Having to do 10's of ElasticSearch v2 -> 6 client requests migration manual deploys of a 10-year old PHP/ Javascript codebase where the gulp build's plugins no longer work, the package dependencies have been .gitignore'd (who does that!), and dev cowboys have frequently bypassed version control by making changes directly in production.

Also, no one knows anything about it because the only dev who was supposed to maintain this app left 3 months ago due to unbearable management.