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Originally published on Forbes.com.

In the summer of 2014, Jonathan Haar became one of my heroes. The story began in 2011, when Mr. Haar extended his 2010 Massachusetts income tax return.  Massachusetts required electronic payment on extensions with $5,000 or more due.  Mr. Haar sent in a paper check in the amount of $19,517 on April 15, 2011 with his extension.  For that he got hit with a $100 penalty.

He Appeals And Wins

I don’t know about you, but I would have sent in the hundred bucks.  Mr. Haar, though, became my hero by representing himself before the Appellate Tax Board and winning.  He maintained that he had a reasonable cause for not paying electronically.  The electronic payment exposes his finances to the risk of cyber attack.

The ATB found in his favor.

On the facts of this appeal, particularly the appellant’s credible testimony concerning his consistent practice of avoiding the payment of his bills electronically, the Board found and ruled that the appellant exercised the degree of care that an ordinary taxpayer in his position would have exercised when he made his timely payment by check, contrary to the Commissioner’s electronic payment mandate.

The Bad News

Something tells me that there is more at stake here than a lousy hundred bucks, because the Mass DOR appealed the ATB decision.  And I am sorry to say that the Appeals Court of Massachusetts ruled in favor of Mass DOR.  The Appeals Court was influenced by the fact that Mr. Haar had been warned when he used a paper check with his 2005 extension and had complied with the mandate when he sent in his 2007 extension.

It is not disputed that the taxpayer was aware of the electronic payment requirement; he received notice from the commissioner for failing to comply as long ago as tax year 2005. It is also clear that he was able to comply with the requirement, as evinced by his compliance during tax year 2007. On this record the commissioner was not required to consider this taxpayer’s professed concerns of privacy (irrelevant, as paper filings are scanned electronically) or security (ignored by the taxpayer himself in 2007) to be reasonable.

There you have it “short and sour”.

Trouble With Being Pro Se

An indication of why Mr. Haar might have lost is in the footnotes.

After the taxpayer filed a brief in this court, he was notified that it was nonconforming in thirteen different respects, including the lack of (1) a statement of facts, (2) a statement of the issues, (3) a statement of the case, (4) a table of authorities, (5) references to the record, and (6) a certificate of service. He did not file a corrected document in the ensuing eight months before the scheduled hearing in this court. On the basis of his oral representation that he would file a conforming brief he nevertheless was allowed to participate in oral argument with the consent of the Commonwealth. Thereafter he filed a second document that was less conforming than the first.

Still, I wouldn’t rule out Mr. Haar appealing.  I hope he does.