Health insurance is by far one of the most complex and frustrating components that people living with chronic health conditions and disability have to navigate. Having access to the right care and the plans that unlock specific treatments can be the difference between being able to try the treatments available to your health condition and falling in between the cracks.

Typically, those who apply for disability and receive end up on Medicare and rather immediately sign up for the drug coverage – Medicare Part D.

But my insurance journey began prior to being on disability.

Since I got sick while I was still in high school and then went off to college, I was still on my parent’s health insurance plan.

Once I left college, we were presented with the first challenge: getting Tricare (my dad’s military insurance) to approve continued insurance for me as “disabled dependent” – a challenge that took far more documentation and paperwork than any of the actual disability process.

As many of you have followed along with this journey you’ve perhaps been privy to some of the other details involved in maintaining my access to Tricare.

The gist however is that as a dependent, both myself and my parents had to go through rigorous reviews after the initial approval that involved tracking of every expense down to the penny to show that I was financially dependent on them.

We had to track all of my own spending – which, by the time I created a budget I incidentally chose to track it based on the Tricare specific categories. We had to track my income, which was pretty simple since I manage my small business so all of that is documented to make tax season easier. But then we had to track my parents household expenses and the expenses which were related to me.

All in all this was a nightmare full of weird rules to try and help us make the calculations make sense and ensure I still fell in line as their dependent.

The rules to me were simple, my parents had to cover more than half of my expenses. Expenses are considered “what I spend on myself and what they spend on me (often indirect with costs of their house).” A secondary rule stated that my income could be no more than half of my expenses.

The secondary part is where things got complicated with social security – I can not cut back my social security so there then was a minimum amount that had to be “spent” on me. Part spent by me, and part (plus a dollar) spent by my parents.

The stress surrounding these calculations and the time dedicated on my mother’s part on tracking it were relentless. Review periods were every 4 years, but the period of tracking included the entire year up to the review meeting. There really was no point in time that my parent’s were not providing for me as required, but complicated spreadsheets and additional considerations without a real understanding of how the program weighted any of the expenses made for a long year. Of course, with the initial application all of that paperwork with all of the financial supporting documents, was submitted.

For the first review, we expected the same thing, only to be asked a few questions confirming the information and that was that.

Having my parents insurance however, was critical. They paid all of the secondary expenses that Medicare didn’t cover, and also provided my drug coverage. Drug coverage that put my copays for ridiculously high migraine medications far lower than most people I knew.

It was the kind of lifeline that kept me tied to living with them, unable to really consider moving out, because losing that insurance would result in the kinds of costs I simply could not imagine. And definitely could not pay for.

As many of you know – maybe you read my last update post – I moved out!

I learned about Medicare Part D costs and ran my numbers and decided I would just have to do it. I would be taking on around $1700 a year in new medical costs.

And then I learned about the Social Security Extra Help Program.

When you initially get approved for Social Security Disability, you’re inundated with lots of pamphlets and information on programs that are available to you. One of those was regarding Extra Help – which likely at the time of applying for Disability I may have been qualified for but by 2021 or so my personal assets would have been too high to be eligible.

Since moving out however, I would be spending down my savings account. A large chunk of that going towards a down payment on my house.

The current income limit is $22,590 – which is a few thousand dollars above my annual income including my social security. The asset limit is $17,220 and does not include things like your primary residence or vehicle.

You can find the current Extra Help Pamphlet here with more details.

So what is Extra Help? Extra Help is available to people on Medicare for additional help towards monthly premiums, copays, and deductibles. You can pay as little as $0 for most of your prescriptions.

Even though I had decided I simply would eat the additional medical costs, learning about this program and learning that I would be eligible was so incredibly beneficial and will help with making living on my own and covering other expenses a good bit easier.

Of course, one has to transition off of insurance and onto another.

Notifying Tricare That I’m No Longer A Dependent

It is a rule that you must notify the department of defense at any point you are no longer a dependent. This makes sense. The process however and the information we were given to do so, was far less clear.

We were told to give them a call and the date when I would no longer be dependent and that would be that, but that not quite the whole story.

Despite not being due for a review, to remove oneself as a dependent you must provide the documentation – on the large scale of the initial application – that you had in fact been a dependent in the year leading up to dependency ending. Since we weren’t in an expected review time, the in depth tracking for all these details simply wasn’t being done which created a tremendous amount of paperwork and time going over bank and credit card statements.

Additionally, the dependency ends the moment I spent the money to put a deposit down on my house. Now, I didn’t even move out of my parents house for another few weeks, so although it makes sense our own dependency considerations were different and I had made a plan on ordering the last of my eligible prescriptions prior to it ending.

I ended up rapidly having to cancel a large prescription order, because the dependency would be backdated and therefore my coverage wouldn’t include the day I ordered.

Should they determine my dependency ended earlier we would be financially liable for anything they had paid for. My Ubrelvy for example is thousands of dollars.

Getting all of that paperwork submitted and then getting me removed from the insurance is a process that can take months – and it was unclear how that may interfere with my ability to start up new insurance.

Because of the unclear information when we started the removal, my start up for getting on a Medicare Part D plan and applying for Extra Help was also delayed – pushing my coverage start back until November 1st.

This created quite the thinly stretched prescription situation and caused for some looming threats of having to pay out of pocket for my medications in the middle of paying for a lot of very expensive household repairs.

Picking a Medicare Part D Plan

Since I am already on Medicare, I have an existing account and the online process is relatively easy to navigate.

There’s special circumstances where you can add on drug coverage outside of the Open Enrollment period, and in my case stopping my other insurance qualified.

They allow you to input your medications and then get a decent picture of what those medications will cost along with what your monthly premium will be. The part I find… difficult… is that doing this in October and getting estimated pricing only gives you information through the end of the year. It made it quite difficult to see what my costs may be going in to 2025.

Now that Open Enrollment has begun, those numbers are a lot easier to access.

What I found confusing was the presentation of what I’d pay for my drugs and when I’d hit various caps and what I’d be looking to pay out of pocket. The numbers were really high and made me really worried that the numbers I was seeing for 3 months would dramatically go up when looking at a whole 12 month period.

I chose the plan which covered all of my meds and seemingly had to lowest costs.

Of course in the back of my mind, I qualify for Extra Help, I just don’t know how the program works yet and when the approval will come. A lot of those numbers in theory will be $0.

After signing up for my plan, I had to prove to the new insurer that I had something called “creditable coverage” in the years since being approved for Medicare and now getting drug coverage. You are penalized if you don’t sign up for Medicare Part D when it is first offered to you. There are exceptions for people who have, for example, secondary insurance that provides drug coverage. There is also an exception for anyone who qualifies for Extra Help if you hadn’t had drug coverage, the penalty will be waived.

This penalty however will increase your monthly premium for life.

I found it incredibly infuriating that I could log in to Medicare’s website and see my Tricare coverage listed, and I was still being expected to provide a whole lot of documentation regarding my proof of coverage… and as anyone who has had Tricare is aware, so much revolves around a military ID and people’s social security numbers the documentation is… not clear.

So I had to snail mail off a bunch of documents with no clear instructions as to how to “prove” it. I included: a copy of my military ID, a copy of my EOB from the mail order pharmacy that has a “Tricare pays” section for the fully available amount of time – not as long as they were requesting, a copy of some Tricare paperwork indicating I was approved – also for the wrong time but still had my info on it, and a letter explaining what the documents were.

Since my premium was processed at the advertised amount on the first of the month, I have to imagine they were able to document my coverage as creditable.

Understanding My New Coverage

I had my first doctor’s visit at the beginning of this week.

The first thing I learned was that I didn’t have a copay. I have to imagine as far as Medicare is concerned I hit my deductible earlier in the year (covered by Tricare) so there was no out of pocket cost for a visit. I found that to be a pleasant surprise.

On the less pleasant side of things, until Extra Help kicks in and is approved, I have to pay for my prescriptions.

And the one I was lowest on? The most expensive one. They wanted $150 for 90 days of my birth control… I instead opted for a 30 day script.

My Part D plan has a special Mail Order Pharmacy. When picking out the plan I was shown a lot of costs through that pharmacy. Fun fact, that pharmacy actually only dispenses 1 of my medications, AND the cheapest one at that. So the “low costs” I’d been shown were kind of a sham.

I am lucky the two other meds I needed more urgent fills on came to $15 total.

My doctor was more than understanding to wait on filling the meds I don’t need right away – some that I’ve successfully stockpiled and others that insurance doesn’t cover that I’ve recently had filled.

I bring up getting prescriptions because I missed a step here! I did look at GoodRx to see if I could get a discount, but I forgot to check with that Mark Cuban pharmacy. Lo and behold they offer my birth control for like $18, so if my Extra Help doesn’t kick in soon I’ll give my doctor a call and have her change where that script is.

So, if you also end up in a coverage gap don’t forget to check there too!

And finally, Extra Help.

I applied for Extra Help at the beginning of October and was given a 4-6 week turn around time with an unclear answer about any possible reimbursements for time I qualified but hadn’t been receiving extra help.

The application was very easy and they outline on their website exactly what forms to have on hand and what information you’ll need. I found that helpful as I could get all my documents in a folder and have them ready to reference while doing the form online.

I did end up giving Social Security a call yesterday to see if there was an update, and they have the application but the person on the phone gave a 45-60 day window for processing. So I guess it could be even longer.

Most people begin Extra Help when they begin receiving Social Security, so there’s not much in the way of gaps – and also not much in the way of information online for people who do have that gap. It certainly isn’t ideal having to pay a couple hundred dollars for my drugs and premiums months after I’ve applied and simply not knowing if I’ll be reimbursed.

I don’t know where I saw it, I thought it was the application that gave the time frame for review that said costs would be reimbursed. But the only people I’ve been able to connect with anecdotally have said there won’t be any reimbursements.

All of that makes for a frustrating line up with doctors – I am glad my new PCP is understanding – but I am scheduled to meet a new Neurologist in December. Will he be as understanding in delaying taking on prescriptions and processing the necessary prior authorizations? Hard to say!

That is the final thing I’ve discovered: all the work I went through over the years getting certain medications approved for certain quantities and certain reduced costs totally goes out the window with new drug coverage.

My lifetime prior authorization for Ubrelvy? That died when I lost my Tricare.

Luckily, that is the only current medication that has special requirements, but what a hassle.

My Tips For Future Drug Coverage Changes:

So much of this process for me was about documentation, so my first tip is to ensure you have saved letters and information you receive about your medical coverages. I think documentation of social security notices and your taxes would also fall in here.

Related to that, I’d recommend knowing where you can find things online. The places you’ve filed your taxes may offer you a pdf you can download of previous years. Social Security lets you download a Benefit Verification Letter. Your banks will let you access a lot of historical information, and if you can’t “scroll” back far enough you can access that information in your bank statements. And your medical insurance providers should provide explanations of benefits, which often let you input a custom timeframe to make cutting down the info to exactly what you need easier.

I’d also highly recommend in times of transition, talking to your doctor. If you move and have to change coverage, and even doctor’s what is your current doctor willing to take on. Mine was more than happy to resubmit any of my prescriptions once I had my new drug coverage if I wasn’t able to line up a doctor in the new location in the right timeframe. They also were happy to manage any new prior auths.

Even if you aren’t planning for changes, there’s some things you can do to insulate yourself for lapses in coverage. For medications you take on an as needed basis, when you’re financially able order the medication as soon as it’s ready for a refill instead of when you need a refill. This is one way to build up a stockpile – which I was quite successful in doing with my Ubrelvy – that will tide you over.

Similarly you can discuss with your doctor adjusting the quantities. Some Neurologists prescribe the 100 mg of Ubrelvy for their patients on the 50mg dose to allow for cost savings. You may also be able to get a slight advance in your prescription with an early fill – like you would for a vacation or in an emergency.

Finally, the shortest term option is to have your doctor switch to 90 day prescriptions instead of 30 days. This doesn’t buy you AS much time for the transition, but it can substantially reduce the stress of other things you may be managing in those first couple of weeks and allow you time to get things sorted.

Of course, it is important to note some medications that are more controlled won’t be able to be managed in this way.

And last but not least, I’d recommend talking to people you know and seeing if anyone can help you understand various things. One of my friends was able to send me some details about how her Extra Help coverage presents on her prescriptions and various bills, which gave me a better picture of how my own coverage might look for my prescriptions.

Changing health plans and messing with parts of your care you may consider to be stable can be so daunting, so at the very least I hope some of my experience will help anyone else prepare for changes they may face. Whether it’s just transitioning off Tricare, or planning for a gap in coverage these are parts of the puzzle I didn’t have clear info on when looking online.

A.