diff --git a/UndoRedo.Test/CompositeCommandTests.cs b/UndoRedo.Test/CompositeCommandTests.cs
index 3223990..be8769d 100644
--- a/UndoRedo.Test/CompositeCommandTests.cs
+++ b/UndoRedo.Test/CompositeCommandTests.cs
@@ -6,6 +6,7 @@ namespace ktsu.UndoRedo.Test;
 using System.Collections.Generic;
 using System.Linq;
 using ktsu.UndoRedo;
+using ktsu.UndoRedo.Core.Services;
 
 [TestClass]
 public class CompositeCommandTests
@@ -74,7 +75,7 @@ public void CompositeCommand_NestedFailure_RollsBackCompleteHierarchy()
 	private static readonly string[] expected = ["A", "B", "C"];
 
 	[TestMethod]
-	public void CompositeCommand_UndoFailure_DoesNotAffectOtherCommands()
+	public void CompositeCommand_UndoFailure_LeavesEveryCommandApplied()
 	{
 		// Arrange
 		List<string> values = [];
@@ -104,12 +105,50 @@ public void CompositeCommand_UndoFailure_DoesNotAffectOtherCommands()
 		// Make undo fail for middle command
 		shouldFailUndo = true;
 
-		// Assert - Undo should throw but still attempt to undo all commands
+		// Assert - Undo should throw and restore C, which it had already undone
 		Assert.ThrowsExactly<InvalidOperationException>(composite.Undo);
+		CollectionAssert.AreEqual(expected, values, "A failed Undo should leave the composite fully applied");
+	}
+
+	[TestMethod]
+	public void CompositeCommand_UndoFailureThenRetry_UndoesEachCommandOnce()
+	{
+		// Arrange: b's undo fails once
+		UndoRedoService stack = new(new StackManager(), new SaveBoundaryManager(), new CommandMerger());
+		int a = 0;
+		int b = 0;
+		bool failUndo = true;
+
+		CompositeCommand composite = new("Move and resize",
+		[
+			new DelegateCommand("a", () => a++, () => a--),
+			new DelegateCommand("b", () => b++, () =>
+			{
+				if (failUndo)
+				{
+					throw new InvalidOperationException("b undo fails");
+				}
+
+				b--;
+			}),
+		]);
+
+		stack.Execute(composite);
+
+		// Act
+		Assert.ThrowsExactly<InvalidOperationException>(() => stack.Undo());
+
+		// Assert: the stack did not move, so nothing may have been undone
+		Assert.AreEqual(0, stack.CurrentPosition);
+		Assert.AreEqual(1, a, "A failed Undo should leave a applied");
+		Assert.AreEqual(1, b, "A failed Undo should leave b applied");
+
+		failUndo = false;
+		stack.Undo();
 
-		// Commands should still be partially undone (C and A undone from end, B failed)
-		Assert.HasCount(1, values);
-		Assert.AreEqual("A", values[0]);  // A remains because B's undo failed, C was undone, A tried to undo but only removes from end
+		Assert.AreEqual(-1, stack.CurrentPosition);
+		Assert.AreEqual(0, a, "Retrying Undo should undo a exactly once");
+		Assert.AreEqual(0, b, "Retrying Undo should undo b exactly once");
 	}
 
 	[TestMethod]
diff --git a/UndoRedo/CompositeCommand.cs b/UndoRedo/CompositeCommand.cs
index 5f66bf7..821e14f 100644
--- a/UndoRedo/CompositeCommand.cs
+++ b/UndoRedo/CompositeCommand.cs
@@ -75,28 +75,37 @@ public override void Execute()
 	/// <inheritdoc />
 	public override void Undo()
 	{
-		List<Exception> undoExceptions = [];
+		List<ICommand> undoneCommands = [];
 
-		// Undo in reverse order, collecting any exceptions
-		for (int i = _commands.Count - 1; i >= 0; i--)
+		try
 		{
-#pragma warning disable CA1031 // Do not catch general exception types
-			try
+			// Undo in reverse order
+			for (int i = _commands.Count - 1; i >= 0; i--)
 			{
 				_commands[i].Undo();
+				undoneCommands.Add(_commands[i]);
 			}
-			catch (Exception ex)
-			{
-				undoExceptions.Add(ex);
-			}
-#pragma warning restore CA1031 // Do not catch general exception types
 		}
-
-		// If any undo operations failed, throw the first exception
-		if (undoExceptions.Count > 0)
+#pragma warning disable CA1031 // Do not catch general exception types
+		catch (Exception)
 		{
-			throw undoExceptions[0];
+			// Re-apply what this call already undid, in forward order, so a failed Undo leaves the
+			// composite fully applied. The stack keeps its position when Undo throws, so it must be
+			// able to rely on nothing having been undone. This mirrors the rollback in Execute().
+			for (int i = undoneCommands.Count - 1; i >= 0; i--)
+			{
+				try
+				{
+					undoneCommands[i].Execute();
+				}
+				catch (Exception)
+				{
+					// Continue restoring even if an individual re-execute fails
+				}
+			}
+			throw; // Re-throw the original exception
 		}
+#pragma warning restore CA1031 // Do not catch general exception types
 	}
 
 	/// <inheritdoc />