Not an embarassing, but definitely a distinctive junior tech experience:
in the outgoing 80ies, when I finished my engineering degree (as an automotive engineer), I started my career as CAD consultant at Control Data. In my very first week (literally my second day), they sat me into a plane to Turkey to hold a CAD training at a Turkish university. Had done the same at home as an intern previously, but this was my very first business trip abroad and my very first training to be held in English language (which obviously isn't my mother tongue). Besides that, the number of words I knew in Turkish was about five or six with no Google translate or Siri at hand as both still had to be invented. You probably can imagine that I started the trip with some mixed feelings...
Anyway, I started to gain some self-confidence as the first day went relatively smooth, training went better than expected (with a lot of nice help from the students that were really eager to learn), only interrupted by several intermittent power cuts while we needed to wait for the mini (I think it was a Cyber 930) to come up again. However, during the following night, there apparently was another power cut and that obviously was one too much for the poor 930 : it refused to come up again.
I didn't have any experience in hardware, neither had seen a 930 in flesh before nor knew any but the most basic NOS/VE commands to bring the CAD system up, but my students looked at me full of expectations since, after all, I was the CDC expert

. With no mobiles, not even a fixed line at their "data center" besides the ultra-modern single phone link that was used for the 930 to call home (which it couldn't since that only worked after it came up), it obviously was my task now to do that (CDC didn't have any mini-capable local services as it was allowed to import such high-tech as the 930 into Turkey only just recently).
Remember: no mobiles, no Internet, no Google, not even a camera to take a picture of the cryptic console messages the sick 930 spit out.
Anyway, with the really nice help of the students, an improvised phone line to the console (a cable running cross-buildings through about half of the campus), my CDC colleagues at the phone remote-controlling my hands, a soldering iron (to repair a broken connector of the replacement disk unit they had which was my very first soldering job) we eventually managed to fix the 930 and bring it up again and lost only like six hours.
My first week as a CAD consultant.