


Ask the community...
I actually know someone who got caught for tax evasion on illegal income. The issue wasn't just not reporting it, but the lifestyle mismatch. They had a minimum wage job but drove an expensive car and bought a house. IRS flagged it, started investigating, and that led to the criminal charges for the original illegal activity. So yeah, damned if you do (admit to illegal activity) and damned if you don't (get caught for tax evasion AND the original crime).
That's exactly why money laundering exists. Not that I'm recommending it! Just pointing out the logical problem in the system.
This is a fascinating legal paradox that highlights the complexity of tax law. The Fifth Amendment protects against self-incrimination, but the Supreme Court ruled in United States v. Sullivan (1927) that this doesn't exempt illegal income from taxation. The practical reality is that the IRS operates under strict confidentiality rules (IRC Section 6103), so they generally can't share your tax information with law enforcement without proper legal process. However, unexplained wealth discrepancies are what typically trigger investigations in the first place. If someone hypothetically had $135k in unreported income, the bigger risk isn't necessarily how you categorize it, but whether your reported lifestyle matches your claimed income sources. The IRS has become very sophisticated at detecting these mismatches through data analytics. The "illegal activities" checkbox exists primarily for legal compliance with Supreme Court rulings, not as a trap. But you're right that it creates an impossible situation - report honestly and potentially incriminate yourself, or misrepresent and risk fraud charges if discovered later. For anyone in genuinely complex income reporting situations, consulting a tax attorney who can provide privileged advice is usually the safest approach.
This is really helpful context about the legal precedents. I've been wondering about this exact situation - not for anything illegal, just curious about how the system works. The Sullivan case explanation makes sense of why the IRS has to collect taxes on all income regardless of source. What I'm still confused about is the practical side though. If someone reports illegal income honestly, does that information stay sealed from law enforcement indefinitely? Or is it more like a ticking time bomb waiting for the right legal circumstances to be accessed? The confidentiality protections sound strong in theory but seem like they could be bypassed pretty easily with the right warrant or investigation.
Thanks everyone for the detailed responses! This has been incredibly helpful. Based on what I'm reading, it sounds like TurboTax Deluxe should handle my Robinhood crypto transactions just fine, especially since I'm only dealing with around 30-40 trades and Robinhood will provide the 1099-B. I think I'll stick with Deluxe for now and see how the import process goes. If I run into any issues or need additional forms, I can always pay the extra fee to add them rather than upgrading to Premier upfront. The suggestion about taxr.ai is interesting too - might give that a try if I find myself getting confused with the cost basis calculations. Really appreciate everyone sharing their experiences, especially those who were in similar situations with Robinhood crypto trading. Makes me feel much more confident about tackling this year's taxes!
@Chloe Wilson Just wanted to add that if you do decide to try taxr.ai, make sure to double-check their calculations against your Robinhood records before importing anything into TurboTax. I ve'heard mixed experiences with third-party crypto tax tools, and while some people swear by them, others have found discrepancies. Since you re'only dealing with 30-40 transactions, you might find it just as easy to work directly with the 1099-B that Robinhood provides. Good luck with your taxes this year!
Just to add another perspective - I've been using TurboTax Deluxe for crypto reporting for the past two years with Robinhood, and it's worked perfectly. The key thing is making sure you wait for Robinhood to send you the consolidated 1099-B (they usually send it by mid-February). This form includes all your crypto transactions with the correct cost basis already calculated. One tip: when you import the 1099-B into TurboTax Deluxe, double-check that all transactions are properly categorized as short-term vs long-term capital gains. With 30-40 transactions, this is manageable to review manually. I found that most of my crypto trades were short-term since I was actively trading, which means they're taxed as ordinary income rather than the lower capital gains rate. Also, keep your own records of all transactions as a backup. While Robinhood's 1099-B is generally accurate, having your own transaction history helps if there are any discrepancies or if you need to reference specific trades during the filing process.
This is really helpful advice! I'm also new to crypto taxes and was wondering - when you mention checking that transactions are properly categorized as short-term vs long-term, does TurboTax Deluxe do this automatically based on the dates in the 1099-B, or do you have to manually review each one? I'm worried about making mistakes since I held some crypto for different lengths of time throughout the year.
Anna, I totally feel your pain with this topic! I went through something very similar when I sold my former primary residence that I had been renting out. The confusion around qualified vs non-qualified use is real, and it sounds like you need a tax professional who can actually explain this stuff clearly. Based on what everyone has shared here, it sounds like you're in a much better position than you initially thought. The key insight is that your work-related relocation means those 4.5 years of renting don't count against you for the non-qualified use calculation - that's huge! Your $63k partial exclusion calculation seems right based on the 2-out-of-5 year rule. Just make sure you have good documentation of your work-related move (job offer letter, employment records, etc.) in case the IRS ever asks questions. One thing I'd add - if you did claim depreciation on the rental during those 4.5 years, you'll need to account for depreciation recapture separately from the capital gains calculation. That gets taxed at a different rate (up to 25%) regardless of the non-qualified use rules. Definitely consider finding a new accountant who specializes in real estate transactions. This stuff is complex but shouldn't be a source of frustration between you and your tax professional. Good luck with everything!
Aurora, thank you for mentioning the depreciation recapture - that's such an important point that often gets overlooked in these discussions! I'm actually dealing with this exact situation right now and hadn't fully considered how the depreciation I claimed during the rental period would be taxed separately. Anna, if you haven't already, make sure to gather all your tax returns from the years you were renting the property. You'll need to calculate the total depreciation you claimed (or were entitled to claim, even if you didn't actually take it) to figure out the depreciation recapture amount. This gets added to your taxable income at rates up to 25%, which is typically higher than long-term capital gains rates. The silver lining is that even though you'll owe taxes on the depreciation recapture, your work-related move exception still protects you from having the non-depreciation portion of your gain allocated to non-qualified use periods. So you're still much better off than if you had just randomly decided to move out and rent the place. I'm definitely taking everyone's advice about finding a specialized real estate tax professional. This thread has been more helpful than months of trying to get clear answers elsewhere!
Anna, I can definitely understand your frustration with this topic - the non-qualified use rules are genuinely one of the more confusing aspects of capital gains tax on primary residences! The good news from reading through all these responses is that your work-related relocation in July 2018 is actually a huge advantage. Since you moved out for employment reasons, those 4.5 years of rental income don't count as "non-qualified use" under Publication 523. This means you avoid the worst-case scenario where part of your gain would be allocated to non-qualified periods and potentially lose exclusion eligibility. Your $63,000 partial exclusion calculation sounds correct based on the 2-out-of-5 year rule (living there only 6 months out of the last 5 years before sale). So here's how it works in practice: 1. Calculate your total capital gain from the sale 2. Subtract your $63,000 partial exclusion 3. Any remaining gain gets taxed as long-term capital gains (plus depreciation recapture if applicable) 4. But thanks to your work-related move, none of that remaining gain gets penalized for the rental period Make sure to keep documentation of your job relocation - employment offer letter, moving records, anything showing the timeline. And honestly, I'd echo what others have said about finding a new accountant. Someone who specializes in real estate transactions should be able to walk through Publication 523 with patience and clarity rather than getting frustrated with legitimate questions about complex tax rules. You're actually in a much better position than many people who rent out former primary residences!
I've been dealing with this exact same frustration! After reading through all these strategies, I wanted to share what finally worked for me last month. I tried the 7am Wednesday approach that everyone's recommending (which is legit - that timing really does matter), but I also discovered you can sometimes get through by calling the IRS International line at 1-267-941-1000. It's technically for taxpayers living abroad, but they can often help with basic domestic issues or transfer you directly to the right department without going through the main phone tree nightmare. The wait times are usually much shorter since fewer people know about it. Worth a shot when you're desperate! Also, that congressional representative tip is gold - I had no idea that was even an option until I read about it here. This whole system is completely broken but at least we can help each other navigate the madness! š¤
This international line tip is brilliant! I never would have thought to try that route. After weeks of getting nowhere with the main lines, I'm definitely going to give this a shot tomorrow along with the 7am Wednesday strategy. It makes total sense that fewer people would know about the international number so the wait times would be shorter. Thanks for sharing this - feels like we're all becoming experts at finding creative ways around this broken phone system! š
I've been battling this exact same issue for over a month now with my 2023 return! Reading through all these strategies gives me so much hope - I had no idea about the 7am Wednesday timing or the international line trick. It's absolutely insane that we need to strategize like we're planning a military operation just to talk to our own tax agency. I'm definitely going to try calling at exactly 7:00am tomorrow (setting multiple alarms for 6:55am) and if that doesn't work, I'll try the international line approach. The congressional representative option is something I never knew existed either - crazy that our elected officials can actually help cut through this bureaucratic nightmare. Thanks to everyone sharing their war stories and tips! This thread has been more helpful than anything else I've found online. It's both comforting and depressing to know so many of us are stuck in this same phone system purgatory, but at least we're all fighting it together. Will definitely report back if I manage to break through the fortress tomorrow! š¤
GamerGirl99
I went through this exact same frustration about 6 months ago! The key thing that finally worked for me was realizing that there are actually TWO separate authorization steps needed for TDS access as a tax professional working for a firm. First, your individual CAF number needs to be active (which it sounds like you already have). But second, and this is the part that trips up a lot of people, your firm needs to have you listed as an authorized delegate in THEIR organizational TDS account. Here's what I'd suggest doing while your manager is out: Contact your firm's office manager or whoever handles the administrative side of things. Ask them who has "e-Services Administrator" access for your firm's IRS accounts. That person needs to log into the firm's e-Services portal and add you to their TDS user list using your PTIN. If nobody at your firm knows who the e-Services admin is, you can actually call the IRS Business and Specialty Tax Line at 1-800-829-4933 (though expect long hold times). They can tell you who the current administrator is for your firm's account. Once you're added by the admin, it usually takes 24-48 hours to show up in the system. The good news is that once it's set up properly, you'll be able to access transcripts for all clients where proper authorization forms have been filed. Don't give up - this is a super common issue for new tax pros and it's definitely solvable!
0 coins
Paolo Conti
ā¢This is incredibly helpful! I'm actually a new tax professional myself and had no idea about the two-step authorization process. I've been struggling with similar access issues for weeks. Quick question - when you say "proper authorization forms," are you referring to the 2848 or 8821 forms that need to be filed for each individual client? And do those need to be processed before I can see them in the TDS system, or will pending authorizations show up too?
0 coins
Danielle Campbell
As someone who's been through this exact situation, I completely understand your frustration! The TDS access issue for tax professionals working at firms is surprisingly common and often poorly explained in the IRS documentation. Here's what I learned from my own experience: Even with an active CAF number, you need your firm to specifically grant you TDS access through their organizational account. This is separate from your individual practitioner credentials. Since your manager is out, try reaching out to whoever handles the firm's administrative functions or IT support. They should be able to identify who has e-Services administrator rights for your firm's IRS accounts. That person can add you to the TDS user list using your PTIN - it's usually a pretty straightforward process once you know who to ask. If you're really stuck and have urgent client deadlines, you might also consider calling the IRS Practitioner Priority Service at 1-866-860-4259. While the wait times can be long, they can sometimes provide immediate guidance or even resolve the access issue over the phone if there's a technical problem with your account linkage. The good news is that once this gets sorted out, you'll have seamless access going forward. It's definitely worth getting properly set up rather than trying to work around it. Hope this helps and you get it resolved quickly!
0 coins