How do you give your user options without overloading them?

I was using WinSCP the other day for transferring files, when I came across this.. umm.. I'll call it a set of options, but it was more like an interview.

Oh boy. I just want to move a file. Now I have to read nine options to determine what I want to do!

The problem is, for the kind of thing WinSCP does, each of these options is sometimes very relevant. Clearly, yes no and cancel are always relevant. When you're moving log files, append is very useful. The option to rename is a common one, particularly when copying output files. When moving code or config or graphic files, newer only is very useful. No to all and yes to all are good for when you're doing a bunch of files at once.

Lord knows they could have added "append all" too. To top it all off, in case you're confused, there's a help button! (The help button doesn't really help either... but that's another story...)

So being that each of these buttons is a good thing at times, how can this problem of overloading be avoided while still giving people the flexibility they need to get high productivity out of your tool?

Edit: here's what the help button does, actually: