In May of last year, I posed a question on Twitter: Do you ever get the feeling that everyone at Medium is drunk? My question had been inspired by the latest release notes for the publishing platform’s iOS app, which had taken the form of a poem:

There’s an iOS app we call Medium
’Tis a great cure for your tedium
You can highlight in story
Add tags for more glory
And many more people be reading ’em

As a limerick, it didn’t quite scan. To the extent it conveyed what was new inside the app, it was hazy and incomplete. And yet given the tedious, perfunctory quality of most release notes — "This app has been updated with bug fixes and performance improvements" — Medium’s slapdash poetry was undeniably refreshing.

Then one day after my latest slander, I received a tweet from Medium itself.

A few weeks later, I found myself inside the company’s headquarters on Market Street in San Francisco. I was met by Nick Fisher, Medium’s community manager, and Greg Gueldner, a member of the company’s trust and safety team. It’s Fisher and Gueldner who are responsible for turning the mundane canvas of an app update into an improbable literary project. They note that the release notes are consistent with Medium's general purpose of inspiring creativity. It isn't the only company to treat release notes as performance art — Tumblr, Trello, Slack, and Yelp are among the companies that routinely infuse their updates with short stories, topical humor, and assorted slapstick. But for sheer gonzo ambition, Medium leads them all.

"We had a previous thing where we took questions over Twitter and dressed up in hard hats and did song responses to them," says Fisher, 34. The hard-hat songs led Fisher to propose writing a song for the next app update. It was a parody of "On The Road Again" entitled "On My Phone Again." "It got such a good response that we just kept doing weird things," he says.

It turns out that iOS is a more inviting canvas than Android — the former offers 4,000 characters for release notes, compared with a mere 500 on the latter. The only other rule is that the notes can’t include special characters, such as emoji. And surely Apple must have some requirement about decency? "They probably do, but we’ve never read it," Fisher says.

The first thing to know about the Medium release notes team is that they do not, for the most part, write drunk. Most app updates ship in the morning; Fisher and Gueldner wouldn’t have time to get drunk even if they wanted to. "The app gets approved, and the engineers want to release it in four minutes," Fisher says. It’s at that point that he grabs Gueldner, and the duo bounce ideas off each other until one makes the other person laugh out loud. "The first idea is always that we should announce we’re going to stop doing this. It’s played out," says Guelder, 43. Fisher smiles. "And we kind of go from there!"

In September, Medium’s updates were rapped on the knuckles by TechCrunch, which described them as "silliness gone awry" as part of a larger indictment of vague release notes. Over the past year, the duo have tried to rein themselves in. "The most common blowback we get is from people who want to know what’s in the release," Fisher says. "They hate these because they have no idea."

The reining in is often done by Gueldner, the more reserved of the two, who appears to be in physical pain during much of the writing process. Gueldner is a former English major and musician — he spent 10 years drumming in the band Stroke 9, which had a modern-rock hit with "Little Black Backpack" in 1999. "He’s the yin to my yang," Fisher says. They both admit to regretting the Kenny Loggins release notes, which in hindsight they agree were incomprehensible. "What was actually introduced in that update was so buried," Guelder says. "I feel bad about that one."

But every new release brings with it the chance for redemption. On the day I visit, the engineers have put the finishing touches on a fairly routine update that fixes a few bugs. We open some beers and survey the changes. The most prominent fix improves "deep links" from the Facebook app — a link clicked in Facebook now opens up properly in the Medium app, if it’s installed. Also, if you get a sudden surge of recommendations and comments — say you've written a traditional Medium post about why you quit your job and shut down your startup and are leaving San Francisco and it goes viral — the app will now roll up that activity into a single notification.

Looking at these updates, Guelder’s mind turns to rap. "A rapping Medium update!" It’s unclear whether he’s serious. "Shoot me," Fisher says. For a few minutes, they play with the idea of parodying Snoop Dogg’s immortal "Gin and Juice," before deciding there’s nothing appropriate they can change the lyric "smoking indo" to. Gueldner, who has a majestic beard, goes to stare out the window. We open a second beer.

A few minutes later, inspiration strikes. "What about Clippy?" Fisher says. The annoyingly chirpy Microsoft Word assistant is a reliable punching bag online, but to date had never made his way into the release notes. Fisher begins to speak in Clippy voice: "Hey, it looks like you’re trying to update your app." Gueldner laughs. The first test has been passed. Fisher opens a Google Doc.

We kick a few ideas around while Fisher locates, then abandons, an ASCII art picture of Clippy himself. Browsing the Clippy entry on Know Your Meme, we pull a few of his stock phrases, trying to get a feel for his voice. We write a script in which the user tries to update the app only to be foiled by Clippy at every turn. I supply the kicker: "Windows has encountered a fatal error and can not perform the update at this time."

Brian Ellin, the iOS product manager at Medium, walks by as we are finishing. The release notes process appears to be somewhat mysterious to him, but he has embraced it. "I entirely trust Nick with my life — and my release notes," Ellin says. "Every single release is different, and that’s what makes it fun."

The updated Medium for iOS is now available in the App Store.