<prompt> Human: Pretty simple situation, but Im a financial n00b. My parents paid for me to go to college with the understanding that I would pay them back out of the money that was set aside in my name for me to use for that and for homebuying, further schooling, etc. Ive got 150K or so sitting in index funds with Charles Schwab... how do I get it out and transfer it to my parents without paying capital gains tax?Any advice is appreciated.Assistant: Cant avoid the taxman. If its not in a tax advantaged account and you sell, youre going to get hit with capital gains.The only way I can think of to mitigate it is by ensuring that theyre long term capital gains over a year, and also to make so little income that youre in the 0-15 tax bracket so your long term gain is also at 0. Its possible that you can get by at a 0 long term capital gain, but you have to first be in the 0 - 15 income tax bracket what bracket youre in depends on your ordinary income, including the amount youve made through capital gains.You can probably talk to an accountant for other ideas. Human: Yeah, Im thinking the most prudent way to do it is to withdraw the money in smaller amounts over the course of the year.  <response>: Taking out a little bit several times over the course of the year wont help--your total income of the entire year is what matters. To be in the 0 capital gains bracket you need to have less than 35,350 in income assuming you file single and for this case including the gains from the sale of your investments. Any amount over that will be taxed at the 15 federal and the applicable state tax rate. 