I had a very similar situation last year where my taxable income was lower but I ended up owing taxes instead of getting a refund. The culprit turned out to be a combination of factors that weren't immediately obvious. First, definitely double-check that Box 12 parser issue you mentioned. I've seen parsers misread codes like "D" (401k contributions) as "DD" (employer-sponsored health coverage), which can dramatically affect your taxable income calculation. Second, when you changed jobs mid-year, did your new employer know about your previous year-to-date earnings? Often they don't, so they calculate withholding as if your new job salary is your only income for the entire year. This frequently results in under-withholding. Also check if you had any life changes that affected your tax situation: got married/divorced, had a child, moved states, or changed health insurance. Even small changes in pre-tax deductions like health insurance premiums or 401k contributions between employers can shift your taxable income enough to change your tax bracket. For Line 23, look specifically at whether you did any gig work, sold investments, or withdrew money from retirement accounts this year that you didn't do last year.

I went through something very similar last year and it was incredibly frustrating! The good news is that Line 16 is actually pretty straightforward - it's just pulling directly from the IRS tax tables based on your taxable income on Line 15. What I found was that even tiny changes in my situation created a domino effect. In my case, I had switched from contributing to a traditional 401k to a Roth 401k mid-year without realizing it would increase my taxable income (traditional contributions reduce taxable income, Roth doesn't). That small change pushed me into a higher tax bracket. Since you mentioned the W-2 parser potentially misreading Box 12, definitely manually verify those entries. I've seen parsers confuse retirement contribution codes with other codes, which can swing your tax calculation by hundreds or even thousands of dollars. For Line 23, check if you did any side work, even small amounts. If you earned more than $400 in self-employment income, you'd owe self-employment tax that shows up there. Also, did you cash out any vacation time when you left your previous job? Sometimes that gets taxed differently and can create unexpected tax obligations. The job change mid-year is probably the biggest factor though. Your new employer's payroll system likely calculated withholding based only on your new salary, not accounting for the income you'd already earned. This almost always results in under-withholding.

Another option worth considering if you have substantial unreimbursed business expenses: talk to your employer about either reimbursing these costs or offering an "accountable plan" for expenses. My company initially wasn't covering our WFH equipment either when we went hybrid, but several of us pointed out the tax disadvantages to employees. They ended up creating a formal expense reimbursement plan that follows IRS "accountable plan" rules. This way, the company gets the deduction and employees receive tax-free reimbursements. Might be worth bringing this up to your HR department with some research on accountable plans. Many employers aren't aware of how these plans benefit both the company and employees.

Just wanted to add another perspective as someone who went through this exact confusion last year. The suspension of miscellaneous itemized deductions really caught a lot of people off guard, especially those of us who had been claiming unreimbursed employee expenses for years. One thing that might help: even though you can't deduct those expenses now, keep detailed records of everything. If the TCJA provisions do expire in 2026 as scheduled, you'll want to have all that documentation ready. Also, some of these expenses might be relevant for other tax situations - like if you change jobs and negotiate expense reimbursement, or if you start any freelance work where they could become legitimate business deductions. The silver lining is that this whole experience taught me to be much more proactive about discussing expense reimbursement with employers upfront. When I started my current job, I made sure to negotiate coverage for professional development and equipment as part of my compensation package rather than assuming I could just deduct it later. Don't feel bad about being confused - the tax code changes have made this area really murky, and even some tax professionals were initially unclear on the implications!

As a tax professional who's been through the software selection process multiple times, I'd echo the recommendations for Drake or TaxAct Pro for your situation. Both are solid choices that won't overwhelm you as a beginner while still being capable enough to handle your expected client mix. One thing I'd add that hasn't been mentioned much - consider the software's diagnostic and error-checking capabilities. When you're new, having software that catches potential issues and explains them clearly can be a huge lifesaver. Drake excels at this with very clear diagnostic messages, while some of the higher-end options assume you already know what various error codes mean. Also think about your workflow preferences. Some preparers love the interview-style approach (great for ensuring you don't miss anything), while others prefer the forms-based method once they're comfortable. Most software offers both, but some do one style much better than the other. Given your 40-50 return volume and mix of return types, you're in that sweet spot where mid-tier software makes the most financial sense. You can always upgrade in future years as your practice grows - and by then you'll have a much better sense of what features matter most to your specific workflow and client base. Good luck with your EA exam! That credential will serve you well in building client trust.

I've been doing tax prep for about 6 years now and want to echo what others have said about Drake being an excellent choice for someone in your situation. What really sold me on Drake when I was starting out wasn't just the price point, but their comprehensive training program. They offer free webinars throughout the year, not just during tax season, which helped me stay current on tax law changes. Their knowledge base is also really well-organized - when you're stuck on something at 9 PM during busy season, being able to quickly find clear explanations and examples is invaluable. One practical tip: whichever software you choose, set up your practice with a few test returns during the off-season using your own tax situation or family members' returns from previous years. This lets you get comfortable with the software's flow without the pressure of client deadlines. I did this with Drake and it made my first real tax season so much smoother. Also, don't underestimate the value of software that integrates well with tax research tools. As you're building your expertise, having quick access to reliable tax resources from within your software can be a real confidence booster when you encounter something unfamiliar. Drake handles this integration really well. Best of luck with your EA exam and your new practice! The combination of good software and that credential should set you up nicely for success.

Has anyone tried using the IRS Transcript service instead? You can request a Wage and Income Transcript as the executor which would show all info reported to the IRS including the SSA benefits. Might be easier than going through SSA directly.

I went through this exact situation with my grandmother's estate two years ago. The IRS Transcript route that Ana mentioned is actually one of the most reliable options - Form 4506-T as the executor will get you a Wage and Income Transcript that includes all the SSA benefit information reported to the IRS. But if you need something faster, I'd recommend the in-person SSA office visit that Victoria suggested. Call ahead to make an appointment and bring your death certificate, letters testamentary, and your ID. They can often print the benefit verification letter on the spot. One thing to keep in mind - if your father received both Social Security retirement benefits AND Medicare premium deductions, make sure whatever document you get shows the net amount actually received, not just the gross benefit amount. The Medicare premiums are deducted before the check is issued, so you want to make sure you're reporting the right taxable amount. Also, don't stress too much about getting the exact form. The IRS is generally understanding about estate situations where original documents aren't available, as long as you can document your efforts to obtain them and use reasonable estimates based on available records.

Be very careful with this strategy - while it can work legally, the IRS scrutinizes income deferral arrangements closely. The key test is whether you have "constructive receipt" of the income in 2023. For your arrangement to pass IRS scrutiny, you need: 1. A formal written agreement stating your employment begins January 1, 2024 2. Clear documentation that you have NO legal right to demand payment in 2023 3. The employer's payroll system should not even have you as an employee until 2024 However, there's a potential red flag in your situation: you mention doing actual work for Company Y in October-December 2023. If the IRS views this as earned compensation that you're artificially deferring, they could challenge the arrangement. The safer approach would be to structure any 2023 activities as unpaid training or onboarding rather than compensable work. Also consider: - Document legitimate business reasons for the January start date (not just tax avoidance) - Ensure Company Y doesn't accrue the expense in 2023 on their books - Keep records of all agreements and communications Given the complexity and your multiple tax goals (student loans, IRA rebates, energy credits), I'd strongly recommend getting professional tax advice before proceeding. The potential savings need to be weighed against audit risk and penalties if the IRS disagrees with your position.

This is a really well-thought-out tax strategy! I've seen similar arrangements work successfully, but there are a few additional considerations that might help strengthen your position: Since you mentioned Company Y is "fine with officially starting employment on 1/1/24 for payroll purposes," I'd recommend getting this in writing as part of a formal offer letter. The documentation should explicitly state that your W-2 employment begins January 1, 2024, and that you have no entitlement to compensation before that date. One thing that caught my attention is your mention of the 24% federal tax bracket. With your strategic income deferral, make sure you're not accidentally pushing yourself into a higher bracket in 2024 when the deferred income hits. You might want to run some projections to ensure the overall tax impact across both years still achieves your goals. Also, regarding the Inflation Reduction Act rebates - double-check the income limits and timing requirements. Some of these programs have specific rules about when income is measured, and you want to make sure your deferral strategy actually helps you qualify. The student loan payment recalculation based on 2023 taxes is probably where you'll see the most immediate benefit from this approach. Just remember that when those payments do go up in 2025 (based on your higher 2024 income), you'll want to be prepared for that adjustment. Overall, with proper documentation and legitimate business reasons for the January start date, this approach should work. The key is making sure everything is structured correctly from the beginning rather than trying to fix it later.