I went to Tavern on the Meta and clicked “load to my last message”. It responded with:
Your last message is too far back; please use the transcript instead
Click here to remove the notification bar
And it links to this message, posted May 10th:
@animuson When you print a page, just set that as the printer’s test page, then print a test page.
That fixed it for me!
However, the correct message is this one, posted May 27th (yesterday):
LOL I SHOULD BE WORKING
Sorry, I thought this room deserved a message after five whole hours of inactivity.
Why can’t it find the right message?
You’re presumably clicking that button to try and load more messages because you’re not satisfied with the messages already on the page. Your most recent message is (currently) on the page already when chat loads, so using that as the point of reference would result in nothing new being loaded – even though you requested something to be.
Clicking the button uses the timestamp of the least-recent message on the page as the starting point of the search, so the message on May 10th is the correct one it should have attempted to load messages from. You could argue that if your most recent message is on the page but sufficiently old that the button should be disabled, but I don’t see a compelling reason to limit the functionality like that.