Here It Is, the Worst Slack Bug

So, here’s a nightmare scenario: You open your work Slack on your phone so you can DM with a few colleagues. You talk with this group regularly, but you don’t see the chat in the list of active DMs on your phone, so you select all of the participants individually to pick the conversation back up. Without thinking too much of it, you accept an odd prompt that asks, “Do you want to include the entire chat history?”

Because yes, you think, of course it should include the chat history of the group DM you’ve been chatting in for ages. Who has time for this? There is business to conduct! Essential facts to convey! But the answer here is no, you do not want to do that. Because if you do, you will have ported your entire DM history with the first person you selected for the chat into the group DM.

This is not a hypothetical. In fact, this screw-up recently happened to me when I tried to DM two of my bosses, Brian Barrett and Tim Marchman. Suddenly, Tim had full access to years of private conversations between me and Brian, with no apparent way to undo it. “lmao andrew,” Brian wrote, “what have you done.”

Dead. I was, at that moment, obliterated by embarrassment—and worry that I’d just made a catastrophic mistake. I couldn’t even explain what had happened, let alone explain it away.

Once I realized I wasn’t going to be escorted into HR and my heart rate dropped back to normal, I was determined to figure out what went wrong and warn the world not to make the same mistake I made.

Turns out, this is definitely not a Slack feature—it’s a bug.

“This sounds like a mobile app sync issue,” says Slack spokesperson Vince Bitong over email. “Sometimes when switching between desktop and mobile Slack, recent conversations (including group DMs) don’t immediately appear in your mobile DM list until the app syncs.”

Because my group DM with Brian and Tim didn’t appear in my list of conversations, Bitong adds, “the app treated this as creating a new group conversation. That’s why you got the chat history prompt—it was asking if you wanted to include your private chat history with the first colleague into this new group.”

My next question, of course, was how Slack users can make sure this never happens—and what to do if it does. “You can go about this in a few ways,” Bitong says. “First, manually pull down to refresh the app. If that doesn’t work, fully close and reopen the app.” That should result in your DM list being up to date, which obviates the problem.

Also, as mentioned, if you see the “Do you want to include the entire chat history?” prompt for a group DM you know already exists, remember to click “no.” (And even for a new group DM, think very carefully about what might be lurking in that history before you share.)