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Gmail image proxy

I'm using Django to send an html email (using gmail account) that includes image tags pointing to static images on my website, like a logo. When I send the email to a gmail account, the gmail image proxy is not loading the images, but when I send to a yahoo mail account the images appear without issue. The filetype for the images is png. Any ideas?

It look like the question to google. If you interact with those email accounts using web interface see what your browser dev tools tell.

Anything on the Pythonanywhere firewall that would be blocking these domains? The Gmail proxy is giving a 404 not found error for my images. ci3.googleusercontent.com ci4.googleusercontent.com ci5.googleusercontent.com ci6.googleusercontent.com

No. You have a paid account, so we do not do anything to the requests you make. If you are getting a 404, it's because there is no page at the URL you are requesting.