OP here - It is all done!
Jenny and I hung out tonight, had some wine, watched old movies, all that fun girly stuff. When she first came in I pulled out the bottle of wine that I had promised her - at which point she let me know that she and Todd had been having disagreements & that I should not be shocked if she suddenly burst into tears. Yeah, that was a little discouraging.
Still, I girded my loins and went forth into the abyss. I told her about the ring incident in particular. A strange thing kind of happened when I said that I wanted to advise her not to use Friend for apartment sitting when she leaves town. I told her how Friend had come over and brought up this ring, but when I started to describe it Jenny exclaimed "oh my gosh that explains so much, we haven't been able to find that ring since that break!" I did quickly say that I had no idea about that & had no reason to think Friend would have taken it. Really I don't think she is a thief & if she is, well I have no knowledge of it and I'm not comfortable commenting on something like that.
Instead, I explained what Friend had told me about the ring & advised her about the dangers of confiding in Friend. Jenny was very upset that such a thing had happened & told me that her expectation when Friend was watching her place was that she would come in, check her pet's food/water & then leave. She shared that she had already been taken aback when she came home to find that Friend had brought an out of town visitor with her into her apartment on one of her visits, & had borrowed movies from Jenny & Todd's collection without asking.
Jenny acknowledged that she and Todd could tell that Friend was not okay with them dating, but had no idea how bad it really was. I tried not to go too far into specifics, but made sure to give some concrete examples so that she would understand the scope of the problem. For example, Jenny said "well, if she says something again, please tell me" I had to tell her that honestly there was no doubt about it happening again, as really it happens multiple times every day. I also let her know that her friends were sticking up for them as best they could. I did not want her to think that people were encouraging Friend in this at all or that people were discussing her behind her back in a negative way.
Ultimately Jenny has said that she has no problem if Friend stops talking to her & Todd altogether after we graduate, but that for the 2 years we have left, Friend'll just have to deal with the fact that they are dating & be civil or just stay away from them. I think Jenny might have a talk with Friend, but she assured me that she would not tell bring me into it at all - apparently Friend shows enough disdain that Todd has stopped being quiet about the snipes she takes at him so it won't exactly come as a shock that they are upset with her. I guess the surprise portion here for Jenny was 1) the ring & 2) that Friend was including Jenny & the relationship so freely in her jibes.
Jenny did thank me for telling her & said that she was glad she knew what was going on. I feel really relieved to have spoken to her about this. I will admit I was especially relieved that she didn't break down - I was worried for a bit because her eyes were turning red & watering but she held it together when I told her to please don't let it upset her too much, because it was unfortunate that such a thing was happening at all, but that now that she knew, she could watch out for herself. I really was worried about piling on to her bad day, but I think it will help her to know when she is so vulnerable that Friend is not someone to trust with deeper feelings. Whew!