Apple added "Announce Messages with Siri" with the release of iOS 13.2 and it was a welcome surprise for me. I missed the feature from the beginning on beta testing for iOS 13. While users happily demonstrated their newly discovered Siri-featured announcements online, I was frustrated to see that I did not have this setting, even though I just upgraded my iPhone to 13.2. So, what's the fix?
Assuming that all other variables are correct, the fix is not at all difficult. There are several ways to make Announce Messages with Siri work. The setting is displayed on one side and the welcome screen on the other side, where you can access the setting.
: Restart your iPhone.
To start, make sure your iPhone is running iOS 13.2. Then just shut down and restart the iPhone. You can use one of two keyboard shortcuts, the Shut Down option in Preferences, the Forced Boot, or AssistiveTouch. After backing up, plug in your AirPods, go to Settings -> Siri & Search -> Announce Messages and turn on "Announce Message with Siri".
Method 2: Forget Your AirPods
If the first method did not work for you, go to Settings -> Bluetooth (or jump there from the Control Center shortcut) and tap ( i). next to your AirPods. Keep in mind that currently only AirPods work with Announce Messages with Siri. Then tap "Forget this device".
Of course, iOS does not trust that you really want to forget your AirPods, so you'll be asked again. Tap "Forgot your device" when it appears. Before you can really forget your AirPods, you must agree that Apple will remove the headphones from all devices in your iCloud account. Again, tap on "forget device" and your AirPods will be forgotten.
Now hold down the back button with your AirPods in the charging case until the green or yellow light disappears to put the case in pairing mode. Open the lid of your AirPods case and your AirPods should appear directly on the display of your iPhone. Tap "Connect" and you should be greeted with the "Message Announcement Welcome" screen. Tap Announce Messages with Siri and your pairing process is complete.
Now all you have to do is go to Settings -> Siri & Search. There you will find your new setting under "Announce Messages". Since you typed "Announce messages with Siri" in the previous step, the option should already be enabled. From here, Siri reads your messages out loud while your AirPods are connected.