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I made a mistake on my taxes and didn't apply the wash rule to one of my trades. Applying the wash sale rule prevented me from declaring a loss on a trade. The IRS wasn't happy and sent me a letter telling me of the error. I refiled with a corrected schedule D and ended up paying some additional tax and penalty. At that point, I thought I was done with it. A couple of months later I get a letter from the IRS demanding more money because I didn't make a quarterly payment of estimated taxes. The deal is that at the time, I was under the impression no tax was due because of the loss on the trade. Applying the wash rule changed that well after the fact.

My question is do I have a chance in hell challenging the additional penalty ($500 +/-) for not filing the quarterly estimated tax since it was the result of an honest mistake, or is it a lost cause?
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