Tuesday, September 17, 2019

Tax Day Apps and More To Start – and Finish – Your Taxes

Jennifer Bosavage
April 11, 2019

2 minute read

If you’ve waited until April to start filing your taxes, you’re not alone. Compared with the same time last year, the number of individual tax returns received by March 29 was down more than 1 percent, according to the IRS.

While tax day is coming on April 15 (or April 17 in Maine and Massachusetts), you still have time to file. To help you make it through tax day, consider utilizing available software tools and apps — from those that will organize receipts and paperwork, to those that will file the return and get you on your way. Here are a few that utilize modern CX technologies to streamline the process.

Free Tax USA

According to FreeTaxUSA’s website, this service offers options to file taxpayers’ completed federal returns for no charge, with state returns at a cost of $14.99, and a deluxe version which, for some, may be worth the $6.99 upcharge. Users can start with the free version and upgrade when needed.

The deluxe version adds priority live chat customer support, lets you file unlimited amended returns, and provides audit assistance. That assistance helps users prepare for a Federal (but not state) audit, but it doesn’t provide a representative to accompany you to an audit or to correspond with the IRS on your behalf.

This app renders nicely on a mobile device, and the mobile site’s help tools are as thorough as the desktop version’s.


You can’t file your taxes with Expensify, but gathering the information needed to do the deed more easily is the aim of this app. During the expense reporting process, Expensify’s SmartScan strives to provide easy entry and simplified reporting. Expensify also advertises automatic sync of your data with other accounting tools, as well as the categorizing and coding of receipts.

According to the company’s website, Expensify can reduce the time it takes to complete an expense report by 83%, uses OCR scanning and automatically records data, and the app can also track mileage via GPS tracking.

Expensify integrates with business systems, including Oracle, and touts usability by companies of “all shapes and sizes“. Various pricing options are available.


Shoeboxed offers functionality similar to Expensify, with 3 pricing plans geared toward independent professionals, small business owners, and midsize businesses. It combines the benefits of receipt trackers with mileage logs.

Like other receipt trackers, Shoeboxed uses a mobile phone camera to capture and digitize receipt images. Shoeboxed also advertises the automatic importing of receipt data from email, and a mobile app that tracks mileage via GPS for employee expense reimbursements and IRS reporting.

For those who are overwhelmed by paper receipts, Shoeboxed also offers a service wherein users can mail receipts directly to Shoeboxed, and the company will “take care of the heavy lifting“.

Whether you utilize one of the above or a number of other existing tech solutions to complete your taxes this year, it’s clear that CX technologies have permeated countless aspects of our lives, helping to streamline even the most complex — and procrastinated — tasks.

Jennifer Bosavage
Jennifer Bosavage
Jennifer Bosavage is a Connecticut native and has been writing about technology since the fax machine debuted. While Jen has covered IT, retail, and customer satisfaction for many years, she also has an undercover history as a Secret Shopper.
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