I noticed that someone attempted to use the text-based “shruggy” in a message recently, and that because Discourse uses markdown, that poor shruggy lost an arm. I’ve added this to the auto-replace list on the site, so the following shruggy should be converted to ¯\\\_(ツ)_/¯ with extra escape \ characters and Just Work:
¯\_(ツ)_/¯
Hmm. It does not.
How about now? ¯\_(ツ)_/¯
I guess I’ll just have to learn the unicode name and use that. Thanks for trying though! 
Edit to add: If you can auto-replace a better unicode graphic, I’d be all for that. 
I feel like if someone has gone to all the trouble to make the text-based shruggy they should get to keep the text. 
¯\_(ツ)_/¯ ?
It works! ¯\_(ツ)_/¯
Just had to use the back tics 
I also tend to always try symbols using the text method of starting a string with : and then letting it complete things. (Force of habit from weechat)
So, : + “shrug” will find the two shrugging emoticons: , 
And there’s also the typing booster that gives lots of options, but I’m not sure if they’re displayed correctly on Discourse: 
A-ha! Got it working!
¯\_(ツ)_/¯
Hammered at it for three hours to get a string of 9 ascii characters to display correctly – now that is “grit”! 
¯\_(ツ)_/¯