I went through this exact situation two years ago and can confirm it's not as scary as it seems! The key thing to remember is that the IRS computer systems are actually pretty sophisticated at identifying these overlaps. What I did was keep a simple spreadsheet showing each payment - the date, amount, client name, and which forms reported it (1099-NEC, 1099-K, or both). This made it super easy to see the total actual income versus what appeared to be "double reporting." On my Schedule C, I just reported my true total income from all clients. The IRS matching system will see that your reported income is reasonable compared to the information returns they received, even if those returns overlap. One thing that gave me peace of mind was talking to my tax preparer about it. She said this happens all the time now with payment processors being required to issue more 1099-Ks. The IRS has definitely seen this pattern before and has procedures to handle it. Keep all your bank statements and client contracts as backup documentation, but honestly you probably won't need them. The system works better than most people think!

I'm dealing with something similar right now and this whole thread has been incredibly helpful! Just to add another perspective - I reached out to my payment processor first before doing anything else, and it turns out they were actually required to send the 1099-K because of how their system categorizes ACH transfers that go through their platform. The customer service rep explained that even though these are direct bank transfers from my clients, because they're processed through their payment infrastructure, they legally have to report them as payment transactions. So getting a corrected form might not be an option depending on your specific processor. What really helped me was creating a simple reconciliation document that shows: - Total income from all sources: $X - Amount reported on 1099-NECs: $Y - Amount reported on 1099-K: $Z - Overlap amount: $Y (assuming all 1099-NEC income is also on the 1099-K) - Actual taxable income: $X (not $Y + $Z) I'm planning to include this as a statement with my return just for extra clarity. It's such a relief to know this is a common issue and not something that will automatically trigger problems. Thanks everyone for sharing your experiences!

This auto-import feature caught me off guard too when I first used TurboTax! What helped me understand it better was realizing that this is actually part of a broader trend in the tax industry toward "pre-populated" returns, similar to what many other countries already do. The IRS has been working on initiatives to make tax filing easier through programs like "Return Free Filing" where your tax information would be pre-filled by the government itself. TurboTax's auto-import is essentially a private sector version of this concept. If you're still concerned about privacy, you might want to consider that the same W-2 data is already being shared with the IRS, Social Security Administration, and state tax agencies automatically by your employer anyway. TurboTax is just tapping into an existing data flow rather than creating a new one. That said, it's totally valid to want more control over your data. The manual entry route gives you complete oversight of what information goes into your return, even if it takes a bit more time.

The auto-import feature definitely seems scary at first! I had the exact same reaction when I saw my W-2 data already loaded. What I learned is that this happens through something called the "IRS e-file system" where your employer electronically submits your tax documents to a network that authorized tax preparers can access. The key word here is "authorized" - TurboTax has to go through IRS certification to participate in this system, so there are actually federal oversight and security requirements they have to meet. It's not like they're just grabbing your data from some random database. That said, I totally understand wanting more transparency about this process. When you first set up your account, there should have been a screen asking about importing documents, but it's easy to click through without fully reading. For future reference, you can always go into your account settings and turn off the auto-import if you prefer to enter everything manually. I ended up keeping it enabled because it saves me so much time, but I make sure to double-check all the imported information before submitting my return. The convenience is nice, but you should definitely verify everything is accurate regardless!

I went through this exact same nightmare last year! What finally worked for me was requesting an "escrow analysis" statement directly from my mortgage servicer - this is different from your regular mortgage statements and shows a detailed breakdown of all payments made from your escrow account throughout the year. Most servicers are required to provide this annually, but you can request it specifically. It will show every property tax payment made, even if your 1098 shows zero. I had to escalate past the first-level customer service (they didn't even know what I was talking about), but once I got to someone in the escrow department, they sent it right over. Also, keep your closing documents handy - they often show prorated property tax amounts that you paid at closing, which are also deductible but easy to overlook. Between the escrow analysis and closing docs, I found over $4,200 in deductible property taxes that weren't on my 1098.

This is such a common and frustrating issue! I went through the same thing when we refinanced our home mid-year. Here's what I learned from my CPA: the 1098 only reports what the lender considers "qualified" property tax payments, and sometimes there are timing issues or coding errors on their end. Your best bet is to get a complete payment history from your county tax collector's office (not just the assessor). They can provide an official statement showing all property tax payments made on your properties during the tax year, regardless of who made them. Most counties now have online portals where you can download these reports instantly using your property address or parcel number. Don't forget about the property taxes you may have prepaid at closing for your new home, or any prorated amounts you were credited for when you sold your old home. These are often overlooked but are legitimate deductions. The key is having documentation that shows the taxes were actually paid during the tax year - the IRS doesn't care that your 1098 is wrong, they just need proof the payments were made.

This is such a helpful thread! I'm dealing with a similar situation where I left my company last year and just sold some ESPP shares. One thing I wanted to add for anyone else in this boat - make sure to check if your old company switched payroll providers or got acquired after you left. I spent weeks trying to get my old W-2s from my former employer's HR, only to find out they had been acquired and all the payroll records moved to a different system. I finally had to request copies directly from the IRS using Form 4506-T, which took about 10 days but was totally worth it to get the exact compensation amounts that were reported. Also, if you're having trouble finding the ESPP compensation on your W-2, sometimes it's not in Box 14 like others mentioned. On mine it was actually included in Box 1 (wages) and I had to look at my final paystub from that year to see the breakdown of regular wages vs. ESPP compensation. Just another place to check if you're coming up empty!

This thread has been incredibly helpful! I'm in a similar situation where I left my job at a tech company about 8 months ago and just sold some ESPP shares. One thing I learned the hard way is to double-check the cost basis calculation even if your broker provides a "Supplemental Information Statement" like Emily mentioned. I found that Schwab had the right compensation amount but applied it to the wrong lot of shares (I had multiple purchase periods). This would have resulted in me overpaying taxes on some lots and underpaying on others. What I ended up doing was creating my own reconciliation spreadsheet using Yuki's method above, then cross-referencing it with both my 1099-B and the supplemental statement. Found a $400 discrepancy that would have cost me about $150 in extra taxes! Also want to second the recommendation about keeping detailed records going forward. I set up a simple Google Sheet now that automatically calculates the discount amount and tracks holding periods. Takes 5 minutes after each ESPP purchase but will save hours during tax season.

Your current system is actually excellent and well above what most delivery drivers maintain! I've been doing multi-app delivery work for over two years and have had my records reviewed by both a CPA and during a random IRS audit. The odometer readings you're tracking are the gold standard - they provide concrete proof of actual business miles driven, which is far more credible than apps that can glitch or estimated calculations. Your method of recording general coverage areas (downtown, university area, etc.) perfectly establishes business purpose without the administrative nightmare of logging every single stop. What you're doing hits all the key IRS requirements: contemporaneous recording (at the time of work), consistent format, business purpose documentation, and actual mileage proof. The IRS specifically recognizes that detailed stop-by-stop logging would be "unreasonably burdensome" for drivers doing 25-30 deliveries per day. Your paper method is not just acceptable - it's often preferred in audits because it clearly shows real-time recording rather than potentially back-dated digital entries. The battery drain issue you mentioned is exactly why many experienced delivery drivers stick with paper logs for those long shifts. If you want to add one small enhancement, consider noting your total delivery count for each shift. But honestly, don't change what's working. Your 20,000+ mile deduction is well-documented with your current system. You're doing this right!

Your current mileage tracking system is actually really solid and meets IRS requirements perfectly! I've been doing delivery driving for about a year now and went through the same research rabbit hole when I started. The IRS doesn't require logging every single pickup and delivery address - that would be completely unreasonable for drivers doing 25+ deliveries per day. What they actually care about is having contemporaneous records (recorded at the time, not reconstructed later) that can substantiate your business mileage deduction. Your paper notebook method with odometer readings, dates, times, and general coverage areas hits all the key requirements. The odometer readings are especially valuable because they provide concrete proof of actual miles driven, which is way more credible than app estimates or guesswork. I had the same battery drain issues when I tried mileage tracking apps - they're just not practical for long delivery shifts when your phone is already working overtime with multiple delivery apps. Paper logs are actually preferred by many tax professionals because they clearly show real-time recording. One small suggestion that might strengthen your records: consider adding a quick note about total deliveries completed each shift (just the number). This adds another layer of business purpose documentation without making your system more complicated. Don't stress about changing your approach mid-year - what you're doing is already more detailed than most drivers maintain. Your 20,000+ mile deduction will be well-supported by your current documentation method. Keep doing exactly what you're doing!