Hey there Matt, welcome aboard.
I also manually send webmentions for each link in an article, but it would be nice to make a script to do that hard work for me. Additionally, I should make accounts on more sites (like Twitter) and join a service like brid.gy to sync my content between them. I would also like to experiment with owning my issues and pull requests, but that’s a thought for another day.
In addition to webmention.js which Jamie already, uh, mentioned, I’ve also written a tool called Pushl which automates the sending of webmentions. I have it set to run as part of my post-publish git hook on my site’s repository, as well as in a cron job that runs every 15 minutes. It requires an RSS or Atom feed at present (adding
h-feed support is on my TODO list) but it only uses the feed for post discovery, rather than for target discovery, so it doesn’t need to be a full-content feed or whatever. It also maintains state so it can handle deletes and edits and so on.
There’s a few other automated Webmention sending things out there, like a lot of IndieWeb folks use webmention.app which can be used in combination with IFTTT, although I can’t speak to the reliability of that solution.