Tip from someone who works with mailed documents: Don't use staples! Use paper clips instead. The IRS scanning centers hate staples because they have to remove them all before scanning, which can damage documents. Also number ALL your pages in the bottom right corner (like "Page 1 of 100", "Page 2 of 100") so if anything gets separated, they know what goes where. And make a detailed table of contents as the first page listing what's included. Makes everyone's life easier.

Based on my experience dealing with IRS audits, I'd strongly recommend against using multiple envelopes. Stick with one secure package to minimize the risk of anything getting lost in their system. For 100 pages, a USPS Priority Mail Medium Flat Rate Box works perfectly. It's sturdy, includes tracking, and has enough space to organize your documents properly without cramming them. I always use certified mail with return receipt requested on top of the Priority Mail service - yes, it's an extra cost, but having that signed receipt is invaluable proof of delivery. Before sealing everything up, make sure to: - Number every single page (1 of 100, 2 of 100, etc.) - Create a detailed cover letter listing all enclosed documents - Use paper clips instead of staples (IRS scanning equipment hates staples) - Write your SSN (last 4 digits only) and name on each page - Take photos of everything before mailing Most importantly, make complete copies of everything before sending. I cannot stress this enough. The IRS processes thousands of documents daily, and things can get misplaced. Having copies and proof of certified delivery will save you if there are any issues later. The extra $10-15 for certified mail with return receipt is the best insurance you can buy for this situation.

Has anyone used TurboTax Self-Employed for handling their LLC quarterly payments? I'm trying to decide if it's worth the cost or if I should just use the free IRS worksheets.

This is super helpful info everyone! I had no idea about the self-employment tax on top of regular income tax - that 15.3% is definitely going to change my budgeting. One thing I'm still confused about though - if I missed the April quarterly payment, do I need to pay the penalty right away or does it just get calculated when I file my 2024 taxes next year? I want to make sure I'm not going to get a surprise bill in the mail before then. Also, for calculating the June payment to cover both quarters like Charlotte mentioned - would that be 50% of my expected annual tax burden, or is there a different calculation for catching up on missed payments?

Has anyone used TurboTax Self-Employed for their 1099 contractor taxes? I'm wondering if it does a good job catching all these vehicle deductions or if I should use something else.

Great question about maximizing vehicle deductions! One thing I haven't seen mentioned yet is keeping a detailed mileage log if you go with the standard mileage rate. The IRS wants to see date, destination, business purpose, and miles for each trip. I use a simple app on my phone that tracks this automatically using GPS. Also, don't overlook parking fees and tolls - these are deductible regardless of whether you use standard mileage or actual expenses method. I was leaving money on the table by not tracking these small expenses that really add up over time. For your lease payments, if you switch to actual expenses method, you can deduct the business percentage of your lease payments. But remember what others mentioned - once you choose actual expenses for a vehicle, you're stuck with that method for the life of that car. The standard mileage rate already includes depreciation/lease costs, so you can't double-dip. One more tip: consider setting up a separate business credit card just for vehicle expenses. Makes tracking so much easier come tax time, and you won't accidentally miss business purchases mixed in with personal spending.

This is exactly why I still do paper returns. Everyone thinks I'm crazy but computers fail, software glitches, systems crash, and suddenly hours of work vanish. With paper, what you write stays written.

I feel your pain - losing hours of tax work is absolutely maddening! I had a similar experience with different software a few years back and it taught me to be paranoid about backups. Beyond what others have suggested about contacting TaxAct support, I'd recommend checking if your browser has any cached data that might help. Sometimes going to your browser history and finding the TaxAct pages you were on can reveal temporary files or cached forms that might have some of your data. Also, if you used any browser autofill features while entering information, check your browser's saved form data - you might be able to recover some of the basic info like names, addresses, and employer information that way. For next time (with any software), I learned to take a screenshot after completing each major section AND save a PDF of the return in progress every 30 minutes or so. It's a bit tedious but saves so much heartache when things go wrong. The tax software companies really need to do better with their autosave and recovery features - this shouldn't be something taxpayers have to worry about!

Does anyone know if tuition reimbursement for a master's degree would also show up in Box 14? My company pays for my MBA classes but I don't see anything on my W-2 about it...should I be worried they're not reporting it correctly?

Thanks everyone for the detailed explanations about Box 14! I've been dealing with something similar and this thread has been incredibly helpful. Just to add another perspective - I work in payroll for a mid-size company and we do put educational assistance in Box 14 with various codes (sometimes "EDU", sometimes "EDUC" or "TUITION"). We're required to report it there even when it's not taxable, mainly for record-keeping purposes and to show employees what benefits they received during the year. The key thing to remember is that if your educational benefit was properly excluded from your Box 1 wages AND it's under the $5,250 annual limit, then you're all set - no additional reporting needed on your tax return. If you're ever unsure, comparing your final paystub totals to your W-2 Box 1 amount can help you verify everything was handled correctly. @Yuki Tanaka - since you mentioned this is your first year with the university, definitely keep track of these benefits throughout the year so you know where you stand relative to that $5,250 limit!