For some reason I can't send iMessages from my Apple Watch! When I text somebody with an iPhone, it sends as a text message instead of an iMessage. Then, I get a notification that the text message failed to send. Has anybody else experienced this?
Thank you, I did have 2FA turned on! That indeed fixed the issue for me. For others, here are the steps:
1. Go to appleid.apple.com
2. Select "Password and Security"
3. Click on Generate App Specific Password
4. Enter "iPhone Messages" or something similar in the "App Name".
5. Click "Generate".
6. Keep this window open.
And now on the iPhone:
1. Go to Settings -> Messages.
2. Turn off iMessage.
3. Turn on iMessage.
4. In the password field, enter the app-specific password generated above.
6. That's it!
Apple Watch will now use iMessages instead of text messages.
It's pretty weird that there's no information on this and Apple even recommends people turn on 2FA.