5 questions to ask tax software vendors before October 15

The useful part

Extension season provides a rare opportunity to assess workflows, test solutions, and prepare teams before peak filing volume returns. That's why extension season is the ideal window for tax software vendor evaluation and testing out new applications ahead of busy season. Not all technology partners can provide the same level of automation, integration, and support.

How it works

• Ask for a live look at how the diagnostics handle a genuinely complex scenario, not a routine one.
• Every SaaS product has its own standalone functionality, but how that solution interacts with the rest of your workflow makes all the difference.
• Ask who you call when a handoff drops or duplicates data mid-season, and whether both vendors will be on that call.
• It also boasts patented text-layer matching combined with AI that removes the need to verify OCR data on roughly 65% of standard documents.
• Ask how much of that switching the software actually eliminates, rather than just making it slightly faster.

What to take from it

During your tax software vendor evaluation, ask for something concrete, tested against documents your clients actually send: scanned 1099s, photographed brokerage statements, PDFs with pages out of order. If each one can only point at the other, your firm owns the problem. To find out what your options are (and whether it's worth looking elsewhere in 2027), here are five questions to ask your tax software vendor ahead of the extension deadline.

Example or evidence

• Then ask the harder second question, which is what that vendor is building on top of it next.
• A basis limitation buried in a multi-year K-1, or a state conformity issue tied to a recent law change might slip under the software's radar.
• Software that claims to update the moment a bill passes is guessing at intent.
• Does the software simply tell you something looks wrong, or does it take you to the exact field where the information is missing and leave the judgment call to you?

Details worth keeping

The run-up to October 15 looks nothing like the sprint to April. Are these solutions actually integrated, or do they just look integrated? What does onboarding actually look like once we commit?

Related coverage

• Thecollegeinvestor: For most, free filing with the IRS or tax prep software is best, but others have complex situations. Here's to know how to do your own taxes.
• Thomsonreuters: Most accounting firms have invested heavily in organizing data but what about the context? They have tax software, document …