I assume you have android phone?
First check if outlook app notifications are blocked on the wearOS app. If you DO recieve notifications, but your watch just doesn't vibrate, then the likely issue may be related to sound. Note: IF the notification sound is "silence" i.e. "show notification silently" or "do not make sound" or similar options (options may be different based on your version of android) then the watch will not vibrate. Watch only vibrates for notifications where the phone would have otherwise made a sound (a ringtone that is 5s of silence is technically a "sound", it's just that SOME kind of ringtone needs to be set rather than the "no ringtone" option). If that isn't the issue then try reinstalling the outlook app on your watch, maybe that'll solve it.
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