Internet postage is OK, but not enough for timely mailing

Postage downloaded from the internet isn’t enough to prove that you timely mailed something to the IRS or a court. You must also prove that your package would have been delivered no later than a package bearing United States Postal Service postage. The Tax Court ruled that taxpayers who, in addition to using private postage, sent their package by certified mail, timely filed their petition, even though the court received it late. (Pearson v. Commissioner, 149 T.C. 20, U.S. Tax Court, 2017)

Seven days late. Taxpayers rang up more than $80,000 in tax deficiencies and accuracy-related penalties. The last day for them to file a petition in the Tax Court to contest the assessment was April 22, 2015. Their lawyer mailed the petition with sufficient postage prepaid through, a USPS-approved commercial vendor, on April 21. Although the envelope wasn’t stamped with official USPS postage, it was sent certified mail and had a tracking number.

The petition arrived at the court seven days late, on April 29. The IRS sought to have the case dismissed, based on the lateness of the petition. The Tax Court ruled against the IRS. Tax Court: The petition was timely filed; it bore an April 21 stamp from and it was late because certified mail often takes up to eight days to deliver.

Postage rules. Until the IRS and courts accept electronic delivery, you have to be concerned with postage and delivery dates. There are three ways to meet the timely-mailing rule:

1. If an item is postmarked by the USPS on the day it is due, the IRS or a court will consider it timely filed, even if they never receive it. Catch: If your envelope is stamped by a private meter and is also stamped at a later date by the USPS, the USPS stamp prevails.

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2. If your envelope bears a private stamp, it will be considered timely filed if it’s received no later than a document contained in an envelope that’s properly addressed, mailed and sent by the same class of mail that would ordinarily be received, if it were postmarked at the same point of origin by the USPS.

3. If your envelope bears a private stamp and is received late, it will be considered timely filed if you can prove that you deposited the envelope with the USPS by the due date, that the delay was the fault of the USPS and the cause of the delay.

PROCRASTINATORS RARELY WIN: If you’re going to tussle with the IRS, it should be over a tax assessment, not whether your documents were filed on time. Don’t wait until the last minute to file. Regularly remind everyone of the deadline and the mailing rules.