IntelliJ Inspection Highlighting Not Syncing With Changes

I'm having an issue where inspection highlighting seems to be broken, but only for a specific file. If I close IntelliJ and restart it the file will appear with the proper highlighting, but as I make updates to the file IntelliJ will highlight things improperly and never update.

A specific example would be an unterminated line issue. Since it is the last character on the line there will be a state when the line isn't terminated, but then once the semi-colon is added, the warning remains until restarting IntelliJ: 

The file in question was recently converted to TypeScript (`.js` --> `.ts`) so that could be related.

I have tried invalidating the caching and restarting and even completely deleting the IntelliJ project and recreating it. The issue persists.

Any thoughts on this weirdness?