Social Security October 2026 payments: Why SSI gets two checks, the calendar twist behind the second deposit and what the 2027 COLA could change

October brings the next round of Social Security payments after the Sept. 23 deposit. Regular benefits will arrive on Oct. 14, 21 and 28, based on birth dates. SSI follows a different calendar, with payments on Oct. 1 and Oct. 30. The latter is November’s benefit, moved forward because Nov. 1 falls on a Sunday.