So its not a bug but a concern. Last year I bought an anonymous pro membership for a DM but had to tell him because the confirmation email had gone to spam. This year I bought from the marketplace instead. Now I want to know will the Modules and compendium entries be added to his account automatically? Or will I need to possibly give away myself again and tell him to check his email?
As someone who has bought Modules and add-ons to the compendium, I can say that you will most probably need to tell him. Even when buying regularly you do not see any popup telling you that you got something new until you actually decide to either make a new game and check the Module or search the compendium and find it there. Unless told otherwise there is a high chance he would not know, but I may be wrong. You can always make a secondary account/email and use those in the guise of a mysterious stranger, at least that's what I did a little while back when I wanted to gift someone while staying anonymous.
Brother Sharp said: You can always make a secondary account/email and use those in the guise of a mysterious stranger, at least that's what I did a little while back when I wanted to gift someone while staying anonymous. +1
Well at least I found out he has it.]. We were playing and he dragged a monster out of the compendium and it gave him the token. However even after I dropped a subtle hint about whether tokens were normal or not he didn't realise. I'd leave it at that, but he won't realise he can search the monsters from Volo's guide if he doesn't check. I can't email him sadly as we met on roll20 and never shared emails, I'll certainly think about making a new account.
Another option would be to ask someone who is uninvolved in the game to Private Message him. I'm sure any one of the moderators would be happy to drop him a "Someone in the community wanted to anonymously let you know..."