I've been following this discussion and wanted to add a perspective that might help simplify things for anyone still feeling overwhelmed by all the options mentioned. While tools like taxr.ai and services like Claimyr can definitely be helpful for complex situations, don't overlook the free resources that are often sufficient for straightforward cases like yours. The IRS Tax Withholding Estimator really is quite good, and for a single person with one main job plus a side gig, it should get you very close to that ideal "break even" target. Here's what I'd suggest as a simple action plan: Start with just Steps 1 and 5 on your W-4 (the basic info), then use your first paycheck to run the IRS estimator with real numbers. At that point, you can add your $7,200 annual side gig income and see what adjustments it recommends. The beauty of this approach is that you're not trying to predict everything perfectly upfront - you're using actual data to make informed adjustments. And remember, owing $200-500 at tax time isn't a failure, it's actually optimal money management since you kept that cash earning interest or invested throughout the year instead of giving the government an interest-free loan. Don't let the complexity paralysis keep you from starting. Get something reasonable submitted, then refine as you learn more about your actual withholding patterns.

This thread has been incredibly helpful! As someone who just went through the W-4 process myself a few months ago, I want to echo what others have said about not overthinking it initially. One thing that really helped me was keeping a simple spreadsheet to track my withholding vs. estimated tax liability as the year progressed. Every few months, I'd plug my year-to-date earnings and withholding into the IRS estimator to see if I was still on track. This made adjustments feel less scary because I could see the impact of small changes before they became big problems. For your delivery gig income specifically, don't forget you can deduct business expenses like gas, phone bills (partially), and vehicle maintenance. These deductions can reduce the tax impact of that side income, so factor them in when calculating how much extra to withhold. I track my delivery expenses in a simple app and it usually saves me a few hundred dollars at tax time. The "break even plus or minus $300" target that several people mentioned is spot-on. I ended up owing $180 last year and felt great about having that extra cash flow throughout the year instead of waiting for a refund. Good luck with your new job!

Something to also consider - check if your 1099-R has a distribution code in Box 7. If it shows code "G" that indicates a direct rollover to a qualified plan, which helps the IRS systems understand it was non-taxable. If it has a different code, you definitely need to amend and provide documentation explaining the rollover.

I went through something very similar with a 401k-to-IRA rollover I missed on my return. One thing that helped me was creating a timeline of events to include with my amendment - dates of the original 401k distribution, when the funds were received by the new IRA custodian, and confirmation that no funds were ever distributed to me personally. Also, if you haven't already, contact both your old employer's plan administrator and your new IRA custodian to get written confirmation that this was a direct trustee-to-trustee transfer. Some custodians will provide a letter specifically for tax purposes that clearly states the rollover was completed according to IRS regulations. Having that documentation attached to your amendment makes it crystal clear to the IRS that this was a non-taxable event. The peace of mind from getting this handled properly is worth the small effort of filing the amendment now rather than potentially dealing with IRS notices later.

I work at a tax prep office and we see these 826 codes fairly regularly. One thing nobody's mentioned yet - check if you have any past due state income taxes. The Treasury Offset Program doesn't just collect federal tax debts, they also collect state tax debts, which would still show up as code 826. Also, the 10-year statute of limitations on tax debt collection is about to expire for 2013 tax returns, which might explain why they're suddenly collecting now. The IRS often gets more aggressive about collection when the statute is about to run out.

I went through almost the exact same thing last year! The 826 code with that specific format (201312) definitely indicates a federal tax debt from December 2013. What helped me was requesting my Account Transcript for tax year 2013 directly from the IRS website - it'll show you exactly what happened that year. In my case, there was an automated adjustment made to my 2013 return that I never knew about because the notice went to an old address. The IRS had corrected something on my original return (I think it was related to education credits) and I apparently owed additional tax plus penalties and interest that had been growing for 10+ years. The good news is that if this is truly the first time you're hearing about this debt, you may have grounds to request penalty abatement for "reasonable cause" since you were never properly notified. I was able to get about 40% of my offset refunded by filing Form 843 and explaining the situation. Definitely get that 2013 Account Transcript first though - it'll give you the full picture of what triggered this debt originally.

One quick tip - make sure you're using the correct form! The IRS changed things a few years ago, and now most contractor payments should be reported on Form 1099-NEC rather than 1099-MISC. The 1099-MISC is now primarily for rent, royalties, and certain other payments, not for services provided by independent contractors. This tripped me up last year and I had to redo all my forms. The 1096 transmittal form is still used for both types though.

Just wanted to share another option that worked for me in a similar situation - many local CPA offices keep a stock of official IRS forms during tax season and are often willing to sell them to small business owners. I called around to a few accounting firms in my area last year when I was in the same bind, and one of them sold me the exact forms I needed for just a few dollars above cost. Also, if you do end up going the electronic route through any of the services mentioned here, make sure you still get signed W-9 forms from your contractors if you don't already have them. The IRS requires you to have these on file regardless of whether you file electronically or on paper, and they can request to see them during an audit. One last thing - if you're paying family members, double-check whether they actually need 1099s. If they're working as employees rather than independent contractors, you'd need to handle payroll taxes differently. The IRS has specific criteria for determining worker classification, and family relationships don't automatically make someone an independent contractor.

One thing that might help ease your stress - the IRS is generally more interested in getting you back into compliance than in punishing you. They see situations like yours all the time, especially after the chaos of the past few years. When you're gathering documents, don't forget about things like state tax refunds you might have received (those can be taxable income), unemployment benefits, or any side gig income from apps like Uber, DoorDash, etc. These smaller income sources are easy to forget but can add up. Also, if you moved during those years, make sure you're filing in the correct states. Some states have no income tax, others do, and you might owe taxes in multiple states depending on when you moved and where you worked. The key is just to start. Pick one year (I'd suggest 2020 since it's the oldest) and focus on getting all the documents together for just that year first. Once you see how the process works for one year, the others will feel much more manageable. You've got this!

I went through something very similar a few years back - hadn't filed 2018-2020 due to job changes and personal issues. The anxiety was honestly the worst part! Here's what worked for me: Start by requesting your wage and income transcripts from the IRS website (irs.gov/individuals/get-transcript). This will show you exactly what income the IRS has on record for each year, which helps you identify any missing documents and gives you a baseline to work from. One thing that really helped my peace of mind was calling the IRS Taxpayer Advocate Service (1-877-777-4778). They're specifically there to help people in situations like yours get back on track. They can't do the filing for you, but they can explain your options and help you understand what to expect in terms of penalties. Don't beat yourself up about this - life happens, and you're taking the right steps now. The IRS would much rather have you file late than not at all. Focus on getting organized first, then tackle one year at a time. You'll feel so much better once you start making progress!