One of the most common mistakes I’ve made with Siri has been speaking to her as if she can understand pronouns. If were to relay a message to my mother through a friend, I’d say “please tell her that…”, after which point my friend would then go on to my mother and say “I’m supposed to tell you that…”
In other words, my friend would be listening for cues in my message, and wouldn’t simply repeat it verbatim to my mother. I understand that Siri can’t do this based on names (especially for names like Morgan and Tracy), but mothers tend to be women, and fathers tend to be men, and from a user’s perspective, it seems like an oversight to not have some code in place for intelligent pronoun identification. I understand that English is a complex and messy language with more exceptions than rules, but this is one of those instances where the reality of Siri’s limitations smacks you in the face. Simple messages with a very specific structure, such as “please tell my mom that she needs to buy me a car” seem like a reasonable thing to expect, given that meeting times, lists, and locations can be specified in other instances.
I’m now trying to simply dictate messages differently, as if the command was separated from the content by a colon (e.g. “tell my mother: sorry, I’ll be late for dinner”), and it is working far more consistently. Unfortunately, it just doesn’t feel quite as natural.