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Can I file a second extension?

In general, you can’t file a second extension. See below for exceptions however.

Once upon a time you could request a second extension (Form 2688) until mid-October if you couldn't file by the first extension's mid-August deadline.

In 2005, the IRS eliminated the second extension and updated the first extension deadline (Form 4868) to October 15.

Exceptions that allow for a second extension include:

For tax year 2019, the extended filing deadline is October 15, 2020.

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