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We currently have an Exchange 2013 setup, which I am in the process of migrating to Office 365, we have a domain which we are going to add for future use for emails. At this moment in time that domain.co.uk has been partly verified (added the TXT records but not the MX records as it may route all live email traffic and cause us to have to do the migration straight away during office hours!) So at the moment only a handful around 4 or 5 users have office 365 business installed, which is connecting to our on-premises Exchange 2013 server which is fine.

The problem comes when users connect via our Watchguard XTM525 firewall from home which logs them in fine, but as soon as they load up their Outlook they get a credentials box pop-up which not only asks for there own email credentials such as [email protected] but then also asks for [email protected].

Is there any way in which I can stop the credentials boxes from popping up ? We are also looking for a cloud only deployment not a hybrid server deployment.

Thanks

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  • Are they logging in on a domain laptop as a domain user or from their personal home computers? Sep 29, 2016 at 10:18
  • Using company laptops logging into the VPN which is attached to the .local domain.
    – Danw
    Sep 29, 2016 at 10:33

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I've had a similar problem with Exchange 2010 in hybrid, except my pop-ups were showing up for on-prem hybrid users. I got rid of them by changing DNS records for autodiscover, i.e., changing where autodiscover pulls its information from.

O365 support says to point autodiscover to Microsoft's Exchange server. That caused problems/pop-ups for me.

Instead, I changed the DNS records for autodiscover.company.com and autodiscover.company.local to point to the on-prem server. In other words: in the DNS server(s) for your VPN connections, add entries to both local and external domains to point to the IP of your on-prem server.

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