Are there any special forms I need to file if Section 965 applies to me? My tax software doesn't seem to have anything specific about this.

Yes, there are specific forms and worksheets required. You'll need to file Form 965 along with your tax return, and potentially several schedules that go with it. Most consumer tax software doesn't handle Section 965 calculations well, which is why professional help is recommended. The IRS also requires a Section 965 Transition Tax Statement to be attached to your return. Additionally, if you elected to pay the tax over installments (which was an option when the law first passed), there's ongoing reporting for that as well. If you're using consumer tax software, this is one area where it might not have the capabilities to properly guide you through the complex requirements.

Thanks for explaining that - makes much more sense now! One quick question: if I already paid foreign taxes on this income in the country where it was earned, can I claim foreign tax credits to offset the Section 965 tax?

For partial work from home situations, you can only deduct the business percentage of your internet if you're self-employed. W-2 employees lost the ability to deduct unreimbursed business expenses after the Tax Cuts and Jobs Act, unless you're certain specific professions like armed forces reservists, qualified performing artists, or fee-basis state/local government officials.

Does requesting all three types of relief make the process take longer? I'm trying to get this resolved as quickly as possible and don't want unnecessary delays.

Requesting all three types actually doesn't extend the processing time at all. The IRS evaluates your case for all types simultaneously, not sequentially. They automatically consider which type you qualify for, starting with innocent spouse relief, then separation of liability, and finally equitable relief. The biggest factors affecting processing time are completeness of documentation and current IRS backlog. Making sure you provide thorough documentation up front is the best way to avoid delays. If you only request one type and don't qualify, they'll reject your case entirely rather than considering if you might qualify under another type.

They process innocent spouse claims year-round, but there's definitely slowdown during filing season. My claim took 9 months last year, with 4 of those months being during tax season when it basically didn't move at all. You might not hear anything until May or June.

5 These are great suggestions. I didn't think about maxing out retirement accounts! I haven't contributed much to my 401k this year so I could definitely increase that. How would I know if I have any investments at a loss that I could sell? Would I just look at my current portfolio and check what's down from my purchase price?

14 Yes, exactly! Just look at your current portfolio and identify any investments that are currently valued lower than what you paid for them. Those are your potential tax-loss harvesting opportunities. Your brokerage should show your cost basis and current value for each position. Remember that if you sell something at a loss and buy the same or a "substantially identical" security within 30 days before or after the sale, that's considered a wash sale and you can't claim the tax loss. You can buy something similar but not identical to maintain market exposure while still harvesting the tax loss.

9 I talked to my Fidelity advisor about almost this exact same situation last year. They basically confirmed what everyone here is saying - you're stuck with the tax bill for the year the gains were realized, but they did help me put together a tax-loss harvesting strategy for the following year to minimize the ongoing impact. Depending on your broker, they might offer free consultations that could be helpful.

Thanks for this advice! I hadn't thought about keeping specific documentation of the tax year designation. Will Fidelity automatically generate a receipt showing the 2020 contribution, or should I request something special when I make the contribution?

When you make the contribution online, you'll receive a confirmation that should clearly indicate the tax year. Print this or save a PDF of it. Additionally, I'd recommend taking a screenshot of the contribution page where you select "2020" as the tax year. Fidelity will also generate a Form 5498-SA in May that officially documents your HSA contributions by tax year. This form is sent to both you and the IRS. While you don't need to include it with your tax return, definitely keep it with your tax records. If you want to be extra careful, you can also call Fidelity after making the contribution to confirm it was properly coded for 2020, and make a note of the date, time, and representative's name from that call.

Generally for online transactions, midnight in your time zone on the deadline day is acceptable. However, different HSA providers might have different cutoff times for processing transactions, especially if they require manual verification or processing. To be safe, I'd recommend making the contribution at least 2-3 business days before the deadline. I made this mistake last year trying to fund my HSA on April 15th at 9pm, and while my provider (not Fidelity) accepted it, they initially coded it for the wrong tax year and it was a hassle to get fixed.