My RSU was 'taxed'/sell-to-cover twice but I haven't sold it yet - help needed

What you're describing sounds like a potential misunderstanding of how RSU taxation works rather than double taxation. Here's what typically happens: When RSUs vest, they're considered income by the IRS at the fair market value on the vesting date. Your employer is required to withhold taxes just like your regular paycheck (federal, state, Social Security, Medicare, etc.). Most companies use a "sell-to-cover" approach where they sell just enough shares to cover the required tax withholding. What might be happening is you're seeing: 1) the original grant amount, 2) the net shares after withholding, and 3) perhaps a separate transaction for the actual sale of shares for tax purposes. This could appear like double taxation, but it's likely just different views of the same withholding event. I'd recommend checking your pay stub for the period when the RSUs vested. You should see the RSU income and corresponding tax withholdings reflected there. Also, in your ETrade account, look at the transaction history to see exactly what happened and when.

After dealing with a very similar situation last year with my RSUs, I discovered taxr.ai (https://taxr.ai) and it was a game-changer for understanding these complicated equity compensation issues. I uploaded my ETrade statements and it immediately identified what was happening with my RSUs and the different withholding transactions. Their tool breaks down exactly how each transaction affects your tax situation and explains when multiple withholdings might occur. In my case, it turned out one withholding was for federal taxes and another was for state taxes, but they happened on different days which made it look like double taxation. The analysis also helped me understand how to properly report everything on my tax return which saved me from potentially making costly mistakes.

Just wanted to follow up about taxr.ai that was mentioned. I decided to try it with my complicated RSU and stock option situation, and it was incredibly helpful! The tool identified that my previous accountant had indeed been reporting my multi-company RSUs incorrectly for 2 years. It showed exactly how each vesting event should be reported and even identified that one of my companies had miscalculated the withholding (they withheld at a flat 22% rate when they should have used my supplemental wage rate). The detailed explanation they provided about the difference between sell-to-cover transactions vs. actual sales I chose to make later really cleared up my confusion. Now I feel much more confident about handling these equity compensation issues on my tax return this year!

If you're still dealing with the frustration of being bounced between your company and ETrade, I had great success using Claimyr (https://claimyr.com) to get through to an actual human at ETrade who could explain what was happening with my RSUs. I was in the exact same situation last year - my 350 shares had what looked like multiple withholdings, and neither my company nor ETrade seemed interested in explaining it. After weeks of frustration, I used Claimyr to get a callback from ETrade (you can see how it works here: https://youtu.be/_kiP6q8DX5c), and I finally got connected to their equity compensation specialist who explained everything. It turned out that in my case, there were separate withholdings for federal and state taxes that happened on different days. The specialist was able to send me documentation showing exactly what happened with each transaction.

I was completely skeptical about Claimyr when I first saw it mentioned here, but after another week of getting nowhere with Fidelity about my RSU withholding issues, I gave it a try. I'm honestly shocked at how well it worked. Instead of spending my lunch break on hold, I put in my request through Claimyr, specified I needed the equity compensation department, and got a call back in about 40 minutes connecting me directly to a specialist. The specialist immediately understood my issue about what looked like multiple withholdings and explained that one was federal withholding (at 22%) and the second was state tax withholding (at 5%) plus a small administrative fee that was taken in fractional shares. They even emailed me documentation showing the breakdown of all withholdings so I can properly report everything on my taxes. Definitely saved me hours of frustration and confusion!

Another thing to check is if your company has an ESPP (Employee Stock Purchase Plan) running simultaneously with your RSU grants. I thought I was being double-taxed on my RSUs, but it turned out some of the shares I was seeing disappear were actually being used to fund my ESPP contributions which were coming out of my after-tax salary. Check your benefits enrollment to see if you might have signed up for an ESPP when you started. Sometimes these are opt-out rather than opt-in at some companies.

Just a heads up that RSU taxation can vary by country too! If you're outside the US or work for a multinational company, the rules might be different. I work for a US company but I'm based in Canada, and my RSU taxation is completely different from my US colleagues.