Is it possible that for shares to be reinvested in a stock you already sold?
I believe this depends on the broker's policies. For example, here is Vanguard's policy (from https://personal.vanguard.com/us/whatweoffer/stocksbondscds/brokeragedividendprogram): Does selling shares affect a distribution? If you sell the entire position two days or more before the dividend-payable date, your distribution will be paid in cash. If, however, you sell an entire position within the two day time frame of the security's payable date, the dividend will be reinvested, resulting in additional shares. Selling these subsequent shares will require another sell order, which will incur additional commission charges. Dividends which would have been reinvested into less than one whole share will be automatically liquidated into cash. If you want to guarantee you receive no fractional shares, I'd call your broker and ask whether selling stock ABC on a particular date will result in the dividend being paid in shares.
You might be right about that, but your previous posts don't say that.  In just the last one you said:  &gt;Because buyback decreases shares outstanding it **also decreases the company's total future dividend payouts as well**  This is indicating that you believe there is a difference somehow, no? You'll need to talk to your broker about registering positions you already hold.  I would personally expect this will cost you a not-insignificant fee.  And I don't think you'll be able to do this on any shares held in a tax-advantaged account. That said, I'd recommend you go to the Investors sections of the company's website in question.  This will usually tell you who the registrar of the company's stock is, and if they offer any direct-purchase, or DRIP, programs.   You should find out from these contacts and program details how the direct program works and what it's costs are. I suspect, but have no firsthand knowledge that this will be true, that you'll end up with lower costs if you just sell the shares in your brokerage, take the cash out, send the cash to the registrar and re-purchase shares that way.   I say this only because I know, from inheritance situations, that de-registering stock cost me a $75 fee at my brokerage, whereas transactions at the registrar were $19.95. My answers to your direct questions: (Edited to fully answer the question with itemized answers.) Ignoring taxes, a share repurchase has exactly the same effect on the company and the shareholders' wealth as a cash dividend. In either case, the company is disbursing cash to its shareholders; in the former, in exchange for shares which shareholders happen to be selling on the market at the time; in the latter, equally to all shareholders. For those shareholders who do not happen to be selling their shares, a share repurchase by a company is equivalent to a shareholder's reinvestment of a cash dividend in additional shares of the same company.  The only difference is the total number of shares left outstanding.  Your shares after a share buyback represent ownership of a greater fraction of the company, since in effect the company is buying out other shareholders on your behalf. Theoretically, a share buyback leaves the price of the stock unchanged, whereas a cash dividend tends to reduce the price of the stock by exactly the amount of the dividend, (notwithstanding underlying earnings.)  This is because a share buyback concentrates your ownership in the company, but at the same time, the company as a whole is devalued by the exact amount of cash disbursed to buy back shares. Taxwise, a share buyback generally allows you to treat your share of the company's profits as capital gains---and quite possibly defer taxes on it as long as you own the stock.  You usually have to pay taxes on dividends at the time they are paid.  However, dividends are sometimes seen as instilling discipline in management, because it's a very public and obvious sign of distress for a company to cut its dividend, whereas a share repurchase plan can often be quietly withdrawn without drawing that much attention. A third alternative to a dividend or a share repurchase is for the company to find profitable projects to reinvest its earnings in, and attempt to grow the company as a whole (in the hopes of even greater earnings in the future) rather than distribute current earnings back to shareholders.  (A company may alse use its earnings to pay down or repurchase debt, as well.) As to your second question, the SEC has certain rules that regulate the timing and price of share repurchases on the open market. No, the dividends can't be exploited like that. Dividends settlement are tied to an ex-dividend date. The ex-dividend, is the day that allows you to get a dividend if you own the stock. Since a buyer of the stock after this date won't get the dividend, the price usually drop by the amount of the dividend. In your case the price of a share would lose $2.65 and you will be credited by $2.65 in cash such that your portfolio won't change in value due to the dividend. Also, you can't exploit the drop in price by short-selling, as you would be owing the dividend to the person lending you the stock for the short sale. Finally, the price of the stock at the ex-dividend will also be affected by the supply and demand, such that you can't be precisely sure of the drop in price of the security. Yes, you often can buy stocks directly from the company at little or no transaction cost.  Many companies have either a Dividend Reinvestment Plan (DRIP) or a Direct Stock Plan (DSP).  With these plans, you purchase shares directly from the company (although, often there is a third party transfer agent that handles the transaction), and the stock is issued in your name.  This differs from purchasing stock from a broker, where the stock normally remains in the name of the broker. Generally, in order to begin participating in a DRIP, you need to already be a registered stockholder.  This means that you need to purchase your first share of stock outside of the DRIP, and get it in your name.  After that, you can register with the DRIP and purchase additional shares directly from the company.  If the company has a DSP, you can begin purchasing shares directly without first being a stockholder. With the advent of discount brokers, DRIPs do not save as much money for regular investors as they once did.  However, they can still sometimes save money for someone who wants to purchase shares on a regular basis over even a discount broker. If you are interested in DRIPs and DSPs and want to learn more, there is an informative website at dripinvesting.org that has lots of information on which DRIPs are available and how to get started. You are still selling one investment and buying another - the fact that they are managed by the same company should be irrelevant.  So yes, it would get the same tax treatment as if they were managed by different companies. How can they reduce the number of shares I hold? They may have purchased them.  You don't say what stock it is, so we can only speculate.  Let's say that the stock is called PENNY.  So they may have taken your 1600 PENNY shares and renamed them to 1600 PENNYOLD shares.  Then they created a new $5 PENNY share and gave you .2357 shares of that in exchange for your 1600 PENNYOLD shares.  This suggests that your old shares were worth $1.1785 or less than a tenth of a cent each.   As an example, MYLAN did this in 2015 as part of their tax inversion (moved official headquarters from the US to Europe).  They did not change the number of shares at that time, but MYLAN is not a penny stock.   This is the kind of thing that might happen in a bankruptcy.   A reverse split (where they give you one share in exchange for more than one share) is also possible, although you received an odd amount for a reverse split.  Usually those produce rounder numbers.  A number like .2357 sounds more like a market price, as those can be bizarre. Investors purchase additional shares all the time. Every investor that adds money to their investments does this every paycheck or every month. Investors do this every time they reinvest dividends, interest or capital gains. They also buy and sell shares when they decide to rebalance their portfolio.  Whether you are investing via a broker, mutual fund or ETF the investment company can handle this issue. You do want to know how they want you to specify which shares you want them to sell. The laws in your country may specify a default procedure, or what needs to be done if you want to use another procedure, or if you are allowed to change once you have specified a procedure. No, this isn't possible, especially not when you're trading a highly liquid stock like Apple. When you put in your buy order at $210, any other traders that have open limit sell orders with the correct parameters, e.g. price and volume, will have their order(s) filled. This will occur before you can put in your own sell order and purchase your own shares because the other orders are listed on the order book first. In the US, many tax-sheltered accounts like IRA's have specific rules against self-dealing, which includes buying and selling assets with yourself, so such a transaction would be prohibited by definition. Although I'm not entirely sure if this applies to stocks, the limitation described in the first paragraph still applies regardless. If this were possible, rest assured that high-frequency traders would take advantage of this tactic to manipulate share prices. (I've heard critics say that this does occur, but I haven't researched it myself or seen any data about it) "Scenario 1 - When you sell the shares in a margin account, you will see your buying power go up, but your ""amount available to withdraw"" stays the same until settlement. Yes, you can reallocate the same day, no need to wait until settlement. There is no margin interest for this scenario.  Scenario 2 -  If that stock is marginable to 50%, and all you have is $10,000 in that stock, you can buy another $10,000. Once done, you are at 50% margin, exactly." "The dividend reinvestment won't change whether the dividends themselves are qualified or not for US income tax purposes.  It's still the holding period on the stock that matters.  If you bought stock in different lots, then you could have a situation where some of the dividends paid are qualified and some are not, but: For completeness, it's worth noting that some dividends cannot be ""qualified"" no matter how long you hold them, but if you've got an investment in a common corporate stock (vs. something more ""exotic""), then what's above should apply." Only if you sell the stock in question, and use the proceeds to buy other stock. (You should probably never feel bad about selling your company stock, even if it goes up a lot later, because from a risk-exposure basis you are already exposed to your company's performance through your career. Unless you have a lot of other savings, you should diversify.) Your question is unanswerable as you haven't provided enough information. I.e. If those shares cost $1000 and you have $50000 ( or any number above $1000) of cash available in the account then you can't possibly free ride. I think your understanding of the free ride rule is incorrect. Basically what this rule is stating is that you have to have the cash when the trade is placed in order to settle the trade. Otherwise you are taking on margin (which you can't do in a cash account). So at order entry you have to have the cash to cover the purchase so it's able to be settled. If you do, no problem and you can sell that stock before trade settlement. There is no law that says you have to hold it past trade settlement. However, you cannot spend the same dollar more than once before it settles.  This site does a good job explaining this more throughly with examples: http://www.invest-faq.com/articles/trade-day-free-ride.html "Something to note is that when a company announces a share buyback program there is usually a time frame and amount of shares that are important details as it isn't like the company will make one big buy back of stock generally.  Rather it may take months or even years as noted in the Wikipedia article about share repurchases. Wikipedia covers some of the technical details here but to give a specific set of answers: When a company announces a share buyback program, who do they actually   buy back the shares from?  From the Wikipedia link: ""Under US corporate law there are five primary methods of stock repurchase: open market, private negotiations, repurchase 'put' rights, and two variants of self-tender repurchase: a fixed price tender offer and a Dutch auction."" Thus, there are open market and a couple of other possibilities. Openly traded shares on a stock exchange?  Possibly, though there are other options. Is there a fixed price that   they buy back at? Sometimes.  I'd think a ""fixed price tender offer"" would imply a fixed price though the open market way may take various prices. If I own shares in that company, can I get them to buy back my shares? Selective Buy-Backs is noted in Wikipedia as: ""In broad terms, a selective buy-back is one in which identical offers are not made to every shareholder, for example, if offers are made to only some of the shareholders in the company. In the US, no special shareholder approval of a selective buy-back is required. In the UK, the scheme must first be approved by all shareholders, or by a special resolution (requiring a 75% majority) of the members in which no vote is cast by selling shareholders or their associates. Selling shareholders may not vote in favor of a special resolution to approve a selective buy-back. The notice to shareholders convening the meeting to vote on a selective buy-back must include a statement setting out all material information that is relevant to the proposal, although it is not necessary for the company to provide information already disclosed to the shareholders, if that would be unreasonable."" Thus it is possible, though how probable is another question. While not in the question, something to consider is how the buybacks can be done as a result of offsetting the dilution of employees who have stock options that may exercise them and spread the earnings over more shares, but this is more on understanding the employee stock option scenario that various big companies use when it comes to giving employees an incentive to help the stock price." Assuming US. The only con that I know of is that hassle factor. You have to remember to sell when you get the new shares, and your taxes become a bit more complicated; the discount that you receive is taxed as ordinary income, and then any change in the price of the stock between when you receive it and you sell it will be considered a capital gain or loss. It's not hard to account for properly if you keep good records.