I Asked ChatGPT Whether Filing an Extension Is a Bad Idea — Here’s What It Said
Written by
Crystal Mayer
Edited by
Amen Oyiboke
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Tax season is in full swing, and the pressure is on to get federal returns filed by April 15. For some, however, that deadline is challenging.
Luckily, most people can file an extension. But is it smart to do so? I asked ChatGPT whether filing an extension is a bad idea — here’s what it said.
When Filing an Extension May Make Sense
ChatGPT didn’t think filing an extension was a big mistake, and in some cases said it may even make sense to do so. For instance, if you’re missing documents like a 1099 filing, an extension can help prevent having to make amendments later. The chatbot also said filing an extension may be a good idea if your taxes are complicated or if you simply need more time.
The experts at Intuit TurboTax noted there may be several good reasons to file an extension. A request for a tax extension is filed through the federal government with Form 4868, and it must be submitted prior to the original tax deadline. Filing an extension can help ensure that taxes are not filed before all documents are received, or if an “unexpected life event” has occurred, such as a natural disaster or the sudden loss of a loved one. The Internal Revenue Service (IRS) does not require an explanation, so any reason is sufficient to extend the filing deadline.
When an Extension May Not Make Sense
There are instances where the AI-assistant said it may not make sense to file an extension, including if your return is simple, you have all of your documents, and you are getting a refund. Also, an extension to file does not equal an extension to pay, explained ChatGPT. Taxpayers must still estimate and pay what they owe by the original tax deadline. Failing to pay taxes in full can result in interest payments and a failure-to-pay penalty.
According to the IRS, filing an extension gives taxpayers an additional six months to file their taxes without penalty. This means that a taxpayer who has successfully filed an extension will have until October 15, 2026, to file instead of the normal tax deadline of April 15. There are three ways to get an extension: pay online and note that you are paying as part of filing for an extension, use IRS Free File, or request an extension by mail.
The IRS, however, reiterates the point made by ChatGPT, that an extension to file is not an extension to pay. Failure to pay by the original deadline can result in fines and penalties.
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