Shirt alert!

A website is like a big old haunted hotel: some things that happen can never be explained, and you never go in the basement if you can avoid it, but the maintenance never ends. The life of a webmaster1 is filled with alerts. Almost all of them tell you that something has broken … again. The fragility of websites is astounding.

I’ve come to dread certain sounds that emanate from my pocket. The ones announcing that PainScience.com is offline makes my heart stumble and skip a beat. Others cause only an eyeroll. But it’s never good news.

This is a story about an alert I really could have done without.

SSL forever! Or at least a week or two

Recently I got me some SSL for my PainScience.com. SSL is about the 79th important subsystem for the site. SSL involves encryption and little locks in the website address, so you know it’s complicated and serious. I know it’s good for a website to have SSL these days, but setting it up is a super dorky chore, notoriously tricksy and error-prone. I didn’t look forward to this, didn’t enjoy doing it, and was relieved when it was over. I knew it was over when I got a nice column full of green checkmarks, proclaiming that all my little SSL ducks were in an SSL row.

But was it really over? In theory, SSL is set-and-forget. But there are two good reasons why I wasn’t sure:

  1. almost everything in tech ends up biting you the arse eventually
  2. I actually don’t know or care what the hell SSL is or how it works

So, just in case, I asked three experts this question: “I need another thing that can break my website like I need my balls in a blender. Will SSL ever fail in some way that gives me a super bad day?” The answers were:

Obviously the third answer was the only honest one. But I was satisfied: as web technologies go, SSL seems sturdy enough. So I declared the SSL installation to be over and done with.

You know where this is going, don’t you?

Alerts are the boss of me

It’s not healthy, and I know it. In the entrepreneurial beginning, the only alert I had was actually good news: I taught my Mac to make a fun sound when I received an order notification. That sound was a cute little “purr.” So my Mac purred when I made money. Seriously. Neat, eh? Business grew steadily, and my Mac purred a lot, life was good.

And I got addicted to that sound.

But as the Mac purred more and more, the stakes went up. Revenue was putting an end to years of debt and mild poverty and it was glorious. I needed my website to be up and running almost as much as I needed my heart to keep beating. And as the business purred along, it also got more complex, and broke more.2 Being a rookie self-taught developer, sometimes I didn’t even know that something important had broken for days, even weeks. Like that one time…

This one time, I tried to quit the purrs, because I feared addiction.3 At the same time I turned them off, I broke something critical on the website, which made sales impossible. Without the alerts, I didn’t know the sales had stopped!4 When I finally realized what happened, days later, I was traumatized by the discovery I’d deliberately cut myself off from the only way of knowing about the the mistake I’d made.

The irony of the timing of blew my mind and changed my life. I got paranoid.

After that, I invested heavily in all kinds of ways of monitoring the health of my virtual business. I’ve gone through many phases of using different kinds of alerts, sometimes more, sometimes less, always seeking the combination that will give me enough information, but not too much, or at the wrong time or volume. Within another year or two, I had succumbed: I always had to know what was going on. I still do.

So about that SSL …

“SSL Installation Alert for www.painscience.com”

That was the subject line that appeared in my inbox.

I filled the air with harsh language. It was inherently exasperating, of course — I’d had the SSL for only a couple weeks, I’d been reassured that it would never give me trouble once it only days before — but this came at a time of seemingly endless bad news, a three month period with more alerts and alarms than the whole year before that.

But here’s what the intallation alert actually said:

Dear Paul,

Congratulations on successfully installing your first DigiCert SSL Certificate! We would like to send you a DigiCert shirt as a token of our appreciation. Click here to see the shirt and let us know where you would like it shipped.

If you have any SSL Certificate questions, please don’t hesitate to call our award-winning support team at 1-800-896-7973.

Sincerely,
Your friends at DigiCert

Unbelievable.

Don’t get shirty with me

A shirt. They wanted to give me…a shirt. It was a shirt alert. Pro tip, DigiCert: never put “alert” in a subject line unless you bloody mean it.


  1. “Webmaster” is a funny old word I associated with the 90s. You don’t see it nearly as often these days, but it’s still in use, and it still works. 

  2. All the more so because my earlier programming efforts were sloppy and amateur. As compared to my modern efforts, which are slightly less sloppy and amateur. 

  3. Happiness and confidence when they were flowing steadily … doubt and dread if they were slow … a flood of relief when they sped up again. Repeat until your nervous system burns out. 

  4. And most defeated ecommerce customers give up and go away rather than asking for help or even complaining. They feel like they’re at a sales counter in a department store with no cashiers in sight. They just stomp away rolling their eyes. I don’t blame them.