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Make sure you’ve added your accounts in the Outlook app on iPhone
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Make sure mail is syncing in the Outlook app on iPhone
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Make sure there’s connectivity between the iPhone app and the Watch (i.e. Bluetooth is turned on for iPhone and the Watch is not in airplane mode; also make sure you don’t see the red icon with the phone crossed out on your Watch: this indicates that the Watch isn’t able to communicate with your Phone
If the Watch app continues to not surface recent information/not stay up to date with incoming mail try the following when there’s connectivity between iPhone and Watch:
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Go to the Watch app on iPhone
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Scroll to the Outlook app
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Toggle the Show App on Apple Watch to OFF to uninstall
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Toggle Show App on Apple Watch to ON to re-install on Watch
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Launch Outlook app on Apple Watch and wait for data to sync to latest
Or
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Press and hold the side button on the Apple Watch
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Slide to Power Off the Watch
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Press and hold the side button on the Apple Watch
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Wait for the device to Power On
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Launch Outlook app on Apple Watch and wait for the latest data to sync