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Recently I've set up Exchange Server 2016, configured external DNS accrodingly. Server itself works fine, can send and receive emails. OWA is working fine aswell (externally and internally).

Issue is that Autodiscover is not working properly. I can open it externally via https://example.com/autodiscover/autodiscover.xml (it prompts for user and password), but cant set up an account automatically in Outlook. Outlook prompts for server address and domain credentials. I have no problem typing those, but I need to solve this issue due users.

When testing Autodiscover in Microsoft Connectivity Analyzer it reports no errors whatsoever.

  • Are you using the same account e-mail address and password in the connectivity analyzer that you are trying to autodiscover in Outlook? – Todd Wilcox Nov 10 '17 at 14:21
  • Yes, made an additional email box from who made those tests. – Jon Nov 10 '17 at 17:17
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Are you setting up the clients externally or internally (and do both fail)? Can you scrub & post output of:

Get-OutlookProvider 
Get-OutlookAnywhere
Get-ClientAccessServer

Most of the time I see problems with those values.

AutodiscoverServiceInternalUri. InternalHostName & ExternalHostName.

Requiring SSL? Authentication method? Assume you have a CA generated certificate installed and it's trusted by clients (some CA's require the Intermediate cert installed too).

  • If the cert(s) were not solid then the MCA wouldn't pass. – Todd Wilcox Nov 10 '17 at 14:56
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Do Outlook works after enter the server name (it's the Exchange GUID for user mailbox normally) and mailbox credential? Does internal Outlook client working fine with autodiscover?

I suppose the autodiscover works (get error 600 when browser autodiscover URL) and has valid certificate for autodiscover.

As we known, the MAPI over HTTP will enabled by default in Exchange 2016. Thus, run "Get-MapiVirtualDirectory" to view the URL and authentication settings of it. Also, check the settings of Outlook provider, Outlook Anywhere as Finny mentioned above. Ensure those FQDNs are valid by DNS resolution.

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