Harry isn't good enough to fool Dumbledore's Legilimency, and he knows that. See Ch. 58:
He had decided to keep the memories. For one thing, they were important. For another, he and the Defense Professor had started planning this a week ago, and Harry wasn't about to obliterate the whole last week, or explain to Bellatrix exactly what needed to be Obliviated. Harry could probably fool Veritaserum, and if Dumbledore insisted that Harry drop his Occlumency shields for a deeper examination... well, Harry had acted heroically throughout.
Harry knows it--or believes it, at least. Does Dumbledore?
Update: Discussion has moved on to a new thread.
After 61 chapters of Harry Potter and the Methods of Rationality and 5 discussion threads with over 500 comments each, HPMOR discussion has graduated from the main page and moved into the Less Wrong discussion section (which seems like a more appropriate location). You can post all of your insights, speculation, and, well, discussion about Eliezer Yudkowsky's Harry Potter fanfic here.
Previous threads are available under the harry_potter tag on the main page (or: one, two, three, four, five); this and future threads will be found under the discussion section tag (since there is a separate tag system for the discussion section). See also the author page for (almost) all things HPMOR, and AdeleneDawner's Author's Notes archive for one thing that the author page is missing.
As a reminder, it's useful to indicate at the start of your comment which chapter you are commenting on. Time passes but your comment stays the same.
Spoiler Warning: this thread is full of spoilers. With few exceptions, spoilers for MOR and canon are fair game to post, without warning or rot13. More specifically: