Dating myself ie showing myself as out of date because no one uses AOL or MSN anymore?

Thaaaaat would make sense :D All of yours from 616 canon, I believe, but since 616 canon is enormous and I'm not really an expert, I went to someone who is! iloome identified the bottom one as being from Captain America V4 #27 where there was a storyline about wasp robots and Tony had to stop his heart - not to be confused with the Madripoor storyline that I originally thought it was from, where there are also wasp robots and Tony has heart issues. The broken shield one I thought was from the vibranium cancer storyline, but iloome pointed out Captain America V3 #15-16 on the slashy moments list: '100. Tony spends roughly eleventy bazillion dollars scouring the ocean for Steve's shield. When it turns up broken, he stays up all hours trying to fix it.' So it sounds like it's from there, although that specific image isn't in the screencaps we have. (EDIT: iloome looked it up and confirmed it's in 15!)

And we're split on the facepalming one, I think it's Tony facepalming out of frustration because he does do that at times, but iloome thinks it may be from CW with Tony being sad. I'm going to have to ask navaan to weigh in, I think, since these three images all came from her :D

Second Edit: Navaan's weighed in, and iloome got it, it's post-CW from Avengers/Invaders #5!