Medicare & Medicaid

Part 1: Planning for Medicare—What to Do Before You Turn 65

Medicare is not one policy, one bill, or one decision. It is a collection of benefits, deadlines, costs, and private-plan choices that can affect a retiree for years. This eight-part Huutri.org series is designed to help older adults, spouses, adult children, and caregivers understand the questions they should ask before enrolling or receiving care.

The figures in this series are for 2026. Medicare costs and private-plan benefits can change each year. Readers should verify current information at Medicare.gov, Social Security, their plan, or their local State Health Insurance Assistance Program (SHIP).

This series is for general education. It is not medical, legal, tax, or insurance advice.


Medicare planning should begin before your birthday

Turning 65 is an important milestone, but Medicare should not be treated like a birthday present that simply arrives and takes care of everything. Some people are enrolled automatically. Others must apply. Some can delay Part B safely because they have insurance from current employment. Others may face a coverage gap and a lasting late-enrollment penalty if they wait.

The safest approach is to begin planning about six months before your 65th birthday.

First, understand the four parts

  • Part A—Hospital Insurance: Helps cover inpatient hospital care, limited skilled nursing facility care, hospice, and certain home health services.
  • Part B—Medical Insurance: Helps cover doctors, outpatient care, durable medical equipment, medically necessary services, and many preventive services.
  • Part C—Medicare Advantage: A private-plan alternative to receiving Part A and Part B through Original Medicare. Most plans include Part D, and some offer extra dental, vision, or hearing benefits. Networks, prior authorization rules, and cost sharing vary.
  • Part D—Prescription drug coverage: Available through a stand-alone drug plan or generally through a Medicare Advantage plan that includes drug coverage.

People who choose Original Medicare may also buy a private Medicare Supplement policy, commonly called Medigap, to help pay certain Part A and Part B deductibles, copayments, and coinsurance. Medigap is not used with Medicare Advantage.

Put your enrollment dates on the calendar

For most people, the Initial Enrollment Period lasts seven months: the three months before the month they turn 65, their birthday month, and the three months afterward. Applying before the birthday month can reduce the chance of a delay in coverage.

If you already receive Social Security or Railroad Retirement Board benefits before 65, you may be enrolled automatically in Part A and Part B. Read every notice and check the effective dates on your Medicare card.

If you are not receiving those benefits, you will generally need to apply through Social Security.

Do not assume every employer plan lets you delay Part B

You may be able to delay Part B without penalty when you or your spouse is still actively working and you have group health coverage based on that current employment. Retiree insurance and COBRA are not the same as coverage based on current employment.

Employer size can also affect which plan pays first. Ask the employer’s benefits office—in writing, if possible:

  1. Is this coverage based on current employment?
  2. Is Medicare expected to be the primary payer when I turn 65?
  3. Can I delay Part B without weakening my employer coverage?
  4. Is the drug coverage “creditable” for Part D?
  5. What date will the employer coverage end?

After current employment or its group coverage ends, many people have an eight-month Special Enrollment Period to enroll in Part B. That period begins when the employment or coverage ends, whichever occurs first—even if the person elects COBRA afterward. Part D has different timing: going 63 days or more without creditable drug coverage can trigger a late penalty.

Protect your Health Savings Account

Once Medicare coverage begins, you can no longer contribute to an HSA. Premium-free Part A can be retroactive for up to six months when a person applies after 65, but not earlier than the first month of Medicare eligibility. Someone working past 65 who wants to keep contributing to an HSA should discuss the timing with the employer and a tax professional and generally stop contributions at least six months before applying for Medicare or Social Security.

Compare the two main coverage paths

Original Medicare path

The common package is Part A + Part B + a stand-alone Part D plan, with an optional Medigap policy.

This may appeal to someone who wants broad access to Medicare-participating providers nationwide and fewer network restrictions. The tradeoff is that the person may pay separate premiums for Part B, Part D, and Medigap.

Medicare Advantage path

The common package is Part A + Part B benefits delivered by a private Medicare Advantage plan, usually with Part D included.

This may appeal to someone who prefers one bundled plan, a yearly medical out-of-pocket limit, and possible extra benefits. The tradeoffs may include provider networks, referrals, prior authorization, and plan benefits that change each year. A “$0 premium” Medicare Advantage plan does not eliminate the Part B premium unless the plan specifically offers a Part B giveback.

Build your decision around your real life

Before comparing premiums, make four lists:

  • Every doctor, specialist, hospital, and pharmacy you want to use.
  • Every prescription, including dosage and frequency.
  • Expected services, such as physical therapy, diabetes supplies, dental work, or hearing aids.
  • Travel patterns, including time spent in another state or outside the United States.

Then estimate the total yearly cost, not only the monthly premium. Include deductibles, copayments, coinsurance, the plan’s maximum out-of-pocket amount, drug costs, and benefits Medicare does not cover.

Do not overlook Medigap timing

Your federal Medigap Open Enrollment Period generally lasts six months, beginning with the first month you are both 65 or older and enrolled in Part B. During that period, insurers generally cannot deny a policy or charge more because of health problems. Outside protected enrollment or guaranteed-issue situations, federal law may allow medical underwriting. State protections vary.

A six-month Medicare planning checklist

Six months before 65: Gather employer-insurance information, create a medication list, check HSA timing, and estimate retirement income.

Four months before 65: Confirm whether enrollment will be automatic. Compare Original Medicare and Medicare Advantage using your doctors and prescriptions.

Three months before 65: Apply if needed. Decide on Part D or Medicare Advantage. Begin comparing Medigap if choosing Original Medicare.

Before coverage begins: Confirm effective dates, provider participation, drug formulary status, pharmacy preference, and plan identification cards.

After enrollment: Create a Medicare.gov account, schedule eligible preventive care, and keep all employer creditable-coverage notices.

Bottom line

The best Medicare plan is not necessarily the plan with the lowest advertised premium. It is the coverage that works with your doctors, medicines, finances, travel, and tolerance for network rules—without leaving a dangerous enrollment gap.

-Phan Trần Hương-

Sources and further reading

Part 1: Planning for Medicare—What to Do Before You Turn 65

Medicare is not one policy, one bill, or one decision. It is a collection of benefits, deadlines, costs, and private-plan choices that can affect a retiree for years. This eight-part Huutri.org series is designed to help older adults, spouses, adult children, and caregivers understand the questions they should ask before enrolling or receiving care.

The figures in this series are for 2026. Medicare costs and private-plan benefits can change each year. Readers should verify current information at Medicare.gov, Social Security, their plan, or their local State Health Insurance Assistance Program (SHIP).

This series is for general education. It is not medical, legal, tax, or insurance advice.


Medicare planning should begin before your birthday

Turning 65 is an important milestone, but Medicare should not be treated like a birthday present that simply arrives and takes care of everything. Some people are enrolled automatically. Others must apply. Some can delay Part B safely because they have insurance from current employment. Others may face a coverage gap and a lasting late-enrollment penalty if they wait.

The safest approach is to begin planning about six months before your 65th birthday.

First, understand the four parts

  • Part A—Hospital Insurance: Helps cover inpatient hospital care, limited skilled nursing facility care, hospice, and certain home health services.
  • Part B—Medical Insurance: Helps cover doctors, outpatient care, durable medical equipment, medically necessary services, and many preventive services.
  • Part C—Medicare Advantage: A private-plan alternative to receiving Part A and Part B through Original Medicare. Most plans include Part D, and some offer extra dental, vision, or hearing benefits. Networks, prior authorization rules, and cost sharing vary.
  • Part D—Prescription drug coverage: Available through a stand-alone drug plan or generally through a Medicare Advantage plan that includes drug coverage.

People who choose Original Medicare may also buy a private Medicare Supplement policy, commonly called Medigap, to help pay certain Part A and Part B deductibles, copayments, and coinsurance. Medigap is not used with Medicare Advantage.

Put your enrollment dates on the calendar

For most people, the Initial Enrollment Period lasts seven months: the three months before the month they turn 65, their birthday month, and the three months afterward. Applying before the birthday month can reduce the chance of a delay in coverage.

If you already receive Social Security or Railroad Retirement Board benefits before 65, you may be enrolled automatically in Part A and Part B. Read every notice and check the effective dates on your Medicare card.

If you are not receiving those benefits, you will generally need to apply through Social Security.

Do not assume every employer plan lets you delay Part B

You may be able to delay Part B without penalty when you or your spouse is still actively working and you have group health coverage based on that current employment. Retiree insurance and COBRA are not the same as coverage based on current employment.

Employer size can also affect which plan pays first. Ask the employer’s benefits office—in writing, if possible:

  1. Is this coverage based on current employment?
  2. Is Medicare expected to be the primary payer when I turn 65?
  3. Can I delay Part B without weakening my employer coverage?
  4. Is the drug coverage “creditable” for Part D?
  5. What date will the employer coverage end?

After current employment or its group coverage ends, many people have an eight-month Special Enrollment Period to enroll in Part B. That period begins when the employment or coverage ends, whichever occurs first—even if the person elects COBRA afterward. Part D has different timing: going 63 days or more without creditable drug coverage can trigger a late penalty.

Protect your Health Savings Account

Once Medicare coverage begins, you can no longer contribute to an HSA. Premium-free Part A can be retroactive for up to six months when a person applies after 65, but not earlier than the first month of Medicare eligibility. Someone working past 65 who wants to keep contributing to an HSA should discuss the timing with the employer and a tax professional and generally stop contributions at least six months before applying for Medicare or Social Security.

Compare the two main coverage paths

Original Medicare path

The common package is Part A + Part B + a stand-alone Part D plan, with an optional Medigap policy.

This may appeal to someone who wants broad access to Medicare-participating providers nationwide and fewer network restrictions. The tradeoff is that the person may pay separate premiums for Part B, Part D, and Medigap.

Medicare Advantage path

The common package is Part A + Part B benefits delivered by a private Medicare Advantage plan, usually with Part D included.

This may appeal to someone who prefers one bundled plan, a yearly medical out-of-pocket limit, and possible extra benefits. The tradeoffs may include provider networks, referrals, prior authorization, and plan benefits that change each year. A “$0 premium” Medicare Advantage plan does not eliminate the Part B premium unless the plan specifically offers a Part B giveback.

Build your decision around your real life

Before comparing premiums, make four lists:

  • Every doctor, specialist, hospital, and pharmacy you want to use.
  • Every prescription, including dosage and frequency.
  • Expected services, such as physical therapy, diabetes supplies, dental work, or hearing aids.
  • Travel patterns, including time spent in another state or outside the United States.

Then estimate the total yearly cost, not only the monthly premium. Include deductibles, copayments, coinsurance, the plan’s maximum out-of-pocket amount, drug costs, and benefits Medicare does not cover.

Do not overlook Medigap timing

Your federal Medigap Open Enrollment Period generally lasts six months, beginning with the first month you are both 65 or older and enrolled in Part B. During that period, insurers generally cannot deny a policy or charge more because of health problems. Outside protected enrollment or guaranteed-issue situations, federal law may allow medical underwriting. State protections vary.

A six-month Medicare planning checklist

Six months before 65: Gather employer-insurance information, create a medication list, check HSA timing, and estimate retirement income.

Four months before 65: Confirm whether enrollment will be automatic. Compare Original Medicare and Medicare Advantage using your doctors and prescriptions.

Three months before 65: Apply if needed. Decide on Part D or Medicare Advantage. Begin comparing Medigap if choosing Original Medicare.

Before coverage begins: Confirm effective dates, provider participation, drug formulary status, pharmacy preference, and plan identification cards.

After enrollment: Create a Medicare.gov account, schedule eligible preventive care, and keep all employer creditable-coverage notices.

Bottom line

The best Medicare plan is not necessarily the plan with the lowest advertised premium. It is the coverage that works with your doctors, medicines, finances, travel, and tolerance for network rules—without leaving a dangerous enrollment gap.

-Phan Trần Hương-

Sources and further reading

Part 1: Planning for Medicare—What to Do Before You Turn 65

Medicare is not one policy, one bill, or one decision. It is a collection of benefits, deadlines, costs, and private-plan choices that can affect a retiree for years. This eight-part Huutri.org series is designed to help older adults, spouses, adult children, and caregivers understand the questions they should ask before enrolling or receiving care.

The figures in this series are for 2026. Medicare costs and private-plan benefits can change each year. Readers should verify current information at Medicare.gov, Social Security, their plan, or their local State Health Insurance Assistance Program (SHIP).

This series is for general education. It is not medical, legal, tax, or insurance advice.


Medicare planning should begin before your birthday

Turning 65 is an important milestone, but Medicare should not be treated like a birthday present that simply arrives and takes care of everything. Some people are enrolled automatically. Others must apply. Some can delay Part B safely because they have insurance from current employment. Others may face a coverage gap and a lasting late-enrollment penalty if they wait.

The safest approach is to begin planning about six months before your 65th birthday.

First, understand the four parts

  • Part A—Hospital Insurance: Helps cover inpatient hospital care, limited skilled nursing facility care, hospice, and certain home health services.
  • Part B—Medical Insurance: Helps cover doctors, outpatient care, durable medical equipment, medically necessary services, and many preventive services.
  • Part C—Medicare Advantage: A private-plan alternative to receiving Part A and Part B through Original Medicare. Most plans include Part D, and some offer extra dental, vision, or hearing benefits. Networks, prior authorization rules, and cost sharing vary.
  • Part D—Prescription drug coverage: Available through a stand-alone drug plan or generally through a Medicare Advantage plan that includes drug coverage.

People who choose Original Medicare may also buy a private Medicare Supplement policy, commonly called Medigap, to help pay certain Part A and Part B deductibles, copayments, and coinsurance. Medigap is not used with Medicare Advantage.

Put your enrollment dates on the calendar

For most people, the Initial Enrollment Period lasts seven months: the three months before the month they turn 65, their birthday month, and the three months afterward. Applying before the birthday month can reduce the chance of a delay in coverage.

If you already receive Social Security or Railroad Retirement Board benefits before 65, you may be enrolled automatically in Part A and Part B. Read every notice and check the effective dates on your Medicare card.

If you are not receiving those benefits, you will generally need to apply through Social Security.

Do not assume every employer plan lets you delay Part B

You may be able to delay Part B without penalty when you or your spouse is still actively working and you have group health coverage based on that current employment. Retiree insurance and COBRA are not the same as coverage based on current employment.

Employer size can also affect which plan pays first. Ask the employer’s benefits office—in writing, if possible:

  1. Is this coverage based on current employment?
  2. Is Medicare expected to be the primary payer when I turn 65?
  3. Can I delay Part B without weakening my employer coverage?
  4. Is the drug coverage “creditable” for Part D?
  5. What date will the employer coverage end?

After current employment or its group coverage ends, many people have an eight-month Special Enrollment Period to enroll in Part B. That period begins when the employment or coverage ends, whichever occurs first—even if the person elects COBRA afterward. Part D has different timing: going 63 days or more without creditable drug coverage can trigger a late penalty.

Protect your Health Savings Account

Once Medicare coverage begins, you can no longer contribute to an HSA. Premium-free Part A can be retroactive for up to six months when a person applies after 65, but not earlier than the first month of Medicare eligibility. Someone working past 65 who wants to keep contributing to an HSA should discuss the timing with the employer and a tax professional and generally stop contributions at least six months before applying for Medicare or Social Security.

Compare the two main coverage paths

Original Medicare path

The common package is Part A + Part B + a stand-alone Part D plan, with an optional Medigap policy.

This may appeal to someone who wants broad access to Medicare-participating providers nationwide and fewer network restrictions. The tradeoff is that the person may pay separate premiums for Part B, Part D, and Medigap.

Medicare Advantage path

The common package is Part A + Part B benefits delivered by a private Medicare Advantage plan, usually with Part D included.

This may appeal to someone who prefers one bundled plan, a yearly medical out-of-pocket limit, and possible extra benefits. The tradeoffs may include provider networks, referrals, prior authorization, and plan benefits that change each year. A “$0 premium” Medicare Advantage plan does not eliminate the Part B premium unless the plan specifically offers a Part B giveback.

Build your decision around your real life

Before comparing premiums, make four lists:

  • Every doctor, specialist, hospital, and pharmacy you want to use.
  • Every prescription, including dosage and frequency.
  • Expected services, such as physical therapy, diabetes supplies, dental work, or hearing aids.
  • Travel patterns, including time spent in another state or outside the United States.

Then estimate the total yearly cost, not only the monthly premium. Include deductibles, copayments, coinsurance, the plan’s maximum out-of-pocket amount, drug costs, and benefits Medicare does not cover.

Do not overlook Medigap timing

Your federal Medigap Open Enrollment Period generally lasts six months, beginning with the first month you are both 65 or older and enrolled in Part B. During that period, insurers generally cannot deny a policy or charge more because of health problems. Outside protected enrollment or guaranteed-issue situations, federal law may allow medical underwriting. State protections vary.

A six-month Medicare planning checklist

Six months before 65: Gather employer-insurance information, create a medication list, check HSA timing, and estimate retirement income.

Four months before 65: Confirm whether enrollment will be automatic. Compare Original Medicare and Medicare Advantage using your doctors and prescriptions.

Three months before 65: Apply if needed. Decide on Part D or Medicare Advantage. Begin comparing Medigap if choosing Original Medicare.

Before coverage begins: Confirm effective dates, provider participation, drug formulary status, pharmacy preference, and plan identification cards.

After enrollment: Create a Medicare.gov account, schedule eligible preventive care, and keep all employer creditable-coverage notices.

Bottom line

The best Medicare plan is not necessarily the plan with the lowest advertised premium. It is the coverage that works with your doctors, medicines, finances, travel, and tolerance for network rules—without leaving a dangerous enrollment gap.

-Phan Trần Hương-

Sources and further reading

Part 1: Planning for Medicare—What to Do Before You Turn 65

Medicare is not one policy, one bill, or one decision. It is a collection of benefits, deadlines, costs, and private-plan choices that can affect a retiree for years. This eight-part Huutri.org series is designed to help older adults, spouses, adult children, and caregivers understand the questions they should ask before enrolling or receiving care.

The figures in this series are for 2026. Medicare costs and private-plan benefits can change each year. Readers should verify current information at Medicare.gov, Social Security, their plan, or their local State Health Insurance Assistance Program (SHIP).

This series is for general education. It is not medical, legal, tax, or insurance advice.


Medicare planning should begin before your birthday

Turning 65 is an important milestone, but Medicare should not be treated like a birthday present that simply arrives and takes care of everything. Some people are enrolled automatically. Others must apply. Some can delay Part B safely because they have insurance from current employment. Others may face a coverage gap and a lasting late-enrollment penalty if they wait.

The safest approach is to begin planning about six months before your 65th birthday.

First, understand the four parts

  • Part A—Hospital Insurance: Helps cover inpatient hospital care, limited skilled nursing facility care, hospice, and certain home health services.
  • Part B—Medical Insurance: Helps cover doctors, outpatient care, durable medical equipment, medically necessary services, and many preventive services.
  • Part C—Medicare Advantage: A private-plan alternative to receiving Part A and Part B through Original Medicare. Most plans include Part D, and some offer extra dental, vision, or hearing benefits. Networks, prior authorization rules, and cost sharing vary.
  • Part D—Prescription drug coverage: Available through a stand-alone drug plan or generally through a Medicare Advantage plan that includes drug coverage.

People who choose Original Medicare may also buy a private Medicare Supplement policy, commonly called Medigap, to help pay certain Part A and Part B deductibles, copayments, and coinsurance. Medigap is not used with Medicare Advantage.

Put your enrollment dates on the calendar

For most people, the Initial Enrollment Period lasts seven months: the three months before the month they turn 65, their birthday month, and the three months afterward. Applying before the birthday month can reduce the chance of a delay in coverage.

If you already receive Social Security or Railroad Retirement Board benefits before 65, you may be enrolled automatically in Part A and Part B. Read every notice and check the effective dates on your Medicare card.

If you are not receiving those benefits, you will generally need to apply through Social Security.

Do not assume every employer plan lets you delay Part B

You may be able to delay Part B without penalty when you or your spouse is still actively working and you have group health coverage based on that current employment. Retiree insurance and COBRA are not the same as coverage based on current employment.

Employer size can also affect which plan pays first. Ask the employer’s benefits office—in writing, if possible:

  1. Is this coverage based on current employment?
  2. Is Medicare expected to be the primary payer when I turn 65?
  3. Can I delay Part B without weakening my employer coverage?
  4. Is the drug coverage “creditable” for Part D?
  5. What date will the employer coverage end?

After current employment or its group coverage ends, many people have an eight-month Special Enrollment Period to enroll in Part B. That period begins when the employment or coverage ends, whichever occurs first—even if the person elects COBRA afterward. Part D has different timing: going 63 days or more without creditable drug coverage can trigger a late penalty.

Protect your Health Savings Account

Once Medicare coverage begins, you can no longer contribute to an HSA. Premium-free Part A can be retroactive for up to six months when a person applies after 65, but not earlier than the first month of Medicare eligibility. Someone working past 65 who wants to keep contributing to an HSA should discuss the timing with the employer and a tax professional and generally stop contributions at least six months before applying for Medicare or Social Security.

Compare the two main coverage paths

Original Medicare path

The common package is Part A + Part B + a stand-alone Part D plan, with an optional Medigap policy.

This may appeal to someone who wants broad access to Medicare-participating providers nationwide and fewer network restrictions. The tradeoff is that the person may pay separate premiums for Part B, Part D, and Medigap.

Medicare Advantage path

The common package is Part A + Part B benefits delivered by a private Medicare Advantage plan, usually with Part D included.

This may appeal to someone who prefers one bundled plan, a yearly medical out-of-pocket limit, and possible extra benefits. The tradeoffs may include provider networks, referrals, prior authorization, and plan benefits that change each year. A “$0 premium” Medicare Advantage plan does not eliminate the Part B premium unless the plan specifically offers a Part B giveback.

Build your decision around your real life

Before comparing premiums, make four lists:

  • Every doctor, specialist, hospital, and pharmacy you want to use.
  • Every prescription, including dosage and frequency.
  • Expected services, such as physical therapy, diabetes supplies, dental work, or hearing aids.
  • Travel patterns, including time spent in another state or outside the United States.

Then estimate the total yearly cost, not only the monthly premium. Include deductibles, copayments, coinsurance, the plan’s maximum out-of-pocket amount, drug costs, and benefits Medicare does not cover.

Do not overlook Medigap timing

Your federal Medigap Open Enrollment Period generally lasts six months, beginning with the first month you are both 65 or older and enrolled in Part B. During that period, insurers generally cannot deny a policy or charge more because of health problems. Outside protected enrollment or guaranteed-issue situations, federal law may allow medical underwriting. State protections vary.

A six-month Medicare planning checklist

Six months before 65: Gather employer-insurance information, create a medication list, check HSA timing, and estimate retirement income.

Four months before 65: Confirm whether enrollment will be automatic. Compare Original Medicare and Medicare Advantage using your doctors and prescriptions.

Three months before 65: Apply if needed. Decide on Part D or Medicare Advantage. Begin comparing Medigap if choosing Original Medicare.

Before coverage begins: Confirm effective dates, provider participation, drug formulary status, pharmacy preference, and plan identification cards.

After enrollment: Create a Medicare.gov account, schedule eligible preventive care, and keep all employer creditable-coverage notices.

Bottom line

The best Medicare plan is not necessarily the plan with the lowest advertised premium. It is the coverage that works with your doctors, medicines, finances, travel, and tolerance for network rules—without leaving a dangerous enrollment gap.

-Phan Trần Hương-

Sources and further reading

Medicare is not one policy, one bill, or one decision. It is a collection of benefits, deadlines, costs, and private-plan choices that can affect a retiree for years. This eight-part Huutri.org series is designed to help older adults, spouses, adult children, and caregivers understand the questions they should ask before enrolling or receiving care.

The figures in this series are for 2026. Medicare costs and private-plan benefits can change each year. Readers should verify current information at Medicare.gov, Social Security, their plan, or their local State Health Insurance Assistance Program (SHIP).

This series is for general education. It is not medical, legal, tax, or insurance advice.


Medicare planning should begin before your birthday

Turning 65 is an important milestone, but Medicare should not be treated like a birthday present that simply arrives and takes care of everything. Some people are enrolled automatically. Others must apply. Some can delay Part B safely because they have insurance from current employment. Others may face a coverage gap and a lasting late-enrollment penalty if they wait.

The safest approach is to begin planning about six months before your 65th birthday.

First, understand the four parts

  • Part A—Hospital Insurance: Helps cover inpatient hospital care, limited skilled nursing facility care, hospice, and certain home health services.
  • Part B—Medical Insurance: Helps cover doctors, outpatient care, durable medical equipment, medically necessary services, and many preventive services.
  • Part C—Medicare Advantage: A private-plan alternative to receiving Part A and Part B through Original Medicare. Most plans include Part D, and some offer extra dental, vision, or hearing benefits. Networks, prior authorization rules, and cost sharing vary.
  • Part D—Prescription drug coverage: Available through a stand-alone drug plan or generally through a Medicare Advantage plan that includes drug coverage.

People who choose Original Medicare may also buy a private Medicare Supplement policy, commonly called Medigap, to help pay certain Part A and Part B deductibles, copayments, and coinsurance. Medigap is not used with Medicare Advantage.

Put your enrollment dates on the calendar

For most people, the Initial Enrollment Period lasts seven months: the three months before the month they turn 65, their birthday month, and the three months afterward. Applying before the birthday month can reduce the chance of a delay in coverage.

If you already receive Social Security or Railroad Retirement Board benefits before 65, you may be enrolled automatically in Part A and Part B. Read every notice and check the effective dates on your Medicare card.

If you are not receiving those benefits, you will generally need to apply through Social Security.

Do not assume every employer plan lets you delay Part B

You may be able to delay Part B without penalty when you or your spouse is still actively working and you have group health coverage based on that current employment. Retiree insurance and COBRA are not the same as coverage based on current employment.

Employer size can also affect which plan pays first. Ask the employer’s benefits office—in writing, if possible:

  1. Is this coverage based on current employment?
  2. Is Medicare expected to be the primary payer when I turn 65?
  3. Can I delay Part B without weakening my employer coverage?
  4. Is the drug coverage “creditable” for Part D?
  5. What date will the employer coverage end?

After current employment or its group coverage ends, many people have an eight-month Special Enrollment Period to enroll in Part B. That period begins when the employment or coverage ends, whichever occurs first—even if the person elects COBRA afterward. Part D has different timing: going 63 days or more without creditable drug coverage can trigger a late penalty.

Protect your Health Savings Account

Once Medicare coverage begins, you can no longer contribute to an HSA. Premium-free Part A can be retroactive for up to six months when a person applies after 65, but not earlier than the first month of Medicare eligibility. Someone working past 65 who wants to keep contributing to an HSA should discuss the timing with the employer and a tax professional and generally stop contributions at least six months before applying for Medicare or Social Security.

Compare the two main coverage paths

Original Medicare path

The common package is Part A + Part B + a stand-alone Part D plan, with an optional Medigap policy.

This may appeal to someone who wants broad access to Medicare-participating providers nationwide and fewer network restrictions. The tradeoff is that the person may pay separate premiums for Part B, Part D, and Medigap.

Medicare Advantage path

The common package is Part A + Part B benefits delivered by a private Medicare Advantage plan, usually with Part D included.

This may appeal to someone who prefers one bundled plan, a yearly medical out-of-pocket limit, and possible extra benefits. The tradeoffs may include provider networks, referrals, prior authorization, and plan benefits that change each year. A “$0 premium” Medicare Advantage plan does not eliminate the Part B premium unless the plan specifically offers a Part B giveback.

Build your decision around your real life

Before comparing premiums, make four lists:

  • Every doctor, specialist, hospital, and pharmacy you want to use.
  • Every prescription, including dosage and frequency.
  • Expected services, such as physical therapy, diabetes supplies, dental work, or hearing aids.
  • Travel patterns, including time spent in another state or outside the United States.

Then estimate the total yearly cost, not only the monthly premium. Include deductibles, copayments, coinsurance, the plan’s maximum out-of-pocket amount, drug costs, and benefits Medicare does not cover.

Do not overlook Medigap timing

Your federal Medigap Open Enrollment Period generally lasts six months, beginning with the first month you are both 65 or older and enrolled in Part B. During that period, insurers generally cannot deny a policy or charge more because of health problems. Outside protected enrollment or guaranteed-issue situations, federal law may allow medical underwriting. State protections vary.

A six-month Medicare planning checklist

Six months before 65: Gather employer-insurance information, create a medication list, check HSA timing, and estimate retirement income.

Four months before 65: Confirm whether enrollment will be automatic. Compare Original Medicare and Medicare Advantage using your doctors and prescriptions.

Three months before 65: Apply if needed. Decide on Part D or Medicare Advantage. Begin comparing Medigap if choosing Original Medicare.

Before coverage begins: Confirm effective dates, provider participation, drug formulary status, pharmacy preference, and plan identification cards.

After enrollment: Create a Medicare.gov account, schedule eligible preventive care, and keep all employer creditable-coverage notices.

Bottom line

The best Medicare plan is not necessarily the plan with the lowest advertised premium. It is the coverage that works with your doctors, medicines, finances, travel, and tolerance for network rules—without leaving a dangerous enrollment gap.

-Phan Trần Hương-

Sources and further reading