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macOS Messages File Transfer Issues

I am having some strange behavior when sending files via macOS Messages app and was wondering if other people have this working. When sending on our internal network, file transfer fails. However sending from external to internal works correctly. When using the spark client file transfer works just fine, so I would assume it’s a port of a config on the macOS client side, but am having trouble sorting it out.

We run Openfire in AWS with ports exposed as needed. Everything works great, except for file transfers.

If anyone has this working and could give me any ideas, I would be very grateful.

file transfer is kind of a known issue. you can work around this by making sure file transfer proxy in openfire is enabled. Once enabled, you’ll need to make sure that the port (default port is 7777) is not being blocked by your firewall for both inbound and outbound traffic.

So I tried to get this working, but using Apple Messages, even when sending files, it seems like it connects over 5223.

Not really sure how to go about fixing this…