Wife and I applied through AA's website many weeks ago, much as we did using UA's and DL's websites, to be enrolled in AA's contactless program. AA's path was not too difficult when we enrolled. We have used UA's contactless multiple times recently on our main route---SFO-ORD. Especially on the reverse leg, ORD-SFO, it has worked like a charm. Especially valuable during the current problem and delays that are nationwide. I am confident it saved 1-2 hrs on return ORD-SFO flights.

So, we've got a trip tomorrow AM, SFO-ORD, and are seated in paid F, together in row 2. I went to check in, and did it on my home computer (same computer I applied for contactless with).
Unfortunately, the little marker that is supposed to show up on our boarding passes, signifying contactless, did not show up. I called, multiple times to get an answer (included multiple HUCA's).
What has resulted, after 2 corroborative calls to the EXP line, is that the system will not bestow the contactless marker on one's boarding pass if one chooses to check in on-line, hoping to use the pathway of having one's boarding pass simply emailed to one's phone---by any other requested pathway other than the AA app.

I inquired about it to an EXP agent now and she admitted that they are having many complaints about this glitch. Whether they fix it or not is anybody's guess. We were offered an alternative path whereby we could go to the check-in area before our flight, request to be unchecked-in, and try to get or boarding pass anew, hopefully with the marker showing we would be good to go as contactless.
We usually use United Terminal 2's check -in lane, since we can roam easily to Terminal 1 for AA flights. The security process there is light years faster than AA's terminal 1. The screeners there are very laborious and often call committee meetings to approve a bag to go through. And worse, they usually delay the approval after one waits quite a bit for an opening of one's bag.

Sum up: Don't risk more delay, if you hope to enjoy the benefit of contactless status, by checking in from any other source other than the AA app on your phone. I was told check in at the kiosks was not good either. Who knew?

Just my hope to share the pain I have have to put up with and not have other pax go through it either. Last AA agent I talked to said they are aware of the avalanche of complaints this has precipitated and are somehow going to address it. I just said, "As a former New Yorker, ask them to try and not take all day".

Check it out for yourselves. Contactless has been a welcome pathway during the terrible TSA delays. I say that from experience.