Sell or hold ESPP stocks? My company has a pretty good employee stock plan. I am able to buy stock at a 15% discount based off a 2 year look back period. So basically, 15% off the lowest it’s been during that 2 year period. The next purchase is in March and I’m looking at 15% off a stock purchase price that is already $20 lower than the trading price. I’m in technology…

It’s tax filing season, so let’s talk about ESPP and how to file your taxes PROPERLY! Every year I sell any shares from my ESPP, I always look for a writeup of how to file them, and can never figure it out. I figured I’d write this up and try to help! I won’t go into the benefits of what ESPPs do, but I want to make sure you don’t get double taxed, which I’m sure thousands of people do every year, because its not up to your emplo…

Does replacing ESPP shares with lower priced shares make sense? Hi, I participated in my employer’s stock purchase plan ESPP which offers a 15% discount on the lowest price during a purchase period. The problem is I now own thousands of shares and the share price has lost 75%. I left the company and am now returning, so all my shares currently in the plan are long term, though at a loss. Does it make sense t…

ESPP – sell after it qualifies as capital gain or hold? The company I work for’s parent company gives us an ESPP. Later this year, I will hit 2 years since the grant date and would qualify for selling that stock and being taxed as a capital gain. However, the stock performs pretty well, 1 year pre-tax return says 46%. Our parent company is large and mature as well. My plan was always to hold until it…

Should I fund ESPP or MBDR? I am already maxing my pre-tax contributions to my 401k, and maxing an HSA but I have access to the following two options and am curious which I should be prioritizing. At this time I cannot afford to fully fund both. 1) Employee Stock Purchase Plan – up to 10% of my salary, stocks are purchased at 85% of the average cost over the pay period (tw…

ELI5 ESPP tax stuff: form 3922 vs form 1099-B? I participated in my company’s ESPP this past year for the first time. I believe the broker they use will send a 1099-B form which I can use to report capital gains since I sold immediately both times. But I also got a form 3922 from the company I work for. I’m not really sure what the difference is or how this all works. Can anyone explain it? …

Do you usually sell your ESPP as soon as they land in your account? I was recently recommended that I sell my ESPP stocks if you don’t see a drastic increase. Any recommendations on what to do with ESPP? submitted by /u/PlentyFar7008

Best strategy regarding ESPP and saving for retirement Working on my savings goals for 2025 and have some questions regarding employee stock purchase plans and how that can fit into my savings. My company offers a 15% discount off the current price at the end of every quarter and is 100% vested, I do know about the requirements for a qualified vs disqualified distribution. Current income/savings in…

ESPP sell off strategy? Hey PF. Over the last 8+ years I have been acquiring company stock through ESPP twice per year. My cost basis ranges from ~$40 – $140 and the current stock price is around $90. My total portfolio is getting a little heavy in this one stock (~15%) and I’d like to start selling some off and throw it into VTWAX. I’ve never really sold stock before…

Just Married: How to Reallocate Savings w Majority in ESPP Throwaway account as I’m discussing my finances I (28M) got married two months ago and I will be taking the lead on finances. We are in good financial standing with little debt (only mortgage and auto loans) and a good savings base. My savings will be a majority of our savings base together but is not allocated well as most is in an ESPP. I am l…

ESPP 5% discount, twice yearly, no holding period. Hello PF, I recently took a position at a new job. They offer a 5% discount on employee stock purchase plan, with buys twice a year, no look back, and no holding period. In comparison, my former employer offered a 15% discount with four buys per year. No look back and no holding period. Both capped at 25% of income. I took advantage of, and ma…

ESPP Sale –> IRS Interest and Penalty Demans I sold ESPP stocks in 2022, however my financial institution Charles Schwab did not include these on my 1099B. I prepare my taxes using TurboTax and it didn’t pull these transactions in and I didn’t realize. Now I received a CP 2000 notice from the IRS declaring that the financial institution reported to them transactions that I didn’t include o…

Is this ESPP worth investing? Below are the details. We have a comfortable emergency fund and while not at all wealthy, are not hurting for money at this time. I am currently already contributing 14% to my 401k: “Earlier this year, our IPO provided the roadmap to offer our employees direct access to an ownership opportunity unique to public companies at a competitive discoun…

Employer Stock ESPP Plan My employer is just stating an ESPP plan. Stock is offered at a 15% discount. Should I do this? My (limited) understanding is that if I sell right after the shared I buy vest then I get a +15% (minus taxes) no matter what… In general what’s the strategy with employee stock purchase plans? submitted by /u/StellarScribe123

What is the optimal way to handle Employee Stock Purchasing Plan (ESPP) money? Our company (Intuit) allows us to purchase stock at a 15% discount, and I’ve been contributing 15% for a while (currently sitting at $120K in stock from ESPP). But, two questions: What is optimal to do when shares are purchased? Sell right away? Is putting this money into VOO superior? What should I do with my $120K available? I thought since …

ESPP – Cash out or hold on I’ve been participating in corporate ESPP plans for 20 years. My current one is a quarterly 5% discounted purchase with a max 10% of gross paycheck contributions. I more or less know the answer to my question, but want confirmation I suppose. Until 2021, I would take my discounted stock and sell it immediately. I have not sold any stock in the p…

Weird company ESPP with 5-year lock-in My company is launching an ESPP but the terms don’t line up with those I find online for this type of plan. The biggest difference appears to be a crazy long lock-in period of 5 years. Employees purchase the stock right away at a rebate of 20% of an already set reference price and then hold it for 5 years. There is also a much higher contributio…

Savings, Taxable Brokerage, or ESPP? Currently I am bringing in $3180 bi-weekly gross. Maxing out 401k, Roth IRA, HSA, and have a budget that fits my needs. I am leftover with $550. How much should I incorporate into taxable brokerage and savings? Am I investing too much and should I save more over a taxable brokerage? My job also offers an ESPP of company stock at a 15% discount w…

Received RSU and ESPP distribution, sold RSU and ESPP shares are now marked as ‘wash sale’. Did I screw myself? In February of this year I received an RSU distribution and, a week later, a distribution from my company’s ESPP. I sold the RSU distribution (sold specifically those shares exclusively), and my remaining ESPP shares are marked as ‘wash sale’. The way the timing worked out, the RSU shares sold at a slight loss (~$100) compared to the cost basis;…

Donating ESPP stock reported as disposition I usually donate some of my RSU stock each year into a DAF, and this year thought I’d donate some ESPP stock instead. I asked my finance department about approving the transfer, and they came back with this: “We are no longer able to simply approve the transfer of ESPP shares due to company tax reporting requirements. If you would still like to …