Personally I'm quite big fan of self-hosting, but if you want less a hassle, def try some of the other suggestions.

Since you're interested in anon file sharing, I'd really recommend you take some time to really think out just what your personal definition of anonymous is, and how well it fits in modern digital infrastructure. True anonymous activity is nearly impossible, you can be fingerprinted by even writing a file to a drive to hand to someone. Every action taken online has some trace to it, while IP is generally not precise information, with enough data overlap you can be reasonably guessed depending on how much effort someone is willing to put into it.

So you know, good luck finding a balance lol.

https://wormhole.app/

E2EE and simple

Ah yes the age old problem

If you're looking for a privacy respecting paid service that's not just a file locker for pirates I have two recommendations: At a previous workplace, we used LiquidFiles. More catered for commercial uses.

Personally I've been using Bitwarden Send. Requires a paid account ($10/year) and limited to 500MB files.

Honestly signal, I however don’t usually share anon outside of torrents

For sharing with your friends you might look into Magic Wormhole. In my case I just put the file on a personal web site, usually.

some PDF with a friend

i would probably just email it

share a PDF or a file with an anonymous lemmy user

onionShare?

protonDrive :/

people here seem to like https://catbox.moe/

Self hosted Project Send: https://www.projectsend.org/ in a Docker environment.

I've been using https://send.vis.ee/

Not anonymous or free but bitwarden send is nice. Thundermail from Mozilla will have this feature too.

An XMPP server. Users with local accounts (long time friends) have almost no restrictions on what can be sent, file size, etc. We have private groups set up, dms, public rooms, etc, more or less like discord. After trying many of the popular chatting and file sharing platforms XMPP seems to be the one that works best for the most people on the most platforms within our group. YMMV.

Depends on the size. If it's small enough I send via Signal. Larger files end up on my Nextcloud instance.

Honestly, it depends. On the size of the file(s), type of files, etc. But usually either Signal or wormhole. If they're standing next to me I've used Android Quick Share.

You can use https://www.swisstransfer.com/ from infomaniak, it's privacy respecting, or https://lufi.ethibox.fr/

I usually use croc, though it requires the receiving party to be around to receive it immediately.

Signal or Proton Drive

SimpleX Chat works for your friends. For anonymous sharing I don't know, Internet Archive?