diff --git a/src/CodeGeneration/DocGenerator/LitUp.cs b/src/CodeGeneration/DocGenerator/LitUp.cs
index 4ad225cb9f4..dfaf25eaaae 100644
--- a/src/CodeGeneration/DocGenerator/LitUp.cs
+++ b/src/CodeGeneration/DocGenerator/LitUp.cs
@@ -66,7 +66,10 @@ public static async Task GoAsync(string[] args)
 			var projects = workspace.CurrentSolution.Projects
 				.ToDictionary(p => p.Name, StringComparer.OrdinalIgnoreCase);
 
-			foreach (var file in GetDocumentFiles(projects).SelectMany(s => s)) await file.SaveToDocumentationFolderAsync();
+			DeleteExistingDocs();
+
+			foreach (var file in GetDocumentFiles(projects).SelectMany(s => s))
+				await file.SaveToDocumentationFolderAsync();
 
 			Console.ForegroundColor = ConsoleColor.Green;
 			Console.WriteLine("Documentation generated.");
@@ -79,6 +82,20 @@ public static async Task GoAsync(string[] args)
 			}
 		}
 
+		private static void DeleteExistingDocs()
+		{
+			var outputDir = new DirectoryInfo(Program.OutputDirPath);
+
+			foreach (var file in outputDir.EnumerateFiles())
+				file.Delete();
+
+			foreach (var dir in outputDir.EnumerateDirectories())
+			{
+				if (!dir.Name.EndsWith("breaking-changes"))
+					dir.Delete(true);
+			}
+		}
+
 		private static void AddDocumentsToWorkspace(AdhocWorkspace workspace)
 		{
 			// we only need source for the Tests project.