Q: Apple Watch text message dictation is not working sometimes

You can try to reset your Apple Watch, it may help you. Turn your watch off and back on. If this does not help, press and hold the side button and the Digital Crown for 10 seconds or more, until the Apple logo appears on the screen.

https://support.apple.com/en-us/HT204510

Hi

The Messages app on Apple Watch can be configured to handle dictated messages in different ways.

To check and, if appropriate, to change your chosen setting:

• On your iPhone, in the Watch app, go to: My Watch (tab) > Messages > for Audio Messages, choose between:
  • Dictation or Audio (to be offered the choice each time you reply);
  • Always Dictation;
  • Always Audio.

If you have not yet done so, it may also help to update your iPhone and Apple Watch to the latest software, starting with your iPhone:

Update the iOS software on your iPhone, iPad, or iPod touch - Apple Support

Update the software on your Apple Watch - Apple Support

If you continue to experience problems with dictation, try these steps:

- On your iPhone, go to: Settings > General > Siri - disable, pause for a few moments and then re-enable Siri.

If that does not immediately help, try also restarting both devices afterwards. Turn both devices off together, then restart your iPhone first.

- To turn off / restart your watch: press and hold the side button until you see the Power Off slider; drag it to turn off.

- When ready to turn back on, press and hold the side button until you see the Apple logo.

D.Cohen wrote:

 

You can try to reset your Apple Watch, it may help you. Turn your watch off and back on. If this does not help, press and hold the side button and the Digital Crown for 10 seconds or more, until the Apple logo appears on the screen.

https://support.apple.com/en-us/HT204510

Note that it is not appropriate to force restart your watch (by pressing and holding both buttons).

Except under certain circumstances (this is not among them), as the linked support article explains, Apple Watch should only be force restarted "as a last resort and only if it's not responding".

You're most welcome!