Long story filled with stupid things by me, but short version IRS did not get my form 1065 LLC tax return sent by USPS via regular mail (again stupid to not use registered mail but never had a problem before). Got a letter saying I have a $440 fine. I did once file late years ago due to confusion about the due date (I thought it was 10/15 with extension it's 9/15 for most 1065 extension filings) and was able to get the fines waived since the actual money was owed on my personal return which was not filed late.
My plan is to now e-file it (again stupid not sure why I didn't do this before although mostly habit - used to include some documentation with my returns when they were more complicated) and pay the fine - sending a check with a letter asking for the fines to be waived and explaining the return was lost in the mail and calling out my stupidity for not using registered mail.
My only question is should I pay the fine or not? Or wait until they read the letter? My thinking is I should pay and they will refund it if they waive the fines but if I don't pay I'll end up paying more in the end if they don't waive it?
