Some companies will allow you to purchase a plan up to six months before turning 65. You can purchase a Medicare Supplement any time during the year, as long as you can qualify health-wise, unless you are in a Medicare Advantage Plan. In that case it would be in your best interest to wait until the Open Enrollment period from October 15th thru December 7th.
You have an automatic guaranteed right to purchase a Medicare supplement policy when you turn 65 or after you have been on Social Security disability income for 2 years.
If you worked past 65 and were covered under an employer group health plan, you have an automatic right to purchase a supplement plan when your group coverage ends.
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If you worked past 65 and were covered under an employer group health plan, you have an automatic right to purchase a supplement plan when your group coverage ends.