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This message is appearing too much frequently when I try to upload a gif.
Sometimes I success after trying like twenty times in a row. Is it normal?

Yes, it happens to me too.
Just reload the page, and the gif should upload in the next minute or so.

Reduce the size of the file. I believe there's a limit of 5 MB.

The limit is 8mb i think, but around 5mb works w/o the 504 sometimes.
theres lots of gifs i made under 8mb that just wont upload.

The gif I was trying to post was 2mb heavy.

Any and All gif files causes a 504 Gateway error, and it's been that way for the past year at least. This mainly has to do with the fact that KYM is trying to shrink your gif into a Thumbnail.

In the case of entries, just be a bit patient with it. I think James may have already been aware of this issue.

But in the case of Avatar uploads, do yourself a favor by resizing and cropping the gif Manually using Photoshop or a similarly capable program. My current avatar I actually shrunk down a 6 something MB Gif (one that crashed the system) into a 1.5 MB Gif simply through cropping and resizing to the 300×300 avatar size.

I've been trying to upload a 2MB GIF, but every time I get the 504 error :(

We really need a better compression procedures.

This was the gif I was trying to upload:

Does it look any large?