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Tried rebooting and it's still not working. I've done a clean install of watchOS as well, so I don't know what's going on here.
 
Which Watch OS are you using? Raise to speak is for Watch OS 5 which only developers have access to.

Version 5 beta 9.
[doublepost=1535578327][/doublepost]Going to try erasing all settings and re-pairing.
[doublepost=1535581140][/doublepost]Hmm, no luck.
 
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Version 5 beta 9.
[doublepost=1535578327][/doublepost]Going to try erasing all settings and re-pairing.
[doublepost=1535581140][/doublepost]Hmm, no luck.

Update. It does appear to be working now. I guess I wasn’t asking Siri the right questions.
 
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