How to send files anonymously

Anonymous, in practice, means the recipient gets the file and not your life story.

Stop using the letter slot

Email will pretend to help and then bounce. A shared drive will succeed and then never leave. A transfer is the third thing: a link with a clock.

A link with a clock beats a folder with no ending.

Do this

It does not mean nobody could ever be asked who uploaded it. If you need cryptographic anonymity, you want a different threat model and probably a different tool. For a client delivery, a link with an expiry is the privacy people actually meant.

On Pink Jeepney: open the site, drop the files, write one sentence on the ticket if they need it, copy the link. Several files can come back down as one zip. Send the link in whatever thread you already have. The transfer does not need to become the relationship.

When this is the wrong tool

If the file must be unreadable to the host, use Wormhole or Tresorit Send. Pink Jeepney will expire, and it will burn after download if you ask. It will not hide the bytes from the machine that stored them. Know which problem you have.