BEGIN:VCALENDAR VERSION:2.0 PRODID:-//Work & Money//Money Calendar//EN CALSCALE:GREGORIAN METHOD:PUBLISH X-WR-CALNAME:Retiree money deadlines (Work & Money) X-WR-CALDESC:Tax deadlines\, benefit dates and enrollment windows from work moneyguide.com. Not tax advice. REFRESH-INTERVAL;VALUE=DURATION:P1D X-PUBLISHED-TTL:P1D BEGIN:VEVENT UID:ma-oep-start-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20260101 DTEND;VALUE=DATE:20260102 SUMMARY:Medicare Advantage open enrollment begins (through March 31) DESCRIPTION:If you're in a Medicare Advantage plan\, you can switch to anot her Advantage plan or go back to Original Medicare (and join a drug plan) once between January 1 and March 31. Medicare's General Enrollment Period\ , for people who missed signing up for Part B\, runs on the same dates.\n\ nMore: https://workmoneyguide.com/medicare-cost-calculator/ URL:https://workmoneyguide.com/medicare-cost-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:forms-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20260202 DTEND;VALUE=DATE:20260203 SUMMARY:W-2s and most 1099s for 2025 due to you DESCRIPTION:Employers must send Form W-2\, and banks and clients most Forms 1099 (interest\, contract pay)\, by this date. Brokers' combined statemen ts (1099-B\, with dividends and interest) are due by mid-February. (Januar y 31 falls on a weekend or holiday\, so it moves to the next business day. )\n\nMore: https://workmoneyguide.com/tax-calendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:ma-oep-end-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20260331 DTEND;VALUE=DATE:20260401 SUMMARY:Last day of Medicare Advantage open enrollment DESCRIPTION:Last day to make your one Medicare Advantage switch for the yea r\, or to sign up for Part B in the General Enrollment Period (coverage st arts the month after you sign up).\n\nMore: https://workmoneyguide.com/tax -calendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:first-rmd-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20260401 DTEND;VALUE=DATE:20260402 SUMMARY:First RMD due if you turned 73 in 2025 DESCRIPTION:If you were born in 1952 and delayed your first required minimu m distribution\, take it by today. You'll then take a second one for 2026 by December 31\, so both are taxed in 2026.\n\nMore: https://workmoneyguid e.com/rmd-calculator/ URL:https://workmoneyguide.com/rmd-calculator/ CATEGORIES:Retirement TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:tax-day-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20260415 DTEND;VALUE=DATE:20260416 SUMMARY:Tax Day: file your 2025 return or an extension DESCRIPTION:File your 2025 Form 1040 and pay any tax due. An extension (For m 4868) gives you until October 15\, 2026 to file\, but not to pay: estima te what you owe and pay it today to avoid penalties and interest. Most sta tes with an income tax use the same date\; check yours.\n\nMore: https://w orkmoneyguide.com/tax-refund-calculator/ URL:https://workmoneyguide.com/tax-refund-calculator/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:ira-hsa-2025@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20260415 DTEND;VALUE=DATE:20260416 SUMMARY:Last day for 2025 IRA and HSA contributions DESCRIPTION:Contributions to a traditional or Roth IRA\, or to an HSA\, mad e by today can count for 2025. Tell the provider which year the money is f or. An extension doesn't extend this deadline.\n\nMore: https://workmoneyg uide.com/roth-vs-traditional-401k-calculator/ URL:https://workmoneyguide.com/roth-vs-traditional-401k-calculator/ CATEGORIES:Retirement TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:extended-2025@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20261015 DTEND;VALUE=DATE:20261016 SUMMARY:Extended 2025 returns due DESCRIPTION:If you filed an extension\, your 2025 Form 1040 is due today. S elf-employed people with an extension can also make 2025 SEP-IRA and solo 401(k) employer contributions until today.\n\nMore: https://workmoneyguide .com/tax-calendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:medicare-aep-start-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20261015 DTEND;VALUE=DATE:20261016 SUMMARY:Medicare open enrollment for 2027 begins DESCRIPTION:From October 15 to December 7 you can change Medicare Advantage or Part D drug plans\, or move between Original Medicare and Advantage\, for coverage starting January 1\, 2027. Plans' 2027 costs and drug lists a re posted by now.\n\nMore: https://workmoneyguide.com/medicare-cost-calcul ator/ URL:https://workmoneyguide.com/medicare-cost-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:medicare-aep-end-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20261207 DTEND;VALUE=DATE:20261208 SUMMARY:Last day for most Medicare plan changes for 2027 DESCRIPTION:Medicare open enrollment ends today. Changes made by today star t January 1\, 2027.\n\nMore: https://workmoneyguide.com/irmaa-calculator/ URL:https://workmoneyguide.com/irmaa-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:gifts-sales-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20261231 DTEND;VALUE=DATE:20270101 SUMMARY:Last day for 2026 charitable gifts and investment sales DESCRIPTION:Donations must be made by December 31 to be deductible for 2026 (from 2026\, people who don't itemize can deduct up to $1\,000\, or $2\,0 00 married filing jointly\, of cash gifts to qualifying public charities\; gifts to donor-advised funds don't count). Stock sales count in the year the trade executes\, so tax-loss sales must execute by the last trading da y.\n\nMore: https://workmoneyguide.com/capital-gains-tax-calculator/ URL:https://workmoneyguide.com/capital-gains-tax-calculator/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:rmd-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20261231 DTEND;VALUE=DATE:20270101 SUMMARY:Take your 2026 RMDs\, QCDs and Roth conversions DESCRIPTION:Required minimum distributions from IRAs and 401(k)s\, qualifie d charitable distributions and Roth conversions must be completed by Decem ber 31 to count for 2026. Custodians often need a week or more.\n\nMore: h ttps://workmoneyguide.com/rmd-calculator/ URL:https://workmoneyguide.com/rmd-calculator/ CATEGORIES:Retirement TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:ma-oep-start-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20270101 DTEND;VALUE=DATE:20270102 SUMMARY:Medicare Advantage open enrollment begins (through March 31) DESCRIPTION:If you're in a Medicare Advantage plan\, you can switch to anot her Advantage plan or go back to Original Medicare (and join a drug plan) once between January 1 and March 31. Medicare's General Enrollment Period\ , for people who missed signing up for Part B\, runs on the same dates.\n\ nMore: https://workmoneyguide.com/medicare-cost-calculator/ URL:https://workmoneyguide.com/medicare-cost-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:forms-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20270201 DTEND;VALUE=DATE:20270202 SUMMARY:W-2s and most 1099s for 2026 due to you DESCRIPTION:Employers must send Form W-2\, and banks and clients most Forms 1099 (interest\, contract pay)\, by this date. Brokers' combined statemen ts (1099-B\, with dividends and interest) are due by mid-February. (Januar y 31 falls on a weekend or holiday\, so it moves to the next business day. ) (Date from the IRS draft calendar.)\n\nMore: https://workmoneyguide.com/ tax-calendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:ma-oep-end-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20270331 DTEND;VALUE=DATE:20270401 SUMMARY:Last day of Medicare Advantage open enrollment DESCRIPTION:Last day to make your one Medicare Advantage switch for the yea r\, or to sign up for Part B in the General Enrollment Period (coverage st arts the month after you sign up).\n\nMore: https://workmoneyguide.com/tax -calendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:first-rmd-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20270401 DTEND;VALUE=DATE:20270402 SUMMARY:First RMD due if you turned 73 in 2026 DESCRIPTION:If you were born in 1953 and delayed your first required minimu m distribution\, take it by today. You'll then take a second one for 2027 by December 31\, so both are taxed in 2027.\n\nMore: https://workmoneyguid e.com/rmd-calculator/ URL:https://workmoneyguide.com/rmd-calculator/ CATEGORIES:Retirement TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:tax-day-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20270415 DTEND;VALUE=DATE:20270416 SUMMARY:Tax Day: file your 2026 return or an extension DESCRIPTION:File your 2026 Form 1040 and pay any tax due. An extension (For m 4868) gives you until October 15\, 2027 to file\, but not to pay: estima te what you owe and pay it today to avoid penalties and interest. Most sta tes with an income tax use the same date\; check yours. (Date from the IRS draft calendar.)\n\nMore: https://workmoneyguide.com/tax-refund-calculato r/ URL:https://workmoneyguide.com/tax-refund-calculator/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:ira-hsa-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20270415 DTEND;VALUE=DATE:20270416 SUMMARY:Last day for 2026 IRA and HSA contributions DESCRIPTION:Contributions to a traditional or Roth IRA\, or to an HSA\, mad e by today can count for 2026. Tell the provider which year the money is f or. An extension doesn't extend this deadline.\n\nMore: https://workmoneyg uide.com/roth-vs-traditional-401k-calculator/ URL:https://workmoneyguide.com/roth-vs-traditional-401k-calculator/ CATEGORIES:Retirement TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:extended-2026@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20271015 DTEND;VALUE=DATE:20271016 SUMMARY:Extended 2026 returns due DESCRIPTION:If you filed an extension\, your 2026 Form 1040 is due today. S elf-employed people with an extension can also make 2026 SEP-IRA and solo 401(k) employer contributions until today. (Date from the IRS draft calend ar.)\n\nMore: https://workmoneyguide.com/tax-calendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:medicare-aep-start-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20271015 DTEND;VALUE=DATE:20271016 SUMMARY:Medicare open enrollment for 2028 begins DESCRIPTION:From October 15 to December 7 you can change Medicare Advantage or Part D drug plans\, or move between Original Medicare and Advantage\, for coverage starting January 1\, 2028. Plans' 2028 costs and drug lists a re posted by now.\n\nMore: https://workmoneyguide.com/medicare-cost-calcul ator/ URL:https://workmoneyguide.com/medicare-cost-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:medicare-aep-end-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20271207 DTEND;VALUE=DATE:20271208 SUMMARY:Last day for most Medicare plan changes for 2028 DESCRIPTION:Medicare open enrollment ends today. Changes made by today star t January 1\, 2028.\n\nMore: https://workmoneyguide.com/irmaa-calculator/ URL:https://workmoneyguide.com/irmaa-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:gifts-sales-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20271231 DTEND;VALUE=DATE:20280101 SUMMARY:Last day for 2027 charitable gifts and investment sales DESCRIPTION:Donations must be made by December 31 to be deductible for 2027 (from 2026\, people who don't itemize can deduct up to $1\,000\, or $2\,0 00 married filing jointly\, of cash gifts to qualifying public charities\; gifts to donor-advised funds don't count). Stock sales count in the year the trade executes\, so tax-loss sales must execute by the last trading da y. December 31\, 2027 is a federal holiday (New Year's Day (observed))\, s o federal offices are closed\; brokers and banks are generally open\, but don't leave it to the last day.\n\nMore: https://workmoneyguide.com/capita l-gains-tax-calculator/ URL:https://workmoneyguide.com/capital-gains-tax-calculator/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:rmd-2027@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20271231 DTEND;VALUE=DATE:20280101 SUMMARY:Take your 2027 RMDs\, QCDs and Roth conversions DESCRIPTION:Required minimum distributions from IRAs and 401(k)s\, qualifie d charitable distributions and Roth conversions must be completed by Decem ber 31 to count for 2027. Custodians often need a week or more. December 3 1\, 2027 is a federal holiday (New Year's Day (observed))\, so federal off ices are closed\; brokers and banks are generally open\, but don't leave i t to the last day.\n\nMore: https://workmoneyguide.com/rmd-calculator/ URL:https://workmoneyguide.com/rmd-calculator/ CATEGORIES:Retirement TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:ma-oep-start-2028@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20280101 DTEND;VALUE=DATE:20280102 SUMMARY:Medicare Advantage open enrollment begins (through March 31) DESCRIPTION:If you're in a Medicare Advantage plan\, you can switch to anot her Advantage plan or go back to Original Medicare (and join a drug plan) once between January 1 and March 31. Medicare's General Enrollment Period\ , for people who missed signing up for Part B\, runs on the same dates.\n\ nMore: https://workmoneyguide.com/medicare-cost-calculator/ URL:https://workmoneyguide.com/medicare-cost-calculator/ CATEGORIES:Health coverage TRANSP:TRANSPARENT END:VEVENT BEGIN:VEVENT UID:forms-2028@workmoneyguide.com DTSTAMP:20261019T000000Z DTSTART;VALUE=DATE:20280131 DTEND;VALUE=DATE:20280201 SUMMARY:W-2s and most 1099s for 2027 due to you DESCRIPTION:Employers must send Form W-2\, and banks and clients most Forms 1099 (interest\, contract pay)\, by this date. Brokers' combined statemen ts (1099-B\, with dividends and interest) are due by mid-February. (Expect ed date\; confirmed each fall.)\n\nMore: https://workmoneyguide.com/tax-ca lendar/ URL:https://workmoneyguide.com/tax-calendar/ CATEGORIES:Tax TRANSP:TRANSPARENT END:VEVENT END:VCALENDAR