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Man, most memorable has to be the lead devops engineer from the first startup I worked at. My immediate team/friends called him Mr. DW - DW being short for Done and Working.

You see, Mr. DW was a brilliant devops engineer. He came up with excellent solutions to a lot of release, deployment, and data storage problems faced at the company (small genetics firm that ships servers with our analysis software on them). I am still very impressed by some of the solutions he came up with, and wish I had more time to study and learn about them before I left that company.

BUT - despite his brilliance, Mr. DW ALWAYS shipped broken stuff. For some reason this guy thinks that only testing a single happiest of happy path scenarios for whatever he is developing constitutes "everything will work as expected!" As soon as he said it was "done", but golly for him was it "done". By fucking God was that never the truth.

So, let me provide a basic example of how things would go:
my team: "Hey DW, we have a problem with X, can you fix this?"
DW: "Oh, sure. I bet it's a problem with <insert long explanations we don't care about we just want it fixed>"
my team: "....uhh, cool! Looking forward to the fix!"
... however long later...
DW: "OK, it's done. Here you go!"
my team: "Thanks! We'll get the fix into the processing pipelines"
... another short time later...
my team: "DW, this thing is broken. Look at all these failures"
DW: "How can that be? It was done! I tested it and it worked!"
my team: "Well, the failures say otherwise. How did you test?"
DW: "I just did <insert super basic thing>"
my team: "...... you know that's, like, not how things actually work for this part of the pipeline. right?"
DW: "..... But I thought it was XYZ?"
my team: "uhhhh, no, not even close. Can you please fix and let us know when it's done and working?"
DW: "... I'll fix it..."

And rinse and repeat the "it's done.. oh wait, it's broken" a good half dozen times on average. But, anyways, the birth of Mr. Done and Working - very often stuff was done, but rarely did it ever work!

I'm still friends with my team mates, and whenever we're talking and someone says something is done, we just have to ask if it's done AND working. We always get a laugh, sadly at the excuse of Mr. DW, but he dug his own hole in this regard.

Little cherry on top: So, the above happened with one of my friends. Mr. DW created installation media for one of our servers that was deployed in China. He tested it and "it was done!" Well, my friend flies out to China for on-site installation. He plugs the install medium in and goes for the install and it crashes and burns in a fire. Thankfully my friend knew the system well enough to be able to get everything installed and configured correctly minus the broken install media, but definitely the most insane example of "it's done!" but sure as he'll "it doesn't work!" we had from Mr. DW.