To minimize your federal penalties, make estimated payments of $5000 now, June 15, Sept 15, and January 15, at www.irs.gov/payments (best to be a few days before each deadline). Your first estimated payment was due April 15, so it's 1 month late, which could result in a penalty of 1%, if the IRS assesses it at all. Making the other estimated payments so that you owe less than $1000 net when you file in April 2024 will eliminate any other penalties. I assume the rules for MA will be similar. Alternatively, you could add extra job withholding by submitting a new W-4 to your employer, so that you pay at least $20,000 extra by December 31. That might be $2500 per month, or $1250 per check if you are paid biweekly or $625 per week if you are paid weekly.
If you make no estimated payments, the penalty will be approximately 1% per month of the amount owed, figuring that you owed $5000 starting in April, $10,000 starting in June, $15,000 starting in September and $20,000 starting in January, up to whenever you pay. The actual penalty is 0.5% per month penalty, plus interest--interest is a variable rate and is around 0.5% per month but since the federal reserve has been increasing interest rates, that is probably gone up too.
