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A Retiree’s Guide to Key Dates in 2019

A Retiree’s Guide to Key Dates in 2019


Jan 1

  • Medicare general enrollment period begins

  • Medicare Advantage’s new open enrollment period begins

Jan 15

  • The final estimated tax payment for 2018 s due

Jan 31

  • By this date, all 10992 and W-2 forms should be mailed out.Once you receive your forms review them closely for any errors.


Mar 31

  • Medicare general enrollment and Medicare Advantage open enrollment periods end.


Apr 1

  • If you turned 70 ½ in 2018, April 1 is the deadline to take your first required minimum distribution from your IRA or 401K.

Apr 15

  • Federal 2018 tax returns are due on April 15 this year.

  • Six month extensions of time to file are also due today, but if you owe money you must remit any balance due with your extension.

  • If you have foreign financial accounts valued at over $10,000.00, this is the deadline to file the FBAR.

  • If you pay estimated taxes, the first payment for 2019 taxes is due.

  • You have until this day to fund your 2018 IRA.


Jun 15

  • This is the deadline to mail the second 2019 estimated tax payment.


Jul 1

  • Now is a good time, at midyear, to examine your tax picture for 2019 and make some moves to keep your tax bill in check such as increasing contributions to tax deferred accounts or for those over 70 ½, making an IRA qualified charitable distribution.


Sep 15

  • The third 2019 estimated tax payment is due

Sep 30

  • By this date you should receive an annual notice of change for your Medicare Advantage or Part D drug plan.Carefully review the notice for changes in cost or coverage beginning January 1.

  • If you inherited an IRA from an owner who died in 2018,, this is the deadline for splitting up the inherited IRA if multiple beneficiaries were named for the account.


Oct 15

  • If you filed an extension to file your 2018 taxes, they are due today.

  • Medicare open enrollment begins today.


Nov 1

  • In most states, early retirees who buy health insurance on exchanges under the ACA can shop for 2020 plans beginning today.


Dec 7

  • Medicare’s open enrollment period ends.

Dec 15

  • The ACA’s open enrollment period ends.

  • This is a good time to make sure all RMDs for IRA and 401K accounts have been taken for 2019.

Dec 31

  • This is the deadline to make 2019 401K contributions or to do Roth conversions.

  • Make sure all charitable donations you wish to make for the year have been mailed.

  • If you want to use the annual gift tax exclusion of $15,000.00 per person, today is the deadline to make those gifts for the year.

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