"Check-in does not check-in". One of the most feared complains from the users. We all check-in files every day (or not, when gauntlet is in use ;)) and everything works fine.But customers are always right (vide Get Latest on Checkout)! So one theory explaining this phenomena say that user encounters conflicts doing check-in.He resolves the conflicts and expects that when Resolve Dialog disappears the files will be checked-in. This is very far from the truth - he needs to try checking in the files again himself.

Why we don't make his life easier by re-attempting to check-in files automatically? Whel, resolving conflicts most probably will change content of the files. Before doing check-in user should at least build sources again to avoid build breaks.

So what we improved in Orcas? It's very psychological feature :)  - Resolve Dialog contains label that inform user that check-in failed. Also, when Check-in Dialog is closed we show extra message box, telling user again that he need to try checking-in files again.