So I tried using the suggested method of updating by dling and overwriting this lackey application file. It got an error saying "SDL2_ttf.dll had some mismatch or something like that"
I fixed it by running the lackey updater
You can't update that way all the time. You can run the lackey updater.exe, or move your old plugins folder to the freshly downloaded lackey.
You often can just take the new exe, but if that doesn't work, try the above.