Questions tagged [espp]

In the United States, an employee stock purchase plan (ESPP) is a tax-efficient means by which employees of a corporation can purchase the corporation's stock, often at a discount.

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31
votes
5answers
5k views

ESPP--any reason not to go all in?

I'm just finishing up paying off my student loans (woohoo!) and am starting to look at places I can put my money to make it work for me. I've read Kobliner's Get a Financial Life and am interested in ...
17
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7answers
20k views

How much percent of my salary should I use to invest in company stock?

My company allows me to purchase stock at 90% of the closing fair market value. My salary is in the 90k-100k range. I am allowed to put in anywhere from 1-15% of my paycheck in company stock up to a ...
16
votes
1answer
1k views

Where Do ESPP stocks come from?

When a company gives its employees an ESPP plan, where do they get the stocks to sell to them? are they being bought in the free market? but then, where does the discount come from? is it stocks that ...
11
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2answers
3k views

ESPP strategy - Sell right away or hold?

I participate in my company's ESPP. Unlike most ESPPs, ours purchases shares on a MONTHLY basis, the price being the average on the last day of the month. A dollar contribution is taken out of each ...
9
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6answers
4k views

Pros/Cons of Buying Discounted Company Stock

For my company (large international software firm) I am allowed to buy company stock at a discounted price. To me all I see are pros such as: Being able to sell the stock right as I buy it, ...
9
votes
1answer
238 views

Is the ESPP discount profit?

My employer offers an ESPP program through which we can buy stocks with some discount. Assume the discount is D and the market price in the day when the stock is purchased is P. The stock is purchased ...
8
votes
3answers
536 views

How can I get the most value from my employer's ESPP?

My employer offers an ESPP with the following details: 15% discount Max contribution is 15% of base salary Purchase transaction occurs on the last business day of the month Transaction settles 3 days ...
7
votes
1answer
395 views

Should I purchase company stock through my ESPP?

I have been contributing several hundred dollars per paycheck to my Employee Stock Purchase Program (stock symbol MDP) at a 15% discount. I was immediately selling at the end of each quarter with ...
7
votes
2answers
749 views

Employer reported ESPP ordinary income on wrong year's W-2

I sold some Employee Stock Purchase Plan shares on 12/31/2014. As far as I understand, the ordinary income portion of the sale should have been reported on my 2014 Form W-2 from my employer but was ...
6
votes
1answer
479 views

what is an ESPP transfer restriction, and why would it be longer than the sales restriction?

I am participating in my company's ESPP. My share lots have two restrictions: A sales restriction of 18 months, which is what it sounds like: I can't sell the shares until I've held them for 18 ...
5
votes
4answers
23k views

Is it worth it to buy TurboTax Premier over Deluxe if I sold investments in a taxable account?

I sold investments in a taxable account in 2013, include shares from an employee stock purchase plan (ESPP). I have always used TurboTax and am planning to again, but I'm trying to decide which ...
5
votes
4answers
400 views

Should I contribute to my employer's Employee Stock Program (ESPP), and if so how much and only during certain times of the year?

Although it is company-specific, what are your experiences when contributing to ESPP (Employee Stock Program)? More specifically, do you recommend contributing to ESPP in max? Or maybe it is only ...
5
votes
3answers
3k views

Tax withholding on ESPP discount

I recently enrolled in my company's employee stock purchase plan (ESPP) with the maximum-allowed 10% of my salary. I get the stock at a 15% discount relative to the purchase date (no look-back ...
4
votes
1answer
385 views

Received W2 from ex-employer for selling shares previously bought under ESPP

My wife used to work at Oracle and quit in January 2016. While she was there, she bought Oracle stock under an ESPP (employee stock purchase plan) that allowed her to buy the stock at a discount. In ...
3
votes
1answer
784 views

Taxes on Income from an Employee Stock Purchase Plan?

My employer offers an ESPP which allows us to purchase company stock at a 5% discount. I signed up for the plan, but was not interested in holding on to the shares for long, so I sold as soon as I ...
3
votes
3answers
253 views

Is this Employee Stock Purchase Plan worth it when adding my student loan into the equation?

Here are the details of my company's Employee Stock Purchase Plan: An automatic 5% purchase discount off the fair market value of the stock. Payroll deductions start on July 1st. The stock purchase ...
3
votes
1answer
1k views

is a forced sale of company stock during Acquisition taxed at short or long term gains

The company i work for was recently bought out; as a result employees are being forced to sell company stock. Some of my ESPP shares are disqualified/Long Term Capital gains and some are disqualified/...
3
votes
1answer
4k views

ESPP in the UK - worth it? Disqualifying / qualifying sales?

I've recently joined a company that offers a ESPP scheme and I just wanted to get a few bits of information as well as confirm that my understanding is correct. You choose a percentage that will be ...
3
votes
1answer
103 views

ESPP and payroll tax

"I participate in my company's stock purchase plan ESPP at a 10% discount. purchases are made quarterly. My company has been adding the 10% discounted amount onto my payroll quarterly and taxing it. ...
3
votes
1answer
166 views

Evaluating worth of ESPP (Startup)

I got an entry offer for an Engineering position: base salary 90K/y at a start up (around 50 employees, got good funding during the last year). The package includes an ESPP for 6000 stocks (1 year ...
3
votes
0answers
135 views

ESPP compounding strategy and taxation?

Let me start off giving some of the details of the ESPP my employer offers: Stock Price Discount: 15% Employee Salary Contribution: 3-10% (in whole value increments) Holding Period: 12 months (...
2
votes
2answers
2k views

ESPP cost basis and taxes

I participated in a qualified employee stock purchase plan (ESPP) and the offering period just ended. I put in $5000 and got a 15% discount on the price at the end of the offering period (no lookback ...
2
votes
3answers
3k views

When filing taxes in Canada, in what cases does box 39 on the T4 get reported as half of box 38?

When filing taxes in Canada, when does box 39 get reported as half of box 38? In my case, I got ESPP amount reported in box 38, with box 39 missing in my T4 altogether. According to my accountant, the ...
2
votes
1answer
168 views

Can I sell my ESPP in a different order than I acquired it, to avoid paying too much tax on profits?

Here is the scenario. Lets say, BATCH_1: My company purchased ESPP on my behalf at $8.50(15% of $10) on JAN 2016. BATCH_2: My company purchased ESPP on my behalf at $10.20(15% of $12) on AUG 2016. ...
2
votes
1answer
281 views

How to calculate profit for ESPP stocks including cost basis, tax, fees etc

I opted for ESPP stock options in my previous company. The plan offered 10% discount on market value. When I opted for the plan the company created a etrade.com account on my behalf and I could see ...
2
votes
1answer
106 views

ESPP stocks taxable in US after moving to US from Singapore

I'm Singapore planning to move to US in 2-3 months. I have some ESPP shares(US Company) that I would like to keep for another year or more. If I sell these shares after moving to US will it be taxed ...
2
votes
2answers
194 views

ESPP cost bases for 2014 taxes

I participated in a qualified employee stock purchase plan (ESPP) and I'm trying to figure out the cost basis of my stock for tax purposes. When I enrolled for the ESPP the stock price was $29.44, ...
2
votes
0answers
90 views

Donating ESPP shares to non-profit organization

In recent years, I've made donations to some non-profit organizations using stock shares. They immediately sell when they receive the shares from my brokerage firm and send me a document at the end ...
2
votes
0answers
73 views

Do I need to pay tax in US that ESPPS and RSUs earned in India

When I was working in India I got some RSUs and also purchased ESPPs from my company by contributing from my salary.Its US based company located in India. I have an account in ETrade. ETrade has ...
1
vote
2answers
59 views

Invest in ESPP Single Stock or General Market

The employee stock purchase program (ESPP) at a US company provides the opportunity to purchase whole or fractional shares of a stock at a 5% discount, or 95% of the stock price at the close of the ...
1
vote
2answers
549 views

ESPP (Employee Stock Purchase Plan) Funds on Mortgage Loan Application

Will the bank count these funds? My company ESPP works like this: 25% of my bi-monthly paycheck (after taxes) is withheld and sent to some kind of company escrow account. This is done for 6 months. ...
1
vote
1answer
364 views

Can compensation income from an employee stock purchase plan be negative?

If I took a loss on my sale of stock from an ESPP (employee stock purchase plan), and the stock had a qualifying disposition, what is my compensation income? I found the following definition: In ...
1
vote
2answers
1k views

How to file income tax returns for profits from ESPP stock?

My company is listed on the NASDAQ. I sold stock under its Employee Stock Purchase Plan (ESPP). I want to know how to file income tax returns for the profit. Which form should I use? What values ...
1
vote
2answers
67 views

Understanding capital gains and taxes on employer stock purchase plan

My company offers employee stock purchase plan at a 15% discount. What I am wondering is how does capital gains come into effect if I only sell my original investment? As an example, using even ...
1
vote
1answer
42 views

ESPP, expat and CGT in which country (Canada/UK)

I participate in my Canadian company's ESPP whilst living and working in Canada as a permanent resident. I'm moving back to the UK in August and will sell my shares when I'm back in the UK. Will the ...
1
vote
1answer
52 views

Mismatched cost basis on 1099-B form for ESPP shares

I have a question about my 1099-B form regarding ESPP sales. My company allows me to buy shares at a 15% discount through an ESPP program. I buy-and-hold for 1 year 1 day so my sales are taxed at ...
1
vote
1answer
184 views

meaning of qualifying/disqualifying distribution as separate from capital gains implications

I have an ESPP and am trying to figure out the difference between a qualifying and disqualifying distribution. I have read the explanation from Intuit here: https://turbotax.intuit.com/tax-tools/tax-...
1
vote
1answer
190 views

Choosing which ESPP stocks to sell?

I participate in the ESPP (Employee Stock Purchase Plan) that my employer provides. Over the years I have accumulated multiple "lots" or positions which all have a different purchase price. I've ...
1
vote
1answer
275 views

Post tax versus pretax (ESPP versus straight investment)

I work at a company that offers a 50% match on 401k contributions, on the first $3500 per year (So $1750 total match possibility). They also have an employee stock purchase plan (ESPP), which ...
1
vote
1answer
118 views

Reporting ESPP ordinary income on shares purchased living in Europe

I have shares acquired through an American company I was working for. They were purchased through the company ESPP plan. I was living and being paid in Europe at the time ( I am not a US citizen). 10 ...
1
vote
1answer
2k views

Tax implications of ESPP shares when company is bought out

I still have ESPP shares in a company I used to work for. This company is getting bought out (deal has been publicly announced and should close soon). Many of these shares have greatly increased in ...
1
vote
1answer
21 views

Dividend from ESOP to Cash - India

I'm Indian and working for a US organisation in India. I have been investing in the Employee Stock Purchase Plan (ESPP) for a while now. During the initial investment period, I had not opted for re-...
1
vote
0answers
38 views

Is it possible to contribute to an ESPP outside the % chosen?

Just curious if it is possible to add additional money to an ESPP during the period before the purchase occurs. I started mine withholding a little lower than I think I want now that I see what I may ...
1
vote
0answers
223 views

For the purpose of filing taxes in Canada, is participating in ESPP considered to exercising stock options?

My tax professional and company payroll department are in a disagreement about what box on the T4 the taxable benefit of my ESPP should be included in. The payroll (Canadian office of a US based ...
0
votes
2answers
240 views

Stock sale cost basis calculations for 2013, now that rules changed, is FIFO or another method the smartest financially?

I was in an employee stock purchase program that auto-bought stock every two weeks at a 15% discount as part of a paycheck deduction. This was BEFORE the 2008 crash and during and after it. This ...
0
votes
1answer
2k views

ESPP: Share vs Payroll withholding

I am considering enrolling in my company's ESPP program during the next offering period. The program is non-qualified, and my employer will withhold taxes on the difference between fair market value ...