Is selling only shares you bought with margin on a margin/unsettled cash purchase free ride?
I'm not 100% sure, but I don't think it would be considered a free ride. The idea of a free ride is that you are engaging in a transaction when you do not actually have the money available to cover it, since the broker is technically giving you a 3 day loan whenever you purchase your stock (3 day rule to settle.) However, if you are using a margin account, and you have enough credit available, then you are not actually using unsettled assets, but rather an additional line of credit which was granted to you. You would just need to make sure that your total transactions are less than your purchasing power. That's my take on it anyway. I hope that helps, and hopefully someone can confirm or reject what I have said. There is no free ride at most brokers. You will likely be charged a margin fee for that trade even though you only held the margin shares for part of one day. The margin fee would be the annual margin interest rate calculated down to a one day holding period,so it would be smaller. Check your broker's policies but most work like this.
You should not have to wait 3 days to sell the stock after purchase. If you are trading with a cash account you will have to wait for the sale to settle (3 business days) before you can use those funds to purchase other stock. If you meet the definition of a pattern day trader which is 4 or more day trades in 5 business days then your brokerage will require you to have a minimum of $25,000 in funds and a margin account. "The price at which a stock was purchased is a sunk cost--that is, you cannot go back in time and reverse the decision you made to purchase that stock.  Another example of a sunk cost would be purchasing a non-refundable, non-transferable movie ticket.  Sunk costs have the tendency to create a cognitive bias in which we feel that the amount we paid at some point in the past should have some sort of bearing on the decision we make now--the purchaser of the ticket feels he must go see the movie even if he no longer wishes too, lest the ticket ""go to waste""... the investor hopelessly clings to a battered stock for that tiny chance that just maybe some day it will return to its former glory.  This is referred to as the ""sunk cost fallacy"" and is considered to be irrational behavior by economists. Keeping this in mind, your hopes and dreams for the stock at the time you purchased it should have no bearing on the decision you make now.  Similarly, whether the stock has risen or fallen in price since your purchase date should have no bearing.  Instead, you must consider what you expect the stock to do from this very moment on into the future--that is, you must act at the margin. You've indicated that you are faced with two choices--sell the stock now, incur the loss, but benefit from the tax break (Option A).  This benefit is quite easily quantifiable--it is your marginal tax rate multiplied by the additive inverse of the loss (assuming you have/will have other gains to offset).  Let's just assume that you incurred a $1000 loss, at a marginal tax rate of 20%, which means your tax benefit for the loss is $200. The second choice--to hold the stock in hopes of it rising in price (Option B)--is a bit harder to quantify.  You must assume that today is day zero, and that every cent in price the stock rises is a gain to you, and every cent in price the stock looses is a loss to you.  If you believe that the stock will rise to a price that will net your more than your tax benefit from option A, then holding the stock is more favorable than selling it at a loss today.  Conversely, if you believe this stock will fall even further in the future, or not rise enough to net you $200 (per the example), then Option A is preferable. Granted, there are some additional complications that play into your decision.  By selling the stock today, you not only get a tax benefit from the loss, but you've also freed up the funds previously used to purchase that stock to be invested elsewhere (in hopefully a better performing asset).  If you choose to stick with your current stock, then the gains you may have netted elsewhere must be considered as an opportunity cost associated with Option B.  Finally, the tax benefit is essentially guaranteed (so in our example, a $200 risk free return), while sticking with the stock in Option B still comes with some risk." It would be nice if the broker could be instructed to clear out the position for you, but in my experience the broker will simply give you the shares that you can't afford, then freeze your account because you are over your margin limit, and issue a margin call. This happened to me recently because of a dumb mistake: options I paid $200 for and expected to expire worthless, ended up slightly ITM, so they were auto-exercised on Friday for about $20k, and my account was frozen (only able to close positions).  By the next Monday, market news had shifted the stock against me and I had to sell it at a loss of $1200 to meet the margin call.  This kind of thing is what gives option trading a reputation for danger: A supposedly max-$200-risk turned into a 6x greater loss.  I see no reason to ever exercise, I always try to close my positions, but these things can happen. "Time for Redditors to not understand that the reason someone is losing cash matters far more than the fact that they're losing cash in the first place.   If you have positive unit economics on every transaction and spend your margins on customer acquisition, you're losing money but gaining market share. Once you stop growing, all of the customer acquisition spend is now pure profit. This is a great reason to be losing money and raising capital from equity/debt.   If you have *negative* unit economics on every transaction and have *no* margins, you are resorting to financing to just keep your operations running. When you stop growing, you're still losing money. The only way you start having a margin is by reducing cost or increasing prices. Uber has experimented with raising prices and it is reducing their losses. But it's also reducing their market share. Revenue growth but market share loss means they're growing slower than the rest of the market. Not great. In fact, catastrophic, because it means people are jumping ship because of increased prices.   People keep comparing Kalanick to Bezos and Jobs, and could not be any more wrong.   Jobs made incredibly high margin, noncommodity premium products that you couldn't get anywhere else. If you're putting companies on a ""commodity-noncommodity"" axis, Apple is going to be on the opposite end of Uber.   Amazon does deliver a lot of commodity goods, but they lost money for so long not just to deliver goods at negative unit economics but to *also* build and scale infrastructure that let them achieve positive economies of scale. They built an infrastructure that rivals the logistics ops of anyone in the world. They also use negative unit economics as a loss leader; so for instance, selling the Fire and Kindle at a loss because people will buy zero marginal cost items like movies, music, ebooks, etc through them, in addition to serving as a portal for Amazon's entire online store. I have bought hundreds of dollars of digital goods through Amazon hardware. That's pure margin for them. How is UberX a loss leader?   Uber shares none of these traits with Amazon or Apple." "Why would people sell below the current price, and not within the range of the bid/ask? There are many scenarios where this is deliberate but all of them boil down to the fact that the top level's bid doesn't support the quantity you're trying to sell (or is otherwise bogus[1]). One scenario as an example: You're day-trading both sides but at the end of the day you accumulated a rather substantial long position in a stock.  You don't want to (or aren't allowed to[2]) be exposed overnight, however.  What do you do? You place an order that is highly likely to go through altogether.  There's several ways to achieve that but a very simple one is to look at the minimum bid level for which the bid side is willing to take all of your shares, then place a limit order for the total quantity at that price.  If your position doesn't fit into the top level bid that price will well be lower than the ""current"" bid. Footnotes: [1] Keyword: quote stuffing [2] Keyword: overnight margin (aka positional margin, as opposed to intraday margin), this is highly broker dependent, exchanges don't usually distinguish between intraday and overnight margins, instead they use the collective term maintenance margin" "I've bought ISO stock over they years -- in NYSE traded companies.  Every time I've done so, they've done what's called ""sell-to-cover"".  And the gubmint treats the difference between FMV and purchase price as if it's part of your salary.  And for me, they've sold some stock extra to pay estimated taxes. So, if I got this right...  20,000 shares at $3 costs you 60,000 to buy them.  In my sell-to-cover at 5 scenario: did I get that right?  Keeping only 4,000 shares out of 20,000 doesn't feel right.  Maybe because I've always sold at a much ratio between strike price and FMV. Note I made some assumptions:  first is that the company will sell some of the stock to pay the taxes for you.  Second is your marginal tax rate.  Before you do anything check these. Is there some reason to exercise immediately?  I'd wait, personally." I used to work at a record keeping company, and while we worked with plan administrators through transitions in investment offerings, we never actually worked through a forced sale.  From what I recall I thought that was illegal, and that all the administrator can do is stop offering the investment (i.e. no new buy ins), but people who still have their money in it can either continue to hold or sell. "Depends on your account. If you have a margin account, then you can ""withdraw"" the margin, and it will get paid off/settled on T+3. However if it's a cash account then you will most likely need to wait. Call your broker and ask, each broker has different rules."