Just as a heads up - my friend who runs an interior design business from home got audited last year and one of the things they specifically looked at was her home office client meal deductions. She got through it fine because she had detailed records - not just receipts but calendar entries showing client names, topics discussed, and outcomes of meetings. IRS apparently gets suspicious of home office food/drink deductions so documenting the business purpose thoroughly is key!

This is all really helpful information! I've been wondering about this exact situation myself. One thing I'd add - make sure you're consistent with how you handle these deductions from year to year. If you start claiming home office client meal deductions, keep doing it the same way each tax season. Also, consider setting up a simple client meeting log where you record the date, client name, business purpose, and what refreshments were provided. This creates a paper trail that shows the business nature of these expenses. I use a basic spreadsheet that takes maybe 30 seconds to update after each client meeting, but it would be invaluable if I ever got audited. The key seems to be showing clear business purpose and keeping personal expenses completely separate. Thanks everyone for sharing your experiences - this gives me confidence to start properly tracking and deducting these legitimate business expenses!

Listen, the IRS site is notoriously glitchy on mobile. Been that way for yrs. Most ppl don't realize their system runs on ancient tech that barely works w/ modern browsers. Quick fixes that work for most: - Try incognito/private browsing mode - Desktop comp > phone ALWAYS - Clear cookies/cache before trying - Try diff browser (Firefox tends to work better) - Log in super early AM or late PM If none of that works, just call the transcript req line (800-908-9946). Takes 5-10 days but way less hassle than fighting w/ their garbage website. Trust me, I've been down this rabbit hole many times.

I've been dealing with this same frustrating issue! What worked for me was switching to a different network entirely - I was on my home WiFi when having problems, but when I tried using my phone's cellular data instead, it worked perfectly. Sometimes the issue isn't just the browser or device, but the network connection itself. The IRS authentication system can be really finicky about certain internet providers or network configurations. If you have access to a different WiFi network (maybe at a library, coffee shop, or friend's house), give that a try. Also, make sure your phone's date and time are set correctly - I know it sounds weird, but security certificates can fail if your device clock is off by more than a few minutes. This happened to me with a different government site last month. Hope this helps! The transcript system really shouldn't be this difficult to use in 2025.

One tip about filing these old returns - don't e-file! The IRS only accepts electronic filing for the current tax year and 2 years prior. For anything older than that, you have to mail paper returns. Also, be sure to mail each tax year in a separate envelope. If you send multiple years together, it increases the chances of processing errors.

Just wanted to add something that might help with your peace of mind - even though you can't recover that 2017 overpayment, filing both returns will at least give you a complete picture of your tax situation from those years. I was in a similar boat with unfiled returns and kept putting it off because I was overwhelmed by all the unknowns. Once I finally bit the bullet and filed everything, it was honestly such a relief to have it done and know exactly where I stood with the IRS. One thing that helped me was creating a simple spreadsheet tracking what I owed for each year including estimated penalties, so I could budget for the payments. The uncertainty was actually worse than the reality of what I ended up owing. Good luck getting everything sorted out - you're already taking the right steps by researching this and planning to file!

Another approach - have you tried explaining to your contractor that they REALLY need to give you their info? If they're a legitimate business, they should understand this is required. I've had success with telling contractors that I'm legally required to report payments over $600, and without their SSN/EIN, they might face issues with the IRS themselves. Sometimes they just don't understand the importance. You might also want to have them complete a W-9 form which officially requests their tax ID information. Send it with a gentle but firm explanation that you cannot make future payments without this completed form.

Great question! I went through this exact situation last year with a freelance graphic designer. You absolutely can e-file your personal return through TurboTax and mail the 1099-NEC/1096 forms separately - they're completely independent processes. For your personal return, just claim the $1,800 deduction on your Schedule C (or Schedule C-EZ) as usual. The IRS doesn't require you to have the contractor's TIN to claim legitimate business expenses. For the 1099-NEC, fill it out with "Applied For" in the TIN field and mail it with Form 1096 to your state's designated IRS processing center (you can find the address in the 1099 instructions). Make sure to keep copies of all your attempts to get their SSN/EIN - emails, texts, certified mail receipts, etc. One tip: Send the contractor a formal W-9 request via certified mail with return receipt. This creates an official paper trail and sometimes the formality finally gets them to respond. You can download the W-9 from IRS.gov. Don't let this contractor's lack of cooperation delay your filing or cost you a legitimate deduction!

Another option worth considering is filing Form 8832 first to elect to be taxed as a C Corporation, then immediately filing Form 2553 for S Corp status. Sometimes this two-step approach can work outside the normal S Corp election deadline. Talk to your accountant about this strategy - it's worked for some clients at our firm.

Don't forget that even if you successfully convert to an S Corp, you need to run payroll and pay yourself a "reasonable salary" before taking any distributions. Many people miss this and end up with IRS problems. My brother tried taking mostly distributions with a tiny salary and got hit with penalties for avoiding payroll taxes.