I think you only get it once on the first Character you log in with
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Just remove the transmutes.gst located in your save folder (place it on your desktop or something) and then load in with the character you want to get the item, get it, exit, and then merge the transmutes.gst on the desktop back into the save folder.
Already tested it and it works.
Hmmm, I equipped the helm and set the clock to 24h and it plays the “Wipe Out” beginning and some Heroes and a Boss spawn. Anything else happen?
Edit: Don’t get me wrong, it’s very cool to see these random Bosses spawn, you never know what you’re going to get! 
How did you get the bosses to spawn? in grim internals i set time to 24 and it hasnt worked.
You need to wear the helm so you get the Passive Curse of Deadly Halloween to affect you. Then on a time basis, they spawn after the “Wipe Out” intro plays. 
I’ve been wearing it for hours and nothing
I think it worked when I wore the helm, then changed the time to something other than 24h, switched to the game, then changed the time to 24h. The curse works every 5(?) minutes or so?
Nothing is working. You set windows time clock to midnight or grim internals?
GrimInternals
I’m going to miss getting ambushed it’s late and I don’t have time to sit around playing with this it isn’t working at all. I played all day with the hat on and nothing ever happened. It says curse is active when I looked at the item but nothing ever happenes.