diff --git a/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcStepTracer.cs b/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcStepTracer.cs
index 0affd47f00..2b71a483f8 100644
--- a/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcStepTracer.cs
+++ b/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcStepTracer.cs
@@ -31,7 +31,7 @@ internal sealed class InProcStepTracer : IStepTracer
     /// <param name="lastStepNumber">The Step Number of the last SuperStep. Note that Step Numbers are 0-indexed.</param>
     public void Reload(int lastStepNumber = 0) => this._nextStepNumber = lastStepNumber + 1;
 
-    public SuperStepStartedEvent Advance(StepContext step)
+    public SuperStepStartedEvent Advance(StepContext step, CheckpointInfo? startCheckpoint = null)
     {
         this._nextStepNumber++;
         this.Activated.Clear();
@@ -57,7 +57,8 @@ public SuperStepStartedEvent Advance(StepContext step)
 
         return new SuperStepStartedEvent(this.StepNumber, new SuperStepStartInfo(sendingExecutors)
         {
-            HasExternalMessages = hasExternalMessages
+            HasExternalMessages = hasExternalMessages,
+            Checkpoint = startCheckpoint
         });
     }
 
diff --git a/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunner.cs b/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunner.cs
index 2a61f80ced..56047a036b 100644
--- a/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunner.cs
+++ b/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunner.cs
@@ -244,7 +244,11 @@ await executor.ExecuteCoreAsync(
 
     private async ValueTask RunSuperstepAsync(StepContext currentStep, CancellationToken cancellationToken)
     {
-        await this.RaiseWorkflowEventAsync(this.StepTracer.Advance(currentStep)).ConfigureAwait(false);
+        // Save a checkpoint before the superstep executes, capturing the pre-delivery state.
+        await this.CheckpointAsync(currentStep, cancellationToken).ConfigureAwait(false);
+        CheckpointInfo? startCheckpoint = this.StepTracer.Checkpoint;
+
+        await this.RaiseWorkflowEventAsync(this.StepTracer.Advance(currentStep, startCheckpoint)).ConfigureAwait(false);
 
         // Deliver the messages and queue the next step
         List<Task> receiverTasks =
@@ -278,7 +282,7 @@ await this.RaiseWorkflowEventAsync(this.StepTracer.Complete(this.RunContext.Next
     private WorkflowInfo? _workflowInfoCache;
     private CheckpointInfo? _lastCheckpointInfo;
     private readonly List<CheckpointInfo> _checkpoints = [];
-    internal async ValueTask CheckpointAsync(CancellationToken cancellationToken = default)
+    internal async ValueTask CheckpointAsync(StepContext? queuedMessagesOverride, CancellationToken cancellationToken = default)
     {
         this.RunContext.CheckEnded();
         if (this.CheckpointManager is null)
@@ -299,7 +303,7 @@ internal async ValueTask CheckpointAsync(CancellationToken cancellationToken = d
         await prepareTask.ConfigureAwait(false);
         await this.RunContext.StateManager.PublishUpdatesAsync(this.StepTracer).ConfigureAwait(false);
 
-        RunnerStateData runnerData = await this.RunContext.ExportStateAsync().ConfigureAwait(false);
+        RunnerStateData runnerData = await this.RunContext.ExportStateAsync(queuedMessagesOverride).ConfigureAwait(false);
         Dictionary<ScopeKey, PortableValue> stateData = await this.RunContext.StateManager.ExportStateAsync().ConfigureAwait(false);
 
         Checkpoint checkpoint = new(this.StepTracer.StepNumber, this._workflowInfoCache, runnerData, stateData, edgeData, this._lastCheckpointInfo);
@@ -308,6 +312,9 @@ internal async ValueTask CheckpointAsync(CancellationToken cancellationToken = d
         this._checkpoints.Add(this._lastCheckpointInfo);
     }
 
+    internal ValueTask CheckpointAsync(CancellationToken cancellationToken = default)
+        => this.CheckpointAsync(null, cancellationToken);
+
     public async ValueTask RestoreCheckpointAsync(CheckpointInfo checkpointInfo, CancellationToken cancellationToken = default)
     {
         this.RunContext.CheckEnded();
diff --git a/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunnerContext.cs b/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunnerContext.cs
index eda7b90a80..e3156715ce 100644
--- a/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunnerContext.cs
+++ b/dotnet/src/Microsoft.Agents.AI.Workflows/InProc/InProcessRunnerContext.cs
@@ -379,11 +379,13 @@ async Task InvokeCheckpointRestoredAsync(Task<Executor> executorTask)
         }
     }
 
-    internal ValueTask<RunnerStateData> ExportStateAsync()
+    internal ValueTask<RunnerStateData> ExportStateAsync(StepContext? queuedMessagesOverride = null)
     {
         this.CheckEnded();
 
-        Dictionary<string, List<PortableMessageEnvelope>> queuedMessages = this._nextStep.ExportMessages();
+        StepContext queuedMessagesSource = queuedMessagesOverride ?? this._nextStep;
+        Dictionary<string, List<PortableMessageEnvelope>> queuedMessages = queuedMessagesSource.ExportMessages();
+
         RunnerStateData result = new(instantiatedExecutors: [.. this._executors.Keys],
                                      queuedMessages,
                                      outstandingRequests: [.. this._externalRequests.Values]);
diff --git a/dotnet/src/Microsoft.Agents.AI.Workflows/SuperStepStartInfo.cs b/dotnet/src/Microsoft.Agents.AI.Workflows/SuperStepStartInfo.cs
index 94ccb06dd1..a6fb85a35d 100644
--- a/dotnet/src/Microsoft.Agents.AI.Workflows/SuperStepStartInfo.cs
+++ b/dotnet/src/Microsoft.Agents.AI.Workflows/SuperStepStartInfo.cs
@@ -18,4 +18,10 @@ public sealed class SuperStepStartInfo(HashSet<string>? sendingExecutors = null)
     /// Gets a value indicating whether there are any external messages queued during the previous SuperStep.
     /// </summary>
     public bool HasExternalMessages { get; init; }
+
+    /// <summary>
+    /// Gets the <see cref="CheckpointInfo"/> corresponding to the checkpoint created at the start of this SuperStep, if any.
+    /// <see langword="null"/> if checkpointing was not enabled when the run was started.
+    /// </summary>
+    public CheckpointInfo? Checkpoint { get; init; }
 }
diff --git a/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/CheckpointParentTests.cs b/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/CheckpointParentTests.cs
index 0ecf3c993f..1f8e79fbb7 100644
--- a/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/CheckpointParentTests.cs
+++ b/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/CheckpointParentTests.cs
@@ -32,13 +32,17 @@ internal async Task Checkpoint_FirstCheckpoint_ShouldHaveNullParentAsync(Executi
         InProcessExecutionEnvironment env = environment.ToWorkflowExecutionEnvironment();
 
         // Act
-        StreamingRun run =
+        await using StreamingRun run =
             await env.WithCheckpointing(checkpointManager).RunStreamingAsync(workflow, "Hello");
 
         List<CheckpointInfo> checkpoints = [];
         await foreach (WorkflowEvent evt in run.WatchStreamAsync())
         {
-            if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                checkpoints.Add(startCp);
+            }
+            else if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
             {
                 checkpoints.Add(cp);
             }
@@ -51,6 +55,14 @@ internal async Task Checkpoint_FirstCheckpoint_ShouldHaveNullParentAsync(Executi
         Checkpoint storedFirst = await ((ICheckpointManager)checkpointManager)
             .LookupCheckpointAsync(firstCheckpoint.SessionId, firstCheckpoint);
         storedFirst.Parent.Should().BeNull("the first checkpoint should have no parent");
+
+        // Assert: The second checkpoint should have 1 parent, the first checkpoint.
+        checkpoints.Should().HaveCountGreaterThanOrEqualTo(2, "multiple checkpoints should have been created, and we can't verify parent checkpoint without at least 2 checkpoints present.");
+        CheckpointInfo secondCheckpoint = checkpoints[1];
+        Checkpoint storedSecond = await ((ICheckpointManager)checkpointManager)
+            .LookupCheckpointAsync(secondCheckpoint.SessionId, secondCheckpoint);
+        storedSecond.Parent.Should().NotBeNull("the second checkpoint should have a parent");
+        storedSecond.Parent.Should().Be(firstCheckpoint, "the second checkpoint's parent should be the first checkpoint");
     }
 
     [Theory]
@@ -79,13 +91,18 @@ internal async Task Checkpoint_SubsequentCheckpoints_ShouldChainParentsAsync(Exe
 
         await foreach (WorkflowEvent evt in run.WatchStreamAsync(cts.Token))
         {
-            if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                checkpoints.Add(startCp);
+            }
+            else if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
             {
                 checkpoints.Add(cp);
-                if (checkpoints.Count >= 3)
-                {
-                    cts.Cancel();
-                }
+            }
+
+            if (checkpoints.Count >= 3)
+            {
+                cts.Cancel();
             }
         }
 
@@ -126,19 +143,24 @@ internal async Task Checkpoint_AfterResume_ShouldHaveResumedCheckpointAsParentAs
         InProcessExecutionEnvironment env = environment.ToWorkflowExecutionEnvironment();
 
         // First run: collect a checkpoint to resume from
-        await using StreamingRun run = await env.WithCheckpointing(checkpointManager).RunStreamingAsync(workflow, "Hello");
+        StreamingRun run = await env.WithCheckpointing(checkpointManager).RunStreamingAsync(workflow, "Hello");
 
         List<CheckpointInfo> firstRunCheckpoints = [];
         using CancellationTokenSource cts = new();
         await foreach (WorkflowEvent evt in run.WatchStreamAsync(cts.Token))
         {
-            if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                firstRunCheckpoints.Add(startCp);
+            }
+            else if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
             {
                 firstRunCheckpoints.Add(cp);
-                if (firstRunCheckpoints.Count >= 2)
-                {
-                    cts.Cancel();
-                }
+            }
+
+            if (firstRunCheckpoints.Count >= 2)
+            {
+                cts.Cancel();
             }
         }
 
@@ -149,19 +171,24 @@ internal async Task Checkpoint_AfterResume_ShouldHaveResumedCheckpointAsParentAs
         await run.DisposeAsync();
 
         // Act: Resume from the first checkpoint
-        StreamingRun resumed = await env.WithCheckpointing(checkpointManager).ResumeStreamingAsync(workflow, resumePoint);
+        await using StreamingRun resumed = await env.WithCheckpointing(checkpointManager).ResumeStreamingAsync(workflow, resumePoint);
 
         List<CheckpointInfo> resumedCheckpoints = [];
         using CancellationTokenSource cts2 = new();
         await foreach (WorkflowEvent evt in resumed.WatchStreamAsync(cts2.Token))
         {
-            if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                resumedCheckpoints.Add(startCp);
+            }
+            else if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
             {
                 resumedCheckpoints.Add(cp);
-                if (resumedCheckpoints.Count >= 1)
-                {
-                    cts2.Cancel();
-                }
+            }
+
+            if (resumedCheckpoints.Count >= 1)
+            {
+                cts2.Cancel();
             }
         }
 
@@ -172,4 +199,118 @@ internal async Task Checkpoint_AfterResume_ShouldHaveResumedCheckpointAsParentAs
         storedResumed.Parent.Should().NotBeNull("checkpoint created after resume should have a parent");
         storedResumed.Parent.Should().Be(resumePoint, "checkpoint after resume should reference the checkpoint we resumed from");
     }
+
+    [Theory]
+    [InlineData(ExecutionEnvironment.InProcess_Lockstep)]
+    [InlineData(ExecutionEnvironment.InProcess_OffThread)]
+    internal async Task Checkpoint_AfterResumeFromSuperstepStart_CountCheckpointsEmittedAsync(ExecutionEnvironment environment)
+    {
+        // Arrange: A basic workflow with 3 executor stages
+        ForwardMessageExecutor<string> executorA = new("A");
+        ForwardMessageExecutor<string> executorB = new("B");
+        ForwardMessageExecutor<string> executorC = new("C");
+
+        Workflow workflow = new WorkflowBuilder(executorA)
+            .AddEdge(executorA, executorB)
+            .AddEdge(executorB, executorC)
+            .Build();
+
+        CheckpointManager checkpointManager = CheckpointManager.CreateInMemory();
+        InProcessExecutionEnvironment env = environment.ToWorkflowExecutionEnvironment();
+
+        // First run: collect a checkpoint to resume from
+        StreamingRun run = await env.WithCheckpointing(checkpointManager).RunStreamingAsync(workflow, "Hello");
+
+        List<CheckpointInfo> firstRunCheckpoints = [];
+        await foreach (WorkflowEvent evt in run.WatchStreamAsync())
+        {
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                firstRunCheckpoints.Add(startCp);
+            }
+        }
+
+        firstRunCheckpoints.Should().HaveCount(3);
+        CheckpointInfo resumePoint = firstRunCheckpoints[1];
+
+        // Dispose the first run to release workflow ownership before resuming.
+        await run.DisposeAsync();
+
+        // Act: Resume from the second checkpoint
+        await using StreamingRun resumed = await env.WithCheckpointing(checkpointManager).ResumeStreamingAsync(workflow, resumePoint);
+
+        List<CheckpointInfo> resumedCheckpoints = [];
+        await foreach (WorkflowEvent evt in resumed.WatchStreamAsync())
+        {
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                resumedCheckpoints.Add(startCp);
+            }
+            else if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
+            {
+                resumedCheckpoints.Add(cp);
+            }
+        }
+
+        // Assert: The workflow should save the right number of checkpoints on re-run.
+        resumedCheckpoints.Should().NotBeEmpty();
+        resumedCheckpoints.Should().HaveCount(4, "the resumed workflow has 2 executors to run, each generating 2 checkpoints");
+    }
+
+    [Theory]
+    [InlineData(ExecutionEnvironment.InProcess_Lockstep)]
+    [InlineData(ExecutionEnvironment.InProcess_OffThread)]
+    internal async Task Checkpoint_AfterResumeFromSuperstepCompleted_CountCheckpointsEmittedAsync(ExecutionEnvironment environment)
+    {
+        // Arrange: A basic workflow with 3 executor stages
+        ForwardMessageExecutor<string> executorA = new("A");
+        ForwardMessageExecutor<string> executorB = new("B");
+        ForwardMessageExecutor<string> executorC = new("C");
+
+        Workflow workflow = new WorkflowBuilder(executorA)
+            .AddEdge(executorA, executorB)
+            .AddEdge(executorB, executorC)
+            .Build();
+
+        CheckpointManager checkpointManager = CheckpointManager.CreateInMemory();
+        InProcessExecutionEnvironment env = environment.ToWorkflowExecutionEnvironment();
+
+        // First run: collect a checkpoint to resume from
+        StreamingRun run = await env.WithCheckpointing(checkpointManager).RunStreamingAsync(workflow, "Hello");
+
+        List<CheckpointInfo> firstRunCheckpoints = [];
+        await foreach (WorkflowEvent evt in run.WatchStreamAsync())
+        {
+            if (evt is SuperStepCompletedEvent completedEvent && completedEvent.CompletionInfo?.Checkpoint is { } completedCp)
+            {
+                firstRunCheckpoints.Add(completedCp);
+            }
+        }
+
+        firstRunCheckpoints.Should().HaveCount(3);
+        CheckpointInfo resumePoint = firstRunCheckpoints[1];
+
+        // Dispose the first run to release workflow ownership before resuming.
+        await run.DisposeAsync();
+
+        // Act: Resume from the second checkpoint
+        await using StreamingRun resumed = await env.WithCheckpointing(checkpointManager).ResumeStreamingAsync(workflow, resumePoint);
+
+        List<CheckpointInfo> resumedCheckpoints = [];
+        await foreach (WorkflowEvent evt in resumed.WatchStreamAsync())
+        {
+            if (evt is SuperStepStartedEvent superStepStartEvt && superStepStartEvt.StartInfo?.Checkpoint is { } startCp)
+            {
+                resumedCheckpoints.Add(startCp);
+            }
+            else if (evt is SuperStepCompletedEvent stepEvt && stepEvt.CompletionInfo?.Checkpoint is { } cp)
+            {
+                resumedCheckpoints.Add(cp);
+            }
+        }
+
+        // Assert: The workflow should save the right number of checkpoints on re-run.
+        resumedCheckpoints.Should().NotBeEmpty();
+        resumedCheckpoints.Should().HaveCount(2, "the resumed workflow has 1 executor to run, generating 2 checkpoints");
+    }
 }
diff --git a/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/InProcessStateTests.cs b/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/InProcessStateTests.cs
index acffbdd336..d93c654730 100644
--- a/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/InProcessStateTests.cs
+++ b/dotnet/tests/Microsoft.Agents.AI.Workflows.UnitTests/InProcessStateTests.cs
@@ -133,7 +133,7 @@ public async Task InProcessRun_StateShouldPersist_CheckpointedAsync()
 
         Run checkpointed = await InProcessExecution.RunAsync<TurnToken>(workflow, new(), CheckpointManager.Default);
 
-        checkpointed.Checkpoints.Should().HaveCount(4);
+        checkpointed.Checkpoints.Should().HaveCount(8);
 
         RunStatus status = await checkpointed.GetStatusAsync();
         status.Should().Be(RunStatus.Idle);