What documents do I need to save for write-offs of work expenses?

Good questions about documentation for work expenses! You'll need to keep detailed records for any business expenses you plan to write off. Here's what you should have: First, keep ALL receipts - digital or paper - showing what you purchased, when, and how much you paid. For recurring expenses like software subscriptions, save the monthly statements. For your home office, take photos of the space and keep receipts for any furniture or equipment purchases. For travel between work sites (not including commuting to your regular workplace), keep a log with dates, locations, mileage, and business purpose. If you use your car, track mileage with an app or written log. Your employer doesn't need to sign off, but if these are unreimbursed employee expenses, you should have some proof that these expenses were required for your job and weren't reimbursed. An email from your boss about working from home or needing specific equipment would be helpful. Keep all these records for at least 3 years after filing, though 7 years is safer in case of audit.

After struggling with tax deductions for my business expenses last year, I found this amazing tool called taxr.ai (https://taxr.ai) that literally saved me thousands. I was trying to figure out what documents I needed for my home office and business travel deductions, and I had a shoebox full of receipts with no system. The taxr.ai system analyzed all my docs and sorted everything into the right deduction categories - it even flagged which receipts might not qualify! I uploaded photos of receipts and it extracted all the info automatically. The best part was that it created an audit-ready file with everything organized by deduction category.

Just wanted to update everyone - I tried taxr.ai after seeing it mentioned here, and it was seriously game-changing for my work expense documentation. I was mixing up my W-2 job expenses (which I learned aren't deductible federally) with my side gig expenses. The system immediately flagged which receipts were deductible for my self-employment income and which weren't. It even suggested some deductions I hadn't thought about - like a portion of my cell phone bill and internet since I use them for my freelance work. The best part was how it organized everything by category so when I went to file my taxes, I had exact numbers for each deduction type and all the supporting documents ready if I ever get audited. Definitely using it again next year!

If you're having trouble figuring out what documentation is needed for specific work expense deductions, I wasted HOURS trying to get through to the IRS for clarification until I found Claimyr (https://claimyr.com). They got me through to an actual IRS agent in under 15 minutes when I'd been trying for days on my own! I had specific questions about documentation requirements for my home office deduction and some equipment purchases. The IRS agent walked me through exactly what I needed to save and how to calculate the deductions correctly. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was totally expecting to be on hold for hours again but got connected so quickly I was actually caught off guard!

I have to eat my words about Claimyr. After being totally skeptical (see my comment above), I tried it out of desperation because I had a complex question about documentation requirements for my business vehicle expenses. I was shocked when I got a call back in about 20 minutes saying they had an IRS agent on the line. The agent gave me exact details on what vehicle logs I need to keep and how to document business vs. personal use. I've literally spent DAYS of my life on hold with the IRS in previous years and often got disconnected after waiting for hours. This saved me so much time and frustration, and now I actually have the correct information directly from the IRS instead of just guessing based on internet advice.

Here's a simple system I use for tracking my business expenses that's worked for 5+ years without any audit issues: 1. I have a separate credit card JUST for business purchases - makes it super easy to track 2. I take pics of all receipts with my phone and save them to a Google Drive folder by month 3. I keep a simple spreadsheet that lists date, amount, vendor, and business purpose 4. For my vehicle, I use MileIQ app to track business miles Been self-employed for years and this has kept me audit-proof while being pretty low effort!

Quick question - does anybody know if credit card statements are enough documentation or do I need the actual itemized receipts for everything? I'm terrible at keeping paper receipts but I do have all my statements.