Share your insights or perspective on the financial matter presented in the input.

Reinvesting dividends and capital gains
First, do you get charged a commission or other fee for reinvesting?   Second, why would capital gains and dividends be grouped together? If the broker charges you for that run away. As Joe explained, it is done as a courtesy. Doesn't this mean if I sell the stock, the profit will be used to buy   that stock right back? No, this is only the capital gains distributions of funds. Lastly, there are two additional checkbox options I was hoping   somebody could explain: "All equity positions currently held in this   account" and "Future equity purchases, transfers, and deposits to this   account". "All equity positions" means your selection will be valid for all the positions you already have. "Future positions" means it will only affect future positions, not the ones you already have. For example: FOLLOW-UP: Looking around, some people suggest not doing this for   taxable accounts because it complicates cost basis reporting. Is this   a valid concern? Doesn't the brokerage handle that and send you the   information when you sell the stock? Yes, because you end up with tons of positions and you need to track the cost basis for each. Brokers are required to report cost-basis on 1099-B now, so its less of a problem, but before 2011 you'd have 10's of positions each year (if you have a monthly dividend, for example) each with different cost basis, and you'd usually sell them all at once. Go figure the gain. So the new 1099-B reporting regulations help a little on this, but it only kicks in for everything starting of 2013 IIRC. Fortunately, for some investments (mutual funds, mainly) you may chose averaging, but it has drawbacks as well.