Escaping Health Connector Hell: How to Fix Your Broken Enrollments

This post originally appeared on Yelp. If you like my reviews, follow me for more snarky points of view.

Well guys, I never wanted to be back in this situation reporting on how terrible the Massachusetts Health Connector can be, but here I am nonetheless! Your response to my ordeal, as well as noise from this post on Universal Hub, has prompted me to write a follow up post detailing how to fight the good fight when your enrollments get screwed up by the Health Connector’s incompetent billing center.

TLDR on the last post: last year, I spent about three months without access to coverage because the Massachusetts Health Connector couldn’t process a simple “retro request” properly. A retro request is when you move your effective date to a date other than when you started the plan, for example, when you leave your job but your enrollment won’t start until the next month, and you need coverage now. 

What I learned during this three month battle is quite simple: the Massachusetts Health Connector’s main line (1-877-623-6765) is operationally incapable of helping you, and that only an inaccessible department called “billing” calls the shots when it comes to modifying your enrollments. Not too surprising, right? I mean, most bloated corporate monstrosities have inaccessible billing departments: I spent a good two weeks dealing with some messed up billing with Bright House, a cable company in Florida, and wasn’t allowed to speak to their money people either. But in that dismal situation, at least there was real communication between the CSRs on the front lines and the accountant robots in the back room. In the Health Connector, not so! Neither the main call center nor your insurer (in my case, this was Neighborhood Health Plan) can pick up a phone and talk to the person screwing up your plan. Be prepared for the fate of your health insurance to be handled by carrier pigeons flying over volcanoes!

Anyway, if you get caught in the unfortunate situation where the Massachusetts Health Connector is threatening to terminate your insurance for nonpayment (when you’ve already paid all your premiums on time), and/or they’ve “restricted” your account without telling you (meaning, you have to pay full cost for your prescriptions) this is what you do to get it fixed in days rather than weeks.

Be Meticulous

First of all, in ALL cases, take down the first name and identifying # of anyone you speak with, whether on your insurer’s side or the Massachusetts Health Connector’s side, and note the time and day you called. If you’re unlucky like me, you may have to call the Connector 32 times, so after that many calls things can get confusing. Most insurers have ID numbers attached to their CSRs, and the Connector does too, though their CSRs will sometimes lie to you and claim they do not. I wish I could recommend recording your phone calls, but since we can’t be certain where the Connector’s or your insurer’s call centers are located, you might run up against two-party consent privacy laws with respect to the recordings.

Make an Ally of Your Insurer

Don’t bother calling the Massachusetts Health Connector directly just yet. Call your insurer and gather all the information they’re aware of. Ask for a supervisor immediately, and demand that the supervisor stay on your case specifically. Explain that the Connector is being intransigent and that you need someone on the insurer’s side to help you get on the case. Confirm that your account has been restricted and verify the dates of enrollment they have on file.

100% of the time, I’ve found that the Massachusetts Connector and the insurer will have a different idea of this, because the Connector is always reporting days or weeks old information to your insurer. This will give you the info you need to keep your story straight in the nightmare you’re about to embark on. While the insurer can’t modify your billing and doesn’t have access to any paper trail of payments you’ve made to the Connector, they can communicate with the Connector’s billing department by email.

Ask them to send a request to the Massachusetts Health Connector’s billing department to review your case, and provide the insurer with any relevant data proving that you’ve made your payments on time. One supervisor I spoke with at my insurer kept insisting that I needed to call the Connector and give them the confirmation number and amount of each on-time premium payment I made, but I was persistent enough to get her to do it for me on the insurer’s side. The Connector’s billing department can’t exactly ignore the insurer, so that’s why we go this route first.

Call the Dreaded Massachusetts Health Connector

Now that you have the insurer on the case, call the Massachusetts Health Connector, choose the Billing option on the robo-menu, and immediately ask for a supervisor. They may tell you there are no supervisors available, or that they can have someone get back to you in 3 days, which is ridiculous. They’re lying. The supervisors are just overworked and don’t want to talk to you. Tell the CSR that you’re willing to wait on the phone however long it takes to talk to someone. They’ll probably want you to explain what your problem is, but don’t bother, because they’re just trying to keep you away from a supervisor, and if you explain your convoluted case to them, it’s just going to get mangled in the game of telephone (if they even explain your problem to the supervisor before they transfer you). Put your phone on speaker and do some other work until they get you someone. Don’t relent.

Once you have a supervisor, explain that you’ve received this termination letter and that you’re disputing it. Explain that you’ve made all your premium payments and can prove it. Give them the dates of all your payments, the confirmations numbers from your bank, and the account IDs you billed them to. If you foolishly used their autopay, give them the dates the money was taken out of your bank (and then promptly turn autopay off! ONLY EVER SEND PAYMENTS MANUALLY TO THE HEALTH CONNECTOR. I use my bank’s autopay to schedule checks to be sent to them, so I can control when money comes out of my account). Ask them to explain why their system is telling them you’re past due and make sure that they write down your explanation for why this is wrong. In my case, on the second go-around this year, the problem was that the billing department was taking months to process a canceled application I submitted during a single day of enrollment in January. That is, whatever system is connected from the website to their billing department is so awful that if you jump into a plan and cancel it, then jump into another plan (all during the open enrollment period), the billing people process each of these events individually, increasing astronomically the possibility of screwing up your enrollment. This meant that they were shuffling me between plans from January to March, all the while demanding payment for the difference between these plans, even though I was never supposed to be enrolled in anything but the one I actually signed up for.

Do not let the Massachusetts Connector initiate any “retro requests,” because that will only make matters worse. The supervisor may insist this is the only way to solve the problem, because it’s the only way they know how to solve the problem. Or, they may also ask you to make the difference in payment, so they can reactivate your insurance now. Don’t do either of these things. If Amazon shipped you an empty box instead of whatever you paid for, would you send them more money before they sent you the actual product? I didn’t think so. Instead, ask them to send all of the information you’ve told them to the billing department for review. Ask the supervisor to re-read what they’re about to send back to you, so they don’t misinterpret anything you’re saying.

Call the Governor’s Constituent Services Office

Finally, this is the all-important step in the process. You are a citizen of the Commonwealth who’s forced to pay for coverage. You paid for coverage, and now because of the State’s technical incompetence, you’re being punished. Doubly punished if you ask me: not only are you being denied the coverage you paid for and that you’re required to pay for as a citizen of the Commonwealth, but you risk being penalized for not having full coverage by year’s end. So this is very much so an issue for the State’s constituent services department. Call the Office of the Governor and you’ll get one of their pleasant phone reps. Don’t use their form—call them. I tried using their form and nothing came of it. When you call, explain simply that you are being denied coverage despite that you’ve made all your premium payments on time, and that you need the restrictions lifted on your insurance immediately. Be polite, and don’t over-explain. The governor’s office will take information from you, and then forward your case down the line.

The end result of this—in the two times I tried it (which, admittedly, isn’t a large sample!)—is that you’ll get a phone call the next day from the Massachusetts Health Connector’s secret “Urgent Care Services” line. As far as I can surmise, the people at this number are a layer of the Connector management that can actually communicate with the billing department, as well as issue requests for technical assistance with the enrollments system. They will immediately lift whatever holds you have while they fix their systems. In the case I described above, it actually required them to make changes to the infrastructure of the system to void out the erroneous enrollment they placed me in. They fixed my problem in two days, in both cases. At the moment, the phone number for this line is 844.558.3454. If you try to call this number directly, however, it may backfire on you as they assign you a “case number” to proceed.


Getting out of Massachusetts Health Connector hell is not easy, but it’s not impossible. You have to talk to the right people, in the right order, as if you’re trapped in some kind of State-mandated insurance version of the horror movie The Cube. Be polite, but firm, like you’re talking to a bunch of airplane pilots who are flying on hallucinogenic drugs. And most importantly: try to keep your story straight. For me, that’s always the hardest part when I venture into the Kafkaesque torments of dealing with labyrinthine customer service.

Health Connector Hell

Massachusetts Health Connector Hell

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  1. Raechel 8 months, 2 weeks ago

    Hi, going through my own hell here. Did you take or do you know of anyone who took any legal action against the Health Connector? What about recouping doctors’ or dentists’ fees that had to be paid out of pocket while the Health Connector still showed no enrollment (despite the fact that enrollment had taken place and all premiums were paid, all checks cancelled, etc.)? Thank you.

    • Daniel Quinn 8 months, 2 weeks ago

      Hi Raechel,

      I’m unaware of anyone who’s tried to sue the Health Connector directly. In my case, they had tried to withdraw extra payments from me because of their screwed up billing process, and managed to royally botch the whole situation. I got around this by filing a merchant dispute through my bank and ultimately got a refund that way. In your case, you’re stuck in the middle of the insurance company and the Connector: the Connector is incompetent and will always have your billing wrong (and report the wrong status of your account to your insurer) while the insurer will do nothing until the Connector gets its act together. What I recommend you do is make sure that you have proof that you made payments to the Connector for your premium during the time you got care. That is, make sure you can demonstrate that you sent a check to them (and that they cashed it) for each month during the time you paid those out of pocket fees. This will prove later on that you should have had coverage when you paid those out of pocket fees.

      Next, don’t bother trying to dispute it directly with the Connector or your insurer. They won’t help you. Instead, contact constituent services at the Governor’s Office: I called them before and they were helpful. Tell them you have a dispute with the Connector and that they are refusing to insure you despite that you paid your premium on time, and that you’ve been forced to pay out of pocket for care. This will cause the Connector to get contacted by the Governor’s Office, and they’ll elevate your case to the “Urgent Care” hotline, which is hidden to the rest of us. The phone number is 844.558.3454 (unless they changed it again). Don’t call that line directly though: it may backfire on you. Just wait; as soon as you set up a case with the Governor’s Office, Urgent Care will call you.

      The Connector is capable of issuing refunds for premiums, but I don’t know about out of pocket $$ you paid because they didn’t activate your coverage when they were supposed to. Most likely, the insurer will need to refund you. Just make sure you’re working with the Urgent Care hotline and not the main callcenter (1-877-623-6765). The main callcenter is run by Dell employees and they are undertrained and misinformed 50% of the time.

  2. K 3 months, 1 week ago

    Call the governors office right away is the most effective route i have found. The connector would not allow me to wait on hold to speak to anyone and calling the urgent number only got me transferred to the connector that does nothing.

    THANK YOU!! For blogging and putting this major issue out there and giving us hope that one day this mess will be sorted out.

    • Daniel Quinn 3 months, 1 week ago

      Hi K, I’m glad this worked for you!

  3. Christina Babin 2 weeks, 5 days ago

    Hi Daniel,
    First of all, thank you for this. I just hung up with the Governor’s Office. They are reaching out to their contact at the Health Connector. Yay, finally feeling some hope.
    I have been dealing with the same issues as you for months now. And promised April 1st my healthcare would be active again. Guess what, its not!!!! And hasn’t been since January 31st!! Such. A. Nightmare. Sadly, I’m happy to know I’m not the only one who has gone through this 🙂 but I’m sorry for everyone’s agony at the same time. The HC sucks. In every way. The hold music sucks too. Anyway, before I start a real rant…THANK YOU for the ideas!
    Christina B.

    • Daniel Quinn 2 weeks, 5 days ago

      Good work! The governor’s office is the first step to forcing the Health Connector to sort out the mess. They have access to people who aren’t part of the general call center.

  4. Joe 2 weeks ago

    I’ve been using the Health Connector off and on for health and/or dental coverage for about 18 months. I have found they usually do the opposite of what I ask. If I ask them to cancel coverage, they do not cancel it and I continue to receive bills. If I tell them not to cancel coverage, they immediately cancel it. Their answer to everything is “it will take 24 to 48 hours for our system to update.” Yet, days or weeks later, there is no update. After about 10 calls with them trying to solve my first (of several) problems, I finally contacted the Ombudsman and the issue was cleared up in about a week. It’s sad that no one else over there can help.

    • Daniel Quinn 2 weeks ago

      It’s worse than sad – it’s a disgrace. The Health Connector needs to get its act together because it’s doing a disservice to so many Massachusetts insured.

  5. Amy 4 days, 16 hours ago

    Hello everyone. I am sad for everyone that is dealing with these issues, however I am so happy to have found you!!! I am going to start off by saying that as sad as this may sound, The Health Connector absolutely ruined my entire summer last year….I am not kidding! I will begin by saying that I stumbled upon this site, while searching for all of the articles that i am sending to Atty Generals Office to yet again explain what has happened to me, and by the looks of it thousands of others. It’s been almost a year now, however the residuals seem to never disappear! That being said I must finish my research to send to them as much evidence of incompetence as possible. I can imagine that it will not be a difficult task, however if anyone has anything that they wouldn’t mind sharing with me, I will send that in with my evidence. I let it go for a while, but I have been stewing about it, the reason I use Health Connector is because it is the law and because of my income. That being said, I don’t have a lot of money, I have just enough and sometimes not even enough for my monthly bills. So when money is taken without my consent….Bad things happen!
    Thank you for any links or anything you can send. I will be writing back with thanks and hopefully we can discuss and get all of this taken care of it. I am sick of them!!!!

    • Daniel Quinn 4 days, 3 hours ago

      The Health Connector strikes again! I wish you the best of luck in your battle with The Beast.

  6. Rhonda Brockman 10 hours, 27 minutes ago

    Nightmare is only the beginning of what I’ve been going through with the Healthconnector. Everywhere from no insurance for two months, to 12 applications/case tickets taken out, to a whopping double payment out of the blue.

    • Daniel Quinn 4 hours, 58 minutes ago

      I’d love to hear your experience. Feel free to leave a rant here for all the world to see!