I was recently asked whether you should send your tax payments to the IRS by certified mail.
It is my rule of thumb that everything you send to the IRS should be sent via Certified Mail Return Receipt Requested. Why? Because you want to be able to prove that you sent what you say you sent and prove that the IRS has received it.
Let’s think about it for a second. The IRS is made up of hundreds of offices all over the country with thousands and thousands of employees. There are millions of letters sent to the IRS each year. Do you think they ever lose a piece of mail? From experience, trust me, the answer is YES!
Especially when you are sending payments to the IRS you want to make sure that they have received your money. But this is also extremely important if you are filing your income tax returns by mail because of the impact penalties and interest can have on the amount you will owe if the IRS believes that your income tax returns were filed late or not filed at all.
I have also been able to have appeals cases reopened after the IRS closed them because they said they never received anything, but I was able to produce the documents I sent along with proof of mailing and proof of receipt by the IRS. This has saved clients lots of money and time over the years.