Outlook and Apple Mail not working with Email Migration

In Outlook, the date of old emails is not showing, so they are sorted incorrectly. For example, a message from 2013 and one from yesterday (and about 100 more with varied dates) say they were received Wednesday 10:47pm (the night before migration). Then hundreds more say Tuesday 1:09pm. 

In Apple Mail, dates and times are accurate back to March 18th, then about 1000 messages are missing as it jumps right to 2015.

Please do not tell me that the solution is to use Gmail - if I wanted to do that I would be using Gmail already. Super frustrated with Telus - no help from support - on the phone with Shaw right now.