First time with options: How did I lose so much money?

All you guys are messed up. I am willing to bet (as I stated in my post) that there were bad prints as shown in the chart I posted and that those trades got busted. How else can it be?
 
He is not playing with pennies, every Brokerage I've traded "Naked Puts" in I had to have $300k min equity, he's either full of %$#$ or clearly messed up! Weird!

I agree...it's impossible to go sell naked options for the premium if you have a tiny account. you must have the ability to cover, just in case. No brokerage will be that dumb to leave themselves open to that gamble/exposure/risk.
 
If he didn't close his position yet, OP may very well have accidentally made money today.

Hopefully he doesn't end up slapping himself on the back about what a genius he was.
 
Maybe you placed a market order instead of limit order and got a bad fill price? That could explain why your account was displaying a negative P/L after you exercised the trade.

BTW, totally agree with the other posters that you seem to be even beyond just a noob trader. I think most noob traders would have at least done some preliminary study of why you aren't automatically "up money" the moment you sell a naked option. You've got a long way to go and a lot of studying to do before you can call yourself a noob trader 0.02$
 
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