5 questions to ask tax software vendors before October 15

The run-up to October 15 looks nothing like the sprint to April. Work volume picks up from the summer, but still pales in comparison to what awaits in spring. That’s why extension season is the ideal window for tax software vendor evaluation and testing out new applications ahead of busy season. 

But not all technology partners can provide the same level of automation, integration, and support. 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.

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1. Where does automation end and review begin?

2. Are these solutions actually integrated, or do they just look integrated?

3. What does onboarding actually look like once we commit?

4. What’s the real extraction rate, and what’s coming after it?

5. Can your staff work through a return without losing their place?

Make the most of the quiet before busy season 

1. Where does automation end and review begin? 

Most vendors boast the ability to automate basic administrative and preparation tasks. But they don’t always provide a clear framework for reviewing that work. A missing W-2 is an easy flag for any system. 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. 

• Ask for a live look at how the diagnostics handle a genuinely complex scenario, not a routine one. 
• Ask what the diagnostic engine is actually tied to. Software that claims to update the moment a bill passes is guessing at intent. A strong diagnostics engine updates when the taxing authority releases its guidance and forms, so the rule applied to your client’s return holds up under review. 
• Ask what happens after a flag. 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? 

Thomson Reuters UltraTax CS runs diagnostics as data is entered, so issues surface while a return is still being built rather than at final review, and each diagnostic links directly to the input screen behind it.  

The preparer goes straight to the gap instead of hunting for it, then decides what’s right for that client. Surfacing the problem and showing you where it lives is the software’s job; the person in the chair stays in charge of the answer. That’s the standard any tax software vendor evaluation should hold every vendor to, including the one you already use.

2. Are these solutions actually integrated, or do they just look integrated? 

Every SaaS product has its own standalone functionality, but how that solution interacts with the rest of your workflow makes all the difference. Your tax software vendor may claim to integrate with certain third-party solutions, but that integration might not be as strong as advertised. 

• Ask whether there is a real partnership between the two vendors, and whether the interfaces have been tested together end to end in the tax scenarios that your firm faces. 
• Ask how the data physically moves. A supported API or a certified import is not the same thing as robotic process automation driving your screen and keyboard the way a staff member would. Screen-level automation breaks with any interface change, carries no validation behind it, and in some cases runs against the other vendor’s terms and conditions. 
• Ask who you call when a handoff drops or duplicates data mid-season, and whether both vendors will be on that call. If each one can only point at the other, your firm owns the problem. 

UltraTax CS integrates directly with SurePrep 1040SCAN for scanned source documents and with SafeSend for electronic return delivery. Each solution lives under the same ecosystem, so files move between intake, preparation, review, and delivery seamlessly with zero confusion when support is needed. 

3. What does onboarding actually look like once we commit? 

Testing out new tools during extension season only pays off if your team can get it running before volume picks back up. During evaluation, ask your tax software vendor what implementation actually looks like, not just what gets promised on a sales call. 

• Ask who owns your onboarding. Will a dedicated specialist walk your firm through setup, or will you be placed in the queue with every other client? 
• Ask how client data and prior-year returns convert from your current system, and what still has to be entered by hand. 
• Ask what training is available for staff who’ve never touched the tool, and whether it’s a one-time session or something they can revisit later. 

Thomson Reuters backs up implementations with dedicated conversion and migration services that move client data over from an existing platform, plus ongoing access to on-demand and live training as staff ramp up. That’s the kind of support that determines whether a new tool is actually ready by the time volume returns. 

4. What’s the real extraction rate, and what’s coming after it?

Every vendor claims to offer extensive automation, but few will boil that down to a precise number. 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. Then ask the harder second question, which is what that vendor is building on top of it next. 

• Ask for an actual accuracy percentage on unstructured documents, measured in production rather than in a demo environment. 
• Ask what happens to a low-confidence match. Does it sit in a queue for someone to check, or does it silently populate the return? 
• Ask what they have shipped in the last three years that firms are running at volume today, and what comes next. A vendor with only a track record is telling you this is as good as it gets. A vendor with only a roadmap is asking your busy season to be the pilot. 

SurePrep 1040SCAN extracts data from over 40 IRS forms along with State K-1s, Federal Organizer pages, grantor letters, margin interest, and investment fees. It also boasts patented text-layer matching combined with AI that removes the need to verify OCR data on roughly 65% of standard documents. That’s real time back for your preparers, especially during peak busy season. 

5. Can your staff work through a return without losing their place? 

Every tax preparer has some version of the same habit: alt-tabbing between a diagnostic flag, the input screen it points to, and last year’s return to check for a discrepancy. Ask how much of that switching the software actually eliminates, rather than just making it slightly faster. 

• Ask whether preparers can view inputs, forms, prior-year data, and diagnostics at the same time, or whether each one requires closing the last. 
• Ask how many clicks it takes to jump from a diagnostic flag to the exact field that caused it, and back again. 
• Ask whether the software supports true multi-monitor layouts, so a preparer can compare this year’s return to last year’s side by side instead of toggling between them. 

UltraTax CS lets preparers view input, forms, prior-year data, and diagnostics simultaneously across as many as four monitors. For a firm running staff through dozens of returns a day, that’s fewer seconds lost per file, and those seconds add up fast once volume returns in the spring. 

Make the most of the quiet before busy season 

Extension season won’t stay quiet for long, but it’s a perfect window to test the opportunities and limitations of your technology partnership.  Your tax software vendor evaluation should look for straightforward answers, hands on implementation, and the functionality your firm needs to thrive in April. The right answers now make next April lighter than this one. 

If your current software partner doesn’t meet the mark, schedule a free, no-commitment UltraTax CS demo to see what a more powerful partnership could look like. 

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