> It's not orthogonal. The agreement usually covers shares owned by employees and former employees

It covers them as equity holders, or people with the right to equity. I’ve negotiated lock-up agreements. Nobody is thinking about RSU holders. Hence how OP winds up in this mess.

OP’s problem stems from a draconian form of RSU. It doesn’t automatically vest on a liquidity event. It has the company collecting taxes. And it has a forfeiture clause.

Yes, it covers them. Hence it's not orthogonal. The fact that there are two agreements doesn't make them orthogonal. Many situations are covered by more than one contract (or law or regulation).

You’re being intentionally obtuse. The source of the problem isn’t the lock-up agreement, which was negotiated independently of the RSUs. And the lock-up agreement is easily (and commonly) circumvented—the problem is intractable because it’s unrelated to the lock-up.

(And pedantically, a 185-day lock-up is not common.)

Ehhh 180 days is 6 months is fairly standard.

Which is why 185 isn’t. (Lock-ups have also gone into and out of vogue. And again, this is a problem with the company’s treatment of withholding. The lock-up agreement could go away and OP would retain their problem.)

The extra 2.7% isn't material to OP's problem. As you note, OP's real problem is the withholding.

Just curious, how is a lock-up commonly circumvented? Might be relevant information for me, I would appreciate any tips