Do the tax consequences make it worth it for me to hold ESPP stock?
To try to answer the three explicit questions: Every share of stock is treated proportionately: each share is assigned the same dollar amount of investment (1/176th part of the contribution in the example), and has the same discount amount (15% of $20 or $25, depending on when you sell, usually). So if you immediately sell 120 shares at $25, you have taxable income on the gain for those shares (120*($25-$17)). Either selling immediately or holding for the long term period (12-18 mo) can be advantageous, just in different ways.   Selling immediately avoids a risk of a decline in the price of the stock, and allows you to invest elsewhere and earn income on the proceeds for the next 12-18 months that you would not otherwise have had.  The downside is that all of your gain ($25-$17 per share) is taxed as ordinary income.   Holding for the full period is advantageous in that only the discount (15% of $20 or $25) will be taxed as ordinary income and the rest of the gain (sell price minus $20 or $25) will be taxed at long-term capital gain tax rates, which generally are lower than ordinary rates (all taxes are due in the year you do sell).  The catch is you will sell at different price, higher or lower, and thus have a risk of loss (or gain). You will never be (Federally) double taxed in any scenario.  The $3000 you put in will not be taxed after all is sold, as it is a return of your capital investment.  All money you receive in excess of the $3000 will be taxed, in all scenarios, just potentially at different rates, ordinary or capital gain.  (All this ignores AMT considerations, which you likely are not subject to.) I think people in general tend to unnecessarily over-complicate this issue.  Here's what I think you should do in any situation like this: First and foremost, put all tax considerations aside and decide whether it makes sense to sell the stock now or hold on to it for the long term based on its merits as an investment.  Tax considerations have absolutely nothing to do with whether the stock is a good investment.  If you consider all non-tax factors and decide to hold on to it for the long term, then you can use the tax considerations as a very minor input to how long you should hold it - in other words, don't set your time horizon to 17.5 months if waiting another 2 weeks gives you better tax treatment. You're going to pay taxes on your gains no matter what.  The only difference is whether you pay capital gains tax or income tax.  Granted, the income tax rate is higher, but wouldn't it suck if you pay a LOT less tax only because you have a LOT less value in your stock? So to answer your question - I would say, absolutely not, tax consequences do not make it worthwhile to hold on to your ESPP shares.  If you decide to hold on to your ESPP for other reasons (and they better be good ones to put that much free profit at risk), only then should you look at the tax consequences to help fine-tune your strategy. Your gain is $1408. The difference between 32% of your gain and 15% of your gain is $236.36 or $1.60 per share. If you sell now, you have $3957.44 after taxes.  Forget about the ESPP for a moment. Are you be willing to wager $4000 on the proposition that your company's stock price won't go down more than $1.60 or so over the next 18 months? I've never felt it was worth it. Also, I never thought it made much sense to own any of my employer's stock. If their business does poorly, I'd prefer not to have both my job and my money at risk. If you sell now: Now assuming you hold for 18 months, pay 15% capital gains tax, and the stock price drops by $1.60 to $23.40:
From the instructions: If you do not need to make any adjustments to the basis or type of   gain or loss (short-term or long-term) reported to you on Form 1099-B   (or substitute statement) or to your gain or loss for any transactions   for which basis has been reported to the IRS (normally reported on   Form 8949 with box A checked), you do not have to include those   transactions on Form 8949. Instead, you can report summary information   for those transactions directly on Schedule D. For more information,   see Exception 1, later. However, in case of ESPP and RSU, it is likely that you actually do need to make adjustments. Since 2014, brokers are no longer required to track basis for these, so you better check that the calculations are correct. If the numbers are right and you just summarized instead of reporting each on a separate line, its probably not an issue. As long as the gains reported are correct, no-one will waste their time on you. If you missed several thousand dollars because of incorrect calculations, some might think you were intentionally trying to hide something by aggregating and may come after you. Does this make sense? I'm concerned that by buying shares with post tax income, I'll have ended up being taxed twice or have increased my taxable income. ... The company will then re-reimburse me for the difference in stock price between the vesting and the purchase share price. Sure.  Assuming you received a 100-share RSU for shares worth $10, and your marginal tax rate is 30% (all made up numbers), either: or So you're in the same spot either way.  You paid $300 to get $1,000 worth of stock. Taxes are the same as well.  The full value of the RSU will count as income either way, and you'll either pay tax on the gains of the 100 shares in your RSU our you'll pay tax on gains on the 70 shares in your RSU and the 30 shares you bought.  Since they're reimbursing you for any difference the cost basis will be the same (although you might get taxed on the reimbursement, but that should be a relatively small amount). This first year I wanted to keep all of the shares, due to tax reasons and because believe the share price will go up. I don't see how this would make a difference from a tax standpoint. You're going to pay tax on the RSU either way - either in shares or in cash.  how does the value of the shares going up make a difference in tax? Additionally I'm concerned that by doing this I'm going to be hit by my bank for GBP->USD exchange fees, foreign money transfer charges, broker purchase fees etc.  That might be true - if that's the case then you need to decide whether to keep fighting or decide if it's worth the transaction costs. I have an ESPP with E*Trade; you can transfer stock like that via a physical (paper) asset-transfer form. Look for one of those, and if you can't find it, call your brokerage (or email / whatever). You own the shares, so you can generally do what you want with them. Just be very careful about recording all the purchase and transfer information so that you can deal properly with the taxes. Note that you're asking about withholding, not about taxing.  Withholding doesn't mean this is exactly the tax you'll pay: it means they're withholding a certain amount to make sure you pay taxes on it, but the tax bill at the end of the year is the same regardless of how you choose to do the withholding.  Your tax bill may be higher or lower than the withholding amount. As far as tax rate, that will be the same regardless - you're just moving the money from one place to the other.   The only difference would be that your tax is based on total shares under the plan - meaning that if you buy 1k shares, for example, at $10, so $1,500 discounted income, if you go the payroll route you get (say) $375 withheld.  If you go the share route, you either get $375 worth of stock (so 38 shares) withheld (and then you would lose out on selling that stock, meaning you don't get quite as much out of it at the end) or you would ask them to actually buy rather more shares to make up for it, meaning you'd have a slightly higher total gain.  That would involve a slightly higher tax at the end of it, of course. Option 1:  Buy and then sell $10000 worth, share-based withholding.  Assuming 15% profit, and $10/share at both points, then buy/sell 1000 shares, $1500 in profit to take into account, 38 shares' worth (=$380) withheld.  You put in $8500, you get back $9620, net $1120.   Option 2:  Buy and then sell $13500 worth, share based withholding.  Same assumptions.  You make about $2000 in pre-tax profit, meaning you owe about $500 in tax withholding.  Put in $11475, get back $13000, net $1525.  Owe 35% more tax at the end of the year, but you have the full $1500 to spend on whatever you are doing with it. Option 3:  Buy and then sell $1000 worth, paycheck withholding.  You get the full $10000-$8500 = $1500 up front, but your next paycheck is $375 lighter.  Same taxes as Option 1 at the end of the year. Good questions. I can only add that it may be valuable if the company is bought, they may buy the options. Happened to me in previous company. Short answer is to put the max 15% contribution into your ESPP. Long answer is that since you want to be saving as much as you can anyway, this is a great way to force you to do it, and pick up at least a 15% return every six months (or however often your plan makes a purchase). I say at least because sometimes an ESPP will give you the lower of the beginning or end period stock price, and then a 15% discount off of that (but check the details of your plan). If you feel like your company's stock is a good long term investment, then hold onto the shares when purchased. Otherwise sell as soon as you get them, and bank that 15% return. For ESPP, the discount that you get is taxed as ordinary income. Capital gains is taxed at the appropriate rate, which is different based on how long you hold it. So, yes, if the stock is going up, Typically, the discount is taxable at sale time But what about taxes?  When the company   buys the shares for you, you do not   owe any taxes. You are exercising your   rights under the ESPP. You have bought   some stock. So far so good. 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. Source: Turbotax.   Second source. Your pretax rate of return would be: 17% (100/85) In your scenario where the stock price is fixed at $100. Your tax rate would be your marginal rate.   If the stock stayed at 100, you would still be taxed as income on $15/share (the discount) and would receive no benefit for holding the stock one year. Assuming you are in the 25% tax bracket, your after tax rate of return would be 13% ((15*.75)+85)/85) You should get a 1099-MISC for the $5000 you got.  And your broker should send you a 1099-B for the $5500 sale of Google stock. These are two totally separate things as far as the US IRS is concerned. 1) You made $5000 in wages. You will pay income tax on this as well as FICA and other state and local taxes. 2) You will report that you paid $5000 for stock, and sold it for $5500 without holding it for one year. Since this was short term, you will pay tax on the $500 in income you made. These numbers will go on different parts of your tax form.  Essentially in your case, you'll have to pay regular income tax rates on the whole $5500, but that's only because short term capital gains are treated as income.  There's always the possibility that could change (unlikely).  It also helps to think of them separately because if you held the stock for a year, you would pay different tax on that $500.  Regardless, you report them in different ways on your taxes. Purchasing stock doesn't affect your immediate taxes any more than purchasing anything else, unless you purchase it through a traditional 401k or some other pre-tax vehicle. Selling stock has tax effects; that's when you have a gain or loss to report. No one can advise you on whether to hold this stock or sell it. Your carried losses can offset short or long term gains, but the long term losses have to be applied to offset long term gains before any remaining losses can offset short term gains. Your question doesn't indicate how long you have to hold before the short term gains become long term gains. Obviously the longer the holding period, the greater the risk. You also must avoid a wash sale (selling to lock in the gains/reset your basis then repurchasing within a month). All of those decisions hold risks that you have to weigh. If you see further upside in holding it longer, keep the investment. Don't sell just to try to maximize tax benefits. You also need to remember that stock options usually become valueless if not exercised while an employee of the company.  So if there is any chance that you will leave the company before an IPO, the effective value of the stock options is zero.  That is the safest and least risky valuation of the stock options.   With a Google or Facebook, stock options can be exercised and immediately sold, as they are publicly traded.  In fact, they may give stock grants where you sell part of the grant to pay tax withholding.  You can then sell the remainder of the grant for money at any time, even after you leave the company.  You only need the option/grant to vest to take advantage of it.  Valuing these at face value (current stock price) makes sense.  That's at least a reasonable guess of future value.   If you are absolutely sure that you will stay with the company until the IPO, then valuing the stock based on earnings can make sense.  A ten million dollar profit can justify a hundred million dollar IPO market capitalization easily.  Divide that by the number of shares outstanding and multiply by how many you get.  If anything, that gives you a conservative estimate.   I would still favor the big company offers though.  As I said, they are immediately tradeable while this offer is effectively contingent on the IPO.  If you leave before then, you get nothing.  If they delay the IPO, you're stuck.  You can't leave the company until then without sacrificing that portion of your compensation.  That seems a big commitment to make. Did you read what I wrote? I sold some stock for a gain, that's a taxable event.  Are you trying to say I just shouldn't have sold it? Do you understand investing at all?   And the second point is moot, I still had to pay the tax, having write offs doesn't change the fact that my taxes were higher(more importantly that they would have been much higher if I couldn't take advantage of capital gains.) There are two things to consider: taxes - beneficial treatment for long-term holding, and for ESPP's you can get lower taxes on higher earnings. Also, depending on local laws, some share schemes allow one to avoid some or all on the income tax. For example, in the UK £2000 in shares is treated differently to 2000 in cash vesting - restricted stocks or options can only be sold/exercised years after being granted, as long as the employee keeps his part of the contract (usually - staying at the same place of works through the vesting period). This means job retention for the employees, that's why they don't really care if you exercise the same day or not, they care that you actually keep working until the day when you can exercise arrives. By then you'll get more grants you'll want to wait to vest, and so on. This would keep you at the same place of work for a long time because by quitting you'd be forfeiting the grants. If you have held the stocks longer than a year, then there is no tax apart from the STT that is already deducted when you sell the shares.  If you have held the stock for less than a year, you would have to pay short term capital gains at the rate of 15% on the profit. Edit: If you buy different shares from the total amount or profits, it makes no difference to taxes.