Hal_Al
Level 15

Education

Q. Should he start making quarterly payments now based on his total tax from last year?

A. Yes.

Q.  Will there be some sort  of penalty for not already doing so in April?

A.  Probably not, since none of the income (apparently) was in received in the first quarter.  You should consider having TurboTax prepare form 2210, using the "annualized method", when he files his tax return.