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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7answers
12k 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 ...
12
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1answer
509 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 ...
9
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2answers
2k 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 ...
8
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6answers
2k 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, ...
6
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1answer
311 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 ...
4
votes
2answers
112 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 ...
4
votes
3answers
83 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 ...
3
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3answers
142 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
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3answers
14k 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 ...
3
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1answer
2k 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
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2answers
1k 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 ...
3
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0answers
57 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
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1answer
354 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/...
2
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1answer
36 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. ...
2
votes
1answer
42 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
1answer
874 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 ...
1
vote
3answers
1k 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 ...
1
vote
1answer
162 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
557 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
1answer
78 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
750 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
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0answers
180 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
191 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
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2answers
47 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 ...
0
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2answers
59 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. ...
0
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2answers
154 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, ...