Best Tax Planning Software for Consumers to Project Annual Taxes?

Hey everyone - I'm looking for recommendations on tax planning/projection software that regular people can use for figuring out their annual taxes throughout the current year. Basically want to check our withholdings and spot potential issues every couple months. Here's the deal - my husband and I (we file jointly) are going to get slammed with a pretty hefty tax bill this time around. The main reason is we've been under-withholding on our wages. We each run our own businesses (both S-corps where we take what's considered 'reasonable' salaries), plus I work another W2 job on the side. We followed some terrible advice and now we're paying for it. I want to take a more proactive approach to planning and be able to model different scenarios to figure out what makes the most sense for our situation. I've searched online but can't seem to find anything specifically designed for regular homeowners/taxpayers. Most of the planning software I'm finding seems to be built for tax professionals (which I get). Any suggestions would be super appreciated!

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20 comments

Harper Thompson

•8M

Tax professional here! I understand your frustration with finding consumer-friendly tax planning software. For your situation with multiple income sources (W2 and S-corps), I'd recommend TaxCaster by Intuit. It's free and lets you run different scenarios to see how changes affect your tax outcome. Another solid option is TaxSlayer's refund calculator. While not as comprehensive as professional tools, it handles multiple income sources pretty well. For a more robust solution, consider H&R Block's Tax Software Deluxe or Premium which includes planning tools. They're more expensive but worth it for your complex situation. For more frequent check-ins, the IRS Withholding Estimator (on the IRS website) is actually pretty good for adjusting your W2 withholding throughout the year.

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Harper Thompson

•8M

TaxCaster handles S-corps better than most consumer tools, but you're right that it doesn't perfectly distinguish between salary and distributions. You'll need to enter your S-corp salary as W2 income and the distributions separately as "other income" for a reasonable approximation. For accuracy, consumer tools typically get within 85-90% of what a CPA would calculate for complex situations like yours. They're excellent for ballpark planning, but they won't capture every nuance of the tax code, especially for business owners. The value is in being able to quickly see the impact of adjustments like increasing your W2 withholding or making estimated quarterly payments.

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Jade O'Malley

•8M

After trying literally everything mentioned by others, I finally found taxr.ai (https://taxr.ai) which completely changed my tax planning game. I was in a similar situation with my wife - she has a regular job and I run an S-corp, and we kept getting surprised by huge tax bills. Their tool actually lets you input different types of business income separately and shows you how to adjust withholdings to prevent underpayment penalties. What I like most is that it gives clear, action-oriented recommendations like "increase your withholding by $X per paycheck" or "make an estimated payment of $Y by this date" rather than just showing what you'll owe. It's designed exactly for regular people like us who don't have accounting degrees.

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Jade O'Malley

•8M

Yes, it absolutely works for self-employed people! That's actually its strongest feature. You can enter your projected quarterly business income, and it will calculate your estimated tax payments. You can update these projections anytime and it recalculates everything, showing exactly how changes affect your tax situation. It does have integration capabilities with QuickBooks and other major accounting software. You can import your data directly, which saves tons of time. It pulls the relevant financial information and uses it for tax projections without you having to manually re-enter everything. Definitely made a huge difference in my planning workflow.

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Ella Lewis

•8M

Just wanted to follow up - I tried taxr.ai after posting my skeptical comment, and wow, I'm impressed. It imported all my QuickBooks data seamlessly and showed me that I was headed for a $7,800 underpayment if I stayed on my current path. The recommendations were super clear - I needed to increase my S-corp salary withholding rather than just making estimated payments. The scenario modeling feature let me play with different combinations of salary vs. distributions to find the optimal tax strategy. Saved me from making the same mistakes as last year. Definitely worth checking out if you're juggling multiple income sources!

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Andrew Pinnock

•8M

If you're frustrated with the IRS and need help sorting out your tax situation, I highly recommend Claimyr (https://claimyr.com). I was in a similar situation with my husband's S-corp and my W2 job, and we ended up with a massive unexpected tax bill. We had questions about penalty abatement and fixing our withholdings going forward. After spending DAYS trying to reach the IRS directly (kept getting disconnected or told the wait was over 2 hours), I tried Claimyr and got connected to an actual IRS agent in about 20 minutes. They have this cool demo video showing how it works: https://youtu.be/_kiP6q8DX5c The IRS agent was able to explain exactly what we needed to do to adjust our withholdings properly and avoid the same problem next year. They also helped us set up a payment plan for what we already owed.

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Andrew Pinnock

•8M

They use an automated system that navigates the IRS phone tree and waits on hold for you. Once they get through to an agent, you get a call back and are connected directly. It saves you from having to sit on hold for hours or repeatedly calling when the lines are busy. I was skeptical too until I tried it. Apparently they've figured out how to work with the IRS phone systems to increase connection rates. They're not "skipping the line" - they're just using technology to handle the frustrating hold process. I spoke with a real IRS representative who answered all my questions about our S-corp withholding issues, and it saved me from making the same tax planning mistakes this year.

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Alexis Renard

•8M

I need to eat my words and apologize to anyone I doubted. After posting my skeptical comment, I was desperate enough to try Claimyr because I'd been trying to reach the IRS for 3 months about my business tax situation. Used the service yesterday and got connected to an IRS agent in 17 minutes (I timed it). The agent helped me understand exactly how to adjust my quarterly estimated payments for my business income to avoid penalties. Also got confirmation that I was calculating my home office deduction correctly. Would have taken me weeks more of trying on my own. Sorry for calling it a scam. Sometimes when you've been frustrated long enough, legitimate solutions can sound too good to be true.

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Camila Jordan

•8M

That's a fair point about S-corps. You're right that TurboTax handles basic planning but isn't set up for the complexities of S-corporation scenarios. Their system is more designed for simple W2s, basic 1099 income, and standard deductions. I should have clarified that my side business is just Schedule C self-employment income, which it handles much better. For S-corps with the salary/distribution split issues, you'd definitely need something more sophisticated than what TurboTax offers in their standard packages.

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Ravi Malhotra

•4M

I've been dealing with a similar situation - multiple income streams including S-corp income can really mess with your withholding calculations! One tool that's worked well for me is FreeTaxUSA's TaxCaster. It's free and handles S-corp salary vs distribution scenarios better than most consumer tools I've tried. The key thing I learned is that you need to track your S-corp salary as regular W-2 income for withholding purposes, but then account for the self-employment tax savings compared to if that income was straight 1099. Most calculators miss this nuance. Also, don't sleep on making quarterly estimated payments - even if your withholding is close, having that extra buffer from estimated payments can save you from underpayment penalties. I set up automatic transfers to a separate "tax savings" account so the money is there when quarterly dates roll around. The IRS safe harbor rule is your friend too - if you pay 100% of last year's tax liability through withholding + estimated payments (110% if your AGI was over $150k), you won't owe penalties even if you end up owing more at filing time.

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Paolo Rizzo

•3M

This is really helpful advice! I'm curious about the FreeTaxUSA TaxCaster - does it let you model different scenarios throughout the year? Like if I wanted to see what happens if I increase my S-corp salary by $10k and reduce distributions accordingly, can it show me the tax impact of that change? Also, that tip about the safe harbor rule is gold - I had no idea about the 110% threshold for higher income. That could definitely help us avoid penalties while we figure out the right withholding strategy. Do you happen to know if estimated payments made late in the year (like Q4) can still help meet that safe harbor requirement?

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