I'm really glad to see this thread has generated so many helpful suggestions! As someone who works in tax preparation, I want to emphasize that the IRS wage and income transcript really is your golden ticket here. It's free, reliable, and contains all the information you need from your missing W2s. One thing I'd add that hasn't been mentioned yet - when you do get your transcript and file that 2017 return, make sure to file it as soon as possible even if you can't pay any taxes owed immediately. The failure-to-file penalty is much steeper than the failure-to-pay penalty (5% per month vs 0.5% per month). You can always set up a payment plan with the IRS later if needed. Also, don't be surprised if the wage transcript shows slightly different numbers than what you remember from your original W2s. Sometimes employers make corrections after issuing the original forms, and the transcript reflects the final reported amounts. This is actually better for your filing since it matches exactly what the IRS has on record. The advice about VITA programs is spot-on too - they're incredibly helpful for situations exactly like this and won't cost you anything. Good luck getting everything sorted out!

This has been such a helpful thread! I'm in a similar situation with missing W2s from 2019 and was feeling pretty overwhelmed about where to start. Reading through everyone's experiences and suggestions has given me a clear roadmap forward. I think I'm going to start with the IRS wage and income transcript like most people suggested, then check my old email accounts and phone photos as backup. The VITA program sounds like a great resource too - I had no idea free help was available for situations like this. One question for anyone who's been through this process - when you requested the wage transcript online, did you need any specific information beyond just your SSN and address to verify your identity? I'm wondering if I need to gather any other documents before I start the online process. Thanks again to everyone who shared their experiences and advice. It's so reassuring to know that other people have successfully gotten through this same situation!

@Maya Patel Yes, you can definitely handwrite directly on the receipt! Most FSA administrators actually prefer when you clearly mark eligible items rather than leaving them to figure out what you're claiming. I usually use a pen or highlighter to circle the eligible items and write the amount next to them. Some people worry about "modifying" receipts, but this is actually considered helpful documentation, not tampering. You're just making it easier for the administrator to process your claim. I've been doing this for over 5 years with multiple FSA providers and never had an issue. Just make sure your handwriting is clear and legible. If you're submitting a photo of the receipt, sometimes it helps to use a darker pen so it shows up well in the image. The goal is to make the reviewer's job as easy as possible so your claim gets approved quickly!

Just to add another perspective from someone who's been through the FSA claim process many times - your Kroger receipt should be perfectly fine for the Claritin! I've submitted similar grocery store receipts for allergy medications, pain relievers, and other OTC items without any problems. One thing that might help streamline your claim: if you plan to buy more OTC medications regularly, consider setting up automatic reimbursement through your FSA debit card if your plan offers it. That way eligible purchases get processed immediately at checkout instead of having to submit receipts later. Not all FSA plans have this feature, but it's worth checking with your administrator. For this current receipt though, definitely circle the Claritin, write the amount, and you should be good to go. The fact that it clearly shows "Claritin" rather than some cryptic product code makes it much easier for them to approve quickly.

Great question! I've been working remotely for about 3 years now and this exact situation comes up all the time. Just to reinforce what others have said - you're definitely on the right track thinking about this upfront. Since you're working from Michigan, that's where you'll pay state taxes regardless of where your employer is based. The federal W-4 is the same everywhere, but you'll need Michigan's state withholding form (MI-W4) for state taxes. One thing I'd add is to double-check your employment contract or offer letter to see if there's any language about tax responsibilities or if they mention anything about "tax equalization" - some companies have policies about handling multi-state tax situations for remote workers. Also, keep in mind that Michigan requires you to pay taxes if you're a resident OR if you earn income from Michigan sources while living there, so you're definitely in Michigan tax territory. Lucky for you that Nevada has no state income tax - makes things much cleaner! The most important thing is making sure your employer's payroll system knows you're physically working from Michigan so they set up the withholdings correctly from day one. Good luck with the new remote position!

Just wanted to add one more consideration that I learned about recently - if you ever work from a different location temporarily (like visiting family in another state for a few weeks while working), you may need to track those days for tax purposes. I found out the hard way that some states consider you liable for taxes if you work there for even a short period. Since you mentioned you might occasionally visit the Nevada office, this shouldn't be an issue since Nevada has no income tax. But if you ever work while traveling to other states, it's worth keeping a simple log of where you're physically located when working. Also, when you do your taxes next year, you'll likely only need to file a Michigan state return (plus federal), which is much simpler than remote workers who have to deal with multiple state filings. The Michigan/Nevada combination is actually pretty ideal from a tax complexity standpoint! One last tip - save all documentation about your remote work arrangement and correspondence with HR about tax withholding. If there are ever any questions from tax authorities about your work location, having that paper trail makes everything much smoother.

Anyone know if TurboTax actually needs the information from these forms entered manually? Or do they just want to know which forms you have? Last year I remember answering questions about insurance but never entering anything from the actual 1095 forms.

Just to add some clarity for future reference - the key difference is really about WHERE you got your insurance from: - 1095-A: You bought insurance through Healthcare.gov or your state's marketplace - 1095-B: You had insurance from a private company, Medicare, Medicaid, or other qualifying coverage - 1095-C: Your employer (with 50+ employees) offered you health insurance Since you have B and C forms, it sounds like you had employer-sponsored insurance. When TurboTax asks about the 1095-A, just answer "No" - you don't need to hunt for one because you wouldn't have received one with employer coverage. The forms are mainly there to help you answer TurboTax's questions about what months you had coverage. You typically don't need to enter specific details from the forms themselves, just use them to confirm your coverage periods were accurate.

22 Has anyone considered the state tax implications? I'm in California, and they don't conform to the federal QSBS exclusion anymore. Made for a really unpleasant surprise when I sold my qualified shares last year and still got hit with a massive CA tax bill despite having the federal exclusion!

This is a really complex area that requires careful planning. One thing to consider is that even if you qualify for QSBS after conversion, the IRS has been scrutinizing these transactions more closely lately. Make sure you have solid documentation showing the conversion was done for legitimate business reasons beyond just tax benefits. Also, with your $60M valuation, you're already above the $50M asset threshold, so you'd need to ensure the business qualifies at the conversion date. The IRS looks at gross assets, not net assets, so factor in any debt when calculating this. I'd strongly recommend getting a detailed tax opinion from a qualified attorney before proceeding. The potential savings are enormous, but the compliance requirements are strict, and any misstep could disqualify the entire benefit.