I really feel for your boyfriend's situation - tax anxiety is so much more common than people realize, and the shame spiral that happens when you fall behind can be absolutely paralyzing. The good news is that he's ready to address this now, which is the hardest part. One approach that might help ease his anxiety is to start by simply requesting his IRS account transcripts online. This will show him exactly what the IRS has on file for each year - what income was reported, whether he actually owes money or is due refunds, and what penalties (if any) have already been assessed. Sometimes seeing the actual numbers instead of imagining worst-case scenarios can be incredibly relieving. Many people in his situation discover they're actually owed refunds for some years, especially if they had taxes withheld from paychecks. The IRS isn't going to "take everything he has" - they're actually quite reasonable about setting up payment plans if he does owe anything. If the anxiety is still too overwhelming, consider starting with just ONE year - preferably the most recent unfiled year since documents will be easier to find. Getting that first return filed successfully can build momentum and confidence for tackling the remaining years. You're being an amazing partner by supporting him through this. Having someone in your corner makes all the difference when dealing with anxiety around these kinds of responsibilities.

As someone who works in tax preparation, I want to reassure you that your boyfriend's situation is incredibly common - I see clients dealing with multiple years of unfiled returns regularly, and it's almost never as catastrophic as people imagine it will be. One thing I'd suggest that hasn't been mentioned yet is having him check if he qualifies for the IRS Fresh Start Program. This program is specifically designed to help taxpayers who've fallen behind, and it can provide significant relief on penalties and payment terms. The criteria aren't as strict as many people think. Also, a practical tip: if he's missing any tax documents from previous years, don't stress about having perfect records. The IRS accepts "reasonable estimates" for things like unreimbursed business expenses or charitable donations if you don't have exact receipts, as long as the amounts are realistic. This can help remove some of the perfectionist paralysis that often keeps people stuck. The fact that he's in a better mental health space now and actively wants to resolve this shows real growth. That motivation is honestly the biggest hurdle - everything else is just paperwork and process. The IRS genuinely wants people to get caught up, and they have systems in place to make it as manageable as possible. You're being an incredible support system for him. Having someone who cares enough to research options and provide emotional support makes this whole process so much less isolating.

Just wanted to add that if you're filing fewer than 10 1099-NECs, the IRS actually has a free online filing system called the FIRE system (Filing Information Returns Electronically). There's a bit of a learning curve, but once you're set up, it's pretty straightforward.

Just to clarify something important that might help others - you absolutely cannot use 2022 forms for 2023 tax year filing. The IRS requires current year forms for all information returns like 1099-NEC and 1096. However, there's good news! You don't need to buy expensive "official" forms anymore. You can download the current 2023 forms directly from the IRS website (irs.gov) and print them on regular white paper as long as they're printed at exactly 100% scale with no adjustments. The IRS scanners can read these just fine. For the 1099-NEC, make sure you're downloading the "Copy A" version for filing with the IRS. The forms are available as fillable PDFs, so you can type directly into them before printing, which makes everything much cleaner and easier to read. This way you can use up those leftover forms for scratch paper and get compliant 2023 forms without spending extra money!

This has been such an enlightening discussion! I've been following along as someone who's been in the US on a J-1 visa for about 8 months and will likely be switching to an H-1B next year. Reading through everyone's experiences has really opened my eyes to how complex the intersection of immigration status and tax status can be. What strikes me most is how many people (myself included) assume that being on a "non-immigrant" visa automatically means you're a non-resident for tax purposes. The substantial presence test seems to be the key factor that many of us overlook. I'm definitely going to bookmark Publication 519 and make sure I understand these rules before my next filing season. For those who discovered they'd been filing the wrong forms - your experiences with amended returns and getting refunds is really encouraging. It shows that the IRS system can work to correct these mistakes, even when the rules are confusing. One thing I'm curious about: for people on J-1 visas, are there any special considerations for the substantial presence test? I know some visa categories have exemptions or different rules. I want to make sure I'm prepared when my situation becomes more complex. Thanks to everyone for sharing such detailed experiences - this thread is going to be incredibly valuable for anyone navigating US tax obligations on work visas!

This thread has been incredibly helpful! I'm currently on an H-1B visa and have been in the US for about 2.5 years. Like many others here, I was completely confused about the difference between immigration status and tax residency status. I've been filing 1040NR forms this whole time because I thought "non-immigrant visa = non-resident for taxes." Reading through everyone's experiences, I now realize I've almost certainly been filing the wrong forms since I clearly meet the substantial presence test. What's really valuable about this discussion is seeing how many people have successfully filed amended returns to correct this mistake. It gives me confidence that I can fix this situation without major penalties. I'm planning to work through Publication 519 this weekend to calculate my exact substantial presence dates and then file 1040X forms for the years I got wrong. One thing I'm wondering about - for those who filed amended returns, did you handle this yourself or work with a tax professional? The process seems straightforward from what you've described, but I'm nervous about making another mistake. Also curious about timing - is it better to get the amended returns filed before preparing this year's return, or can I handle them together? Thanks to everyone for sharing such detailed experiences. This community has probably saved me thousands of dollars in missed deductions and credits!

Just a heads up - I talked to my international student advisor about this exact issue last semester. She said that technically Form 8843 is supposed to be attached to your tax return, but submitting it separately isn't a major issue. The most important thing is making sure it gets submitted before the filing deadline. She also mentioned that some students who forget to file it have submitted it in later years without penalty, but obviously it's better to do it on time. The key is that Form 8843 establishes your non-resident status for tax purposes, which can matter in the long run for immigration purposes.

I went through this exact same situation two years ago and can confirm that mailing Form 8843 separately after e-filing is completely fine! I was panicking just like you are now, but it turned out to be much simpler than I thought. Here's what I did: I printed out Form 8843, filled it out completely, and included a brief cover letter stating "Please find attached Form 8843 for tax year [YEAR]. My federal tax return was already e-filed and accepted on [DATE]." I included my name, SSN/ITIN, and address at the top of the letter. I sent it via certified mail to the IRS processing center for my state and got the delivery confirmation about a week later. Never heard anything back from the IRS, which in this case is good news - it means they received it and processed it without issues. The important thing is to get it postmarked before the tax deadline (April 15th). Since you're on OPT, maintaining proper tax compliance is definitely important for your status, so good on you for catching this and taking action. Don't stress too much - this is a common oversight and the IRS is used to receiving these forms separately from international students.

This has been such an enlightening thread! I'm working on my first year of self-filing after years of paying someone else to do my taxes, and Box 14 was honestly making me consider going back to a tax preparer. The breakdown everyone provided about informational vs. actionable entries is a game-changer. I was getting so frustrated trying to figure out where to input every single Box 14 item in my tax software, not realizing that most of them (like the employer health insurance contributions) don't actually need to go anywhere. I just went back through my W-2 with fresh eyes after reading all these responses. The "Health" entry that was stressing me out is definitely just my employer's premium contribution - informational only. But I did spot something labeled "NY-PFL" that I now realize might be New York Paid Family Leave and could potentially be deductible on my state return. It's really frustrating that there isn't clearer guidance from the IRS on this stuff. Box 14 feels like this mysterious catch-all that every employer uses differently, and we're all left to figure it out ourselves. Thank goodness for communities like this where people actually share practical advice instead of just telling you to "consult a tax professional" for every little question!

As someone who's been preparing taxes for family and friends for a few years now, I wanted to add that the confusion around Box 14 is totally understandable - it really is one of the most poorly explained parts of the W-2 form. One thing I've learned is to always check if your employer includes a legend or explanation somewhere on the W-2 or in their year-end documentation that explains what their specific Box 14 codes mean. Some employers are better than others at providing this context. Also, if you're using tax software and it has an "import W-2" feature where you can take a photo or upload the form, those tools are getting pretty good at automatically categorizing Box 14 entries and telling you which ones need action versus which are just informational. It can save you from having to manually decode each entry. The state-specific deduction advice everyone's shared here is spot-on though - those are definitely the ones to watch for since they can actually impact your tax liability. Everything else (health premiums, parking, most fringe benefits) you can generally ignore for tax purposes even though your employer felt compelled to report it.