I think with slack the danger is exacerbated by the fact that this value gets stored in a cookie that is a lot easier to gain access to - and, once you have it it has a much better documented format than whatever MSN Messanger might roll in-house. We're essentially just talking about an added layer of security by obscurity when it comes to the format - but actually nabbing a cookie is easier than gaining arbitrary file access.
But the problem goes beyond that. Many organizations have disabled sharing executable file formats in attachments over e-mail. GMail flat-out prevents you from sharing executables, and macro enabled word documents as attachments, even when put into a zip file.
But on Microsoft teams? I sent a zip file with 8 unsigned executables to a colleague a few days ago. No warnings, no messages, no nothing :)
As for me, I really hate this "feature". I work with IHVs and often have to share private binaries and it's a chore using xcopy/sfpcopy to their bespoke network path, from where I guess then someone manually copies over to their local subnet.
We should have a more robust mechanism in place than to outright ban sharing of executable files. Windows Smartscreen and Mac's Gatekeeper method of online checksum/signature verification is sort of interesting.
You need to build security for the lowest common denominator.
This is like banning guns and cars because they can kill people.
Also, you do 24 hours of lemons?
I don't think the signing itself does much.
Was bored the other week and found a ton of slack web hook urls in public github repos. I think it would be a pretty great way to do some phishing, just need to scrape the urls and brute force channel names with messages with links to websites you own.