Update: Whoop representative was able to reach out and resolve this issue.
I recently upgraded to MD while I was at 1821 total logged recoveries. When I upgraded I asked the bot if I would still be eligible for the milestone gift. It said yes, and to reach back out when I reached them.
Turns out, that is not correct. So if you’re thinking about upgrading to the life membership, and are close to 1825, just wait. Otherwise you’ll have to pay +$200 to receive the milestone collection. The customer service has all been repetitive and no resolution.