


Ask the community...
This is a great breakdown of ESPP tax implications! I've been participating in my company's ESPP for about 6 months now and honestly had no idea about the difference between qualifying and disqualifying dispositions until reading this thread. I'm in a similar situation where our stock price has dropped about 15% since my offering date. Based on what everyone's explaining here, it sounds like there's really no point in me holding these shares for the full qualifying period since the tax benefit would be minimal and I'd be taking on unnecessary risk. One question though - when you calculate the "discount you received" for tax purposes, is that based on the actual percentage discount from the plan (like if it's a 15% discount plan) or is it the dollar amount difference between what you paid and the fair market value? My plan offers 15% off the lower of offering date or purchase date price, so I'm trying to figure out exactly how much would be taxable as ordinary income. Also wondering if anyone has experience with RSUs vs ESPP from a tax planning perspective? I have both and trying to figure out the best strategy for managing the tax impact when I eventually sell.
Great question about the discount calculation! For tax purposes, it's the actual dollar amount difference, not the percentage. So if your plan gives 15% off and you bought shares at $85 when the FMV was $100, your taxable discount is $15 per share, not necessarily 15% of the purchase price. Regarding RSUs vs ESPP - they're taxed very differently. RSUs are taxed as ordinary income when they vest (included in your W-2), then any gains/losses from there are capital gains when you sell. With ESPP, you get to control the timing of when the discount becomes taxable income by choosing when to sell. From a tax planning perspective, you might want to coordinate the timing. For example, if you have a big RSU vesting event pushing you into a higher bracket this year, it might make sense to delay ESPP sales until next year. Or conversely, if you're in a lower bracket year, it could be a good time for disqualifying dispositions. The tools others mentioned like taxr.ai could help you model different scenarios with both types of equity comp.
Your analysis is spot on! You're absolutely right that when stock price drops during the offering period, the tax advantages of qualifying dispositions become pretty minimal. I went through the exact same decision process with my ESPP shares last year. One thing that helped me decide was calculating the actual dollar amounts rather than just thinking about percentages. In your 24% bracket, if you're only saving 9% on capital gains treatment, you need to ask yourself: is that 9% savings worth the risk of the stock dropping further while you wait for qualifying disposition status? I ended up selling most of my shares from periods where the stock had declined, but kept a small portion from one purchase where there was a meaningful tax benefit to holding. The key is running the numbers for your specific situation rather than following a one-size-fits-all approach. Also worth noting - make sure you understand your company's specific ESPP terms. Some plans have a "lookback" feature that can affect the tax calculations, and the discount percentage might vary. Your plan documents should spell out exactly how the purchase price is determined, which will help you calculate the exact ordinary income portion for each lot of shares.
This is exactly the kind of practical advice I was looking for! Running the actual dollar amounts makes so much more sense than just looking at percentages. One follow-up question - when you mention the "lookback" feature, how does that typically work? I think my plan might have something like that but I haven't dug into the details. Does it change which price they use as the baseline for calculating the discount? Also, did you end up using any specific method to track which lots came from which purchase periods? With quarterly purchases, I'm worried I'll lose track of the tax implications for each batch of shares, especially if I do partial sales like you mentioned.
My father-in-law fell for this exact scam last year with his "accountant" and lost over $24,000 from his business account. The person seemed totally legitimate - office, website, everything. After getting his login info, they slowly transferred money out over several months while sending him fake bank statements showing the correct balances. By the time he discovered it during tax season, the bank refused to cover the losses because he had willingly shared his credentials, which violated their terms of service. Please tell your brother to run away from this accountant and find someone legitimate who uses proper accounting software and secure document sharing. This isn't just unusual - it's a common scam targeting small business owners.
That's terrifying! Did they ever catch the person? Did your father-in-law report them to the IRS or state board of accountancy? I'd be interested to know what happened afterward.
This is absolutely a red flag and your instincts are correct! As someone who works in financial fraud prevention, I can tell you that legitimate accountants NEVER need full login credentials to bank accounts. There are multiple secure alternatives like QuickBooks bank feeds, Xero connections, or simply providing monthly statements. The refusal to provide her SSN for read-only access is particularly suspicious - any legitimate tax professional is required to have a PTIN (Preparer Tax Identification Number) and routinely provides identification to financial institutions. This is standard practice, not something to avoid. Your brother should immediately: 1) Find a new CPA or EA with proper credentials, 2) Change all his banking passwords if he's shared them, 3) Monitor his accounts closely for any unauthorized activity, and 4) Consider reporting this person to your state's board of accountancy. Small business owners are frequent targets for this type of scam because they often feel overwhelmed by tax requirements and trust too easily. Don't let him brush this off as "normal practice" - protecting his business finances is worth more than the inconvenience of finding a new accountant.
Just wanted to add my experience - I was in a very similar situation with a CP21B after my divorce. The $60k amount you mentioned is substantial, so I'd strongly recommend getting everything in writing before splitting it. Even though your divorce decree specifies 50/50, I'd suggest both of you sign a simple agreement acknowledging the refund amount, the split, and who received the original check. This protects both parties if questions arise later, especially with an amount this large. Also, keep copies of the CP21B notice, your divorce decree section about tax refunds, and any bank records showing the transfer. The IRS might ask questions years later about large deposits, and having clear documentation makes everything much easier to explain. One more tip - if the check comes made out to both names with "AND" between them (not "OR"), you'll definitely need both signatures. Some banks are strict about this even for divorced couples.
I went through something very similar last year with a CP21B notice for about $45k after my divorce was finalized. A few things I learned that might help: First, the timing of when you separated matters more than you might think. Even though your divorce was finalized in 2020, if you separated earlier in 2019, that could affect how the refund should be split according to your decree. Some courts consider the separation date, not the divorce date, for financial matters. Second, make sure you understand what triggered the CP21B. In my case, it was missed business deductions from my ex's side business that we had forgotten to claim. This changed our negotiation since those deductions were directly related to her income, not our joint expenses. Third, consider opening a temporary joint account just for this transaction if the check comes in both names. It's cleaner than trying to get dual signatures at the bank, and you can close it immediately after splitting the funds. The person at work who mentioned taxation was definitely wrong - this is your money being returned to you, not new income. But definitely keep detailed records since $60k will likely trigger some banking reporting requirements. Good luck with the split - having it spelled out clearly in your decree should make this relatively straightforward!
This is really helpful advice, especially about the separation vs divorce date distinction! I hadn't thought about that aspect. We actually separated in late 2019 but didn't finalize until 2020, so I should probably review our decree language more carefully to see if that matters for this refund. The temporary joint account idea is brilliant - much simpler than trying to coordinate bank visits for dual signatures. Did you have any issues opening an account specifically for this purpose, or were banks pretty understanding about the situation? Also, you mentioned banking reporting requirements for the $60k - should I expect any 1099s or other tax forms to be generated from this, even though it's not taxable income?
I completely understand your frustration with getting such a vague notice about something from 7 years ago! The LTR 672C is notorious for being unhelpfully brief, but this situation is actually more common than you'd think. The timing delay could be due to several factors - the IRS has been working through massive backlogs since 2020, or they may have recently completed an internal review/audit of your 2018 return that resulted in this adjustment. Sometimes it's as simple as them finally getting around to processing a correction they identified years ago. My recommendation would be to start by requesting your tax account transcript for 2018 from the IRS website (IRS.gov - search for "Get Transcript Online"). This will show you exactly what the IRS processed versus what you originally filed, including any adjustments they made that created the overpayment. The transcript should also indicate which tax year or type of debt they applied your overpayment to. Most of the time these situations involve relatively minor issues - math errors, duplicate income reporting, or small penalties you weren't aware of. While the 7-year delay is unusual, it's likely just bureaucratic cleanup rather than anything serious. The transcript should give you all the details you need to understand what happened without having to spend hours trying to reach someone by phone. Don't stress too much - this is probably just the IRS finally getting their paperwork in order!
This is exactly the kind of reassuring and practical advice I needed! You're right that the LTR 672C notices are frustratingly vague - it's almost like they're designed to create confusion rather than provide clarity. The fact that this is more common than I realized definitely makes me feel better about the situation. Your explanation about the IRS backlogs and delayed processing makes a lot of sense. I hadn't really considered that they might have been sitting on a correction for years and are just now getting around to sending the notice. It's actually kind of amazing that they're still working through stuff from that far back! I'm definitely going to start with getting that tax account transcript like you and several others have suggested. It sounds like that's really the key to understanding what actually happened. I appreciate you emphasizing that it's likely something minor - I was starting to worry that maybe I had some huge unknown tax debt, but hearing from everyone's experiences here suggests it's probably just a small calculation error or something similar. Thanks for the clear step-by-step approach and for helping put this in perspective. Much better than sitting here anxious about it!
I can definitely relate to your confusion about getting a LTR 672C notice for something from 2018! These notices are frustratingly vague by design, but don't panic - this situation happens more often than you'd think. The 7-year delay is definitely unusual, but given the IRS's massive processing backlogs since the pandemic, they're still working through older adjustments and corrections. It's likely they found a discrepancy during a routine review or audit that just got processed. Here's what I'd suggest: First, get your tax account transcript for 2018 from the IRS website (go to IRS.gov and search for "Get Transcript Online"). This will show you exactly what the IRS processed versus what you originally filed, including any adjustments that created the overpayment. The transcript should also indicate which tax year they applied your overpayment to. Common causes for these situations include math errors, duplicate income reporting (like accidentally including the same 1099 twice), or small penalties from other years that you weren't aware of. In most cases, we're talking about relatively minor amounts - maybe a few hundred dollars at most. The transcript will give you way more detail than that vague notice ever could. Once you understand what adjustment they made, you'll probably realize it's just routine administrative cleanup rather than anything serious. If you still need clarification after reviewing the transcript, then you can consider calling the IRS with specific questions rather than going in blind. Don't stress too much - this is likely just the government finally getting their paperwork sorted out!
This is such a helpful and thorough explanation! I really appreciate how you've laid out the most likely scenarios and given such clear next steps. The point about these notices being "frustratingly vague by design" really resonates - it almost feels like they want to keep you guessing about what actually happened. Your explanation about the pandemic-related backlogs makes total sense. I hadn't really thought about how something from 2018 could still be sitting in their processing queue after all this time, but given everything that's happened with the IRS over the past few years, it's actually not that surprising. I'm definitely going to get that tax account transcript first thing - it sounds like that's really the magic bullet for understanding what's going on. The examples you and others have given about duplicate 1099 reporting or small math errors are exactly the kind of thing I could see myself having done without realizing it. It's so reassuring to hear that these situations usually involve relatively minor amounts. I was starting to imagine worst-case scenarios about having some massive unknown tax debt, but hearing from everyone's real experiences here has really put my mind at ease. Thanks for taking the time to break this down so clearly!
Oscar Murphy
Pro tip: set up alerts on your banking app instead of manually checking. Your neck will thank you later š
0 coins
William Rivera
ā¢good idea fr thank u
0 coins
Clay blendedgen
Been there! The waiting game is brutal but totally normal. TurboTax advance usually hits within 1-2 business days after your return gets accepted. Since yours was accepted 1/22, you're probably looking at Thursday or Friday at the latest. I know it feels like forever when you need the money, but try to distract yourself - obsessively checking won't make it come faster! š
0 coins