Outlook 2011/365 connectivity to Exchange 2010

Hey Everybody,
I'm running into a little bit of jam with Outlook 2011/365 from my Mac population to Exchange 2010 SP3 Rollup 8 v2. I have read many articles and discussion forums regarding the issues with SSL and TLS connectivity. I have verified that my windows host with
Outlook are just fine in setup and use of the Exchange server.
The Mac systems are having the issues. Autodiscover is working ok and IPhone/Ipad configure just fine. We really only have two, so this is why it was a surprise.
If I browse to the EWS directory it is just a blank page receive from any browser on the Mac's.
What is the issue with Outlook 2011 and 365 connecting to a exchange system during configuration?
Would joining the Mac's to the domain make a difference?
With Poodle being one of the most recent risks, what should Mac user be configured as to not bring a security risk to the rest of the environment.
Is reseting the virtual directories a possible action or is the most common issue just SSL and TLS compatibility?
Is there anyways around this without having to turn on basic security on EWS and fall back to SSL instead of TLS?
What is the best ways of testing connectivity with logging other then just seeing the error 17997 from Outlook on the Mac.
Thoughts? Recommendations? Tips?
Thanks,
Matthew

Hi Matthew,
According to your description, I noticed that the issue doesn’t happen in Outlook for Windows but occurs in Outlook 2011 for Mac.
Please access the EWS URL from Internet Explore in Windows instead of Mac machine, and check whether a proper XML file is returned. If the XML file returns in Windows for the problematic account, it indicates the EWS service should be working in Server side.
The issue may be related to client side in Outlook 2011 for Mac machine, I suggest we can ask a question in Outlook for Mac forum for more help:
http://answers.microsoft.com/en-us/mac/forum/macoutlook?tab=Threads
If the EWS service doesn’t work in Windows either, please check whether users can view free/busy information in OWA. Then run the following command to check the EWS configuration in server:
Get-WebServicesVirtualDirectory | FL Identity,*AUTH*,*url*
Regards,
Winnie Liang
TechNet Community Support

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Hi,
Don´t disable IPV6 on an Exchange Server, it is, in my opinion not necessary - also applies for AD.
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In dns you want two host A records: mail.domain.com and autodiscover.domain.com
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Outlook 2011 not connecting to exchange server

Hi,
I am trying to use outlook 2011 with my Mac to connect to my Company server Exchange with no success
while I can do it fine with the Mac native aplication "Mail".
Here after the Exchange Server Connectivity Test (in italian) which has been passed:
Altri dettagli Impostazioni account del servizio di individuazione automatica Risposta XML: <?xml version="1.0"?>
<Autodiscover xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns="http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006"> <Response xmlns="http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a">
<User> <DisplayName>GGGGG GIAMBERTO</DisplayName> <LegacyDN>/o=Messaging/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=U333</LegacyDN> <DeploymentId>4e25f968-2a52-4b3e-a495-85893d549218</DeploymentId>
</User> <Account> <AccountType>email</AccountType> <Action>settings</Action> <Protocol> <Type>EXCH</Type> <Server>outlook-to.sede.corp.NN.com</Server> <ServerDN>/o=Messaging/ou=Exchange
Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=outlook-to.sede.corp.NN.com</ServerDN> <ServerVersion>7383807B</ServerVersion> <MdbDN>/o=Messaging/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=outlook-to.sede.corp.NN.com/cn=Microsoft
Private MDB</MdbDN> <ASUrl>https://webmail-01.XX.com/ews/exchange.asmx</ASUrl> <OOFUrl>https://webmail-01.XX.com/ews/exchange.asmx</OOFUrl> <OABUrl>https://webmail-01.XX.com/OAB/8b29a335-91f9-459d-8226-af3af35a0f11/</OABUrl>
<UMUrl>https://webmail-01.XX.com/ews/UM2007Legacy.asmx</UMUrl> <Port>0</Port> <DirectoryPort>0</DirectoryPort> <ReferralPort>0</ReferralPort> <PublicFolderServer>EXC10TSPPF00.sede.corp.NN.com</PublicFolderServer>
<AD>RSDCFTS008.filiali.corp.NN.com</AD> <EwsUrl>https://webmail-01.XX.com/ews/exchange.asmx</EwsUrl> <EcpUrl>https://webmail-01.XX.com/ecp/</EcpUrl> <EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
<EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr> <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt> <EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
</Protocol> <Protocol> <Type>EXPR</Type> <Server>webmail.XX.com</Server> <ASUrl>https://webmail-01.XX.com/ews/exchange.asmx</ASUrl> <OOFUrl>https://webmail-01.XX.com/ews/exchange.asmx</OOFUrl> <OABUrl>https://webmail-01.XX.com/OAB/8b29a335-91f9-459d-8226-af3af35a0f11/</OABUrl>
<UMUrl>https://webmail-01.XX.com/ews/UM2007Legacy.asmx</UMUrl> <Port>0</Port> <DirectoryPort>0</DirectoryPort> <ReferralPort>0</ReferralPort> <SSL>On</SSL> <AuthPackage>Ntlm</AuthPackage>
<CertPrincipalName>msstd:webmail.XX.com</CertPrincipalName> <EwsUrl>https://webmail-01.XX.com/ews/exchange.asmx</EwsUrl> <EcpUrl>https://webmail-01.XX.com/ecp/</EcpUrl> <EcpUrl-um>?p=customize/voicemail.aspx&exsvurl=1</EcpUrl-um>
<EcpUrl-aggr>?p=personalsettings/EmailSubscriptions.slab&exsvurl=1</EcpUrl-aggr> <EcpUrl-mt>PersonalSettings/DeliveryReport.aspx?exsvurl=1&IsOWA=<IsOWA>&MsgID=<MsgID>&Mbx=<Mbx></EcpUrl-mt> <EcpUrl-ret>?p=organize/retentionpolicytags.slab&exsvurl=1</EcpUrl-ret>
</Protocol> <Protocol> <Type>WEB</Type> <Port>0</Port> <DirectoryPort>0</DirectoryPort> <ReferralPort>0</ReferralPort> <Internal> <OWAUrl AuthenticationMethod="Basic, Ntlm, Fba, WindowsIntegrated">https://webmail-01.XX.com/owa/</OWAUrl>
<OWAUrl AuthenticationMethod="Ntlm, WindowsIntegrated">https://webmailint-01.XX.com/owa/</OWAUrl> <OWAUrl AuthenticationMethod="Basic, Ntlm, WindowsIntegrated">https://webmailint-01.XX.com/owa/</OWAUrl> <Protocol>
<Type>EXCH</Type> <ASUrl>https://webmail-01.XX.com/ews/exchange.asmx</ASUrl> </Protocol> </Internal> <External> <OWAUrl AuthenticationMethod="Fba">https://webmail-01.XX.com/owa/</OWAUrl> <Protocol>
<Type>EXPR</Type> <ASUrl>https://webmail-01.XX.com/ews/exchange.asmx</ASUrl> </Protocol> </External> </Protocol> </Account> </Response> </Autodiscover> Intestazioni risposte HTTP: Connection: Keep-Alive
Transfer-Encoding: chunked Persistent-Auth: true Cache-Control: private Content-Type: text/xml; charset=utf-8 Date: Wed, 11 Feb 2015 05:31:48 GMT Server: Microsoft-IIS/7.5 X-AspNet-Version: 2.0.50727 X-Powered-By: ASP.NET Tempo trascorso: 1894 ms.
And hereafter the Trouble shooting log of Outlook 2011:
Outlook Exchange Auto Configure,Verbose,=== Performing autodiscover for [email protected]
Outlook Exchange Auto Configure,Verbose,--- HTTPS endpoints
Outlook Exchange Auto Configure,Verbose,Querying https://xx.com/autodiscover/autodiscover.xml
Outlook Exchange Web Services,Verbose,"EWS: Request data on thread=0x7a2bf264, XML data=
<?xml version=""1.0"" encoding=""UTF-8""?><soap:Envelope xmlns:soap=""http://schemas.xmlsoap.org/soap/envelope/"" xmlns:t=""http://schemas.microsoft.com/exchange/services/2006/types""
xmlns:m=""http://schemas.microsoft.com/exchange/services/2006/messages""><soap:Header><t:RequestServerVersion Version=""Exchange2007_SP1"" /><t:MailboxCulture>it-IT</t:MailboxCulture><t:TimeZoneContext><t:TimeZoneDefinition
Id=""XXX Standard Time""/></t:TimeZoneContext></soap:Header><soap:Body><GetFolder xmlns=""http://schemas.microsoft.com/exchange/services/2006/messages""><FolderShape><t:BaseShape>IdOnly</t:BaseShape></FolderShape><FolderIds><t:DistinguishedFolderId
Id=""inbox""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId Id=""outbox""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId
Id=""contacts""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId Id=""calendar""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId
Id=""notes""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId Id=""tasks""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId
Id=""journal""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId Id=""sentitems""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId
Id=""deleteditems""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId Id=""drafts""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId
Id=""junkemail""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId><t:DistinguishedFolderId Id=""root""><t:Mailbox><t:EmailAddress>[email protected]</t:EmailAddress></t:Mailbox></t:DistinguishedFolderId></FolderIds></GetFolder>"
2015-02-28 11:44:10.075,0xFFFFFFFF,Outlook Exchange Web Services,Info,"EWS: Sending request on connection=0x7a399eb8, URL=/ews/Exchange.asmx, SoapAction=""http://schemas.microsoft.com/exchange/services/2006/messages/GetFolder"""
Outlook Exchange Auto Configure,Error, Error code: -3259
Outlook Exchange Auto Configure,Verbose,Querying https://autodiscover.xx.com/autodiscover/autodiscover.xml
Outlook Exchange Auto Configure,Error, Error code: -39
Outlook Exchange Auto Configure,Verbose,--- HTTP redirect endpoint
Outlook Exchange Auto Configure,Info, Error code: -3259
Outlook Exchange Auto Configure,Verbose,--- DNS SRV method
Outlook Exchange Auto Configure,Error, Error code: -3176
Outlook Exchange Auto Configure,Verbose,No _autodiscover._tcp.xx.com service found
Outlook Exchange Auto Configure,Verbose,--- HTTPS endpoints
Outlook Exchange Auto Configure,Verbose,Querying https://webmail.xx.com/autodiscover/autodiscover.xml
Outlook Exchange Auto Configure,Error, Error code: -39
Outlook Exchange Auto Configure,Verbose,Querying https://autodiscover.webmail.xx.com/autodiscover/autodiscover.xml
Outlook Exchange Auto Configure,Error, Error code: -3259
Outlook Exchange Auto Configure,Verbose,=== Failed to retrieve autodiscover settings for [email protected]
Outlook Exchange Web Services,Verbose,"EWS: Request data on thread=0x7c20cee4, XML data=
Can somebody help?
Thank you in advance

Hi,
The connection in Outlook 2011 for Mac is difference from the Exchange connection in Outlook for Windows. The Outlook for Mac is using EWS for Exchange connection.
According to your original posting, there seems to be some issue with your autodiscover service. And some Exchange services (such as OAB, OOF, OWA etc.) are using webmail-01.xx.com namespace in the URL. Please double confirm the configuration in your Exchange
server.
Additionally, please check the autodiscover service on Outlook for Windows machine. If all configurations in server side are correct but the issue persists, I suggest we can ask a question in Outlook 2011 for Mac forum for more help:
http://answers.microsoft.com/en-us/mac/forum/macoutlook?tab=Threads
Regards,
Winnie Liang
TechNet Community Support

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At this point, We high recommand that we run Microsoft Connectivity Analyzer Tool from the folloing link to check what was happening
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Come back and mark the replies as answers if they help and unmark them if they provide no help.
If you have any feedback on our support, please contact
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Hi,
Firstly, I’d like to explain, same with external users, internal users use Outlook Anywhere to connect with Exchange server and use Autodiscover get all settings.
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Angela Shi
TechNet Community Support

Outlook Can't connect to Exchange Server

Dear All;
I install the exchange server 2013 in our Environment with basic configurations, it was work correctly in out look and OWA.
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Here are the default permissions for the Exchange virtual directories:
http://technet.microsoft.com/en-us/library/gg247612(v=exchg.150).aspx
I found that the print in the screenshots was not clear - maybe it's me or my browser.
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Say for instance i am coexisting exchange 2010 with exchange 2013 .Unfortunately if all of my exchange 2013 servers goes down .
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http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx<o:p></o:p>
Internal Outlook Connectivity
For internal Outlook clients using RPC/TCP connectivity whose mailboxes exist on Exchange 2010, they will still connect to the Exchange 2010 RPC Client Access array endpoint.
For internal Outlook clients using RPC/TCP connectivity whose mailboxes exist on Exchange 2007, they will still connect directly to the Exchange 2007 Mailbox server instance hosting the mailbox.
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S.Nithyanandham

Hi Winnie Liang ,
Thanks a lot for your reply.
Scenario 1 : for internal outlook connectivity
We have below settings for exchange 2010 autodiscover.
mail.domain.com - will be the namespace for internal autodiscover URI for all the exchange 2010 cas serves
We are going to have below settings for exchange 2013 autodiscover.
mail.domain.com - will be the namespace for internal autodiscover URI for all the exchange 2013 cas serves
During coexistence mail.domain.com will be pointed to exchange 2013 cas servers . I mean to say if we try to resolve the mail.domain.com it will get resolved in to the exchange 2013 cas servers.
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servers for autodiscover request.During the whole exchange 2013 environemnt failure whenever the user tries to close and open outlook .Outlook will first queries the autodiscover service for any changes happened on that particular mailbox and it will try to
get it updated on user profile.
http://blogs.technet.com/b/exchange/archive/2014/03/12/client-connectivity-in-an-exchange-2013-coexistence-environment.aspx
Would it be possible to make the exchange 2010 mailbox users to query only the scp points which belongs to the exchange 2010 cas servers for autodiscover request ?
Scenario 2: For exchange services
mail.domain.com - will be the namespace for all the exchange 2010 services (i.e owa,activesync,external outlook anywhere,pop,imap)
mail.domain.com - will be the namespace for all the exchange 2013 services (i.e owa,activesync,external outlook anywhere,pop,imap)
What about the above services will it get affected during whole exchange 2013 environment failure ?
Note : We are not facing this issue , i hope everything goes well in my environment while doing coexistence i am just asking this question on my own interest?
Regards
S.Nithyanandham
Thanks S.Nithyanandham

Cannot connect my exchange 2010 from outlook outside of my LAN

I have problem connecting to my exchange 2010 server from outside of my LAN.
I have configured Outlook Anywhere and its working.
After i enter all the details it is asking again for password and once i entered the password i receive the error "The action cannot be completed. The Connection to Microsoft Exchange is unavailable etc ... "
Kindly suggest

Hi Angela,
Thanks for the support, kindly check the requested.
[PS] C:\Windows\system32>Get-ExchangeCertificate |fl
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule}
CertificateDomains : {autodiscover.mydomain.com, mydomain.com}
HasPrivateKey : True
IsSelfSigned : False
Issuer : CN=StartCom Class 1 Primary Intermediate Server CA, OU=Secure Digital Certificate Signing, O=Start
Com Ltd., C=IL
NotAfter : 2/25/2015 3:41:54 AM
NotBefore : 2/24/2014 9:47:31 AM
PublicKeySize : 2048
RootCAType : ThirdParty
SerialNumber : 0EB79F
Services : IIS
Status : Valid
Subject : [email protected], CN=autodiscover.mydomain.com, C=KW, Description=vlkZ61QVKE36hUW5
Thumbprint : 2687AAECFD7C53DA14DDEB421D547B42A33E67BA
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule}
CertificateDomains : {*.mydomain.com}
HasPrivateKey : True
IsSelfSigned : True
Issuer : C=KW, S=Kuwait, L=Kuwait, O=mydomain.com, OU=IT, CN=*.mydomain.com
NotAfter : 2/11/2015 3:58:45 PM
NotBefore : 2/11/2014 3:38:45 PM
PublicKeySize : 2048
RootCAType : None
SerialNumber : 6DFCB427D57AE58746B5DF8B070E6455
Services : None
Status : Valid
Subject : C=KW, S=Kuwait, L=Kuwait, O=mydomain.com, OU=IT, CN=*.mydomain.com
Thumbprint : 4A90303EBFA71BB73928E9BFB9FD5D129EEC9270
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule, System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAcc
essRule}
CertificateDomains : {exchange, exchange.mydomain.com}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=exchange
NotAfter : 2/11/2019 6:30:52 AM
NotBefore : 2/11/2014 6:30:52 AM
PublicKeySize : 2048
RootCAType : None
SerialNumber : 7BBA32A69E5DC2B2404406700225B006
Services : IMAP, POP, SMTP
Status : Valid
Subject : CN=exchange
Thumbprint : 565B3D127A98DB2D25FAE71864E58B427F17FC3C
AccessRules : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {WMSvc-EXCHANGE}
HasPrivateKey : True
IsSelfSigned : True
Issuer : CN=WMSvc-EXCHANGE
NotAfter : 2/8/2024 3:44:28 PM
NotBefore : 2/10/2014 3:44:28 PM
PublicKeySize : 2048
RootCAType : Registry
SerialNumber : 168EC4DED2C01B874C8BD6F16E231229
Services : None
Status : Valid
Subject : CN=WMSvc-EXCHANGE
Thumbprint : 736EF13159F0F851EFCC20709C00AE60D5A54C94
Thanks

No calendar connection for Exchange 2010 + Outlook 2013

My environment is this:
Running Outlook 2013 (as part of Office 2013 Suite) connecting to Exchange Server 2010
Both cached and non-cached modes
Connecting using RPC
With both existing profile for last 1yr+ and with a new profile
Outlook v 15.0.4649.1001
The issue I'm having is a room/resource calendar that I was once able to see I can't anymore.
Running Outlook 2010 as the same user from a different computer works fine.
OWA works as well.
Other calendars work
Running Outlook 2013 vs 15.0.4420.1017 also works on a different computer!!!
So this seems to be an issue with my particular version of Outlook, and I did read where a security update seems to have gotten in the way (regression test lately?) but a December patch of 2013 was supposed to fix that. I didn't specifically install the
patch, rather I downloaded from my vendor the latest available version they had.
So is there a patch that will work for me. The only one I've come across tells me it isn't for my machine.
Thanks,
Joe

Hi,
According to your description and test, I understand that the room/resource calendar is invisible in Outlook.
How about changing another user to log on your Outlook?
How about the same version of Outlook on another computer?
Please try to run Outlook under safe mode to avoid some AVs and add-ins.
Please try to re-create profile for testing.
If all method above doesn’t work, please re-install Outlook.
Best Regards,
Allen Wang

Issues connecting Outlook 2011 for Mac to Exchange Server 2013

Could someone help me with the bellow please:
I have a Mac with outlook 2011 on it.
We have recently set up Exchange Server 2013, and all of the Windows Workstation just required the trusted root certificate to be installed and they were working.
However I have spent hours reading different forums trying to get this working on the Mac and no luck.
The auto discover does not work when setting up the exchange email, therefore I have also tried setting up manually but it still will not connect to the server.

Hi,
Please check if the links below help:
How the Autodiscover service works with Outlook for Mac 2011:
http://technet.microsoft.com/en-us/library/jj984202(v=office.14).aspx
A great tool for troubleshooting Autodiscover and Outlook 2011 for Mac connectivity issue:
http://blogs.technet.com/b/johnmak/archive/2012/04/01/a-great-tool-for-troubleshooting-autodiscover-and-outlook-2011-for-mac-connectivity-issue.aspx
Since this forum is for general questions and feedback related to Outlook for Windows, it's better to post your question to the forum for Exchange or for Mac:
Exchange forum:
http://social.technet.microsoft.com/Forums/exchange/en-US/home?category=exchangeserver
Office for Mac forum:
http://answers.microsoft.com/en-us/mac/forum/macoffice2011?tab=Threads
The reason why we recommend posting appropriately is you will get the most qualified pool of respondents, and other partners who read the forums regularly
can either share their knowledge or learn from your interaction with us. Thank you for your understanding.
Steve Fan
TechNet Community Support

Outlook 2010 won't connect to exchange 2010 - logon box appears

Users can't connect to Exchange server from outlook 2010. The domain\user and password boxes keep popping up and will not accept the details. It ends with "the connection to exchange is unavailable. Outlook needs to be online to perform
this action"
I've searched high and low for an answer and none work. Anyone any ideas?
Exchange is behind Threat Management Gateway 2010, with applicable rules setup. Strangeley, Outlook Web Access works fine with no problems what so ever.
Thanks in advance
Andy

Ok. Done some reading and made some adjustments but still pretty much the same. Microsofts Exchange analyser tool come up with the folowing errors and does indeed pinpoint it down to the autodiscover service. The srv record for the autodiscover
service - should that be on my own internal DNS or on my web host DNS?
The results of the connectivity test are below:
Testing RPC/HTTP connectivity.
The RPC/HTTP test failed.
Test Steps
ExRCA is attempting to test Autodiscover for [email protected].
Testing Autodiscover failed.
Test Steps
Attempting each method of contacting the Autodiscover service.
The Autodiscover service couldn't be contacted successfully by any method.
Test Steps
Attempting to test potential Autodiscover URL https://owa.optima-ws.co.uk/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name owa.optima-ws.co.uk in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 78.33.247.168
Testing TCP port 443 on host owa.optima-ws.co.uk to ensure it's listening and open.
The port was opened successfully.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Test Steps
ExRCA is attempting to obtain the SSL certificate from remote server owa.optima-ws.co.uk on port 443.
ExRCA successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=owa.optima-ws.co.uk, OU=Domain Control Validated - GeoTrust(R) SSL Trial, OU=www.geotrust.com/resources/cps, OU=GT52908676, SERIALNUMBER=OyRDVCpo58GRaYQL5CORIFnTYn4Odw9G, Issuer: CN=GeoTrust DV SSL CA, OU=Domain Validated
SSL, O=GeoTrust Inc., C=US.
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
Host name owa.optima-ws.co.uk was found in the Certificate Subject Common name.
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
Test Steps
ExRCA is attempting to build certificate chains for certificate CN=owa.optima-ws.co.uk, OU=Domain Control Validated - GeoTrust(R) SSL Trial, OU=www.geotrust.com/resources/cps, OU=GT52908676, SERIALNUMBER=OyRDVCpo58GRaYQL5CORIFnTYn4Odw9G.
One or more certificate chains were constructed successfully.
Additional Details
A total of 1 chains were built. The highest quality chain ends in root certificate CN=GeoTrust Global CA, O=GeoTrust Inc., C=US.
Analyzing the certificate chains for compatibility problems with versions of Windows.
Potential compatibility problems were identified with some versions of Windows.
Additional Details
ExRCA can only validate the certificate chain using the Root Certificate Update functionality from Windows Update. Your certificate may not be trusted on Windows if the "Update Root Certificates" feature isn't enabled.
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
Additional Details
The certificate is valid. NotBefore = 7/24/2012 7:35:43 PM, NotAfter = 8/25/2012 12:31:49 PM
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Accept/Require Client Certificates isn't configured.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
Test Steps
ExRCA is attempting to retrieve an XML Autodiscover response from URL https://owa.optima-ws.co.uk/AutoDiscover/AutoDiscover.xml for user [email protected].
ExRCA failed to obtain an Autodiscover XML response.
Additional Details
An HTTP 500 response was returned from Unknown.
Attempting to test potential Autodiscover URL https://autodiscover.owa.optima-ws.co.uk/AutoDiscover/AutoDiscover.xml
Testing of this potential Autodiscover URL failed.
Test Steps
Attempting to resolve the host name autodiscover.owa.optima-ws.co.uk in DNS.
The host name couldn't be resolved.
<label for="testSelectWizard_ctl12_ctl06_ctl00_ctl00_ctl01_ctl00_tmmArrow">Tell
me more about this issue and how to resolve it</label>
Additional Details
Host autodiscover.owa.optima-ws.co.uk couldn't be resolved in DNS InfoDomainNonexistent.
Attempting to contact the Autodiscover service using the HTTP redirect method.
The attempt to contact Autodiscover using the HTTP Redirect method failed.
Test Steps
Attempting to resolve the host name autodiscover.owa.optima-ws.co.uk in DNS.
The host name couldn't be resolved.
<label for="testSelectWizard_ctl12_ctl06_ctl00_ctl00_ctl02_ctl00_tmmArrow">Tell
me more about this issue and how to resolve it</label>
Additional Details
Host autodiscover.owa.optima-ws.co.uk couldn't be resolved in DNS InfoDomainNonexistent.
Attempting to contact the Autodiscover service using the DNS SRV redirect method.
ExRCA failed to contact the Autodiscover service using the DNS SRV redirect method.
Test Steps
Attempting to locate SRV record _autodiscover._tcp.owa.optima-ws.co.uk in DNS.
The Autodiscover SRV record wasn't found in DNS.
<label for="testSelectWizard_ctl12_ctl06_ctl00_ctl00_ctl03_ctl00_tmmArrow">Tell
me more about this issue and how to resolve it</label>

Outlook client in different subnet unable to connect to Exchange 2010 CAS using Windows 2008 R2 NLB multicast mode

Hi all,
need urgent assistance on the following issue
this is my Exchange 2010 setup
2 x CAS/Hub servers with HP network teaming, and load balanced using Windows NLB multicast mode. There are 2 VIPs on the NLB, one for outlook anywhere, one for autodiscover
2 DNS records were created for the 2 VIPs
Clients use Outlook Anywhere (HTTPS) to connect to the CAS servers from external segment via a Palo Alto firewall, which also acts as a layer 3 router
static arp was set on the Palo Alto firewall, with both virtual MACs pointing to the primary virtual MAC used by the NLB.
Observations
1. within same segment - no issue accessing Exchange servers, even when one CAS node is offline
2. external segment (via firewall)
a. when both nodes are up
outlook client able to connect to Exchange CAS VIP on 443, but will disconnect after around 30 seconds. Client will retry and the pattern will repeat
Exchange CAS RPC logs shows client connections and disconnections to the outlook anywhere VIP address
Firewall logs shows allowed traffic from client to the VIPs
unable to complete profile creation
b. with only CAS2 (CAS1 stopped/deleted from NLB cluster)
no issues accessing Exchange servers, creating profiles etc
c. with only CAS1
same behaviour as (a)
reinstalled NLB, but doesn't resolve
deleted CAS1 from NLB cluster, and re-add. issue remain
Q1. is teaming supported? Teaming is currently set to automatic mode, instead of specified Fault Tolerant
Q2. are there additional settings we need to set or verify on the Palo Alto firewall, since the issue only happen to external segment? Thanks!

Yes - I've been scarred with this for many years :(
If it is just CAS 1 that is causing issues, then focus in on that. The support statement for Win 2008 R2 is that NLB is still a 3rd party component and support may ask for it to be disabled.
http://support.microsoft.com/kb/278431
Does CAS1 and CAS2 have the same NICs (firmware as well), driver, teaming software, and teaming config?
I also want to ask what the network team did for configuring the switch ports on the servers? This will vary from vendor to vendor - did they do the same config on both?
Cheers,
Rhoderick
Microsoft Senior Exchange PFE
Blog:
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Thanks Rhoderick, issue still persists
can you also help clarify what you meant by "configuring the switch ports on the servers"?
thanks again

Outlook 2011/365 connectivity to Exchange 2010

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