I have 2 phones with separate Nsec. Both connected the same way to the same servers. I should be able to send a DM from one phone to another via my private server. That’s what I think anyway. But it keeps failing. I have tried multiple settings, with Orbot on and off. If I use the supplied DM servers then the message goes through. Trying to use my private server fails.

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I see, I think you should also check your server to see whether it suports kind 1059 events

Ok. Thank you for the advice. Much appreciated.