I just went through this exact situation this past tax season and wanted to share my experience. Like you, I received several W-2Gs throughout the year but was net negative overall from my casino visits. The most important thing I learned is that the win/loss statement is NOT what determines your tax liability - it's purely supporting documentation. You must report every dollar from your W-2Gs as income, period. The IRS already has copies of those forms, so there's no way around it. Here's what really helped me: I calculated whether itemizing my deductions (including gambling losses) would be more beneficial than taking the standard deduction. In my case, I had mortgage interest and charitable donations that, combined with my gambling losses, pushed me well over the standard deduction threshold. This allowed me to offset my gambling winnings with my losses. However, if you don't have enough other itemized deductions, you could end up in the unfortunate situation of paying taxes on winnings while being unable to deduct your losses. This is why keeping detailed session logs throughout the year is crucial - not just for substantiating your losses, but for making informed decisions about your gambling activity from a tax perspective. My advice: Start keeping meticulous records now for next year, and definitely consult with a tax professional who understands gambling taxes. The rules are more complex than most people realize.

I went through this exact same confusion when I started gambling more frequently and getting W-2Gs. The biggest misconception I had was thinking the win/loss statement somehow "netted out" my taxes - it doesn't work that way at all. Here's the reality: Every W-2G you received must be reported as income on your tax return, even if you're down overall for the year. The IRS already has copies of those forms, so they know about every jackpot you hit. Your win/loss statement showing you're down $3,800 doesn't change the fact that you still have taxable income from those W-2Gs. The good news is you can potentially deduct your gambling losses, but only if you itemize deductions on Schedule A, and only up to the amount of your gambling winnings. So if your W-2Gs total $2,000 and you lost $3,800 overall, you can deduct up to $2,000 in losses - but only if itemizing makes sense for your overall tax situation. This is where it gets tricky for casual gamblers. If your total itemized deductions (including gambling losses, mortgage interest, charitable donations, etc.) don't exceed the standard deduction, you're better off taking the standard deduction. But that means you pay tax on your gambling winnings with no offset for losses. My advice: Add up all your potential itemized deductions first to see if it's worth it, and definitely start keeping detailed session logs going forward. The win/loss statement helps, but the IRS wants to see your own contemporaneous records of each gambling session.

This is an incredibly useful guide! As someone who's relatively new to dealing with IRS issues, I really appreciate having these step-by-step navigation instructions laid out so clearly. I've been putting off calling about a question regarding my tax withholdings because the thought of getting lost in their phone system was so intimidating. One quick question - for the main customer service line, after you enter your SSN, does the system typically ask for any additional verification information like your filing status or AGI from your last return? I want to make sure I have all my documents ready before I call. Also, does anyone know if there are particular days of the week that tend to have shorter wait times, or is it pretty much always going to be a long hold regardless of when you call during tax season?

This is exactly what I needed! I've been struggling to reach the IRS about my 2023 tax return that shows a processing delay. The step-by-step navigation for the main customer service line is incredibly helpful - I've been making the mistake of not knowing which prompts to select and ending up in the wrong department. One thing I'd add is to have your Individual Taxpayer Identification Number (ITIN) ready if you don't have an SSN, as they'll accept that for verification too. Also, for anyone dealing with tax transcript requests, you can sometimes get faster service by calling 800-908-9946 directly rather than going through the main line. The automated system there can often provide transcript information without needing to speak to a representative, which saves time during peak season. Thanks for compiling this resource - it's going to save me so much frustration!

This is such a great question! I went through the exact same confusion last year. Just to add to what Grant mentioned - make sure you're also considering the timing of your HSA contributions for maximum benefit. If you make HSA contributions through payroll deduction, those reduce your MAGI automatically since they're pre-tax. But if you make direct contributions to your HSA (like if you have a better investment platform with your own HSA provider), you'll need to deduct those on your tax return to get the MAGI reduction. Also, don't forget about the catch-up contribution! If either you or your wife are 55 or older, you can contribute an additional $1,000 to your HSA, which would further reduce your MAGI and help with that Roth IRA phase-out range. One more tip - consider making your HSA contributions early in the year if possible. Unlike IRA contributions which you can make up until the tax filing deadline, HSA contributions for 2025 need to be made by December 31, 2025. Planning ahead will help you optimize both your HSA and Roth IRA strategies!

Great discussion everyone! I wanted to add one more consideration that might help with your planning - the backdoor Roth IRA strategy. Even if your MAGI ends up being too high for direct Roth IRA contributions after accounting for HSA contributions, you can still do a backdoor Roth conversion. This involves contributing to a traditional IRA (which has no income limits) and then converting it to a Roth IRA. The key thing to watch out for is the pro-rata rule if you have existing traditional IRA balances. But if you don't have any traditional IRA assets, the backdoor Roth is a clean way to get that $7,000 per person into Roth accounts regardless of your income level. This might give you more flexibility in your HSA contribution strategy too - you could prioritize maxing out your HSA for the triple tax advantage (deductible, tax-free growth, tax-free withdrawals for medical expenses) and then use the backdoor Roth for your retirement savings goals. Just make sure to keep good records of the conversion for tax purposes!

Has anyone dealt with a situation where the deceased owner hadn't been taking depreciation properly before death? My uncle passed and left me his rental property, but I discovered he hadn't claimed depreciation for 3 years even though he should have. Does the step-up basis just make all that irrelevant now?

Great question about the depreciation situation! I went through something very similar when my grandmother passed and left me her duplex. She had also missed claiming depreciation for several years before her death. The good news is that @Libby Hassan and @Eva St. Cyr are absolutely right - the step-up in basis at death essentially gives you a clean slate. All the missed depreciation from before becomes irrelevant because you're starting with a fresh basis equal to the fair market value at the date of death. One thing I'd add is that you might want to consider filing an amended return for your uncle's estate if the missed depreciation deductions were significant. While it doesn't affect your stepped-up basis, it could result in refunds for the estate that the beneficiaries would receive. My CPA helped us recover about $4,200 in missed deductions from my grandmother's final three years. Also, make sure to start your depreciation schedule immediately once you inherit - don't repeat your uncle's mistake! The IRS expects you to claim depreciation whether you actually take it or not, so there's no benefit to skipping it.

Welcome to the community, StarSailor! Your action plan sounds perfect - starting with the EFTPS technical support line and having Firefox as a backup is exactly what I'd recommend based on all the success stories shared here. One additional tip I'd like to add for newcomers dealing with EFTPS issues: if you do end up calling the tech support line, have your EIN and EFTPS PIN ready before you dial. The techs can resolve most account-level issues (like the flagging problems several people mentioned) much faster when they can immediately verify your identity and pull up your account details. Also, when you set up Firefox with Paolo's security settings, I'd suggest testing your login a few times over the course of a day to make sure it's consistently working before your actual payment deadline. That way you'll know for certain that your backup solution is reliable. It's great seeing how this community has developed such a comprehensive troubleshooting guide through everyone's shared experiences. These kinds of technical issues with government sites are so frustrating when you're dealing with tax deadlines, but having multiple proven solutions makes it much less stressful!

As someone who's been dealing with EFTPS access issues on and off for the past year, I wanted to add another potential solution that hasn't been mentioned yet. Sometimes the problem isn't with your browser settings or account flags, but with your local network configuration. I discovered this when I was having login issues at my office but could access EFTPS perfectly fine from my home computer. It turned out our office firewall was blocking certain SSL certificates that EFTPS requires for the login.gov integration. Our IT person had to whitelist specific government certificate authorities in our firewall settings. If you're accessing EFTPS from a business network (especially if you have robust security software or firewalls), you might want to try logging in from a different network - like your phone's hotspot or a home internet connection - to see if that resolves the issue. If it works from a different network, then you know it's a firewall/network configuration problem rather than a browser or account issue. This could be particularly helpful for people who have tried all the browser fixes and called tech support but are still having problems. Sometimes the issue is at a completely different layer of the technology stack than what most troubleshooting guides address.