How to send files to someone remotely

Remote only means they are not here. The link does not care. What cares is the clock and whether their connection can finish a 20 GB download before the link dies.

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

Give them more days than you think. People are in other time zones, on other jobs, on planes.

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.