Is there a good template for tracking this? My company has done RSUs, ISOs, and ESPPs over the years and I'm already losing track of which shares came from where and when each lot vested.

I don't have a specific template, but I created one in Google Sheets that works well. The key columns I use are: Grant Type (RSU/ISO/ESPP), Grant Date, Vest Date, Shares Granted, Shares Vested, FMV at Grant, FMV at Vest, Shares Sold for Taxes, Net Shares Received, and Cost Basis per Share. I also add notes for any corporate actions like splits or mergers that affected share counts. This has saved me countless hours at tax time. The most important thing is to update it immediately when new shares vest, because trying to reconstruct this later is a nightmare.

E*Trade is awful for this! I switched jobs and my new company uses Fidelity, which is SO much better. They provide a supplemental tax statement that shows your original W-2 income amount for RSUs and the corresponding cost basis adjustment. Made my taxes 100x easier this year.

Did you end up having to amend your return or pay any penalties for the Form 1116 mistake? I'm leaning toward just not claiming the credit at all at this point.

No penalties or amendments needed, thankfully. I just had to send in some additional documentation to clarify how I calculated the credit. But it was definitely an unnecessary hassle for $8! For your $1.99 credit, I absolutely wouldn't bother claiming it if it requires paying for software upgrades. Even beyond the immediate cost, the potential for questions or confusion just isn't worth it for such a small amount. The IRS certainly won't flag you for not claiming a credit you're entitled to - that's your choice.

FreeTaxUSA has been my go-to for years. So much cheaper than TurboTax and includes most forms. I've claimed foreign tax credit with them without issues.

Thanks for the suggestion! I've been with TurboTax for so long I guess I just assumed all tax software had similar pricing tiers. I'll definitely check out FreeTaxUSA for next year. For now I think I'll just skip claiming the tiny credit since it's literally less than my lunch cost today lol.

How exactly do you calculate this "insurance amount"? I've tried to do this before but always end up way off, either getting much bigger refunds than I planned or owing a little.

I use what I call the "10% buffer rule." I calculate what my ideal withholding should be for zero refund/zero amount due, then I add 10% extra to that amount as my safety margin. For example, if my calculated correct withholding is $1,000 per month, I'll actually withhold $1,100 per month. This typically results in a refund of about $1,200 at year end, which I'm comfortable with. It's small enough that I'm not giving a huge interest-free loan to the government, but large enough to absorb unexpected tax changes or calculation errors.

I've done this for the past three years with no issues. Applied about $8K of my refund to the next year's taxes each time, then adjusted my withholding way down for Q1 and part of Q2. Never triggered any special review or audit flags. The IRS systems treat it as a perfectly normal transaction because it is - it's a built-in option on the tax forms for a reason.

My health insurance is still through my employer, same plan as last year. But you know what, I'm going to go back and check those health insurance questions again to make sure I answered them the same way. I honestly tend to click through those sections pretty quickly since nothing changed, but maybe I did check something different. Thanks for the suggestion!

Not OP but this happened to me! I had 8 weeks of unemployment and had NO idea they barely withhold any taxes. Got absolutely wrecked at tax time. Now I always select the maximum withholding on unemployment.

No unemployment for me - been at the same job the whole time. But that's good to know about unemployment withholding being low. I actually might have some temporary layoffs coming up later this year, so I'll definitely remember to adjust the withholding if that happens. Thanks for the heads up!

I actually did ask the dealer about this yesterday! They seemed open to the idea but weren't sure about the legal implications. Did you have any issues with the financing company or insurance when they delayed the official delivery date? What documentation did you end up using to prove the January delivery date to the IRS?

I didn't have any issues with financing or insurance. The dealer simply scheduled the "delivery appointment" for January 2nd, and all paperwork was dated that day - including the sale agreement, registration application, and delivery receipt. The loan wasn't finalized until that day either. For IRS documentation, I used the dated purchase agreement, the vehicle registration that showed the January date, and made sure the dealer noted "delivery date" specifically on the paperwork. I took pictures of me picking up the car on that date too, just to be safe. The key is having all official paperwork consistently show the January date.

That's not accurate advice and could potentially cause problems for the OP. The IRS is clear that "placed in service" is generally when you take possession and the vehicle is ready for use, not the registration date. Your situation may have worked out, but that doesn't mean it follows IRS guidelines. Registration timing doesn't determine the placed in service date.