The Marketplace window, and the part of it that gets missed. The general rule at 45 C.F.R. 155.420(c)(1) gives a qualified individual 60 days from the triggering event to select a plan. Paragraph (c)(2) adds "advanced availability": where the trigger is a loss of coverage, the individual has 60 days before the event as well, which is the mechanism that lets somebody whose coverage ends on the 31st arrange a replacement starting on the 1st. Paragraph (c)(5) protects a person who was reasonably unaware the event had happened, running the 60 days from when they knew or should have known.
But the start date is set by paragraph (b), not paragraph (c), and it does not follow the same logic. The default at 155.420(b)(1) is that coverage takes effect on the first day of the month following plan selection, so the gap depends on when you choose rather than on when the event occurred. Three departures matter. For a birth, an adoption, a placement for adoption or in foster care, or a court order, paragraph (b)(2)(i) requires the Exchange to make coverage effective on the date of the event itself, or to let the individual elect the first of the following month instead. For marriage, paragraph (b)(2)(ii) gives only the first day of the month following selection, with no retroactivity at all. And for a loss of coverage, paragraph (b)(2)(iv) provides that if the plan selection is made on or before the day of the triggering event, coverage is effective the first day of the month following that event; select afterwards and the ordinary rule applies. That single sentence is the whole practical value of the 60-days-before window, and using the window without using it early gets none of the benefit.
The employer window is shorter, and the same statute contains two different numbers. Under 29 U.S.C. 1181(f)(1)(D), an employee who lost other coverage must request enrollment "not later than 30 days" after the exhaustion or termination of that coverage, and 1181(f)(2)(B) sets a dependent special enrollment period of "not less than 30 days" after a marriage, birth, adoption or placement for adoption. The regulation restates both as "a period of at least 30 days". Then paragraph (f)(3), added for Medicaid and the Children's Health Insurance Program, gives 60 days: 60 days after Medicaid or CHIP coverage terminates for loss of eligibility, and 60 days after the employee or a dependent is determined eligible for premium assistance under one of those programs. So the same subsection of the same statute runs a 30-day clock for a birth and a 60-day clock for a CHIP determination, and the employer window for a life event is half the Marketplace window for the same event.
The employer plan's start dates are again separate. Under 29 C.F.R. 2590.701-6(a)(4)(ii), coverage after a loss of other coverage must begin no later than the first day of the first calendar month beginning after the plan receives the request. For a new dependent, 2590.701-6(b)(3)(iii) is more generous in one direction and not the other: marriage gets the first day of the first month after the request, while a birth gets coverage as of the date of birth, and an adoption or placement for adoption as of that date. So the newborn is covered from day one on both the employer plan and the Marketplace, and the new spouse is not covered on either until the following month.
Medicare's window is eight months, and it is the one where a mistake is permanent. 42 C.F.R. 406.24(b)(1) provides that the special enrollment period includes any month during any part of which the individual is enrolled in a group health plan by reason of their own or a spouse's current employment status, and (b)(2) that it "ends on the last day of the eighth consecutive month during which the individual is at no time enrolled in a GHP or an LGHP by reason of current employment status". Two conditions in paragraph (c) qualify it: the individual must have had that employment-based coverage when first eligible to enroll, and must have maintained either Medicare hospital insurance or such coverage in the months since. Paragraph (d) closes the door behind them, since someone who fails to enroll during an available window generally gets no further one, unless the failure happened because group coverage was restored before that window ended. And the start date follows its own rule at paragraph (e): enrolling in a month partly covered by the group plan, or in the first full month after it ends, allows coverage to begin the first of that month or, at the individual's option, the first of any of the three following months; enrolling later in the window means coverage begins the first day of the month after enrollment. Note the words the regulation keeps repeating: by reason of current employment status. Retiree coverage and continuation coverage are not employment-based in that sense, so neither one extends this window.
Two things that are not special enrollment periods. Changing a pre-tax election under an employer's cafeteria plan is governed by Treasury Regulation section 1.125-4, which is a different list of events and, as the qualifying life event page explains, a permission to the plan rather than a right of the employee. And Medicaid and the Children's Health Insurance Program accept applications year-round, so a household that may qualify for either never needs a window or a trigger at all.