Dear Governor Baker: Good morning. I hope you like the look of your new office, and thanks for pulling this letter out of the stack on your first day.

The only thing you need to know about me is that I’m a Democrat, the gooey sort who agrees the Redskins really should change their name. But I promise here at the very start of your first term that I’ll vote for your re-election — indeed, I’ll send you money and appear in a Lefties for Baker ad — if you’ll do just one thing for me, and by extension the rest of the commonwealth:

Throw away the Massachusetts Health Connector website and start all over again.

I realized I was up against it when I first tried to apply for health insurance six weeks ago and the website informed me that I must first download a new internet browser because the health connector page did not support Safari, the default browser of Apple — a biggish company that builds computers, tablets and phones whose main virtues are that they connect to the internet and work with every other page I’ve ever visited. Using, I point out again, Safari.

But I’m pleased to report that, afterwards, none of the problems that hobbled me as I applied for insurance through the health connector had anything to do with the browser. (Except one, see below.) They had to do with everything else about the health connector. For example, though I’ve had a Massachusetts driver’s license since June, been registered to vote since July and paid quarterly taxes twice in the last six months, the state evidently did not tell the federal government any of this, and so the federal government told the health connector not to believe a word of it.

When I mailed in the requisite proof of residency, the folks at the hard-copy end of the health connector website readily agreed that the Tom who sent in this paperwork by mail must indeed be a Massachusetts resident. They mailed me back a letter that said so. But I guess they declined to share the news with the folks at the digital end of the health connector website, because to this day, a month and a half later, the website says it is still awaiting conclusive evidence that mail-sending Tom and website-applying Tom are one and the same Tom.

Then there was the matter of my estimated income for 2015. I estimated it. But the health connector said my estimate was wrong because it was different from the income I actually reported on my 2013 federal taxes. So I entered the figures from my 2013 federal taxes. To my surprise, the health connector said these figures were wrong too, because, well, the figures from my 2013 federal taxes somehow also differed from my 2013 federal taxes. Hoping to finish before I made things worse by filing my 2014 federal taxes, which would be more different still, I pressed on.

I might call it a triumph that the health connector let me sign up for a plan anyway. I say “might,” because the health connector then refused to let me pay for it — which kept me from activating the plan I signed up for. On the third attempt to file an online payment from my checking account, the page published a notice saying that “some of you” may have received a notice saying that the page would not let us pay using the page.

I suspect that “some of you” might actually have meant “most of you,” and more probably “all of you,” because the notice was placed in a bright blue box, appeared suddenly on the last day a payment was allowed for coverage starting Jan. 1 and took up half the page from which the payment was supposed to be sent. I also believe that it really meant “all of you” because on the last day to file, the online billing system crashed.

I know this because the woman I spoke with on the phone said she hoped the system might be up and running again by noon that day, and she suggested I try again after that, when the remaining time would be less and the situation that much more desperate and hopeless. Of course, “desperate and hopeless” were my words, not hers, but when I tried them out on her, she did not disagree.

This brings me to the subject of tech support. I am delighted to report that online tech support worked brilliantly in comparison to the rest of the features on the health connector website, chiefly because it does not exist. Which meant using telephone support, which meant an hour-long wait every time I tried it, which meant listening to a tape loop urging me every five seconds to try a walk-in center instead, which meant looking up the nearest one by typing in my zip code on the website, which meant I couldn’t because — wait for it, and I use the phrase ironically — to access that part of the health connector website, you can’t use Safari. (See above.)

Don’t get me wrong, Governor. I’m a huge supporter of Romneycare and Obamacare, and I’ll be your heartiest lefty supporter in 2018 if Bakercare figures out how to set up a website that actually allows us to land the health insurance we want to apply for. Then lets us pay for it. And receive it. Using, you know, the health connector.

Desperately and hopelessly,

Tom Dunlop
Edgartown

Editor’s Note: During a deadline extension, the health connector suddenly and mysteriously granted the writer health insurance. He has no idea how or why.