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

Thank you for this. This seems to have solved the issue for me. since there is still no patch from Apple I'm going to go ahead and mark this as the solution for anyone else tying to land on it.

I did use both the image url and base 64 url as in this example and that seems to get the signature to work in apple mail, gmail an outlook as well.

Appreciate everyone's contributions.

I have found another little Gem in this. The Base 64code for an image is very long. if you are like me and used 3 images ( company logo, 2 social icons) the resulting code was "too long" to paste into gmails signature setting. Some of my coworkers don't use the apple mail client at all. However the issue of the images not showing in apple mail is the problem for everyone so this code needs to go everywhere including in gmail.

Just an issue to know about if you are on a Gmail client, and i assume outlook as well if gmail takes issue with it.

Annoying since the problem is still really only an apple mail issue that they simply have not patched.

The dropbox route has worked for me and the rest of my team so far. I'm not sure where it might be failing on your end.

If you are only using the signature in apple mail then I would suggest trying Janneman84's base64 method posted here. This works very well to install the signature for OS and IOS Mail.

I may actually go back to the dual image version ( base 64 and url on top) for my OS Mail as the images do load pretty instantaneously. I have noticed a very very small delay in image loading with the dropbox version, its really not much but Personal preference there since there's a split second I think it's broken again. I have not had it break again yet however.

Thank you P.Phillips, I am familiar with this process but if you are wanting more options with your signature, html will give you more control and layout options and is supported. Apple I don't think gives the directions to do it but any search will guide you to steps. Apple mail has the most confusing method to add an html signature for OS but it has always worked. in iOS it's more in line with other mail apps and you simply paste it into your signature section in settings.

I am realizing maybe it wasn't clear that this html signature has always been in apple mail on my desktops and on my iPhone and worked perfectly until the updates (iOS 15 and Os Monterey ), so I wanted to clarify that.

I have not found a solution, sorry. Most of what im finding is about reinstalling everything which seems a little silly since I ts effecting all my updated devices and to just one machine. Hopefully will be an update patch fix if enough people having the issue report it.

Thank you for all the links.

I would agree the method in the html signature link you sent is the most robust way I've found to add an html signature on OS. This is how I do it and I have tried simply redoing the signature and even a very basic one but the issue remains.

I do not have an "unable to load remote content" warning and attachments are working just fine.

cycling Mail privacy settings don't have any effect on it either and deleting and reconnecting the mail account yields the same results.

restarting mail holding shift has also not reset this issue.

This particular account is gmail and the signature is fine in gmail its a different system but same html so it isn't the links. Testing it on an my icloud account has the same problem so it seems specifically related to apple mails handling of html image links and Monterey related.

You will notice the only mail feature mentioned for Monterey is the privacy feature. This seems to make sense as something that could create this kind of conflict but so far even turning it fully off has yielded no change but a road to look further down I think.

Just as an update I've made sure all 32 bit apps have been removed and all other software is up to date. It has not changed the issue and wouldn't explain why it is same issue on my iPhone where I noticed it first directly after updating the IOS. Still seems more plausible the issue is related to Mail's new privacy updates.

Another progress update. restarting in safe mode the issue persists. reinstalling Monterey, issue persists.

on iPhone, the 15.1 update did not resolve the issue but mail wasn't mentioned in the big fixes either.