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Matt: Wayback Machine Joint
Automattic has been working with the Internet Archive to develop a plugin to combat link rot, and it’s a plugin I’d encourage you to install. As the plugin says:
When a linked page disappears, the plugin helps preserve your user experience by redirecting visitors to a reliable archived version. It also works proactively by archiving your own posts every time they’re updated, creating a consistent backup of your content’s history.
I’ve been doing this manually on my old archives, fixing broken links and tending the garden. But we can make it all automatic. 
https://shorturl.fm/GubC3