Android MS Outlook notifications stopped showing up on Wear.

I've been using Outlook on my Galaxy S5 for a while now and was getting email notification on my watch (Moto 360 2nd gen) without difficult. Then I just stopped getting email notifications. I appear to still be getting calendar notifications, but not email.

I did two things around the time when the notifications stopped:
1.) Installed an app on my phone create extra vibrations on the watch when notifications were received (Feel the Wear).
2.) Setup the default sammy calendar to sync with my work's Exchange calendar so I could get calendar info in WatchMaker.

To trouble shoot I've tried:
a.) Uninstalling the app listed above and removing the calendar sync setup.
b.) Uninstalling and re-installing MS Outlook
c.) Verifying that Outlook is not listed as a block/ignore app in Android Wear
d.) Forgetting and reconnecting my watch
e.) Verified that I'm getting outlook notifications properly on my phone.
f.) Searching google and xda... couldn't find anything, but I'll admit I didn't do a super huge search here in xda.

Anyone have any ideas? I'm working around this right now by using eNotify, but I hate to use additional programs to do something that I should be able to do without them.

Download from this link