After speaking to multiple Rabonim, I just wanted to let people know of a second advantage of donating appreciated stock to a DAF. In addition to not having to pay taxes on the appreciation since the IRS views that all that gain was given away to tzedaka, you also do not consider the growth in your obligation of maiser, as halachah does not view the avoidance of tax in this scenario as a halachicaly tangible gain. Scenario: You have a w2 job, you have a net profit of 10k this month and have to give 1k in maiser. You also have a taxable brokerage account with appreciated stock. If you take $1000 of stock that you purchased for only $500 and transfer it into your DAF, you: • consider the 1k maiser obligation of your w2 income as fulfilled via your stock transfer • do not need to give 50$ of maiser from the $500 of growth you donated • can deduct the 1k off your taxes if you itemize deductions • can use the 1k that would have gone to maiser off your salary and repurchase the stocks you gave away at the new price resetting your tax basis, wiping out all that tax burden completely that you previously had.

Your rabbi doesn't want you to know: Jews are saving thousands with this simple trick!

If you're rebuying the same stock, it's a bit of a waste - since you could just keep it and give it later. It works a bit better to give assets that you don't want anymore and then buy different assets that you like more. Of course, if you follow Baruch's idea and put everything in the S&P, this is moot.

how is it a waste? you are resettting your cost basis using your maiser. If you did it later you wouldn’t be able to count it as maiser because you don’t make enough in one year to donate that much stock to charity

If I buy XOM at $100, donate it at $150 and replace it at $150 and then donate it again at $200, I would have gotten the same benefit by holding the initial shares until $200 and donating them then. In the meantime, I missed the opportunity to donate a different appreciated stock.

You are forgetting the limited maiser component. You are correct only from a tax perspective, but you're missing the maiser benefit.

I don't think so. With both m'assar and tax, I get the benefit each time I give something. Giving and replacing a stock uses up the opportunity to give a different stock and shelter those profits from either a tax or m'assar obligation.

But maiser benefit not captured each year is gone as opposed to the tax benefit which is deferred

I'm assuming that I have multiple appreciated stocks. In that case, I am arguing to give the one you don't want to own anymore rather than one that you would replace.

I am only talking about a scenario where you want to own the stocks you currently own. Obviously if you want to get rid of something then you should do that.

One twist on this - for REIT's and MLP's, most of the dividend payouts are treated (for taxes) as a return on capital and they lower the cost basis so that when they are sold, there will be more capital gains. Donating these stocks is more helpful, as there are more capital gains to avoid. I'm guessing that for m'assar we would treat the dividends the same way that taxes treat them.