If you're having trouble with using Outlook on the Apple Watch, here are some handy troubleshooting steps.
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Go to the Watch app on your iPhone.
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Scroll to the Outlook app.
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Toggle Show App on Apple Watch to OFF to uninstall.
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Toggle Show App on Apple Watch to ON to reinstall on your watch.
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Launch the Outlook app on the Apple Watch and wait for your data to sync.
If your problem isn't resolved, we'd be happy to help. In the Outlook app, select Settings > Help & Feedback > Contact Support.