I think the focus shouldn't be on whether such syntax is possibly confusing or not because a) People will always remember that's *either* one way or the other, but are very unlikely to just assume one; hence they can always check what it does, and more importantly, b) It's actually pretty easy to remember which way it is, by just considering that a syntax feature exists for scenarios that can't be easily solved otherwise. For `for ... else` it's actually more tricky than for the proposed syntax because that doesn't let you distinguish between "`else` is only executed if the loop didn't `break`" and "`else` is only executed if the loop didn't execute at all". But for `for ... except` or `while ... except` it will be even more obvious because `try ... except`ing the body is just as easy as, well, `try ... except`ing the body; it's pretty clear that no new syntax would be required for that and hence it must concern the statement itself since that's not easy to work around. The only possible confusion I see is when people look at something like this: for ...: LENGTHY BODY except ...: HANDLER else: SOMETHING_ELSE and only look at the `except ... else` part and readily assume that the two are complementary. But that's easy to prevent by only allowing the opposite order, i.e. `for ... else ... except`, stressing that the two are unrelated in this case. In the end a feature should be driven by its usefulness to the community and whether it provides a solution for an otherwise (hard|awkward)-to-solve problem. I could imagine that due to the awkward workaround, especially regarding `with`, corresponding "self-made" code is either error-prone or people will not even try to work around it in the first place. This feature will probably be among the less prominent ones, but someone who needs it will be glad that it exists and they're also likely to be well aware of what it does (just like with `for ... else`). Someone who encounters that feature for the first time, e.g. when reviewing some code, will probably check what it does and even if not, the assumption that it `except`s the whole body should be perplexing since (a) excepting whole blocks by default is not really best practice and (b) it's pretty easy to accomplish that with existing syntax.