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@santiago
Ha-ha, interesting! I had licenses for both: Painter 10/11 and CS2 and I always did a clean install, never bothered to check if just copying would suffice.
Ableton is actually not a bad company — they even legally allowed you to have software installed on multiple machines if you don't use them simultaneously, so you could e.g. have it on your Mac Pro/PowerMac in your home studio and on your MacBook Pro/PowerBook for field recording sessions.
@santiago
And they allowed up to 10 activations for each license to proceed automatically, after that you could email them and after confirming you as a valid license holder, reset the counter.
I even remember those on tighter budget chipping in to buy one license — just to not mess with cracks😅
The problem isn't their unwillingness, but lack of commitment to support old SW in general — not specific to them, they might even not be the worst, I just never had to experience this in person before.