What are my chances of being audited with self-employment income and multiple W-2s?

Your risk of audit is actually still pretty low. The IRS audits less than 1% of all returns, and while certain factors can increase your risk, what you've described isn't throwing major red flags. Multiple W-2s are very common and not an audit trigger. The self-employment income on Schedule C does slightly increase audit risk, but $2,700 in business expenses against significantly higher contractor income is a reasonable ratio that shouldn't raise eyebrows. The IRS tends to scrutinize returns with unusually high deductions relative to income, which doesn't sound like your case. Two-state returns and backdoor Roth contributions are also fairly routine these days. Making your quarterly estimated tax payments shows good compliance, which actually works in your favor. If you've been careful documenting your business expenses and have receipts for everything you're deducting, you're in good shape. The tax software should handle all the forms correctly if you've input everything accurately.

After reading your situation, I was in a similar boat last year with multiple income sources and state tax issues. After tons of stress, I found this AI tax review service at https://taxr.ai that completely saved me. They analyzed all my documents and flagged errors in my Schedule C that I would have missed. What's cool is you can upload your draft return before filing and their system reviews everything for audit risks and mistakes. For me, they caught that I had categorized some business expenses in the wrong sections, which could have raised red flags.

I was skeptical about AI tax tools too until I tried that taxr.ai service after seeing it mentioned here. I had a complicated situation with rental income, self-employment, and multiple state filings. The regular tax software I was using missed several things that could have triggered an audit. What impressed me was how it caught a specific issue with my home office deduction where I had calculated square footage incorrectly. It also identified that I had missed claiming some qualified business income deductions that saved me about $1,700. The review highlighted specific audit risk factors based on my return, not just generic advice. I ended up paying a lot less than what a CPA would have charged me, and I felt much more confident filing my return. For someone in a situation like yours with new self-employment income, it's definitely worth checking out.

Hey! I see you're worried about an audit. My brother got audited last year after having a similar jump in income. We tried for WEEKS to get through to the IRS for clarification on some issues - literally called 30+ times and couldn't get a human. Then someone told us about https://claimyr.com which got him through to an IRS agent in about 15 minutes! You can see how it works here: https://youtu.be/_kiP6q8DX5c Not saying you'll get audited, but if you have questions or concerns before filing, it might be worth having them answered directly by the IRS instead of guessing. The peace of mind was totally worth it for my brother.

I need to apologize for my skepticism about that Claimyr service. After struggling with some questions about my 1099 income, I decided to give it a shot as a last resort. I was honestly shocked when I got a call back connecting me to an actual IRS representative after about 40 minutes. The agent was able to clarify some specific questions I had about home office deductions that were relevant to my situation. She also explained exactly what documentation I should keep on hand in case of an audit. Getting definitive answers directly from the IRS gave me so much more confidence in filing my return. For anyone on the fence - it actually works as advertised. Would have saved me hours of frustration if I'd tried it sooner instead of playing the endless redial game on my own.

I think you'll be fine filing with the tax software if you've been careful inputting everything. I was in an almost identical situation 2 years ago (multiple W2s, new 1099 income, two states) and filed with TurboTax without issues. The biggest thing is making sure you have documentation for all your self-employment deductions. Keep detailed records of what each expense was for and how it relates to your business. If you're deducting any home office expenses, make sure you've measured the space accurately and it's used exclusively for work. Also, double check that your quarterly estimated payments are all properly credited in the software. Sometimes those can get missed if the dates or amounts aren't entered correctly.

Has anyone here actually been audited? I filed with 1099 income for years and always worried but never got flagged.

My advice - file electronically through the software if you're confident, but pay the extra fee for audit protection. Most tax software offers this now for like $40-50 extra, and it gives you representation if you do get audited. Way cheaper than hiring a CPA now and the software is pretty good at handling all the forms you mentioned. Just make absolutely sure you double check all your entries before submitting!

I've been through a similar situation and wanted to share what worked for me. Your audit risk is genuinely low - the combination of factors you described (multiple W-2s, reasonable business expenses relative to income, proper quarterly payments) actually shows good tax compliance rather than red flags. That said, I'd strongly recommend doing a final review of your return before filing. Whether that's through one of those AI tax services people mentioned, a quick consultation with a CPA, or just methodically going through each form line by line depends on your budget and comfort level. The most important thing is having solid documentation for every business deduction. Since you mentioned keeping receipts digitally, make sure you also have a clear business purpose documented for each expense. For mixed personal/business items, only deduct the business portion and keep notes on how you calculated that percentage. Your income jump from adding contractor work is actually pretty normal and explainable, so don't stress too much about that aspect. The IRS sees career changes all the time, especially with the gig economy boom.