Taxaway

Filing extensions / making extension payments

An extension only avoids the late filing penalty; there is late payment penalty and interest on any balance due.*
If you expect to owe, you can make a payment online. This is easier than having the direct debit transmitted via my software when I efile the extension, because in that situation I would need you to sign a signature page before the extension can be efiled/debited.
In addition to direct debit, both Federal and MA offer payment via credit card but a service fee is charged.

Websites:

Federal Direct Pay

MATaxConnect (you don't need to register, see quick links: make a payment)

If you have a refund and didn't file an extension, no penalty is assessed since it's calculated on the balance due. However, you might decide to be cautious and have an extension filed.

*If 90% of the Federal tax is prepaid before the initial deadline, the late payment penalty is waived if the remaining tax is paid by the extension deadline.

Important to realize: If you have a Federal extension to Oct 15 but do not file by then, the late penalties/interest are assessed retroactive to the April filing deadline: as if you didn't have an extension. If for some reason you cannot meet even the Oct 15 deadline, pay what might be any balance due.
MA automatically grants an extension if 80% of the tax is paid by the initial deadline, but on the other hand, the extension will be invalid if 80% of the tax is not prepaid by the initial deadline. So it's important to prepay your MA tax liability as much as possible.

A few details on the numbers if balances due:

Late filing penalty: Fed 5% per month / MA 1% per month, each up to 25%.
Late payment penalty: Fed 1/2% per month / MA 1% per month, each up to 25%.
Late interest is 7% APR for Fed, 8% APR for MA (as of 2026).
You can see even if you owe, it's more important to at least get the extension filed and worry about the tax later, if necessary. An installment agreement can reduce the late payment penalties being assessed on the balance.
For the Federal, there is a minimum late filing penalty of 100% tax or $525 (as of 2026), whichever is less, if you file 60 days past your applicable original or extension deadline. For example, if you owe $850 and file four months late without an extension, the penalty will be $525 not $170 (5% x 4 months). If you had owed $400, the penalty is 'capped' at $400 but that's still a 100% penalty! It's just as important with an extension, to meet that extension deadline.

My fee is just $15 for extension efiling, +$5 if extension signatures needed for direct debit, added to the final tax prep fee. I can also efile CA, LA and NY extensions, other states you would need to visit their websites; many states automatically grant theirs if the Federal is on extension.

First Time Abatement

Taxpayers who are current with prior tax filings and prior year tax liabilities may be eligible to request a first-time abatement of assessed penalties. We can discuss this procedure if applicable.