Redirects/URL aliases not working as expected

Do you have redirects enabled as souce/target in the settings page?
As soon as you have a redirect in the middle it starts becoming one extra entity in the chain, so that needs to be tracked as a separate entity.

Yes, redirect and URL alias are enabled as both source and target. One thing I forgot to mention in my post (I'll update it) is that these links are not properly linked using Linkit or some other tool, they are hardcoded in the source in a/href tags. <a href="/title-1A">cool page</a> They work as expected and appear in usage, but if you recreate usage settings after switching the page to /title-1B, those hardcoded links to /title-1A disappear from the usage tab.

Side note: Needing to have redirect enabled to track redirects isn't ideal UX for our authors. They see "- Restricted access -" "Redirect: redirect," which can be confusing. Admins already can see redirects from inside the node edit screen. It would be nice to be able to granularly exclude the actual redirect entity from appearing in the usage table but still be able to view the actual links that happen to be redirected. If you think this request has legs, I can open a separate ticket.