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I was having issues with my Exchange installation in that I was being prompted for SSL certificates for the wrong domain which I managed to resolve via this: post Outlook SSL error when connecting to new exchange 2013 installation. Now that I've updated all my internal / external Urls for the virtual directories some users are being prompted (Constantly) for their User / password which when entered doesn't seem to care and re-prompts seconds later. Everything works as it should when pressing cancel on the dialogue (as though it didn't need to authenticate) but I'm not sure what's causing it.

Another issue which might be related is when trying to activate Automatic Replies from Outlook 2013 a message comes up saying the Server is unavailable which is odd because we can receive / send mail etc.

The commands I ran to update the urls are:

Get-ActiveSyncVirtualDirectory -server EXCHANGE | Set-ActiveSyncVirtualDirectory -ExternalUrl 'https://mail.example.com/Microsoft-Server-ActiveSync' -InternalUrl 'https://mail.example.com/Microsoft-Server-ActiveSync'
Get-AutodiscoverVirtualDirectory -server EXCHANGE | Set-AutodiscoverVirtualDirectory -ExternalUrl 'https://mail.example.com/Autodiscover/Autodiscover.xml' -InternalUrl 'https://mail.example.com/Autodiscover/Autodiscover.xml'
Get-ECPVirtualDirectory -server EXCHANGE | Set-ECPVirtualDirectory -ExternalUrl 'https://mail.example.com/ECP' -InternalUrl 'https://mail.example.com/ECP'
Get-OabVirtualDirectory -server EXCHANGE | Set-OabVirtualDirectory -ExternalUrl 'https://mail.example.com/OAB' -InternalUrl 'https://mail.example.com/OAB'
Get-WebServicesVirtualDirectory -server EXCHANGE | Set-WebServicesVirtualDirectory -ExternalUrl 'https://mail.example.com/EWS/Exchange.asmx' -InternalUrl 'https://mail.example.com/EWS/Exchange.asmx'

Any ideas as to where to start looking into these issues as I'm a little baffled.

Edit: I've tried removing the account / profile and re-adding it (For outlook via Control Panel - Mail) again but it doesn't auto fill the information based on the domain account any more. Adding manually doesn't appear to work either now.

Results from the following:

Get-ClientAccessServer | FT Name,AutodiscoverServiceInternalUri,AutodiscoverServiceExternalUri -Autosize
    Name:           myserver
    InternalUri:    https://my.external.com/AutoDiscover/Autodiscover.xml (This is the same value I have in the internal and external Urls for the above commands I ran
    External:       

Get-OutlookAnywhere | FT Name,EXCHANGE -Autosize
    Name:       Rpc (Default Website)
    EXCHAGE:        

Get-OutlookProvider (3 lines returned)
    Name:   EXCH, EXPR and WEB  
    Server:     
    Cert:       
    TTL:    1 on all
Community
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webnoob
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1 Answers1

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Check output for following cmdlets:

Get-ClientAccessServer | FT Name,AutodiscoverServiceInternalUri,AutodiscoverServiceExternalUri -Autosize

Get-OutlookAnywhere | FT Name,EXCHANGE -Autosize

Get-OutlookProvider

In addition, make sure the version of the Outlook client is properly patched to the minimum required Exchange version.

•Outlook 2013

•Outlook 2010 SP1 with November 2012 Cumulative Update ( available from http://support.microsoft.com/kb/2687623 )

•Outlook 2007 SP3 with November 2012 Cumulative Update ( available from http://support.microsoft.com/kb/2687404 )

•Entourage 2008 for Mac, Web Services Edition

•Outlook for Mac 2011

Vick Vega
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  • I've posted the results of those commands in my OP. I'll look at the links now. – webnoob Jan 15 '15 at 13:49
  • You need to set all these values. I don't have access to the computer at the moment, however please look up for the examles for the following : 1. Set-ClientAccessServer 2.Set-OutlookAnywhere 3. Setting Outlook Provider. Setting those to correct values will resolve your issue. – Vick Vega Jan 15 '15 at 13:53
  • I'm sorry but I don't know what I should be changing them to. Any guidance? – webnoob Jan 15 '15 at 14:12
  • Ok, thanks. It's working out what values I need to set that I am having issues with at the moment (I'm not a full time sys admin so excuse my lack of knowledge). There are lots of options available to set against each of those settings. Do I just need to change the ones you've specfically selected in your calls? – webnoob Jan 15 '15 at 16:07
  • I'll get you the exact info later today. – Vick Vega Jan 15 '15 at 16:40
  • Thanks Vick, I really appreciate your time (in the mean time, it seems all access to outlook has now stopped saying the SSL cert doesn't match (it's looking for the server fqdn, not the remote.mycompany.com that the SSL is set up for). It's voodoo I tell you. – webnoob Jan 15 '15 at 16:42
  • Sorry I can't help any sooner, traveling right now. – Vick Vega Jan 15 '15 at 16:45
  • No need to apologise, I've told people to untick the Require SSL in the proxy settings for now which has allowed connections temporarily. – webnoob Jan 15 '15 at 16:59
  • Let us [continue this discussion in chat](http://chat.stackexchange.com/rooms/20276/discussion-between-vick-vega-and-webnoob). – Vick Vega Jan 15 '15 at 19:29
  • Can you please try entering the chat: http://chat.stackexchange.com/rooms/20276/discussion-between-vick-vega-and-webnoob I'm available now to assist. – Vick Vega Jan 15 '15 at 19:34