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Slightly off topic but I've never had success with self hosted prosody and the "conversations" app being able to share photos/memes as one would in WhatsApp or telegram. This is the one thing keeping me from being able to sell my non-tech friends on it, has anyone had any luck in this regard?

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Enable the "http_upload" module if you have not yet done so.

I'm using it with self-hosted ejabberd and have no issues. It just works.

That's a standard module included in ejabberd. It may not be enabled by default in others, such as prosody

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