Remote Events not connecting in Studio

Remote events are not always connecting on the server-side when testing in Roblox Studio. I have an event that is firing from the client to the server, indicating when a monster is damaged.

Video showing expected behavior
robloxapp-20230220-1952377.wmv (2.0 MB)

Video showing remote event not connecting on server side
(no changes were made to any code at all)

robloxapp-20230220-1953148.wmv (2.9 MB)

When this issue does happen, it seems to show up during testing, and when I stop the game and play again, sometimes this resolves itself, sometimes it does not. It is sort of difficult to diagnose where this issue is coming from, since no errors are being thrown and this does not happen 100% of the time. I am not sure if this is a Studio bug. Is there a way I can figure out why this is happening?

If I only add a print() to the function that is supposed to connect on the server side, then run the game again, the function always goes back to working as expected and the print() outputs normally.