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!

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.

I've been dealing with similar Direct Pay frustrations for years, and one thing that's often overlooked is checking if you have any outstanding IRS correspondence or notices that might be putting a hold on your payment processing. Even something as simple as an unresolved notice about a minor discrepancy from a previous year can silently block new payments. Here's what I'd suggest trying before your deadline: 1. **Log into your IRS online account** (not the guest payment system) and check for any notices or account alerts that might explain the rejections 2. **Try the payment at exactly 6 AM Eastern** when their systems reset for the day - I've had success with this timing when afternoon attempts failed 3. **Use a private browsing window** with all extensions disabled to eliminate any cached data issues But honestly, after reading through everyone's experiences here, I think the smartest move is just using the phone payment system at 1-888-PAY-1040. That $3.99 fee is nothing compared to the stress you're dealing with, and you'll have confirmation within minutes. The IRS payment systems are notoriously unreliable during busy periods, so don't take it personally - you're doing everything right! Sometimes the path of least resistance is worth a few extra dollars for peace of mind.

I've been experiencing the exact same Direct Pay issues and want to share what finally worked for me after reading through all these helpful suggestions. After trying multiple browsers, different times of day, and checking my bank account details, I discovered the problem was actually a combination of two things: my VPN was running (which I didn't even think about) and my bank had flagged the previous IRS payment attempts as potentially fraudulent. Here's what solved it for me: 1. Called my bank first to remove the fraud flags and pre-authorize the IRS payment 2. Disabled my VPN completely 3. Used Safari in private browsing mode with all extensions disabled 4. Made the payment at 6:30 AM Eastern when system traffic is lowest The payment went through immediately and I got confirmation within minutes. That said, if you're cutting it close to your deadline, I'd honestly just recommend calling 1-888-PAY-1040 and paying the $3.99 fee. After spending hours troubleshooting this, that small fee is absolutely worth the guaranteed processing and peace of mind. The IRS payment systems are just unreliable during busy periods, and it's not worth risking penalties over a technical glitch. Don't stress too much about it - this thread shows how incredibly common these issues are, and there are definitely reliable alternatives available!

Great question! I went through this exact same situation when I started renting out a room in my condo. Your 12% calculation based on square footage is the right approach - that's the standard method the IRS expects. One thing I learned the hard way: make sure you're using the correct square footage. Only count livable space, not garages, unfinished basements, or storage areas. Also, if your tenant has access to common areas like the kitchen or living room, some tax professionals suggest you might be able to claim a slightly higher percentage, but definitely document your reasoning. For the utilities you split with your tenant - you'll want to be careful here. If they pay you directly for half the electric bill, don't include that as rental income. Just report the $12,500 rent and deduct your portion of the utilities. Since you mentioned the house is new, remember that you can't depreciate the land value, only the structure. Your property tax assessment should break this down, or you can use local assessment ratios (typically 80% structure, 20% land, but varies by location). One last tip: consider setting up a separate checking account for rental income and expenses. Makes tracking everything so much easier come tax time!

I'm dealing with a very similar situation - just started renting out a bedroom in my house this year! One thing that hasn't been mentioned yet is keeping detailed records of your tenant screening and advertising costs. Those are 100% deductible business expenses. Also, for the depreciation calculation that's confusing you - you'll need your home's purchase price minus the land value. If your closing documents don't break this down clearly, you can often find the land-to-building ratio on your county assessor's website or property tax records. Quick tip: Since you mentioned splitting electricity with your tenant, make sure you're tracking this consistently. I keep a simple spreadsheet each month showing the total bill, what my tenant pays me, and what I actually pay out of pocket. This makes the tax calculations much cleaner. The 12% calculation you're using sounds right for deductions, but remember that percentage will be crucial for depreciation too - you can only depreciate the rental portion of the home's value over 27.5 years. Good luck with your first year of rental income taxes!