That's a great point I hadn't considered! I did confirm with the parents that the names on the Social Security cards match exactly what we're entering on the return, including middle initials and spelling. Birth dates also match perfectly. The only unusual aspect is that these are twins born in December, but they didn't receive their actual SSN cards until February this year. I'm wondering if maybe the SSA records could have some discrepancy even though the physical cards look correct?

Twins born in December with SSNs issued in February definitely points to the "new SSN not in database" issue. But it's always worth double-checking with SSA directly just to rule out any other problems. You can verify the SSNs with the Social Security Administration by going to their office with your clients (with proper authorization forms) or by having your clients request a Social Security Statement. If everything checks out with SSA, then it's almost certainly just the delay in the information transfer between SSA and IRS systems. Given that information and the timing, I'd probably recommend paper filing now rather than waiting for an extension. Even with the current backlog, the paper return should still be processed well before October.

Which processing center handles returns from Florida? My client is in Miami and I'm helping them with a similar issue.

I've heard that you could potentially make a case that the primary purpose is business if the conference is in a location you wouldn't typically vacation in. Like if it's in a random midwest city in winter versus a beach destination. Does that actually hold up with the IRS?

There's some truth to that, but it's more nuanced. The location factor is one element the IRS might consider, but it's not determinative by itself. The ratio of business to personal days is usually given more weight. However, if you can demonstrate that you wouldn't have made the trip at all except for the business purpose, it strengthens your position. But with a 4:26 day ratio of business to personal, that's going to be a tough argument to win regardless of location. The overwhelming personal time makes it clear that personal pleasure was a major consideration in the trip.

Yikes, that's definitely not what I want! How detailed was the audit? Did they ask for specific documentation about what you did each day of your trip? I think I'll follow the allocation advice, better safe than sorry.

The audit was surprisingly thorough. They asked for a daily itinerary showing exactly which hours were spent on business activities, names and business relationships of people I met with, and how each meeting related to my business. They also wanted to see emails setting up business meetings, conference registration receipts, and even questioned why I stayed extra days if I didn't have business activities scheduled. Good call on being conservative with your deductions. The few hundred dollars you might save taking an aggressive position isn't worth the headache of an audit, potential penalties, and interest if they disallow the deductions later.

Thanks for bringing this up! I do have about $3,000 a year from a small side gig. Should I be accounting for that directly on the W4 or should I be doing those quarterly payments you mentioned?

For $3,000 in side income, you have two options. You can include it on your W4 by adding the estimated tax amount in Step 4(a) as "other income" which will increase your withholding from your main job to cover it. Alternatively, you could make quarterly estimated payments. This is often better if your side income fluctuates a lot. The rule of thumb is if you expect to owe more than $1,000 at tax time, you should make estimated payments to avoid an underpayment penalty. For $3,000 in extra income, you're probably looking at around $500-700 in additional tax depending on your tax bracket.

This is bad advice. Blanket recommendations like "put an extra $50" don't account for specific situations. That could be way too much or too little depending on income level and other factors. The whole point of the new W4 is to be more precise.

Is there any way to verify directly with the IRS that your 1099s were properly filed? Or do you just have to trust the service you used?

Unfortunately, the IRS doesn't have a simple verification system for confirming 1099-NEC filings. This is why getting the acknowledgment receipt with submission ID from your e-filing provider is so crucial. You can call the IRS Business & Specialty Tax Line (800-829-4933) and ask them to check if your forms were received, but be prepared for long wait times and potentially inconclusive answers. Sometimes they can confirm receipt, but they often tell you to just wait to see if you receive any non-filing notices, which isn't very helpful when you're trying to be proactive.

That's incorrect information that could cause serious problems. The threshold change to 250 (not 25) forms was actually implemented years ago, then reduced back to 10 forms for 1099-NEC specifically. For the 2024 tax year (filing in 2025), the threshold is still 10 forms, meaning OP must e-file since they have 12 forms. Filing incorrectly based on misunderstood future rule changes could result in penalties. The safest approach is to follow current requirements and use an authorized e-file provider as suggested earlier.

I completely forgot about state taxes! Do I need to make quarterly payments to the state too, or is that a different process from the federal estimated payments?

Yes, many states require quarterly estimated tax payments similar to the federal system, though the due dates and calculation methods might be slightly different. Your state's department of revenue or taxation website should have forms and information specifically for estimated taxes. Some states even have lower thresholds than the federal government for when you're required to make estimated payments, so don't assume the rules are identical.

I've heard good things about FreeTaxUSA too. Much cheaper than TurboTax but still handles self-employment well. Anyone tried it?