dmertz
Level 15

Get your taxes done using TurboTax

Given that the investment income occurred early in the year, it's likely that annualizing income would increase the underpayment penalty for the earlier quarters rather than reduce it.

 

About the only way to reduce the underpayment penalty for earlier quarters would be to have taxes withheld from income during the remainder of the year.  Unlike estimated tax payments, tax withholding is treated by default as having been paid evenly throughout the year no matter when during the year the withholding is made.