Depends on the demographic I think. And also tells you surprisingly much about how the brain of person uttering it works.
There are people that almost feel physical pain if something is unnecessarily incorrect.
+ That if the mental model of something is accurate, it is actually _more_ work to say something that is incorrect than just saying the correct thing.
> tells you surprisingly much about how the brain of person uttering it works
That's ridiculous. You wouldn't respond to "I went to visit my doctor yesterday" with "but slavery has been illegal since forever!" Similarly it would be foolish to respond to "where should we meet? my place or yours" with "but we both rent!"
In my mental model, "my Outlook" is the outlook instance running on my computer, on my data. My outlook crashed today. Yours might not have crashed. Similarly, my Jira contains tickets about my work, your Jira does not contain those same tickets. That might be technically the same instance on the same SaaS server, but the server I'm routed to accessing my data with my credentials turns it into "my Jira". My Jira is slow. Maybe you are lucky and get routed to a faster server, or your company is self-hosting. Then your Jira might be reasonably fast