Oh, I see. You are treating the sentence as if it were a complete idea (an independent clause). While I agree that the two sentences you posted can be translated as 'you should have asked ...', I didn't think the original context was a complete sentence. I assumed there was more to it, and that we were only given the dependent clause. As such, it would be translated as 'you have/had asked'. I invented a main clause that requires the subjunctive mood in the secondary clause, and placed the dependent clause in it. The English translation of the invented sentence is "It surprised me that you have/had asked for more vacation time."
I think we're both correct, depending on our point of view.
