diff --git a/src/Elastic.Markdown/DocumentationGenerator.cs b/src/Elastic.Markdown/DocumentationGenerator.cs
index 49168cca1..ff957f6c8 100644
--- a/src/Elastic.Markdown/DocumentationGenerator.cs
+++ b/src/Elastic.Markdown/DocumentationGenerator.cs
@@ -99,6 +99,36 @@ public async Task ResolveDirectoryTree(Cancel ctx)
 		_logger.LogInformation("Resolving tree");
 		await DocumentationSet.Tree.Resolve(ctx);
 		_logger.LogInformation("Resolved tree");
+		ReportDuplicateTitles(DocumentationSet.Tree.ResolvedMarkdownFiles);
+	}
+
+	private void ReportDuplicateTitles(List<MarkdownFile> files)
+	{
+		// Create a dictionary where keys are the titles
+		// and values are files with that title
+		var titleMap = new Dictionary<string, List<MarkdownFile>>(StringComparer.OrdinalIgnoreCase);
+		foreach (var file in files)
+		{
+			if (string.IsNullOrWhiteSpace(file.Title))
+				continue;
+			// If there is no entry for this title, create it and
+			// initialize it to an empty list
+			if (!titleMap.TryGetValue(file.Title, out var list))
+				titleMap[file.Title] = [];
+			titleMap[file.Title].Add(file);
+		}
+		// Go through all the titles and if a title has multiple files, report it
+		foreach (var kv in titleMap)
+		{
+			var documentFiles = kv.Value;
+			if (documentFiles.Count > 1)
+			{
+				var fileList = string.Join(", ", documentFiles.Select(f => f.RelativePath));
+				foreach (var documentFile in documentFiles)
+					Context.Collector.EmitHint(documentFile.RelativePath,
+						$"Duplicate titles found. The title '{kv.Key}' is used in files: {{{fileList}}}");
+			}
+		}
 	}
 
 	public async Task<GenerationResult> GenerateAll(Cancel ctx)
diff --git a/src/Elastic.Markdown/IO/Navigation/DocumentationGroup.cs b/src/Elastic.Markdown/IO/Navigation/DocumentationGroup.cs
index 038b857be..442901c67 100644
--- a/src/Elastic.Markdown/IO/Navigation/DocumentationGroup.cs
+++ b/src/Elastic.Markdown/IO/Navigation/DocumentationGroup.cs
@@ -46,6 +46,8 @@ public class DocumentationGroup : INodeNavigationItem<MarkdownFile, INavigationI
 
 	private readonly IRootNavigationItem<MarkdownFile, INavigationItem>? _root;
 
+	public List<MarkdownFile> ResolvedMarkdownFiles { get; set; }
+
 	protected virtual IRootNavigationItem<MarkdownFile, INavigationItem> DefaultNavigation =>
 		_root ?? throw new InvalidOperationException("root navigation's model is not of type MarkdownFile");
 
@@ -70,6 +72,7 @@ protected DocumentationGroup(string folderName,
 		// We'll need to address this more structurally
 		// ReSharper disable VirtualMemberCallInConstructor
 		_root = toplevelTree;
+		ResolvedMarkdownFiles = [];
 		toplevelTree ??= DefaultNavigation;
 		if (parent?.Depth == 0)
 			toplevelTree = DefaultNavigation;
@@ -225,10 +228,22 @@ public async Task Resolve(Cancel ctx = default)
 		if (_resolved)
 			return;
 
-		await Parallel.ForEachAsync(FilesInOrder, ctx, async (file, token) => await file.MinimalParseAsync(token));
-		await Parallel.ForEachAsync(GroupsInOrder, ctx, async (group, token) => await group.Resolve(token));
+		// First add the index file
+		ResolvedMarkdownFiles.Add(Index);
+		// Then add all the files in this group
+		ResolvedMarkdownFiles.AddRange(FilesInOrder);
+		// Then add all files in subgroups, breadth first
+		var treeGroups = new Queue<DocumentationGroup>(GroupsInOrder);
+		while (treeGroups.Count > 0)
+		{
+			var group = treeGroups.Dequeue();
+			ResolvedMarkdownFiles.Add(group.Index);
+			ResolvedMarkdownFiles.AddRange(group.FilesInOrder);
+			foreach (var subgroup in group.GroupsInOrder)
+				treeGroups.Enqueue(subgroup);
+		}
 
-		_ = await Index.MinimalParseAsync(ctx);
+		await Parallel.ForEachAsync(ResolvedMarkdownFiles, ctx, async (file, token) => await file.MinimalParseAsync(token));
 
 		_resolved = true;
 	}