We had a rough time with a customers Outlook 2016. It wouldn’t start and would give us the “Cannot start Microsoft Outlook” error. We repaired the OST and reinstalled Office 2016, but this didn’t fix the issue. It would seem like the error was fixed, but after a restart the issue would come back.

We used the following link to lead us to the right resolution.
https://support.office.com/en-us/article/Fix-your-Outlook-email-connection-by-repairing-your-profile-4D5FEBF6-7623-486B-9A9F-D5CFC4264AF3

We then downloaded the repair tool from this page.

https://support.office.com/en-us/article/Fix-your-Outlook-email-connection-by-repairing-your-profile-4D5FEBF6-7623-486B-9A9F-D5CFC4264AF3

We ran the tool and got the following message.

Which lead us to turn off IPV6.

• Go to Control Panel
• Click on “Network and Sharing Center”.
• Click on the given “Network Connection”.
• Click “Properties”.
• On the “Networking” tab, clear the “Internet Protocol Version 6 (TCP/IPv6) check box, and then click “OK”.

Let us know if this helped your issue…