Thank you so much!! I tired searching before and didn't find that.
Thank you for updating this!
It's now March 2020 & INDESIGN is the problem, not photoshop.
Proportional resize using shift key on object or text box still not working Indesign cc 14.0.3 mac, mojave.
neither is CMD shift (using only a corner handle, yes of course)
just updated but this doesnt work correctly, needed all the time ... also scaling with CMD tool ... duplicating with OPT-CMD fails ... any news?
I have found the the Opt key stops working periodically, just in the past few months. I reboot and then all is good again.
We know that other applications will interfere with the modifier keys, and while I am well aware of that, I haven't figured out which application is causing the issue for me yet.
TL;DR: Try rebooting.
Well I'll be darned, that fixed all three of em! I tend to reboot only when its really needed. THANKS!