Meanwhile in Linux with luls, which I've had since a pre-pre-pre version somewhere back in the early 2000's, I can have multiple keys, all works like sunshine, never had problems.
On windows... So we work with highly sensitive data, and ever since I came in I thought it insane that people working remote don't have that highly sensitive data encrypted. We can't switch Linux yet, so okay, we go for BitLocker.
Boy oh boy oh boy was that a mistake.
50 remote users, 5 get encrypted devices with BitLocker as a trial and within a month, 3 of them already got locked up permanently because apparently it'll pwrma lock itself after x amounts of invalid passwords which is just incredibly stupid. But don't worry, there is a backup key! Yeah, that is lie 48 characters that we'd had to pass by phone and they have to type it flawlessly.
Suffice to say, the remote users will be running Linux soon, like it or not.