Filing Form SSA-44 after retirement is worth considering for most United pilots, because retirement is a qualifying life-changing event that causes a significant income drop. The Social Security Administration uses income from the previous two years to set Medicare premiums — meaning a pilot retiring in 2026 could initially be charged surcharges based on peak 2024 earnings. SSA-44, filed with documentation of the income change, may result in premiums being adjusted to reflect current, lower retirement income — potentially saving hundreds of dollars per month in IRMAA surcharges.