This has been a bug for years. I can’t find the old thread(s) so I am making a new one.
If Internet Upload Speed is set and you try to download a picture you will get an error. This has been happening for years without a fix.
I don’t normally set the Upload speed, but I just tried it and, yeah, I see the same problem for large images. It seems to be okay for small files, like 1 or 2 MP, but not for 36 MP.
I think I found your old thread:
That is the one.
It has been 6 years 
I feel like anything I want Plex to implement / fix takes at least a decade or more to get done. 
This is just basic. The hole reason I bought the plexpass was a solution for storing my pictures. Now I had the idea to download now and then one of my own. Silly me 
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