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Exchange 2013 and Outlook 2016

We are running exchange server 2013. We have a security certificate created by Microsoft that allows users outside our office to use Outlook and eliminate the security warning when using OWA. Some users who have Outlook 2016 are not able to connect to their email because of autodiscover service needs to active. Is this a simple process and how does it affect users of Outlook 2013 or 2010 who have installed a security certificate which has allowed them to use Outlook?

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