Buying company stock at a discount and immediately selling?

[DK82]

First time working for a publicly traded company.  I recently learned that I can buy company stock at an X% discount.  Doesn't seem like there's anything preventing me from immediately selling (thus making a quick X% return on my money).  Are there tax implications that'd stop me from simply doing this over and over and over and (slowly but surely) accumulating a decent amount of "free money"?

Sorry if this is a dumb question, this is all new to me.   

[PDXTabs]

That's pretty normal. But it usually takes at least a day to pull off, so if X is a small number it might not be worth it due to market volatility.

[Telecaster]

First time working for a publicly traded company.  I recently learned that I can buy company stock at an X% discount.  Doesn't seem like there's anything preventing me from immediately selling (thus making a quick X% return on my money).  Are there tax implications that'd stop me from simply doing this over and over and over and (slowly but surely) accumulating a decent amount of "free money"?

Sorry if this is a dumb question, this is all new to me.   

No, you've got it right.   

[lutorm]

The tax rules are a bit complicated, though: https://www.hrblock.com/tax-center/income/investments/employee-stock-purchase-plan-taxes/. (But if you sell it immediately, all the gain is income anyway.)

Typically an ESPP also requires you to agree to a deduction over something like 6 months before you get the stock, and there's a cap to how much you can buy.

[Grow Stacks]

It'll chalk up as short term capital gains (sale of asset held for less than 1 year), and you'd follow your tax-table as you would for other 'ordinary income'. At least you don't pay FICA tax on capital gains (even if they are short term).

[shuffler]

It'll chalk up as short term capital gains (sale of asset held for less than 1 year), and you'd follow your tax-table as you would for other 'ordinary income'. At least you don't pay FICA tax on capital gains (even if they are short term).

The gain (i.e. the "discount" given by the employer) is treated as income.  You'll pay your marginal rate on it, not capital gains (short or otherwise).