Everyone's making this more complicated than it needs to be. An Accountable Plan is just a fancy way of saying "we reimburse business expenses properly." On the 1120S, you just put the expenses wherever they'd normally go. Travel on Line 12, repairs on Line 14, etc. The IRS doesn't care that it was reimbursed under an Accountable Plan - they just care that it was a legitimate business expense properly documented. The Accountable Plan benefits the EMPLOYEE by making the reimbursement non-taxable to them.

Thanks everyone for the helpful responses! I just wanted to add one more tip that helped me with our S-corp Accountable Plan setup. Make sure you're keeping separate records for your Accountable Plan reimbursements versus regular payroll expenses, even though they both end up as business deductions on the 1120S. I learned this the hard way when our bookkeeper mixed some reimbursements in with regular wages on our payroll records. It created a mess because those reimbursements were supposed to be non-taxable to the employee under the Accountable Plan, but they got processed as taxable wages instead. We had to file corrected W-2s and it was a nightmare. Now I have a completely separate tracking system for all Accountable Plan activity - receipts, approval documentation, reimbursement records, everything. It makes tax preparation much smoother and gives you rock-solid documentation if you ever get audited. The IRS really focuses on whether you can prove the plan was administered correctly, not just that you had one on paper.

Has anyone tried the Free File Fillable Forms on the IRS website for older returns? I wonder if that would work instead of paying for old TurboTax versions.

For anyone still struggling with this, I want to emphasize what others have said about the 3-year E-File window. The IRS is very strict about this - once October 15th passes for any given tax year, that year's E-File system permanently closes. However, there's one important thing to keep in mind: if you're filing these old returns because you owe money, interest and penalties continue to accrue until you file and pay. So even though you have to mail paper returns, don't delay getting them submitted. Also, if you're expecting refunds on these old returns, be aware that you generally only have 3 years from the original due date to claim a refund. For 2018, that deadline was April 15, 2022 (with some COVID extensions), so any 2018 refunds may already be forfeited. You should still file for record-keeping purposes, but don't expect a refund check. Make sure to send your paper returns via certified mail so you have proof the IRS received them!

Great discussion here! I've been managing multiple Roth IRAs for years and learned some of these lessons the hard way. One additional tip I'd add is to set up automatic contribution limits within each brokerage account if they offer that feature. For example, if you know you want to split your $6,500 annual limit between two accounts, you can often set up automatic investments that will stop once you hit your predetermined amount for each account (like $3,250 each). This prevents the accidental over-contribution scenario that Maria faced. Also, keep in mind that if your income changes during the year and you become ineligible for Roth contributions due to income limits, that's another way to accidentally over-contribute even if you're tracking the dollar amounts correctly. The income limits for 2025 phase out between $146,000-$161,000 for single filers, so it's worth double-checking your projected income if you're anywhere near those thresholds.

This has been such an informative thread! As someone who just opened my second Roth IRA account at a different brokerage, I was completely unaware of how easy it would be to accidentally over-contribute. The point about Form 5498 not being available until May is particularly eye-opening - I always file my taxes in February, so I would have never caught an over-contribution through those forms. I'm definitely going to set up that contribution limit tracking that was mentioned. It's reassuring to know that the major brokerages have built-in features to help prevent this issue. I think I'll also start using a simple tracking spreadsheet as a backup, just to be extra safe. One question I have: if someone realizes they over-contributed but it's a relatively small amount (like $50-100), is it still worth going through the hassle of the excess contribution withdrawal? Or would it sometimes make more sense to just pay the 6% penalty, especially if the withdrawal process is complicated?

I actually had this exact issue with a /ES futures spread last year. The trick is to reverse how you think about the short position. For Form 6781: 1. For the short position: Put the amount you RECEIVED when opening the position as the PROCEEDS, and the amount you PAID to close it as the COST. 2. For the long position: Put the amount you PAID when opening as the COST, and the amount you RECEIVED when closing as the PROCEEDS. This way both will calculate correctly - the long showing a gain and the short showing a loss.

I ran into this exact same issue with SPX spreads last year and it was incredibly frustrating until I figured out the correct approach. The key insight that finally made it click for me was understanding that for short positions on Form 6781, you're essentially reporting a "reverse transaction" - what you received becomes proceeds, what you paid becomes cost. For your specific situation with the SPX put spread: - Short 4950 put: Proceeds = amount you received when opening the short position, Cost = amount you paid to close it (resulting in your $320 loss) - Long 4850 put: Cost = amount you paid when opening, Proceeds = amount you received when closing (resulting in your $215 gain) The mark-to-market rule is crucial here. Since you held these past December 31st, you need to report the "deemed sale" at fair market value on Dec 31 for this tax year's return. Then when you file next year, you'll report the actual closing transactions using the Dec 31 values as your new basis. Most tax software struggles with this, but the underlying tax treatment is straightforward once you understand the mechanics. The 60/40 split applies to each leg separately, so you'll get the favorable tax treatment on both the gain and loss portions.

This has been such an incredibly thorough and helpful discussion! I'm in a very similar situation with my company's non-standard benefit year, and reading through everyone's experiences has given me so much confidence about navigating this transition. A few key takeaways that I think are worth highlighting for anyone else in this situation: 1. **Month-by-month eligibility is the golden rule** - You can absolutely have HSA contributions for part of the year and FSA contributions for another part, as long as they don't overlap in the same month. 2. **Proration is crucial** - If you're only HSA-eligible for 4 months (Jan-Apr), you can only contribute 4/12 of the annual limit, not the full amount. 3. **Documentation is your friend** - Keep detailed records of everything, especially if your HR department is as confused as mine has been! 4. **Strategic timing matters** - Think about when to incur medical expenses based on which account will give you the best tax advantage and fund availability. The practical tips about record-keeping, the IRS Publication 969 reference, and especially the real-world calculation examples have been invaluable. It's amazing how much clearer this all becomes when you see people who have actually been through it share their experiences. Thanks to everyone for making this such a comprehensive resource - this thread should be required reading for anyone dealing with HSA/FSA transitions and non-calendar benefit years!

This has been an absolutely fantastic thread! As someone who's been lurking in this community for a while, I'm impressed by the depth and quality of advice shared here. I wanted to add one small detail that might help others - when you're making the HSA to FSA transition, double-check whether your employer offers any "bridge" coverage options during the transition period. Some larger employers have supplemental plans or gap coverage that can help ensure there's no interruption in your benefits eligibility. Also, for anyone still feeling overwhelmed by all the calculations and rules, I'd recommend scheduling a quick call with your HSA provider's customer service team in addition to reading IRS Publication 969. Many HSA administrators have specialists who deal with exactly these transition scenarios and can walk you through the math specific to your situation. They often have internal tools that make the proration calculations much simpler than doing it manually. The community knowledge sharing here has been incredible - from the practical record-keeping tips to the strategic expense timing advice. It's clear that many of us have learned these lessons the hard way, so sharing that experience really helps others avoid common pitfalls. Thanks to @Julia Hall for starting such an important discussion, and to everyone who contributed their expertise. This thread is going to help so many people navigate these complex benefit transitions!