I tried SimpleX but the VPN kill switch on my phone prevents syncing with my computer.

I use telegram primarily as a note taking app with sync features.

Occasionally I send files to friends, so having easy set up for tech illiterate would be great.

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I’ve gone this route. Not for the faint of heart. If you’re not self-hosting savvy, but you know someone that hosts a server, absolutely sign up with them. Or use a local public server like pikaviestin.fi, which provides accounts for finnish citizens.

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7 points

This. I‘m hosting a couple matrix servers and have many friends who have a ton of issues. It really depends on the admin and how tech savvy everyone involved is. If you cant be arsed to understand how key sharing works and check out which is the best client for you, matrix might bot be the best choice. I love it, personally but I suggest it rarely since tech illiterate users tend to get really upset about a free product not matching their insane standards.

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