Disconnect: Missing Map, but then player rejoins and map downloads fine

So on my server, I mount maps by simply adding them to the linked workshop collection. No .bsp’s, no fastdl, I don’t even resource.AddWorkshop them because this is a TTT server and I need the maps to download one at a time.

And this works, except that when I deleted all my personal addons and tried rejoining the other day I got Disconnect: Missing Map as soon as I was about to load in. I then immediately re-clicked the join server button and was able to get in without issue.

This is weird- obviously the server allowed me to download the map automatically, but why’d I have to join a second time for this to take effect? I don’t want this to deter players who will most likely not try clicking a second time.

Any help would be appreciated.
Thank you!