Hmm, good point. "My outlook" might actually be correct.
Depending on if it is a webapp or the real one running on your device that is.
Similiar to "My game just crashed".
Jira otoh is not yours, because it's in the cloud. It might be "my internet connection", "my browser" or "my account" that is having trouble.
___
Hm. "My train got delayed" is interesting in this context.
I don't find that offensive. But that also might be because trains don't seek rent the way SaaS does? Not sure.
I guess trains do not hold me hostage. They might just be a container in which someone does that.
Jira, cloud LLM inference or similar otoh..