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CMS has recently released a new fact sheet that encourages early-in-month enrollments.
Generally, if a person with Medicare enrolls in a Medicare drug plan at the beginning of the month, they will be able to get the most out of their coverage, from the first day it is effective. Enrollments early in the month give Medicare and drug plans time to update their systems, and mail important information like a membership card, acknowledgement letter, and welcome package to enrollees before their coverage becomes effective. In these cases, even if a person with Medicare goes to the pharmacy on the first day of coverage, they can get their prescriptions quickly and accurately.
Please see the fact sheet below for more information.

Information Partners Can Use on: Encouraging Early-in-Month Enrollments
New Medicare Prescription Drug Coverage, As of February 2006
As you help people with Medicare compare Medicare drug plans and make a choice
that works for them, it is also important to consider the timing of each enrollment.
Generally, if a person with Medicare enrolls in a Medicare drug plan at the beginning
of the month, they will be able to get the most out of their coverage, from the first
day it is effective. Enrollments early in the month give Medicare and drug plans time
to update their systems, and mail important information like a membership card,
acknowledgement letter, and welcome package to enrollees before their coverage
becomes effective. In these cases, even if a person with Medicare goes to the
pharmacy on the first day of coverage, they can get their prescriptions quickly and
accurately.
Enrollments later in the month make it far less likely that all of the information
needed to file the claim correctly will be available at the pharmacy or the plan.
For enrollments being processed later in the month, it is important to provide the
enrollee with some extra information to help manage expectations and help the
person successfully fill prescriptions. This information is especially important because
a person who enrolls late in the month might not receive an acknowledgement or
confirmation letter, or a membership card by the day the coverage starts.
In these cases, if the enrollee needs to fill a prescription, he or she should know:
- Take the acknowledgement or confirmation letter to the pharmacy until they
receive a membership card.
- If they haven’t gotten a letter yet, they might have one or more of the
following to bring to the pharmacy: a welcome letter from the plan, or an
enrollment confirmation number.
- If the person has both Medicare and Medicaid or has been approved for the
low-income subsidy (extra help paying for prescriptions), they should bring a
copy of the yellow automatic enrollment letter from Medicare, a Medicaid card,
an approval letter from the Social Security Administration, or other proof that
they qualify for extra help.
- If they need to get a prescription before receiving a letter or membership card,
they should let the pharmacist know the Medicare drug plan name and bring
one of the items above to get prescriptions filled, and be aware that it may take
some extra time.
- As a last resort, if a person must pay out-of-pocket for the prescription, they
should save the receipts and work with their Medicare drug plan to be
reimbursed.
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