And you are the person who replied to my earlier post saying "don't do things that do not have intuitively clear semantics." Do integer promotion rules count as intuitively clear semantics? Most C programmers never learned them and therefore the semantics is confusing. For the few C programmers who learned them, the semantics is clearer when they can remember the rules, and confusing otherwise.
Now I hope I've convinced you that there are a lot of such subtle semantics issues in C, and hardly anything is intuitively clear, unless you've been a language lawyer or programmed in C for long enough.
It seems I've never really done "overshifting", otherwise I would have easily noticed that the shifted value is promoted first. If you don't overshift there's no way to trigger the undefined behaviour, even when you shift multiple times - since by assigning to the smaller type the result gets cut down again, effectively leading to the behaviour I'd assumed. I would hardly call this a gotcha.
Where it might be confusing is in a situation like this:
char x = 42;
printf("%d\n", x << 4);
If ubyte is greater than or equal to 128, then converting it to a signed 32-bit integer (as on a 32 bit machine) and then shifting it left by 24 causes signed integer overflow. This is undefined behavior. Therefore the compiler is allowed to make optimizations that assume ubyte is less than 128.