Just a heads up on the marketplace HDHP option - make sure you check the deductible amounts carefully! Not all "high deductible" plans on healthcare.gov actually qualify as HDHPs for HSA purposes. For 2024, a qualifying HDHP needs to have a minimum deductible of $1,650 for self-only coverage and a maximum out-of-pocket limit of $8,050. I nearly messed this up when I was shopping for plans.

Great question about the HSA last-month rule and job transitions! I went through something similar a few years ago and learned a lot about maintaining eligibility during the testing period. One thing I'd add to the excellent advice already given is to consider the network differences between your current plan and potential new coverage. If you have any ongoing medical needs or preferred providers, COBRA might be worth the extra cost to maintain your existing network relationships through the end of the year. Also, when comparing marketplace HDHPs, pay close attention to the HSA contribution limits if the plan comes with an HSA from a different provider. Some HSA administrators have higher fees or limited investment options compared to others. Since you're only looking at a few months of coverage, the fees might not matter much, but it's worth checking. The timing advice others have shared is spot-on - you have until October 31st to remain HSA-eligible after your coverage ends on the 10th, and you'll want new HDHP coverage starting November 1st. This gives you a comfortable window to shop and compare options without rushing into a decision.

Isn't TurboTax supposed to catch things like the Saver's Credit automatically? I thought that was the whole point of using tax software!

This is exactly why I love this community - so much helpful information! I had no idea about the Saver's Credit either. For anyone else who might be confused like Omar and I were, I found that TurboTax does have a section for retirement savings contributions, but it's easy to miss if you're rushing through the interview. It's usually under the "Deductions & Credits" section, and they ask about contributions to IRAs, 401(k)s, etc. The key thing is that even though Roth contributions aren't deductible, you still need to report them IF you're eligible for the Saver's Credit. It's one of those situations where the same contribution serves two different purposes - your financial institution reports it to the IRS via Form 5498 (so they know you made the contribution), but you also need to report it on your tax return to claim the credit if you qualify. Thanks everyone for clearing this up - definitely going to check if I missed out on this credit in previous years!

As someone who works in tax preparation, I can confirm that all the advice here about the EIN being the primary matching element is absolutely correct. The IRS automated systems use the EIN (Employer Identification Number) from Box 9a as the main identifier when matching your return against the information they received from Fidelity. For your specific situation with "FIDELITY INVESTMENTS INSTITUTIONAL OPERATIONS CO.", you should definitely enter the full name exactly as it appears on your 1099-R. While minor variations in the payer name usually won't cause issues as long as the EIN matches, using the exact name helps ensure the smoothest processing. One additional tip I'd add: when you're entering this information in FreeTaxUSA, make sure you also double-check that you're entering the correct distribution code from Box 7. This is almost as important as getting the payer information right, since it tells the IRS (and your tax software) how to treat the distribution for tax purposes. You're being very thorough by asking these questions upfront - that's exactly the right approach for your first 1099-R filing!

Great thread everyone! As a newcomer to this community, I really appreciate all the detailed advice about handling 1099-R forms. I'm in a similar situation with my first retirement distribution and was getting overwhelmed by all the boxes and codes. Reading through all these responses, it's clear that the EIN is the critical piece for IRS matching, but entering the payer name exactly as shown is the safest approach. I love that people shared their actual experiences - especially hearing from the tax prep professional about what constitutes "minor" vs "problematic" variations in payer names. The tips about double-checking federal withholding in Box 4 and state withholding in Box 12 are gold - I almost missed those on my form! And I had no idea about the distribution codes in Box 7 being so important for determining tax treatment. This kind of detailed, experienced-based advice is exactly why I joined this community. Looking forward to contributing back once I get more familiar with all these tax forms and processes. Thanks again everyone for making this less intimidating for us newcomers!

Has anyone used FreeTaxUSA for filing back taxes? Their prior year returns are only $15 each and I've heard good things, but not sure how they handle situations with missing documents.

I'm dealing with a similar situation but for 2019-2021. One thing I learned from my tax preparer is that you should prioritize getting your wage and income transcripts from the IRS before you start filing. You can request these online through the IRS website or by calling them. These transcripts will show you exactly what income the IRS has on record for each year, which is super helpful if you're missing W-2s or 1099s. It also helps you verify that you're not missing any income sources you might have forgotten about. For the Recovery Rebate Credit specifically, the transcript will show if you received any stimulus payments that year, so you'll know exactly how much credit you can still claim. I discovered I was eligible for an extra $600 from the second stimulus that I never received. The transcript is free and gives you a complete picture before you start the actual filing process. Much better than guessing what your income was!

Has anyone tried MileIQ for retroactively creating logs? My accountant mentioned it but I'm not sure if it can help with past years or just going forward.

One thing that really helped me when I had to reconstruct my 2017 mileage logs was creating a "typical week" template first. I looked at my calendar patterns and identified my regular business destinations, then calculated standard routes between them. For example, if I went to Client A every Monday and Client B every Wednesday, I could establish those as baseline trips and then look for variations. This approach helped me avoid over-estimating miles while still capturing the bulk of my business travel. Also, don't forget to check your car insurance records - sometimes they have annual mileage estimates that can help validate your totals. And if you had any major car repairs or oil changes, those service records often include odometer readings that can serve as checkpoints for your reconstruction. The IRS generally accepts reasonable reconstructions as long as you can show you made a good faith effort using available evidence. Document your methodology clearly - explain what sources you used and how you calculated the mileage. This transparency actually helps your case if you're ever questioned about it.