Direct Message conversation not updating after upgrade

I don't know what info to include, but all of my rooms seem to be updating except a 1:1 conversation I was having with my partner. It has some messages from "The day before yesterday" but doesn't seem to be downloading any more.

I probably haven't opened Spectral since then, and I just updated to the 2019-05-22 build a few minutes ago.

Let me know if there's more info I can include.