Rav Dovid Grossman
Answer: There is no obligation to give ma'aser at any specific time. Some people take ma'aser off of every paycheck, while others take every few months or once a year. According to halacha, all these ways are acceptable.
Whichever way one chooses to separate his ma'aser, it is important to make a good calculation and to be exact. The Gemara says that there is a guarantee that if one gives ma'aser, he will become rich. Some people ask, I give ma'aser; why am I not rich?
One answer offered for this question is that this guarantee applies only to people who make an exact calculation and give the precise amount of ma'aser.
Accordingly, it is a good idea for many people who are paid by the month to make an exact calculation every time they receive a paycheck and put aside that amount of money for ma'aser. (One need not take off ma'aser from earnings that were deducted from his paycheck for taxes.)
In short, one can arrange any setup he wants for how and when he separates his ma'aser, as long as he is careful to keep precise calculations. If he has no reason not to, it might be a good idea to separate ma'aser from each paycheck, but if one has a reason why a different arrangement works better for him, he may do whatever is easiest. The Chofetz Chaim suggests that it is better to calculate ma'aser twice a year as it says "Asser t'asser". He suggests two specific times, the month of Nissan and before Rosh Hashanah. If this works for you, you can do it that way, if this does not work for you, you may do it any time that does.
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