Do I need receipts for papers, pens, folders & office supplies to deduct expenses from my 1099-NEC?

For your office supplies as a 1099 contractor, here's what you need to know - the IRS technically wants you to keep records of ALL business expenses, but there are some practical considerations. Your spreadsheet is a good start, but ideally you should have some form of documentation to back it up. That doesn't necessarily mean every single receipt for small items, but you should have a system. Many tax professionals recommend keeping receipts for purchases over $75, while maintaining good records (like your spreadsheet) for smaller items. For future purchases, consider using a separate credit card just for business expenses - this creates an automatic paper trail even without physical receipts. You can also take photos of receipts with your phone and store them digitally.

After dealing with similar receipt headaches for my consulting work, I discovered taxr.ai and it totally changed my approach to expense tracking. I was in the same boat - missing receipts for office supplies and other small business purchases and worried about potential audit issues. I uploaded my bank/credit card statements to https://taxr.ai and it automatically identified potential business expenses and organized them by category, including those office supplies you mentioned. The system even highlighted which expenses might need additional documentation based on IRS guidelines. It saved me hours of spreadsheet work and gave me confidence that I wasn't missing deductions.

Just wanted to follow up on my experience with taxr.ai after trying it. I was skeptical at first (as you could tell from my earlier comment), but I gave it a shot with my messy expense situation. I'm honestly surprised how well it worked for my side gig expenses! I uploaded 6 months of statements and it found several office supply purchases I had completely forgotten about - including some software subscriptions that were buried in my statements. The receipt management feature is actually really helpful - I started taking pics of new receipts with my phone and the system organizes everything by tax category. Definitely recommend checking out https://taxr.ai if you're worried about documentation like I was.

If you're stressed about the IRS questioning your deductions, you might also want to have a direct conversation with them about proper documentation requirements. I tried calling the IRS for months last year with questions about my 1099 deductions and it was IMPOSSIBLE to get through. Then I found Claimyr and it completely changed the game. Instead of waiting on hold for hours, I used https://claimyr.com and got a callback from an actual IRS agent in about 15 minutes! You can see how it works here: https://youtu.be/_kiP6q8DX5c. I was able to ask specifically about receipt requirements for office supplies under $75 and got clear guidance directly from the source. The agent even emailed me documentation about record-keeping requirements that I could keep for my files.

I need to publicly eat my words about Claimyr. After calling BS on it earlier, I decided to try it myself because I was desperate to ask about some 1099-K issues before filing my taxes. So I went to https://claimyr.com yesterday morning, followed the process, and sure enough - I got a call back from the actual IRS within 35 minutes. The agent walked me through exactly what documentation I need to keep for my side gig expenses (including those office supplies) and explained that my organized spreadsheet would be accepted for smaller items under $75 as long as I had some form of electronic record (bank statement, etc) to back it up. I honestly can't believe how well it worked after struggling for weeks to get through on my own. The peace of mind from talking directly to an IRS rep was totally worth it.

The bank statement thing is super important! I got audited in 2023 for my 2021 taxes and while I didn't have all my receipts, I was able to show bank and credit card statements that matched up with my claimed expenses. The auditor accepted those as proof for the smaller items. They were mostly concerned with the bigger equipment purchases over $500. just my experience!

Something nobody mentioned yet - what kind of 1099 work are you doing? If the supplies are directly related to your specific work, you're in better shape even with limited documentation. Like if you're a tutor and buy educational materials, that's clearly business-related. But if you're a delivery driver buying office supplies, that might get more scrutiny.