I think there's a problem in how Microsoft communicates with outside of the campus.
For example, calling a technology "legacy" doesn't mean that it's obsolete or abandoned. The day after Vista shipped, for example, everybody in the Windows team called it (Vista) legacy, as opposed to the new OS that was in development, to avoid internal confusion.
That makes perfect sense within the organization, but when exposed to the outside world, where these words have different attached connotations, it creates confusion.
Another aspect is the continued effort from all the industry to use acronyms and shorthands to indicate concepts that could be very well communicated in a plainer fashion. Just yesterday, an architect in my team kept using a couple of acronyms (because that's what they do all day in their job) when in a meeting with the business team. I noticed that their eyes were glazing away and I interrupted with "hang on a sec. Guys, do you know what <xxx> means? No? It stands for blah blah blah". Took two seconds and everyone was happy. But that happened because there was an immediate interaction and explanation, and that's hard when you communicate via email or press releases.