First of all, could you please wrap your console output in a code block instead of a quote block? There’s Markdown syntax being interpreted in there.
Secondly, no, I’m not seeing it.
notriddle@wsl:~$ ssh ubuntu@52.26.80.122
Welcome to Ubuntu 16.04.3 LTS (GNU/Linux 4.4.0-92-generic x86_64)
* Documentation: https://help.ubuntu.com
* Management: https://landscape.canonical.com
* Support: https://ubuntu.com/advantage
Get cloud support with Ubuntu Advantage Cloud Guest:
http://www.ubuntu.com/business/services/cloud
68 packages can be updated.
0 updates are security updates.
*** System restart required ***
Last login: Thu Jan 4 00:59:09 2018 from 70.184.74.19
ubuntu@ip-172-31-27-237:~$ sudo -i
root@ip-172-31-27-237:~# cd /var/discourse/
root@ip-172-31-27-237:/var/discourse# ls
bin cids containers discourse-setup image launcher README.md samples scripts shared templates Vagrantfile
root@ip-172-31-27-237:/var/discourse# ./launcher enter app
root@ip-172-31-27-237-app:/var/www/discourse# rails c
[1] pry(main)>
It did take me like a minute after hitting enter at “rails c” before the pry prompt came up. Maybe wait longer?