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7 One thing nobody's mentioned yet - remember you can choose SPECIFIC LOTS when selling RSUs. You don't have to sell entire batches. Many brokers default to FIFO (first in, first out) but you can typically select exactly which shares to sell. This lets you fine-tune your tax strategy even further.
13 How exactly do you select specific lots? Is that something you do through your broker platform or when filing taxes?
7 You do this through your broker at the time of sale. Most major platforms (Fidelity, E*TRADE, Schwab, etc.) let you choose "Sell specified lots" instead of the default FIFO method when placing a sell order. You'll see a list of your lots with their purchase dates and costs, and can select exactly which ones to sell. You need to do this BEFORE executing the sale - you can't change it when filing taxes. If you don't specify, your broker will use their default method (usually FIFO) and report that to the IRS.
5 Just adding another consideration - if you've got other income/loss events this year, that might influence your decision. I ended up selling some underwater RSUs (at a loss) to offset gains from other investments. Tax-loss harvesting can be a powerful strategy!
17 Can you actually claim losses on RSUs? I thought since you're taxed on the value when they vest, your cost basis is that vesting price, so if they go down after vesting and you sell, you can claim that as a capital loss?
Exactly right! Your cost basis for RSUs is indeed the fair market value on the vesting date (which you already paid ordinary income tax on). So if the stock price drops after vesting and you sell below that vesting price, you can absolutely claim a capital loss. This is actually a common situation in volatile markets - you get taxed on the full vesting value as ordinary income, but then can offset other gains with the capital loss if the stock drops. Just remember the $3,000 annual limit on deducting net capital losses against ordinary income, though unused losses carry forward to future years.
Has anyone addressed the Roth IRA overcontribution issue? I had a similar problem last year when a bonus unexpectedly pushed me over the income limit after I'd already contributed. The cleanest solution is a "recharacterization" to a Traditional IRA. Call your IRA provider and tell them you need to recharacterize your Roth contribution to a Traditional IRA due to income limits. They'll handle the paperwork and move the money (including any earnings/losses). Do this before your filing deadline (including extensions). Since your income is above the deduction limits for Traditional IRAs, you'll have a non-deductible contribution, which means you need to file Form 8606 with your tax return to track the basis. This gets a bit complicated if you already have Traditional IRA money, due to the "pro-rata rule." Alternatively, you could withdraw the excess contribution plus earnings before your filing deadline. You'll pay income tax on the earnings portion only (plus a 10% early withdrawal penalty on the earnings if you're under 59½), but no 6% excess contribution penalty.
This is a really frustrating situation, and you're absolutely right to be stressed about it. The retroactive nature of this change is particularly unfair since you made a major financial commitment based on their previous policy. A few additional thoughts beyond what others have shared: 1. Document everything from when you enrolled - any emails, benefit summaries, or enrollment materials that indicated the tax treatment. If you have anything in writing suggesting the reimbursements would be non-taxable, that strengthens your position significantly. 2. Consider consulting with a tax attorney who specializes in employment benefits. The retroactive application of a policy change that affects substantial financial commitments could potentially violate reasonable reliance principles, especially if you can show you wouldn't have enrolled knowing the true tax consequences. 3. For immediate relief, you might want to adjust your W-4 withholdings now to account for the additional tax burden over the remaining years of your program. This will help avoid a massive tax bill at filing time. 4. Some companies have hardship provisions in their benefits policies. Given that this change creates unexpected financial hardship, it might be worth asking HR if there are any exceptions or payment plan options for the additional taxes. The Roth IRA issue is definitely fixable through recharacterization as others mentioned, but make sure to act before your filing deadline. This whole situation is a good reminder of how important it is to get benefit details in writing, even when policies seem well-established.
This is excellent advice, especially about documenting everything from enrollment. I'm dealing with a similar situation where my company changed their tuition policy mid-program, and I wish I had been more proactive about saving all the initial communications. One thing I'd add - if you do end up consulting with a tax attorney, make sure they have specific experience with educational benefit disputes. I initially went to a general employment lawyer who wasn't familiar with the nuances between Section 127 and Section 132(d), and it wasn't very helpful. Also, regarding the hardship provisions - some companies will allow you to spread the additional tax burden over multiple years or even provide interest-free loans to cover the unexpected tax liability. It's definitely worth having that conversation with HR, especially if you can frame it as the company's policy change creating an undue financial burden that you couldn't have reasonably anticipated. The W-4 adjustment suggestion is spot-on too. Better to have smaller amounts withheld throughout the year than get hit with a massive bill plus potential underpayment penalties come tax time.
I went through this exact situation last year! The key thing to remember is that Social Security survivor benefits for children are generally not taxable UNLESS your child has other significant income. You'll get a SSA-1099 form showing the total benefits received. As long as your child doesn't have other income sources (like significant investment income or wages), you typically won't need to report it. The threshold is pretty high - around $25,000 total income including half the SS benefits. Keep all your paperwork though, just in case you need it later. Hope this helps ease some stress during an already difficult time! š
My sister-in-law works at the IRS and said they NEVER just freeze accounts out of nowhere for simply filing late. They have to send multiple notices including a final certified letter with 30 days to respond before taking any action like that. The whole process takes at least 6+ months minimum, often years. The only time they move faster is if they suspect actual tax fraud or if someone is actively hiding assets, which doesn't sound like your situation at all. Just file ASAP, pay what you can, and respond to any notices you get.
Thank you so much for this! I've been stressing for days thinking they could just take my money without warning. I'm going to file this weekend for sure and set up a payment plan. Really appreciate the inside perspective.
I totally understand your panic - I was in almost the exact same situation two years ago. Missed the deadline by about 6 weeks and was convinced the IRS was going to empty my account overnight. Here's what actually happened: I filed late (with penalties), set up a payment plan for what I owed, and never heard from them again except for the monthly payment confirmations. No scary letters, no account freezing, nothing dramatic at all. The key things that helped me: 1) Filed as soon as I realized my mistake, 2) Paid what I could upfront (even though it was only about 30% of what I owed), and 3) set up an automatic payment plan for the rest. The IRS website makes it pretty easy to do the payment plan online. Your $5,300 estimate sounds very manageable for a payment plan. Even if you could only pay $200/month, that would show good faith and keep you in compliance. The relief you'll feel once you just file and get it sorted is incredible.
Omar Hassan
Does anyone know how the audit rates compare between CRA and IRS? I've heard the IRS is much more likely to audit low-income taxpayers while the CRA focuses more on wealthy individuals and businesses. Is that accurate?
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Chloe Robinson
ā¢That used to be true about the IRS targeting lower-income filers, especially those claiming the Earned Income Tax Credit, but they've been shifting focus in recent years. The CRA has definitely been more aggressive with wealthy individuals, particularly with their "High Net Worth Compliance Program" that targets Canadians with assets over $50 million.
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Miguel Castro
Having dealt with both agencies as a US expat living in Canada, I think the key difference comes down to resources and scope. The IRS operates on a massive scale - they process nearly 10x more returns than the CRA - but they're chronically underfunded relative to their mandate. This creates the paradox where they're technically sophisticated but often inaccessible. The CRA benefits from serving a smaller population and generally has better funding per capita. Canadian taxpayers can usually reach someone by phone within a reasonable time, while getting through to the IRS can take hours or days of trying. From a compliance perspective, both agencies are getting more aggressive, but the IRS has always had more of a "fear factor" in American culture. Movies, TV shows, and political rhetoric have built up the IRS as this intimidating enforcement agency, while the CRA maintains a more bureaucratic, less threatening public image. Interestingly, both agencies are dealing with similar challenges around cryptocurrency, digital assets, and remote work taxation that became huge issues during the pandemic.
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Alexander Evans
ā¢This is such a helpful perspective! As someone new to cross-border tax issues, I'm curious about those pandemic-era challenges you mentioned. How did remote work complicate things for both agencies? I imagine people working from home in different countries than their employers created a lot of confusion about tax residency and filing requirements.
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