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But it's not just achievements, when I check my mission menu it doesn't have a record of me completing anything past Regret even though I completed the whole campaign on legendary.
If you have Reach, does the "I'm Sorry, Dave." achievement work for you? That and "Remember Reach" (tried it yesterday) don't work either for me. I randomly got some of the Halo 2 collectible achievements yesterday (which i don't remember to have ever picked up back when i played on Xbox One).
These are the skulls with the x0.0 multiplier on them and these disable achievements related to completing missions, par score and par time
Also, the person I was co-oping with did recieve the achievements/ progress.
I also just tried using a different Xbox Live account, not getting any achievements with that one either, I'm guessing the problem is with connecting to the Xbox Live servers and them not being reachable for our PCs to upload and register achievements/stats/progress/whichever most of the time. Did any of you change your internet connection in some way between when it works/doesn't work?
My brother and I probably re-played Regret 4 times before it counted (Back in like 2015). I don't know if this is true but we read online somewhere that if you play with the original graphics it has a better chance of working.
Maybe we should move this over to the Halo Waypoint discussions and create an official bug report about stats not being properly synchronised with the Steam version?
while some achievements remain broken for me (wihtout unlocking, including many of Halo: Reach's side achievements) I figured out what was breaking most achievements to unlock for me (actually I feel kind of dumb now, there is a support page mentioning it on halowaypoint[support.halowaypoint.com] after all) - if any of you are using a dns adblocker, try disabling that and check if progress/achievements will sync with it disabled.
Good luck with the issue everyone!