ESPP 101

Employee Stock Purchase Plans (ESPP) usually gives employee the opportunity to buy company stock at a discount, usually it is 15%.

Two dates to remember:
Grant date (offering date)
Purchase date (exercise date)

Two price to remember for tax purpose:Grant price
Purchase price

Two years to remember for qualified disposition:
2 years since grant date
1 years since purchase date

When the company buys the shares for you, you do not owe any taxes.
When you sell the stock, the discount that you received when you bought the stock is generally considered additional compensation to you, so you have to pay taxes on it as regular income.  The 15% discount applies to the lower price, and the discount amount will be considered ordinary income in sale year's w2 for qualified disposition. (Remember to adjust the cost basis in tax return)

To get favorable long-term capital gains treatment, you have to hold the shares purchased more than one year from the purchase date and more than two years from the grant date.

US Tax return

Key Dates:
April 15th (Deadline unless it falls on weekend/holiday)
June 15th (for foreign workers outside of USA)
October 15th (for those filed Extension)

Popular software:
TurboTaxH&R Block
TaxACT

Less known software:
TaxSlayer
eSmart
FreeTaxUSA

Upgrade to TurboTax Premier

This year I installed TurboTax Deluxe, but realized it didn't support Stock/ESPP investment during my filing. I had to get a new Premier copy. However, new download Premier copy always show TurboTax Deluxe after open the premier application.

After search and talking to intuit technical support, found TurboTax cached files impacted different versions. It is an obvious bug which Intuit doesn't cover, and it also implies they use configuration or temp files to differentiate Deluxe or Premier edition. If they implement in this way, we might be able to get a free upgrade from Deluxe to Premier or even Business and Home edition. :-)

I did the following which resolved the issue
1. Delete previous installed Deluxe application
2. Delete ~/Library/Application Support/TurboTax 2014 folder
3. Delete ~/Library/Caches/TurboTax 2014 folder
4. Reboot my macbook
5. Reinstall the premier application

Above also implies Mac OSX un-installation actually includes application itself and system caches.