[waferbaby]

As the person who runs usesthis.com, let me tell you it's a massive pain in the ass (I have a JSON file for every item I link to, and so many just... die.)

[pabs3]

Have you considered automatically submitting the links to the archive.org save API? Unfortunately it doesn't support HEAD anymore, only GET but basically just request this URL:

https://web.archive.org/save/$URLoflink

[waferbaby]

Ooh, neat!

[j88439h84]

Have you considered linking to a Wayback Machine archive page instead?

[waferbaby]

It's funny, I was seriously considering doing just that a day or so ago. I think I might.

[all2]

You could have a service that runs in the background (say once a week) on all outbound links that checks for 404s and then automatically updates the outbound link to the archive.org link. That or have both links.