The Last-minute Tax Extension Decision: Stop Worrying & Talk to a Tax Expert


As the April 15th tax filing deadline rapidly approaches, for most small business owners  who haven’t filed there are two options:  either finish your tax return, or consider an extension.

Small business owners and freelancers should consider speaking to a tax preparer regarding their situation to decide if there’s enough time to make a last-minute dash to submit your return.  Otherwise, the preparer will be able to file an extension, which will give the taxpayer an additional six months of breathing room.

But there’s a catch:  this only applies to the paperwork, and you are still responsible for estimating and submitting payment for your taxes. If the IRS considers your payment estimate to be incorrect, it’s possible that the IRS will assess a late penalty.  The IRS charges an interest of 0.5%/month on any portion of your taxes not paid by April 15th.

According to, an online tax preparation website, most of their customers requiring an extension often complain about not being organized enough to submit their small business returns—generally overwhelmed by the amount of tax paperwork that needs to be found and organized before meeting with an accountant.

In order to get everything squared away properly, Teaspiller recommends sites like Shoeboxed to help organize business receipts.  This makes it easier once tax season approaches for the customer, and also makes it easy to automatically upload all of the information directly into Teaspiller and share with your selected tax preparer.

Teaspiller’s certified experts (CPAs and IRS Enrolled Agents) can then help a Shoeboxed customer decide if an extension is needed, and whether or not you need to make a payment to the IRS–helping small business owners get the reassurance they need before making an extension decision.

Tax Day!

If you are just learning that today is Tax Day, you may be in a bit of trouble. For everyone trying to get them finished today, good luck! And to everyone already done, congrats!

If you think you’ll need more time, make sure to check out FileLater, an easy way to get a tax extension in just a couple of minutes.

Tax Extensions: Do They Increase Your Chances of Being Audited?

This is a guest post from our friends at FileLater, which offers and easy way to get a tax extension. They explore the question of whether or not filing for a tax extension increases your chances of being audited later. The answer may surprise you!

Continue reading “Tax Extensions: Do They Increase Your Chances of Being Audited?”