Do I need to make added estimated Fed Tax payments in 2019 because of unusually increased income? I retire in 13 days, and will get a monthly severance for 14 months, on the 25th of each month, with normal withholding from it, as if the only income. My pension will start 8/1 on the first of each month, with taxes withheld as if IT was the only income. Plus I will get a severance incentive, paid for unused vacation, bonus, etc. Wife gets pensions plus SS with no taxes withheld. Basically, until Sept, I will not really know what my exact total Fed taxes will be via Taxcaster, though I made a decent estimate. Are the circumstances and income differential increase compared to last year, (about $60k or 30%) enough to not worry about a penalty for the larger tax bill in April 2020, or am I required to make estimated payments last quarter or 2019? If I don’t HAVE to make payments in 2019, I am ok with the large tax bill in 2020.