Why did an image included in my email signature suddenly turn into a question mark?

Hi Rmandree,

Thank you for using the Apple Support Communities! Does the same issue occur on another user account? Being able to see if the issue occurs in another user account will to identify if it is something that is affecting your entire system or just one particular user account. To do this, you'll want to set up a Test User account and then try to replicate the issue in that account.

1. Choose Apple menu > System Preferences, then click Users & Groups.

2. Click the lock icon, then enter an administrator name and password.

3. Click the add button (+) below the list of users.

4. Complete the fields shown for a Standard or Administrator account, then click Create Account (or OK).

5. Go back up to the Apple menu in the upper left of the computer and select "Log Out". At the login screen, choose the "Test User" just made.

6. Once inside the Test Account, try to replicate the issue to determine if it just occurs in one account or on the whole computer.

Thank you.

Don't bother. Anything fancy in an e-mail signature, whether custom fonts, text styling, or especially images, is going to cause you no end of trouble. As an added bonus, it makes your e-mails look low-quality when they reach the recipient. Just don't do it.

I can't give you a technical explanation because I don't know the details of how your signature is constructed, your e-mail service, spam filters, system security settings, 3rd party system modifications, etc. etc. It's really, really complicated. Literally the entire system has been designed specially to block images. And you're trying to attach an image.