:
+                          - name: local-postgre-sql
+                            postgre-sql-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendCommandPostgreSqlEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendCommandPostgreSqlEndToEndTests.cs
index a4475578..9c040cee 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendCommandPostgreSqlEndToEndTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendCommandPostgreSqlEndToEndTests.cs
@@ -38,34 +38,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-postgre-sql
-                        transports:
-                          - name: local-postgre-sql
-                            postgre-sql-transport-config:
-                              connection-string: {Container.GetConnectionString()}
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendTimeoutCommandPostgreSqlEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendTimeoutCommandPostgreSqlEndToEndTests.cs
new file mode 100644
index 00000000..5c72c48b
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/PostgreSql/SendTimeoutCommandPostgreSqlEndToEndTests.cs
@@ -0,0 +1,72 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.PostgreSql;
+
+[TestFixture]
+public class SendTimeoutCommandPostgreSqlEndToEndTests : PostgreSqlEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldReturnErrorWhenSendingTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-postgre-sql
+                        transports:
+                          - name: local-postgre-sql
+                            postgre-sql-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(TestEndpoint.TryReceiveMessage(), Is.Null);
+    }
+
+    [Test]
+    public async Task ShouldReturnErrorWhenSendingTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-postgre-sql
+                        transports:
+                          - name: local-postgre-sql
+                            postgre-sql-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(TestEndpoint.TryReceiveMessage(), Is.Null);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/PublishEventCommandRabbitMqEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/PublishEventCommandRabbitMqEndToEndTests.cs
new file mode 100644
index 00000000..741fa885
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/PublishEventCommandRabbitMqEndToEndTests.cs
@@ -0,0 +1,41 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.RabbitMQ;
+
+[TestFixture]
+public class PublishEventCommandRabbitMqEndToEndTests : RabbitMqEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-rabbitmq
+                        transports:
+                          - name: local-rabbitmq
+                            rabbitmq-transport-config:
+                              amqp-connection-string: {Container.GetConnectionString()}
+                              management-api:
+                                url: http://{Container.Hostname}:{Container.GetMappedPublicPort(15672)}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendCommandRabbitMqEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendCommandRabbitMqEndToEndTests.cs
index c80bc8e8..cabd4249 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendCommandRabbitMqEndToEndTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendCommandRabbitMqEndToEndTests.cs
@@ -39,36 +39,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-rabbitmq
-                        transports:
-                          - name: local-rabbitmq
-                            rabbitmq-transport-config:
-                              amqp-connection-string: {Container.GetConnectionString()}
-                              management-api:
-                                url: http://{Container.Hostname}:{Container.GetMappedPublicPort(15672)}
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendTimeoutCommandRabbitMqEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendTimeoutCommandRabbitMqEndToEndTests.cs
new file mode 100644
index 00000000..bd585d8a
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/RabbitMQ/SendTimeoutCommandRabbitMqEndToEndTests.cs
@@ -0,0 +1,76 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.RabbitMQ;
+
+[TestFixture]
+public class SendTimeoutCommandRabbitMqEndToEndTests : RabbitMqEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldSendTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-rabbitmq
+                        transports:
+                          - name: local-rabbitmq
+                            rabbitmq-transport-config:
+                              amqp-connection-string: {Container.GetConnectionString()}
+                              management-api:
+                                url: http://{Container.Hostname}:{Container.GetMappedPublicPort(15672)}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+
+    [Test]
+    public async Task ShouldSendTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-rabbitmq
+                        transports:
+                          - name: local-rabbitmq
+                            rabbitmq-transport-config:
+                              amqp-connection-string: {Container.GetConnectionString()}
+                              management-api:
+                                url: http://{Container.Hostname}:{Container.GetMappedPublicPort(15672)}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Timeouts.OrderTimeout", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/PublishEventCommandSqlServerEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/PublishEventCommandSqlServerEndToEndTests.cs
new file mode 100644
index 00000000..0cd6c1f7
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/PublishEventCommandSqlServerEndToEndTests.cs
@@ -0,0 +1,39 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.SqlServer;
+
+[TestFixture]
+public class PublishEventCommandSqlServerEndToEndTests : SqlServerEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldPublishEvent()
+    {
+        // Arrange
+        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-sql-server
+                        transports:
+                          - name: local-sql-server
+                            sql-server-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "event",
+            "publish",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
+            "--message-body", json,
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(0));
+        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
+    }
+}
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendCommandSqlServerEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendCommandSqlServerEndToEndTests.cs
index d9dd784e..fcdb6fec 100644
--- a/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendCommandSqlServerEndToEndTests.cs
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendCommandSqlServerEndToEndTests.cs
@@ -37,34 +37,4 @@ public async Task ShouldSendCommand()
         AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Commands.CreateOrder", json);
     }
 
-    [Test]
-    public async Task ShouldPublishEvent()
-    {
-        // Arrange
-        await TestEndpoint.Subscribe("MessageContracts.Events.OrderCreated");
-        var messageBody = new { OrderNumber = Guid.NewGuid() };
-        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
-        var yamlFile = $"""
-                        ---
-                        current-transport: local-sql-server
-                        transports:
-                          - name: local-sql-server
-                            sql-server-transport-config:
-                              connection-string: {Container.GetConnectionString()}
-                        """;
-        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
-
-        // Act
-        var result = Sut.Run(
-            "event",
-            "publish",
-            "--content-type", "application/json",
-            "--enclosed-message-type", "MessageContracts.Events.OrderCreated",
-            "--message-body", json,
-            "--config", configFile.FilePath);
-
-        // Assert
-        Assert.That(result.ExitCode, Is.EqualTo(0));
-        AssertMessageReceived(TestEndpoint.TryReceiveMessage(), "MessageContracts.Events.OrderCreated", json);
-    }
 }
\ No newline at end of file
diff --git a/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendTimeoutCommandSqlServerEndToEndTests.cs b/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendTimeoutCommandSqlServerEndToEndTests.cs
new file mode 100644
index 00000000..4026a77b
--- /dev/null
+++ b/tests/BuslyCLI.Console.Tests/EndToEnd/SqlServer/SendTimeoutCommandSqlServerEndToEndTests.cs
@@ -0,0 +1,72 @@
+using System.Text.Json;
+using BuslyCLI.Console.Tests.TestHelpers;
+
+namespace BuslyCLI.Console.Tests.EndToEnd.SqlServer;
+
+[TestFixture]
+public class SendTimeoutCommandSqlServerEndToEndTests : SqlServerEndToEndTestBase
+{
+    [Test]
+    public async Task ShouldReturnErrorWhenSendingTimeoutWithDelayDeliveryWith()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-sql-server
+                        transports:
+                          - name: local-sql-server
+                            sql-server-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--delay-delivery-with", "00:00:01",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(TestEndpoint.TryReceiveMessage(), Is.Null);
+    }
+
+    [Test]
+    public async Task ShouldReturnErrorWhenSendingTimeoutWithDoNotDeliverBefore()
+    {
+        // Arrange
+        var messageBody = new { OrderNumber = Guid.NewGuid() };
+        var json = JsonSerializer.Serialize(messageBody, _jsonObjectOptions);
+        var yamlFile = $"""
+                        ---
+                        current-transport: local-sql-server
+                        transports:
+                          - name: local-sql-server
+                            sql-server-transport-config:
+                              connection-string: {Container.GetConnectionString()}
+                        """;
+        using var configFile = new TestableNServiceBusConfigurationFile(yamlFile);
+
+        // Act
+        var result = Sut.Run(
+            "timeout",
+            "send",
+            "--content-type", "application/json",
+            "--enclosed-message-type", "MessageContracts.Timeouts.OrderTimeout",
+            "--destination-endpoint", TestEndpoint.EndpointName,
+            "--message-body", json,
+            "--do-not-deliver-before", "2020-01-01T00:00:00Z",
+            "--config", configFile.FilePath);
+
+        // Assert
+        Assert.That(result.ExitCode, Is.EqualTo(1));
+        Assert.That(TestEndpoint.TryReceiveMessage(), Is.Null);
+    }
+}
\ No newline at end of file
diff --git a/website/docs/cli-reference/cli-reference.md b/website/docs/cli-reference/cli-reference.md
index 4da41839..1aba0307 100644
--- a/website/docs/cli-reference/cli-reference.md
+++ b/website/docs/cli-reference/cli-reference.md
@@ -8,6 +8,7 @@ This document contains information about all commands and settings available in
 -   `busly transport set`
 -   `busly command send`
 -   `busly event publish`
+-   `busly timeout send`
 
 ## Global Options
 
diff --git a/website/docs/cli-reference/timeout/index.mdx b/website/docs/cli-reference/timeout/index.mdx
new file mode 100644
index 00000000..7fc20e95
--- /dev/null
+++ b/website/docs/cli-reference/timeout/index.mdx
@@ -0,0 +1,7 @@
+import DocCardList from "@theme/DocCardList";
+
+# busly timeout
+
+Use `busly timeout` to send timeouts to NServiceBus endpoints.
+
+<DocCardList />
\ No newline at end of file
diff --git a/website/docs/cli-reference/timeout/send.md b/website/docs/cli-reference/timeout/send.md
new file mode 100644
index 00000000..7c46bb68
--- /dev/null
+++ b/website/docs/cli-reference/timeout/send.md
@@ -0,0 +1,40 @@
+# busly timeout send
+
+Send a timeout message to an endpoint.
+
+## Usage
+
+```
+busly timeout send
+```
+
+## Options
+
+| Option                          | Description                                                                                                       |
+| ------------------------------- | ----------------------------------------------------------------------------------------------------------------- |
+| `-c`, `--content-type`          | The fully qualified .NET type name of the enclosed message (ex: Ordering.Commands.CreateOrder )                   |
+| `-e`, `--enclosed-message-type` | The type of serialization used for the message                                                                    |
+| `-m`, `--message-body`          | The content of the message body                                                                                   |
+| `-d`, `--destination-endpoint`  | The destination endpoint to send a message to                                                                     |
+| `--do-not-deliver-before`       | Allows specifying a date before which the delivery should not occur, using ISO-8601 format (YYYY-MM-DDTHH:mm:ssZ) |
+| `--delay-delivery-with`         | Specifies the delay before the timeout is delivered, using a TimeSpan format                                      |
+
+## Transport Support
+
+Not all transports support sending timeouts. Transports that delegate delayed delivery to the broker work fine. Transports that rely on an in-process poller to forward deferred messages are not compatible with the CLI's fire-and-forget execution model — the process exits before the poller has a chance to dispatch the message.
+
+| Transport              | Supported | Reason                                                              |
+| ---------------------- | --------- | ------------------------------------------------------------------- |
+| Learning               | ✅         | Broker-side delayed delivery                                        |
+| RabbitMQ               | ✅         | Broker-side delayed delivery via TTL                                |
+| Azure Service Bus      | ✅         | Broker-side scheduled messages                                      |
+| Amazon SQS             | ✅         | Native SQS message delay                                            |
+| Azure Storage Queues   | ❌         | Requires an in-process poller; exits before messages become due     |
+| PostgreSQL             | ❌         | Requires an in-process poller; send-only endpoints not supported    |
+| SQL Server             | ❌         | Requires an in-process poller; send-only endpoints not supported    |
+
+## Examples
+
+```
+
+```
\ No newline at end of file
diff --git a/website/docs/introduction/quick-start.mdx b/website/docs/introduction/quick-start.mdx
index 82791026..05ce6a20 100644
--- a/website/docs/introduction/quick-start.mdx
+++ b/website/docs/introduction/quick-start.mdx
@@ -222,10 +222,70 @@ docker run --rm `
   --network host `
   -v "$HOME/.busly-cli/config.yaml:/app/config.yaml" `
   tragiccode/busly-cli `
-  event publish `
+    --message-body ('{"OrderNumber":"3f2d6c8a-b7a2-4c3f-9c3e-12ab45ef6789"}'-replace '"', '\"') `
+    --config ./config.yaml
+```
+
+</TabItem>
+</Tabs>
+
+## Send a Timeout
+
+<Tabs>
+<TabItem value="bash" label="Bash">
+
+```bash
+busly timeout send \
+  --content-type 'text/json' \
+  --enclosed-message-type "Messages.Timeouts.OrderTimeout" \
+  --destination-endpoint "BuslyCLI.DemoEndpoint" \
+  --message-body '{"OrderNumber":"3f2d6c8a-b7a2-4c3f-9c3e-12ab45ef6789"}' \
+  --delay-delivery-with "00:00:05"
+```
+
+</TabItem>
+<TabItem value="powershell" label="Powershell">
+
+```bash
+busly timeout send `
+  --content-type 'text/json' `
+  --enclosed-message-type "Messages.Timeouts.OrderTimeout" `
+  --destination-endpoint "BuslyCLI.DemoEndpoint" `
+  --message-body ('{"OrderNumber":"3f2d6c8a-b7a2-4c3f-9c3e-12ab45ef6789"}'-replace '"', '\"') `
+  --delay-delivery-with "00:00:05"
+```
+
+</TabItem>
+<TabItem value="docker bash" label="Docker (Bash)">
+
+```bash
+docker run --rm \
+  --network host \
+  -v "$HOME/.busly-cli/config.yaml:/app/config.yaml" \
+  tragiccode/busly-cli \
+  timeout send \
+    --content-type "text/json" \
+    --enclosed-message-type "Messages.Timeouts.OrderTimeout" \
+    --destination-endpoint "BuslyCLI.DemoEndpoint" \
+    --message-body '{"OrderNumber":"3f2d6c8a-b7a2-4c3f-9c3e-12ab45ef6789"}' \
+    --delay-delivery-with "00:00:05" \
+    --config ./config.yaml
+```
+
+</TabItem>
+<TabItem value="docker powershell" label="Docker (Powershell)">
+
+```bash
+docker run --rm `
+  --network host `
+  -v "$HOME/.busly-cli/config.yaml:/app/config.yaml" `
+  tragiccode/busly-cli `
+  timeout send `
     --content-type "text/json" `
-    --enclosed-message-type "Messages.Events.OrderPlaced" `
+    --enclosed-message-type "Messages.Timeouts.OrderTimeout" `
+    --destination-endpoint "BuslyCLI.DemoEndpoint" `
     --message-body ('{"OrderNumber":"3f2d6c8a-b7a2-4c3f-9c3e-12ab45ef6789"}'-replace '"', '\"') `
+    --delay-delivery-with "00:00:05" `
     --config ./config.yaml
 ```
 
diff --git a/website/docs/transports/azure-storage-queues.md b/website/docs/transports/azure-storage-queues.md
index d0bc085e..90c4aea3 100644
--- a/website/docs/transports/azure-storage-queues.md
+++ b/website/docs/transports/azure-storage-queues.md
@@ -38,3 +38,9 @@ Examples:
 ```yaml
 connection-string: UseDevelopmentStorage=true
 ```
+
+## Limitations
+
+### Timeout Send Not Supported
+
+The `timeout send` command is not supported with the Azure Storage Queues transport. Native delayed delivery is disabled in busly's transport configuration because it requires an in-process background poller (`NativeDelayedDeliveryProcessor`) to forward due messages from an Azure Table to the destination queue. Because busly exits immediately after dispatching a message, the poller is stopped before it can forward the deferred message. Enabling native delayed delivery for send-only endpoints also requires a dedicated poison queue and would still not resolve the fundamental timing incompatibility.
diff --git a/website/docs/transports/postgre-sql.md b/website/docs/transports/postgre-sql.md
index 8f723cfa..eb0ba8df 100644
--- a/website/docs/transports/postgre-sql.md
+++ b/website/docs/transports/postgre-sql.md
@@ -38,3 +38,9 @@ Examples:
 ```yaml
 connection-string: Data Source=(local);Initial Catalog=Ordering;Integrated Security=SSPI;Application Name=Busly-CLI;TrustServerCertificate=true
 ```
+
+## Limitations
+
+### Timeout Send Not Supported
+
+The `timeout send` command is not supported with the PostgreSQL transport. PostgreSQL implements delayed delivery using a database table polled by an in-process background worker. Because busly exits immediately after dispatching a message, the poller is stopped before it can forward the deferred message to the destination queue. Additionally, the transport explicitly blocks delayed delivery from send-only endpoints.
diff --git a/website/docs/transports/sql-server.md b/website/docs/transports/sql-server.md
index c6101e37..8e462c4c 100644
--- a/website/docs/transports/sql-server.md
+++ b/website/docs/transports/sql-server.md
@@ -38,3 +38,9 @@ Examples:
 ```yaml
 connection-string: Data Source=(local);Initial Catalog=Ordering;Integrated Security=SSPI;Application Name=Busly-CLI;TrustServerCertificate=true
 ```
+
+## Limitations
+
+### Timeout Send Not Supported
+
+The `timeout send` command is not supported with the SQL Server transport. SQL Server implements delayed delivery using a database table polled by an in-process background worker. Because busly exits immediately after dispatching a message, the poller is stopped before it can forward the deferred message to the destination queue. Additionally, the transport explicitly blocks delayed delivery from send-only endpoints.