Last week, with great fanfare, I announced that I’d switched from using MailChimp to using Buttondown to power the ability to subscribe to a daily digest of my blog posts by email.
A week later, Buttondown suffered a technical meltdown, something that resulted in some of my 94 subscribers receiving 8 copies of that day’s email, and some—like me—not receiving it at all.
Needless to say, I was pissed off and frustrated, all the more so when the reply I received from Buttondown support was disappointingly “we’ll get back to you about this, but don’t hold your breath”:
Thank you for raising this issue about the duplicate emails going out. I have filed your experience on the Buttondown Roadmap page to be investigated and addressed. I have also associated your message to support with the ticket so that when it is resolved we can reach out directly to update you.
I was frustrated enough that I started to look elsewhere for alternative providers, to the point where I got pretty deep into setting up Moosend, a process that involved its own frustrations and limitations.
Today, before continuing down this road, I thought to look and see if Buttondown has a status page. It does. And on that page I read a very detailed blow-by-blow about what had happened, in part:
Bad configuration on one of our self-hosted SMTP servers caused a crash that proved difficult to recover from, leaving lots of emails “stuck” in varying degrees – and their being stuck manifested in a slew of unpleasant ways. We’ve fixed the configuration, are investing (literally, right at this very moment) in better tooling and alerting, and are architecting a way to prevent this from ever happening again.
and then, later on, in more detail:
Over the course of the afternoon, approximately 13,000 subscribers across 40 authors experienced some combination of the following:
- Multiple hour delays before receiving a message
- Not receiving an email at all (though we’ve redriven these.)
- Multiple sends of the same email
And that’s the fate that befell my subscribers and me.
Having managed servers professionally for more than 30 years, I am no stranger to confounding cascading technical meltdowns: some of my most challenging and frustrating hours have been spent in the wee hours, trying to diagnose some combination of web and database servers being overwhelmed. I was religious about telling my clients, when this sort of thing happened, exactly what happened and why; I treated that responsibility as seriously as my responsibility to actually fix the problem.
As I wrote last week:
I’d been reading the blog of Buttondown’s founder for awhile, and liked the cut of his jib.
Posts like this, with a photo of his office, and his bicycle, remind me that he’s a person like me, and he’s likely had a really shitty week.
This all combines to me unusually sympathetic to the Buttondown’s plight, and so I’m going to stick with them.
Comments
I've had a weird issue, probably unconnected, whereby a few people who have Gift subscriptions, but not all of them, received a new "you've been Gifted ..." message on Thursday. I use Gifted as a mechanism to give (the very few) perks to people who support me other than directly on Buttondown, and of course I need to apologise to them, but I'm torn about whether to do that immediately or wait until I get some sort of explanation.
It seems I got lucky since my newsletter which is run with Buttondown only goes out on weekends this didn’t affect me. I sent a link to your post to Justin. I do think the thing you highlight, that I've also highlighted, is how important the support experience is. I use three Indieweb services a LOT: Pinboard, Micro.blog, and Buttondown. They are all run by one or a couple of people. And supporting services is always hard.
- Pinboard is famously challenging for support, but the service almost never changes and is very stable so I VERY rarely need support.
- Micro.blog is, to me, impressively robust. Given the complexity of managing Hugo at the heart of it I’m always impressed at how little support I have needed. And generally Manton and team are really fast and engage directly. There are some issues I know only I've experienced and those took a long time to get resolved.
- Buttondown I've had the most support engagement of all with. I suspect some of that is the nature of email. I also have run into way more bugs than others. And the act of sending a thousand plus emails each week has ongoing issues. I always wish for Buttondown to focus more on stability and support over new features.
I am 
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