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Thanks for the reply.

 

-Is it worth sending in a statement explaining my scenario to the IRS regarding the underpayment and see if I can claim a waiver?

 

-Is it better to pay the estimated underpayment penalty when I file my tax returns? Or wait until the IRS send me the bill with the actual penalty amount? 

 

-If the estimated penalty that I end up paying upfront is less than the actual penalty that I owe, will this incur any late fee or even more penalty?

 

Thanks again.