Apple Mail Signature images loading as Question Marks after updates on desktop and iOS

None of the trouble shooting has worked for me or other people from my team having the same problem.

Just got back an iMac that had drive failure, it was fixed by apple and had nothing but Monterey on it when I got it back so I wanted to test this before fully setting the thing up. won't even let me add signature so far ( they delete when mail closes and there is no signatures folder created). so that's fun, but I can see from the email threads that the signature issue remains.

when I look at through icloud's webmail it also doesn't work at first but gives the notice "this email contains remote content." after selecting "load remote content" the signature does show. so even though I have turned all those privacy features off in the desktop app it does seem to be a bug that still blocks the signature. However, newsletters iCloud blocks the remote content on through web are coming in just fine in the desktop app.

Thank you Matthew, I’m glad it is working a bit better for you. that is not the case for me in iOS or the desktop app. I’m also finding I will get newsletters with and without the warning where images load fine but people with html signatures images are broken and don’t have the load remote content option. On desktop and iOS newsletters don’t even ask for remote content loading but the images aren’t broken either.

even if this was the case (sent e-mails gave the option) that’s a strange feature to just trust the signature is sending out fine but appears broken for the user. I appreciate the new privacy features but html email signatures aren’t exactly a novel item so a bit odd to throw a wrench in there without some guidance or an alternative.

i will attempt Apple support next to see what I might be missing