The best examples that come to mind are when ordering food. As examples:
• You speak English and Spanish and are ordering a burrito
• You speak Thai and English and are ordering Tom Yum
I imagine it could depend on numerous things:
• You primary language or ethnicity
• What sort of restaurant
• Who you’re dining with
• Who you’re ordering from
• and probably a lot more…
The old ones do, but young people think I’m cringe. I personally find it way more cringe if I pronounce the rest of the sentence with a strong American accent though, so my friends can call me cringe and I’m okay with it. Regarding my other example, „der Song,“ I tend to just say „das lied” instead, because I recognize that pronouncing it like „der (Minne)sang“ with an o is wrong and hard to understand.
But why do you get an American accent when you pronounce “Microsoft” like a German who speaks English with a German accent? “ai” and sharp s are common sounds in German.
My brain just gets confused, and it automatically switches. I’d like to be able to go back and forth easily, but I can’t. It might come in time, but for now I just stick with the pronunciation that leads from the spelling and standard German pronunciation rules (somewhat tailored to the local dialect)