https://xkcd.com/949/ has a few good hints.

Do you have a public-facing internet-presence? If so, then I've heard good things about copyparty.

I'm using Nextcloud for this, but that seems a bit overkill for your usecase.

Edit: they explain how to use a cloudflare tunnel, so no public IP needed, actually.

Copyparty is amazing

Are both parties online at the same time?

Maybe something like this is a good solution: https://github.com/magic-wormhole/magic-wormhole

It will figure out the fastest p2p connection and send even very large files without hassle.

Just run a web server and expose the specific files you want to share through that?

Try nextcloud. It can generate links to files like this.

https://file.pizza/ just because the pizza toppings URLs are fun and nasty

Do you have a domain? If you do, maybe try Nginx Proxy Manager and SFTPGo. I previously used File Browser but the developers made some fairly large breaking changes and I never went back. SFTPGo lets you add accounts easily and I have specific folder setup for sharing with friends. It has a clean interface too. If you don't have a domain, maybe try Tailscale?

You can consider using a Pikapods service for this. It's dead simple to strand up a server when you need one.

https://www.pikapods.com/apps#storage

They have Gokapi and/or PrivateBin for just about a buck per month. You can turn the service on and off whenever you like. Good company to work with, IME, too.

croc is really easy to setup as well, https://github.com/schollz/croc

Not selfhosted but after I found catbox.Moe I haven't had yo worry about sharing files.

There are a few implementations of wormhole that might work.

If you're ok with exposing a server to the internet, I've had good luck with sharry. https://eikek.github.io/sharry/

I've also had good luck running a Nextcloud instance to share with friends and family. But that is probably overkill here.

https://selfh.st/apps/?tag=File+Sharing

I use Filebrowser Quantum if you are happy opening up a port for it. It supports 2fa. Also requires Docker which isn't too difficult.

Another vote for Syncthing. Might be a little too complicated for some though

It's not quite self hosted, but Soulseek allows you to share share private directories with buddies. Soulseek might require a port forward.

Other than that, there are the many pasteboard solutions that have been mentioned. They'll either require a port forward or reverse proxy (nginx etc.) to access outside the network though.

Any particular reason why you can't do something like host a Send instance instead? Better to treat "filesystem behind the network" and "files to share" as two different things: one is imanent, the other is punctual and sporadic.

I use Pingvin. You upload a file to it and it generates a link. Has expiration on the link.

You can allow anonymous uploads or not, give friends logins etc.

I have it locked down to just me with a login and I use it to let others download the files.

I haven't bothered to set up anything that complex, but mega.nz gives you an encrypted 50GB of free space. I'm not crazy about supporting Kim Dotcom's crazy ass, but it periodically solves problems for me.

I was also a founding member of box.com so there's another free 50.

Does anyone use Blaze? ( https://github.com/blenderskool/blaze )

I always thought it looked promising, even supporting peer-peer transfer, so in theory if you are transferring to multiple destinations multiple folks would seed.

Edit: ah, ni commits for the last 2 years

I’ve been looking for something like this as well. Hopefully someone has a solution.

I use Warpinator in combination with tailscale

https://zipline.diced.sh/

you might configure Syncthing in that way

Onion share might be an option.