It’s Tax Filing Season—Mail Correctly to Avoid IRS Trouble

Parts of this article are published with permission from Bradford Tax Institute, © 2021 Daniel Morris, Morris + D’Angelo

During your taxable life, you need to mail various documents to the IRS.

You likely find the idea of taking a trip to the post office distasteful because you can suffer long lines and unhelpful postal people.

What can make you endure that ugly trip to the post office? The IRS. The federal courts. Your wallet.

How One Taxpayer Suffered

The IRS claimed that Charles Crispino owed $134,327 in taxes (due to an inadvertent rollover of his traditional IRA to a SIMPLE IRA) and collected the money by levying on Crispino’s assets.

Crispino wanted to contest the IRS’s action in federal court. But first he had to timely file an administrative claim for refund with the IRS.

The claim for refund was due by June 3. Crispino’s accountant mailed the claim for refund by First-Class Mail on April 15. This probably seemed like plenty of time (49 days in advance). What could go wrong? In a word, everything.

The IRS claimed it never received the refund claim. It likely lost it, but no one knows for sure. The accountant mailed another copy in November, which the IRS received, but that was too late.

Crispino went ahead and filed his suit in federal court, but the court ultimately dismissed it because he had failed to file a timely claim for a refund with the IRS. He had to kiss $134,327 of his hard-earned money goodbye.

Crispino and his accountant could have avoided this unfortunate and expensive outcome if they had understood the IRS’s rules about when documents are deemed filed for legal purposes. Had they understood these rules, they never would have sent that claim for refund by regular first-class mail.

Under the IRS’s rules, the date a document is deemed filed with the IRS is not necessarily the date the agency receives it. You can make the IRS receipt date the date you mail or send the document if you do it right, as we explain in this article.

Regular U.S. Mail

IRS regulations provide that if you send the IRS a document or payment by Regular U.S. Mail (to the correct address with adequate postage), it is legally deemed to be filed with the agency on the date of the postmark stamped on the envelope.

But this is the case only if the IRS actually receives the document, even if it’s months late. Thus, if the envelope has a timely postmark, the document or payment is considered timely filed or paid even if the IRS receives it after the deadline for filing the document or making the payment.

The postmark on Crispino’s claim for a refund was six weeks before the filing deadline, but the IRS said it never received the first-class mailing. Thus, under the IRS regulation, Crispino did not timely file his claim for a refund.

The Mailbox Rule

Crispino argued that the IRS’s regulation does not provide the only way to establish timely filing by mail. He asked the court to apply the “Mailbox Rule.”

This common-law rule, which has been in use for generations, says that if a document is properly mailed, a court will “presume the United States Postal Service delivered the document to the addressee in the usual time.” You can present testimony from the person who mailed it to prove the date of mailing.

This is what Crispino wanted to do—present testimony from his accountant that the claim for refund was mailed on April 15 and must have been received long before the June 3 deadline.

Some courts have allowed taxpayers to rely on the common law mailbox rule.

But the court in Crispino’s case refused to do so, holding that the IRS’s regulation supplanted the old rule. Since Crispino could not prove that the IRS received his April 15 mailing, his claim for a refund was untimely filed and his case was dismissed.

Other courts also have held that the old common law mailbox rule is a dead letter and the IRS’s regulation governs. So it is highly unwise for any taxpayer to rely on the mailbox rule when they file documents with the IRS.

Registered and Certified Mail

You have available two significant exceptions to the requirement that the IRS receives the document to declare it filed on the postmark date.

  • Documents sent by registered mail are deemed filed on the registration date.
  • Documents sent by certified mail are deemed filed on the postmark date.


You need to keep the receipt. For both certified and registered mail, you want your receipt postmarked by the postal employee at the post office. (Yes, you need to make that ugly trip to the post office so you have that receipt postmarked by the postal employee.)

Key Point: If Crispino’s accountant had sent the claim for refund on April 15 by registered or certified mail, it would have been deemed received on April 15 despite the fact that the IRS claimed it never received the claim. This simple error potentially cost Crispino $134,327.

Key Point: Note that when you use registered or certified mail, you don’t need to prove that the IRS received the item you sent. It’s deemed sent on the postmark or registration date. Thus, you don’t need to obtain a signed return receipt from the IRS. But for your peace of mind, send items by certified mail using the “return receipt requested” option anyway.

Priority Mail

What about the U.S. Postal Service and come with a receipt to track other forms of mailing? These include Priority Mail, Certificate of Mailing, Express Mail Receipt, Delivery Confirmation Receipt, and Signature Confirmation. Logically, these should also qualify for “timely mailed, timely filed” treatment. But the IRS says no.

The IRS claims it lacks authority to extend such treatment to any form of U.S. mail other than registered or certified mail. Thus, forms of mailing other than registered or certified mail are treated the same as regular U.S. mail— such forms must be received by the IRS for the postmark date to serve as the filing date.

Private Delivery Services

You don’t have to use the U.S. Postal Service to file physical documents with the IRS. You can use one of the IRS- approved private delivery services listed below:

Federal Express (FedEx): FedEx First Overnight, FedEx International Next Flight Out, FedEx International Economy, FedEx Priority Overnight, FedEx Standard Overnight, FedEx 2Day, FedEx International Priority, and FedEx International First

United Parcel Service (UPS): UPS Next Day Air, UPS Next Day Air Saver, UPS 2nd Day Air, UPS 2nd Day Air A.M., UPS Next Day Air Early AM, UPS Worldwide Express Plus, and UPS Worldwide Express

DHL Express: DHL Express 9:00, DHL Express 10:30, DHL Express 12:00, DHL Express Worldwide, DHL Express Envelope, DHL Import Express 10:30, DHL Import Express 12:00, DHL Import Express Worldwide

When you use one of these delivery services, the “timely mailed, timely filed” rule applies, the same as for registered or certified U.S. mail.

Key Point: Although the private delivery services are more expensive, they are likely a more convenient option than certified or registered U.S. mail.

Electronic Mail

When the electronic mail option is available, it’s a great way to file documents because the date of the electronic postmark is deemed to be the date of filing. Thus, the IRS deems the document filed if the electronic postmark date is on or before the filing date.


Here are five takeaways from this article:

  1. Never rely on regular U.S. mail to send the IRS a document that you must file by a deadline. If the IRS loses the document or never receives it, you have no way to prove that the IRS got it. And remember, most courts won’t accept your testimony (or anyone else’s) that the document was timely mailed.
  2. Send your documents to the IRS by registered or certified mail because then the IRS deems them timely mailed, timely filed on the postmarked date.
  3. Alternatively, send your documents using one of the IRS-approved private delivery services because documents sent by these approved deliveries also receive “timely mailed, timely filed” treatment.
  4. Do not rely on Priority Mail, Express Mail, and other tracked U.S. mail because such mail does not receive “timely mailed, timely filed” treatment.
  5. When allowed, use electronic mail because it receives “timely mailed, timely filed” treatment.

Because the IRS is understaffed and has many challenges processing all the documents it receives, you need to protect yourself when you send an important tax filing due by a specific deadline.

In this article, I shared with you several strategies to avoid tardy delivery of your tax documents; like filing physical documents by certified or registered U.S. mail, or using an IRS-approved private delivery service (generally, two-day or better service from FedEx, UPS, or DHL Express). If you need guidance regarding these mail delivery strategies, please contact us at Morris + D’Angelo. This is our Expertise!

At Morris + D’Angelo, we believe that Tax Optimization is one of the most empowering and responsible things you can do to protect your growing financial assets. Tax optimization looks at a multi-year approach to minimizing tax costs. Tax avoidance is integral to tax optimization.

Parts of this article are published with permission from Bradford Tax Institute, © 2021 Daniel Morris, Morris + D’Angelo

Daniel Morris
Daniel frequently provides Media Content via Workshops, Podcasts, and Printed Articles on topics like Bitcoin and Cryptocurrency, Wealth Preservation and Planning, Global Banking, and many other high-level financial topics that serve and demonstrate the Value of our Global Network that should be of interest to those who need Private High-Wealth Services.

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Daniel Morris, Dan Morris, CPA, Portland Oregon, Dragon Slayer

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