Here's 12 Sysadmin/DevOps (they're synonyms now!) challenges, straight from the day job:

  1.  Get a user to stop logging in as root.
  2.  Get all users to stop sharing the same login and password for all servers.
  3.  Get a user to upgrade their app's dependencies to versions newer than 2010.
  4.  Get a user to use configuration management rather than scp'ing config files from their laptop to the server.
  5.  Get a user to bake immutable images w/configuration rather than using configuration management.
  6.  Get a user to switch from Jenkins to GitHub Actions.
  7.  Get a user to stop keeping one file with all production secrets in S3, and use a secrets vault instead.
  8.  Convince a user (and management) you need to buy new servers, because although "we haven't had one go down in years", every one has faulty power supply, hard drive, network card, RAM, etc, and the hardware's so old you can't find spare parts.
  9.  Get management to give you the authority to force users to rotate their AWS access keys which are 8 years old.
  10. Get a user to stop using the aws root account's access keys for their application.
  11. Get a user to build their application in a container.
  12. Get a user to deploy their application without you.

After you complete each one, you get a glass of scotch. Happy Holidays!