Hi
Audio messages are not sent:
- When Siri is used to create and send a new message (for example: "Hey Siri, send a message to whom saying what" ), or;
- When sending a message via SMS (text message) / MMS (such as to someone who does not have an Apple device) rather than via iMessage (Apple's messaging service).
To check that your iPhone and watch are configured for using iMessage - including using Siri and audio messages - check these settings:
- iMessage: on your iPhone, go to Settings > Messages - turn on iMessage (it may help to toggle this off and on again, with a pause in between).
- Dictation: on your iPhone, go to Settings > General > Keyboard - turn on Enable Dictation.
- Siri: on your iPhone, go to Settings > General > Siri - turn on (it may help to toggle this off and on again, with a pause in between).
- As you have explained, your watch is already configured to send audio messages rather than dictated text when applicable (via the Watch app: My Watch > Messages > Audio Messages > Always Audio).
With these settings, audio messages can be sent when:
- Sending a new message using the Messages app on your watch (rather than entirely via Siri);
- Replying to a message on your watch (tap on Reply, then on the Microphone symbol to record your message).
For more instructions on using each method, see this support article:
Use Messages with your Apple Watch - Apple Support
More information:
If you can't send or receive messages on your iPhone, iPad, or iPod touch - Apple Support
Use Messages with your iPhone, iPad, or iPod touch - Apple Support