Chapter 8 — How to Enroll and Get the Most Benefits
A step-by-step field manual for maximizing your veteran advantages
1. Your Pre-Enrollment Battle Plan
Before we dive into the enrollment process, let’s make sure you have everything you need. Just like any military operation, proper preparation prevents poor performance. Complete these preparations before enrolling:
Required Documents You’ll Need
- Social Security login (create account at ssa.gov if you don’t have one)
- DD-214 or retirement orders (proves service dates if questions arise)
- Current VA or TRICARE ID card (confirms existing coverage levels)
- 2023 tax return (determines possible IRMAA surcharges for 2025)
- Current prescription list (for plan comparisons if you use civilian pharmacies)
- Preferred doctors’ information (to verify network participation)
With your documents organized and creditable coverage status confirmed, you’re ready to understand exactly when you can and must enroll.
Important: The Creditable Coverage Question
This is where I see many veterans get tripped up by standard advice. If you’re still working and have employer health insurance, you need to determine if it’s “creditable coverage” that allows you to delay Medicare Part B without penalties.
Creditable coverage requires:
- Employer group plan with 20+ employees
- You must be actively working (not retired or on COBRA)
- The coverage must be through current employment
(Source: Medicare.gov, https://www.medicare.gov/basics/get-started-with-medicare/medicare-basics/working-past-65)
If you have creditable employer coverage, you should likely delay Part B enrollment until you lose that coverage. TRICARE for Life doesn’t work with employer group coverage, so you can’t use both simultaneously. TRICARE for Life only begins when you have Medicare Parts A and B, not while you’re covered by an employer plan.
To determine if you have creditable coverage, contact your HR department or group administrator for clarification. Important note: TRICARE Prime or Select will work with employer coverage, but TRICARE for Life will not.
(Source: TRICARE.mil, https://tricare.mil/Plans/HealthPlans/TFL)
If you don’t have creditable coverage (which includes most veterans using VA benefits), you must enroll in Medicare Parts A and B during your Initial Enrollment Period to avoid penalties. If you’re unsure about your specific situation, we can help clarify this at 888-960-8387 (VETS). (Source: VA.gov, https://www.va.gov/health-care/about-va-health-benefits/va-health-care-and-other-insurance/)
2. Your Personal Enrollment Timeline
Understanding enrollment timing is crucial for veterans:
Initial Enrollment Period (IEP): Your Primary Window
CMS officially defines the IEP as “a 7-month period that begins 3 months before the month a person turns 65, includes their birthday month, and ends 3 months after the person turns 65.” (Source: CMS.gov, https://www.cms.gov/medicare/enrollment-renewal/original-part-a-b)
- Begins: 3 months before the month you turn 65
- Ends: 3 months after the month you turn 65
- Total window: 7 months
- Best practice: Enroll during the first 3 months for coverage to start on your 65th birthday
- Important Exception: If you were born on the 1st of the month, your Medicare and TRICARE for Life become effective a month early.
(Source: Medicare.gov, https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start)
Example Timeline for June Birthday:
- March-May (age 64): First 3 months of IEP, coverage starts June 1st
- June (turning 65): Birthday month, coverage starts July 1st if you enroll this month
- July-September (age 65): Last 3 months of IEP, coverage starts 1st of the month after enrollment
Special Enrollment Period (SEP): For Working Veterans Only
- Available only if you have creditable employer coverage (20+ employee group plan)
- Lasts 8 months after your employment ends OR your creditable coverage ends
- Critical: Must be actively working, not receiving retiree benefits
- Veterans with TRICARE should note that military retirement benefits are NOT considered creditable employer coverage.
(Source: Medicare.gov, https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-can-i-sign-up-for-medicare)
Annual Election Period (AEP): Your Yearly Optimization Window
- October 15 – December 7 every year
- Change Medicare Advantage (Part C) plans or switch between Original Medicare and Medicare Advantage (Part C)
- Add or change Part D prescription drug coverage
- Coverage changes take effect January 1st
This is when we help veterans review their plans to ensure they’re still getting maximum Part B premium refunds and the best benefits available.
Medicare Advantage Open Enrollment Period (MA OEP)
- January 1 – March 31 every year
- Only for those already enrolled in Medicare Advantage plans
- Switch between Medicare Advantage plans OR return to Original Medicare
- Coverage changes take effect the 1st of the month after enrollment
General Enrollment Period (GEP): Last Resort
- January 1 – March 31 each year
- Coverage starts July 1st
- Late enrollment penalties highly likely to apply
- Critical for veterans: If you missed your Initial Enrollment Period and don’t qualify for a Special Enrollment Period, this is your annual chance to enroll
According to the Social Security Administration: “This is the ‘General Enrollment Period,’ and there is typically a life-long penalty if you sign up during this time.” (Source: SSA.gov, https://www.ssa.gov/medicare/plan/when-to-sign-up)
(Source: Medicare.gov, https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-can-i-sign-up-for-medicare)
Most veterans who are not currently working full time and receiving medical benefits from their employer should enroll during their Initial Enrollment Period to avoid any penalty risk. We regularly work with veterans who could have avoided penalties entirely by understanding these critical timelines.
3. Step-by-Step Medicare Enrollment Process
Important: Are You Already Receiving Social Security?
If you’re already receiving Social Security or Railroad Retirement Board benefits at least 4 months before turning 65, you’ll be automatically enrolled in Medicare Parts A and B. Your Medicare card will arrive about 3 months before your 65th birthday. You don’t need to take any action unless you want to decline Part B (which most veterans should NOT do). If automatically enrolled, skip to Step 2.
(Source: Medicare.gov, https://www.medicare.gov/basics/get-started-with-medicare/sign-up/when-does-medicare-coverage-start)
Step 1: Enroll in Medicare Parts A and B (If Not Automatically Enrolled)
For most veterans not receiving Social Security, this is mandatory regardless of VA coverage.
Online Enrollment (Fastest Method):
- Log in to ssa.gov
- Select “Apply for Medicare Only”
- Complete the 15-minute application
- Confirm Part A start date (usually first day of birth month)
- Elect Part B (accept the $185/month premium for 2025)
- Choose premium payment method (deducted from Social Security if you’re receiving benefits, or quarterly billing/automatic payment if not)
- Print confirmation and Medicare Beneficiary Identifier (MBI)
(Source: SSA.gov, https://www.ssa.gov/medicare/applying-for-medicare)
Need Help? Call 1-800-772-1213 or visit your local Social Security office (appointments fill quickly).
Step 2: Verify Military Benefit Integration
For TRICARE for Life Users:
- DEERS automatically updates when you enroll in Medicare
- Verify your status at milConnect or call 1-800-538-9552
- No separate TFL application needed, enrollment is automatic
(Source: TRICARE.mil, https://tricare.mil/Plans/Eligibility/DEERS)
For VA Users:
- No changes needed to your VA benefits
- Continue using your VA ID card for VA facility care
- Medicare and VA operate independently, you can use both systems strategically
If you have questions about how these benefits complement each other, we help veterans understand this relationship daily. Many veterans don’t realize they can strategically use both systems. For example, routine care at the VA, emergency coverage through Medicare when traveling.
4. Finding the Right Medicare Advantage (Part C) Plan for Veterans
This is where the specialist versus generalist distinction becomes absolutely critical. Traditional advisors often recommend Original Medicare with a Supplement plan, missing the substantial benefits available through Medicare Advantage (Part C) plans designed for veterans.
If you have TRICARE for Life or comprehensive VA benefits, buying a Medicare Supplement is often throwing money away on duplicate coverage.
What to Look for in Medicare Advantage (Part C) Plans
Part B Premium Reductions (Priority #1):
- Look for plans offering $25-$185 monthly premium refunds
- Our clients average $110 monthly in premium refunds
- This money goes directly back into your Social Security check or simply lowers your Medicare bill if paying directly
In 2025, 32% of Medicare Advantage plans offer some level of Part B premium reduction, with many offering $100 or more monthly. (Source: KFF.org, https://www.kff.org/medicare/issue-brief/medicare-advantage-2025-spotlight-a-first-look-at-plan-premiums-and-benefits/)
Network Flexibility:
- PPO plans offer the most flexibility for veterans who travel (Over 90% of our veteran clients choose PPO plans specifically for this flexibility)
- HMO plans typically offer higher premium refunds but limit you to local networks
Extra Benefits Many Veterans Value:
- Comprehensive dental coverage (cleanings, fillings, crowns, dentures)
- Vision benefits (annual exams, glasses, contacts, frames allowance)
- Hearing aids and audiology services
- Over-the-counter allowances ($50-$200 quarterly)
- Fitness benefits (gym memberships, home fitness equipment)
- Transportation to medical appointments (including VA appointments)
- Home-delivered meals after hospital stays
How to Evaluate Plans Like a Specialist
When we work with veterans, we don’t just look at premium refunds or provider networks. We evaluate the total value proposition based on your specific military benefits and situation.
The Veteran-Focused Evaluation Process:
- Identify maximum premium refunds available in your ZIP code
- Verify network adequacy for your preferred providers and travel patterns
- Calculate total annual value including premium refunds and extra benefits
- Check plan stability and insurance company ratings
This is the same process we use when evaluating plans for veterans.
Real Example: The Strategic Choice
A military retiree had been paying $245/month for a Medigap Plan G plus the standard $185 Part B premium, total monthly cost of $430.
When she worked with us, we found her a Medicare Advantage (Part C) plan that provided:
- $125 monthly Part B premium refund
- Comprehensive dental and vision coverage
- $100 quarterly OTC allowance
- Nationwide PPO network
- TRICARE for Life pays all deductibles, copays, and coinsurance
Her new monthly cost: $60 ($185 Part B minus $125 refund) Monthly savings: $370 Annual savings: $4,440 Added benefits value: $2,400 annually
Total annual advantage: $6,840 while maintaining her full TRICARE for Life benefits.
This example shows what’s possible when you work with specialists who understand veteran benefits. But finding these opportunities requires more than just knowing what to look for. It requires working with someone who truly understands the unique intersection of military and Medicare benefits.
5. Why Veteran Medicare Specialists Make the Difference at Enrollment
You’ve learned the enrollment process, you understand the timelines, and you know what Medicare Advantage plans can offer. But there’s a critical difference between knowing what to do and actually getting it done right.
You wouldn’t trust a general practice doctor to perform specialized surgery. Why would you trust your Medicare enrollment to someone who doesn’t specialize in veteran benefits?
The Enrollment Mistakes That Cost Veterans Money
I’ve seen the same enrollment errors happen when veterans work with advisors who treat them like any other person turning 65. These aren’t minor oversights. They’re financial errors that compound over decades.
A traditional Medicare advisor sees you approaching 65 and follows their standard playbook. They enroll you in Parts A and B, maybe suggest a Supplement plan, remind you about Part D. They check their boxes and move on to the next client. What they miss could cost you tens of thousands of dollars.
What typically happens is they don’t ask about your military service. They don’t understand that your VA coverage isn’t creditable for Part B penalties. They have no idea that TRICARE for Life makes Medigap redundant. They’ve never heard of Part B premium refunds, so they can’t tell you that Medicare Advantage plans in your area might put $100 or more back in your pocket every month.
The Specialist Difference During Enrollment
When my team and I work with veterans during enrollment, we start with questions that generic advisors don’t even know to ask. We need to understand your complete benefits picture: your VA priority group, whether you have TRICARE for Life, how far you live from VA facilities, whether you travel frequently, and your income situation for potential IRMAA surcharges.
These aren’t just conversation starters. Your answers determine your entire Medicare strategy. A veteran with TRICARE for Life needs a completely different approach than a veteran relying primarily on VA care. A veteran living 140 miles from the nearest VA facility has different priorities than one living next door to a VA medical center.
We understand that timing matters differently for veterans. If you’re still working and have employer coverage, we know how that affects your TRICARE benefits differently than it affects civilians. We know that missing your Initial Enrollment Period doesn’t just mean a late enrollment penalty; for military retirees, it means losing TRICARE for Life until you get Medicare in place.
Independence Means Better Options
Most veterans don’t realize that many Medicare advisors can only offer plans from one or two insurance companies. They’re employees or contracted agents with quotas to meet and limited options to offer. When they say “this is the best plan available,” they really mean “this is the best plan my company offers.”
As independent specialists, we aren’t tied to any insurance company. We can evaluate every Medicare Advantage plan available in your ZIP code. This independence consistently results in finding higher Part B premium refunds and better benefits because we’re not limited by corporate relationships.
For example, while a company-tied advisor might only show you their employer’s plan with a $50 monthly refund, we can show you that regional insurer offering $150 refunds in the same area. That’s $100 extra in your pocket every month, $1,200 annually, simply because we have access to all available options.
Ongoing Support vs. One-Time Sales
Standard Medicare enrollment typically follows this pattern. You meet with an advisor, they help you pick a plan, you enroll, and then you never hear from them again unless they’re trying to sell you something else. When you have questions six months later about a billing issue or need help with an unexpected IRMAA notice, they’ve moved on to the next enrollment season.
Veteran Medicare specialists understand that enrollment is just the beginning. Military benefits change. VA policies shift. New Medicare Advantage plans enter your market with better benefits. IRMAA situations arise when you retire or have income changes. You need ongoing guidance, not just one-time enrollment help.
We conduct annual reviews with our veteran clients because we know that the best plan this year might not be optimal next year. We help with IRMAA appeals when your income drops. We assist with billing issues when providers don’t understand how Medicare works with military benefits. This ongoing relationship is what separates specialists from salespeople.
The Real Cost of Traditional Advice
Let me share what traditional enrollment advice typically costs veterans. If you work with someone who doesn’t understand military benefits, you might face these unnecessary expenses.
- Unnecessary Medigap premiums when you have TRICARE for Life: $2,000-$3,000 annually
- Missed Part B premium refunds: $1,320 annually (based on our average client refund of $110 monthly)
- Preventable late enrollment penalties: Hundreds or thousands in lifetime costs
- Lack of IRMAA appeal guidance: Potentially $3,000-$5,000 annually in unnecessary surcharges
- Poor benefit integration: Confusion, billing issues, and gaps in coverage
Add these up over a 20-year retirement, and traditional advice could cost you $50,000 or more. That’s real money that could stay in your pocket with proper guidance.
Making the Right Choice for Your Enrollment
You’ve served your country. You’ve earned unique benefits through that service. Your Medicare enrollment should honor that service by maximizing every advantage available to you. That requires working with specialists who understand not just Medicare, but how Medicare works specifically for veterans.
The enrollment decisions you make now will affect your healthcare and finances for the rest of your life. You can’t afford to get this wrong, and you shouldn’t have to figure it out alone. Whether you’re approaching 65 or already enrolled and realizing you might have missed opportunities, specialist guidance makes the difference between adequate coverage and optimized benefits that put money back in your pocket while providing comprehensive protection.
6. Introducing Veterans Advantage Financial™: Your Veteran Medicare Specialists
I founded Veterans Advantage Financial™ with one mission: to provide Medicare guidance that truly demonstrates We Speak Veteran™. We work exclusively with veterans, not seniors in general, not “anyone over 65,” just veterans and their families.
Why We’re Different
Exclusive Veteran Focus. While other Medicare companies try to serve everyone, we focus solely on veterans. This specialization allows us to understand the nuances of military benefits that traditional advisors miss.
Complete Independence. We don’t work for any insurance company. We’re not bound by corporate quotas or pressured to recommend specific plans. This independence gives us the freedom to find the absolute best Medicare solution for each veteran’s unique situation.
Proven Results.
- Our clients average $110 monthly in Medicare Part B premium refunds
- We’ve helped countless veterans avoid financial errors
- We provide ongoing support and annual reviews, not just one-time enrollment
- My own dad, Wallace Duncan, receives $175 monthly through our guidance
Comprehensive Service.
- Free Medicare reviews and plan comparisons
- IRMAA appeal guidance and documentation support
- Annual plan optimization during Annual (Oct 15 to Dec 7) and Open Enrollment (Jan 1 to Mar 31)
- Ongoing support and guidance for benefit questions
- Educational resources through our social media channels
Our Process: How We Maximize Your Benefits
Phase 1: Comprehensive Veterans Analysis
We start by reviewing your complete situation, your current VA, TRICARE, and Medicare benefits. We analyze your priority group, service-connected disabilities, and how you actually use your benefits. We also assess your geographic location, travel patterns, and evaluate any potential IRMAA issues that might need appeals.
Phase 2: Strategic Plan Development
Next, we identify the maximum Part B premium refunds available in your area and compare all Medicare Advantage options against Original Medicare. We calculate the total value including premium refunds and extra benefits, ensuring everything works optimally with your existing military benefits.
Phase 3: Implementation and Optimization
We handle the entire enrollment process and monitor your premium refund activation to resolve any issues. But our service doesn’t stop there. We provide ongoing support for billing questions and benefit integration, plus conduct annual reviews to ensure your benefits stay optimized as plans change.
Veterans share their experiences working with us:
These aren’t just testimonials. They represent the many veterans we’ve helped navigate Medicare successfully, avoiding financial pitfalls while maximizing every benefit they’ve earned through their service.
7. How to Get Started: Your Next Steps
Option 1 – Free Medicare Review Call
Call us at 888-960-8387 (VETS) for a complimentary 15-minute Medicare review. We’ll discuss your current situation and identify veteran-specific opportunities and strategies you might be missing. No pressure, no sales pitch, just honest guidance that demonstrates what We Speak Veteran™ really means.
Best for: Veterans who want to understand their options before making any changes.
Option 2 – Educational Resources
Follow our educational content covering Medicare strategies, veteran benefits optimization, and enrollment guidance.
- YouTube: https://www.youtube.com/@ChrisDuncan-WeSpeakVeteran
- Facebook: https://facebook.com/veteransadvantagefinancial
- Instagram: https://www.instagram.com/wespeakveteranchrisduncan/
- X/Twitter: https://x.com/wespeakveteran
- TikTok: https://www.tiktok.com/@christopherduncanvaf
Option 3 – Comprehensive Veterans Medicare Strategy Session
For veterans with complex situations involving multiple family members, IRMAA issues, or significant benefit integration challenges, we offer detailed strategy sessions to optimize your entire healthcare approach.
Best for: Veterans approaching major Medicare decisions or those with complex benefit situations.
What to Expect When You Call
No High-Pressure Sales Tactics
Our focus is understanding your situation and providing guidance that actually helps you maximize your benefits. We provide education and recommendations that make sense for your specific needs, never high-pressure sales tactics.
Veteran-Specific Questions
We’ll ask about your military service, current benefits, health status, and goals to develop a strategy that works specifically for your situation. These aren’t questions that standard Medicare advisors think to ask.
Clear Options and Plain English Explanations
We’ll explain your options clearly, show you the real numbers, and help you understand exactly how different choices impact your finances and coverage. No confusing jargon or hidden details.
Ongoing Support Commitment
Unlike advisors who disappear after enrollment, we provide ongoing support and annual reviews to ensure your benefits stay optimized. We’re building long-term relationships, not making one-time sales.
8. Common Questions About Working with Veteran Medicare Specialists
Q: “How much do your services cost?” A: Our services are provided at no cost to veterans. Medicare regulations allow us to receive standard compensation from Medicare Advantage (Part C) plans regardless of which plan you choose, so we have no financial incentive to steer you toward any particular option.
Q: “Are you licensed in my state?” A: Yes, we’re licensed in all 50 states and work with veterans nationwide via phone consultations.
Q: “What if I’m not satisfied with the plan you recommend?” A: You can change Medicare Advantage (Part C) plans every year during the Annual Election Period (Oct 15 to Dec 7), and Open Enrollment (Jan 1 to Mar 31). Those with TRICARE for Life can cancel their Part C anytime during the year without penalties. We also provide ongoing support to resolve any issues that arise.
Q: “Do I have to switch from my current Medicare plan?” A: Absolutely not. We’ll review your current situation and only recommend changes if they provide clear benefits. Sometimes the best advice is to stay with what you have.
Q: “How do I know you’re legitimate?” A: We’re fully licensed Medicare specialists. I have nearly 20 years of Medicare experience and hold credentials as a Certified Medicare Insurance Planner™ and Retirement Income Certified Professional®. You can verify our licenses through your state insurance department, and we encourage you to check our reputation through online reviews and testimonials.
You can verify our licenses at https://veteransadvantagefinancial.vet/licenses-lines-of-authority/ and read testimonials from veterans we’ve helped at https://veteransadvantagefinancial.vet/our-veteran-client-testimonials/
Q: “Why should I work with you instead of going directly to Medicare or an insurance company?” A: When you go directly to an insurance company, you only see their plans. We’re independent and can compare all available plans in your area to find the best fit for your specific veteran benefits. Plus, you pay the same price whether you work with us or go direct, but with us you get expert guidance at no additional cost.
9. Key Takeaways for Veterans
✓ Timing is critical—enroll during your Initial Enrollment Period unless you have creditable employer coverage
✓ Medicare Advantage (Part C) often provides better value for veterans—especially plans with Part B premium refunds and extra benefits
✓ Generic Medicare advice consistently fails veterans—you need specialists like my team and me who understand military benefits
✓ Independence matters—advisors tied to specific companies can’t offer you the best available options
✓ Ongoing support is needed—Medicare optimization requires annual reviews and expert guidance
✓ The financial stakes are enormous—proper guidance can save tens of thousands over your retirement
✓ You pay the same price whether you work with us or go direct—but with specialist guidance you get expert support at no additional cost
✓ You’ve earned and already paid for these benefits—don’t let generic advice prevent you from maximizing what you’ve rightfully earned through decades of service and Medicare contributions
10. What’s Coming Next
You now understand the complete enrollment process and how to find veteran-specialized guidance that maximizes your benefits. But enrollment is just the beginning. Once you’re enrolled in Medicare, how do you ensure you’re getting maximum value from what you’ve already paid for through decades of payroll taxes?
In Chapter 9, we’ll shift from enrollment strategy to financial optimization. You’ll discover why generic financial advisors’ healthcare projections don’t apply to veterans and how your military benefits create unique financial advantages that most retirement planners completely miss.
You’ll learn how strategic Medicare planning can dramatically reduce those inflated healthcare cost projections you’ve been hearing about. We’ll explore the hidden drains on veterans’ fixed income and show you how different veteran categories, from high service-connected disabilities to military retirees with TRICARE for Life, each have distinct Medicare advantages.
Most importantly, you’ll understand why working with Medicare specialists who understand military benefits provides more accurate financial planning than generic advisors who use civilian assumptions and miss veteran-specific opportunities.
The difference between generic retirement planning and veteran-specific Medicare optimization could mean tens of thousands of dollars staying in your pocket rather than going to unnecessary healthcare costs.
11. Your Medicare Mission Starts Now
You’ve served your country with distinction. You’ve mastered complex military systems and succeeded in challenging environments. Now you’re facing Medicare, another complex system that requires specialized knowledge to navigate successfully.
The choice is simple: you can get generic Medicare advice that treats you like any other 65-year-old, or you can work with specialists who understand your unique veteran situation and can help you maximize every benefit available.
You wouldn’t trust your brain surgery to a knee specialist. Don’t trust your Medicare decisions to advisors who don’t specialize in veteran benefits.
Your Medicare strategy should honor your service by maximizing the benefits you’ve earned. That’s exactly what we help veterans accomplish every day. You now have the knowledge to make informed decisions. The next step is putting that knowledge into action with guidance from specialists who truly understand your unique situation.
Ready to turn your Medicare knowledge into action with guidance designed specifically for veterans? My team and I specialize exclusively in helping veterans navigate these critical enrollment decisions. Call us at 888-960-8387 (VETS) to experience what WE SPEAK VETERAN™ really means.
Your service earned these benefits. Now let us serve you by ensuring you maximize every one of them.