1065 mailed return lost by USPS

[DARROW]

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?

[xmasbaby0]

@DARROW 

"My plan is to now e-file it "

E-filing is closed for 2022 returns.  You have to file by mail.  Use a mailing service that will track it so you will know it was received.

[DARROW]

I just e-filed - I know normally it would be closed by now I'm guessing it's still alive because of delays (CA has later deadlines due to disasters for example).  

[Mike9241]

i would think it's best to pay the penalty on or before the due date - make sure the postmark is on or before the due date and I would even suggest using a tracking method. if you pay and the IRS rejects your explanation then additional penalties and interest tack on. If the IRS accepts it, they should refund the payment.