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So I’ve been seeing this woman for a few months. Kind of casual. She knows a bit about my cheating ex etc. not all the details obviously.
Today when talking with her she said she is going to meet her firmed tomorrow as she wants her to meet a guy she likes. She then said her friend was married and she said she can only say so much. This really bothered me for some reason.

If I had a married friend I would never want to meet their potential affair partner or someone they liked.

Am I overthinking this ?

Personally, I don't think you are. I would not be comfortable with her being so accepting of her friend's situation. I think it would be a deal breaker for me because it would make me wonder about how they really feel about being faithful in relationships.

I don't have time to worry about someone I've only been seeing for a few months. Onto the next, that's what I'd do.

Yeah that’s what I think and feel as well. It’s a major red flag. I want nothing to do with anyone or anything that supports that level of dishonesty. I wouldn’t be or stay friends with anyone that is in to that. It turns my stomach.

I think what you can infer here is that she doesn't have a boundary with cheaters and cheating. That's troubling. She missed a cue here with you as well in terms of empathy by treating it like it's no big deal even though she knows your recent history. I think it's okay to continue casual dating, but you can't really change anyone. She is who she is. If you have that discussion with her and she really likes you, she might blow a bunch of sunshine up your skirt to convince you that she's not that way, but you saw what you saw and you can't unsee it. It doesn't sound like she's just meeting a friend whose actions she disapproves of either. It sounds like she's meeting the married boyfriend for the sake of validating the relationship.

If you decide to keep seeing her, you might want to make it clear that you're just there for the laughs and no intention to get serious. In fact, I'd make sure she understood that it's not exclusive. You're a free man. Date. Have fun. Keep your options open, be picky. Why not?

I personally don't feel comfortable with people who (currently) cheat or support cheating. There are many people in this group who are former waywards that I would be comfortable with. But cheater supporters are a personal no go for me. It's a matter of values alignment for me. People for whom cheating is a hard "no" seem to have values that align better with my values.
Your mileage may vary as far as your experiences with people who are ok with cheating...
My experiences were very negative (ex mil was a serial ow, lots of can't be ex wh's friends are cheater supporters). I want nothing to do with any of them. As in if I saw them walking down the street I would cross to the other side..again this is my feelings only and not giving advice

Oops typo what I meant to type was can't be ex SOON Enough WH's friends

Am I overthinking this ?

No, trust your spidey-senses.

I think you are under-questioning it though. I would have been like "Oh...does she have an open M?" or "Does she do this frequently?", "Oh, is she getting D?" etc. If you wanted to leave the friend out of it entirely, then more like "Wow - what a tough spot to put you in....how do you feel about that?"

I would not have dropped it because she said ".....she can only say so much" because she opened that door for discussion once she even told you.

Maybe it was a test to see how you would respond?

I would wait until I got some questions answered before I let her know how much this bothered you and that it is a dealbreaker for you, etc.