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hypertown@lemmy.world to Lemmy Shitpost@lemmy.world – 1737 points –
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Years ago, as far as I can tell. Are you using an older version of the app maybe? I've not had Discord outright refuse to send pictures for ~2 years now, for a while it would ask to compress them, now it'll just automatically compress them (unless it's so big it can't of course).

Back in April they also increased the limit to 25MB, so even less stuff should need to get compressed anyway.

I believe it doesn't always work for whatever reason. I had images from my phone get the 'over 8mb' message sometimes only a few months ago as well, sometimes it worked but other times it didn't

Maybe he send the full file and not just the photo via the photo option.