At the federal level, up to 85% of Social Security benefits are taxable if your provisional income exceeds $34,000 (single) or $44,000 (married). Provisional income is your adjusted gross income plus tax-exempt interest plus half your SS benefit.
Connecticut adds state income tax on Social Security benefits on top of federal. At a $1,900/month benefit ($22,800/year) with $40,000 in other retirement income, the CT state tax on SS is $1,594/year. Roth conversions before retirement can lower provisional income and reduce federal SS taxation.
The 2026 maximum Social Security benefit at Full Retirement Age is $3,822/month ($45,864/year). Delaying to age 70 increases benefits by 8%/year past FRA, resulting in a $4,739/month maximum. The break-even age for delaying from 62 to 70 is typically around 81.