Outlook 2007 won't connect / Autodiscover issues

Hello Foristas,
I'm stuck ... so I hope someone will point me in the right direction. This is the scenario:
Target: Migrate 2003SBS to EX2013. SBS hat been migrated to 2008R2 AD Server plus EX2010. This went without problems. Outlook and OWA worked just fine. A 2012 AD Server has been added.
EX2013 has been installed on a fresh 2012 Server. Still everything worked. Mailboxes were moved and still everything worked. EX2010 was decomissioned (seemingly in a hurry :-( ) and now users can't connect via Outlook.
Outlook Version (2007) is up to date, OWA works fine. I can't use the external Connectivity Test because I have no access to either external DNS nor Firewallconfiguration. The customer also doesn't need external access.
Internally I have A-Records for
exchsrv.intdom.local
autodiscover.intdom.local
Lookups work fine. I can access https://autodiscover/autodiscover/autodiscover.xml as well as https://autodiscover.intdom.local/.... and exchsrv/autodiscover (I get the invalid request answer)
Certificates are signed by a domain CA, the root certificate is installed and there is no certificate warning when accessing OWA (or EWS, for that matter).
When trying to connect Outlook, I get that "no connection to Exchange - outlook ha to be online" error (like many others ...). When trying to create a new profile, Outlook barfs at "logging on to server" (wording might be different, I'm
on a german system).
I've double-checked that AutoDiscoverInternalURI is correct (it's autodiscover.intdom.local/autodiscover/autodiscover.xml) as well as AutodiscoverVirtualDirectory InternalUrl is set and correct.
Now here is what is really strange: Out of despair, I just clicked "repair account" and I was able to connect. Once. I could send Mails and receive internally. After restarting Outlook, it was and stayed disconnected. But at least I was able to
run the Outlook Autodiscover diagnostics and what I see: Outlook tries lots of autodiscover.EXTdom.com URIs, but net even tries the internal one. So for testing, I created a host entry on the client pointing autodiscover.EXTdom.com to the internal IP of the
Exchange-Server. I created a new profile and the ran through the assistant and had a working outlook. Once. After restarting, Outlook was disconnected again andcreating a new profile doesn't help. I've recreated that scenario and I'm able to create a working
profile just once and it will only work for the first start.
With the host entry present, when I open https://autodiscover.EXTdom.com/aut.... , a login prompt appears ...
I suspect something fishy in the AD, but I have no more ideas where to look after trying to track that down since yesterday morning.
Any help would be greatly appreciated!
Chris

Hi,
Glad that you have resolved the connectivity issue.
According to your description, there is something wrong with your OAB. And I recommend the following articles which can help you troubleshoot the OAB issue:
http://blogs.technet.com/b/exchange/archive/2012/10/26/oab-in-exchange-server-2013.aspx
http://msexchangeguru.com/2013/12/04/e2013-oab/
Note: Microsoft is providing this information as a convenience to you. The sites are not controlled by Microsoft. Microsoft cannot make any representations regarding the quality, safety, or suitability of any software or information found there. Please make
sure that you completely understand the risk before retrieving any suggestions from the above link.
Thanks,
If you have feedback for TechNet Subscriber Support, contact
[email protected]
Angela Shi
TechNet Community Support

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Testing RPC/HTTP connectivity.
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Test Steps
ExRCA is attempting to test Autodiscover for [email protected].
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Test Steps
Attempting each method of contacting the Autodiscover service.
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Test Steps
Attempting to test potential Autodiscover URL https://owa.optima-ws.co.uk/AutoDiscover/AutoDiscover.xml
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Testing TCP port 443 on host owa.optima-ws.co.uk to ensure it's listening and open.
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Testing the SSL certificate to make sure it's valid.
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Test Steps
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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
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Additional Details
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Test Steps
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Testing the certificate date to confirm the certificate is valid.
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Additional Details
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Attempting to test potential Autodiscover URL https://autodiscover.owa.optima-ws.co.uk/AutoDiscover/AutoDiscover.xml
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Attempting to resolve the host name autodiscover.owa.optima-ws.co.uk in DNS.
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<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.
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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.
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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>

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Testing RPC/HTTP connectivity.
The RPC/HTTP test failed.
Additional Details
Elapsed Time: 3221 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for
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Autodiscover was tested successfully.
Additional Details
Elapsed Time: 3219 ms.
Test Steps
Attempting each method of contacting the Autodiscover service.
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Additional Details
Elapsed Time: 3218 ms.
Test Steps
Attempting to test potential Autodiscover URL
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Additional Details
Elapsed Time: 835 ms.
Test Steps
Attempting to resolve the host name pickardconstruction.com in DNS.
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Additional Details
IP addresses returned: 205.204.84.106
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Additional Details
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Test Steps
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Attempting to test potential Autodiscover URL
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Additional Details
Elapsed Time: 609 ms.
Test Steps
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Additional Details
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Additional Details
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Test Steps
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IP addresses returned: 205.204.84.106
Elapsed Time: 21 ms.
Testing TCP port 80 on host autodiscover.pickardconstruction.com to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 100 ms.
The Microsoft Connectivity Analyzer is checking the host autodiscover.pickardconstruction.com for an HTTP redirect to the Autodiscover service.
The redirect (HTTP 301/302) response was received successfully.
Additional Details
Redirect URL:
https://cpanelemaildiscovery.cpanel.net/autodiscover/autodiscover.xml HTTP Response Headers: Keep-Alive: timeout=5, max=100 Connection: Keep-Alive Content-Length: 0 Content-Type: application/xml Date: Fri, 28 Feb 2014 01:49:00 GMT Location:
https://cpanelemaildiscovery.cpanel.net/autodiscover/autodiscover.xml Server: Apache/2.2.23 (Unix) mod_ssl/2.2.23 OpenSSL/0.9.8e-fips-rhel5 mod_auth_passthrough/2.1 mod_bwlimited/1.4
FrontPage/5.0.2.2635 PHP/5.3.21
Elapsed Time: 184 ms.
Attempting to test potential Autodiscover URL
https://cpanelemaildiscovery.cpanel.net/autodiscover/autodiscover.xml
Testing of the Autodiscover URL was successful.
Additional Details
Elapsed Time: 1463 ms.
Test Steps
Attempting to resolve the host name cpanelemaildiscovery.cpanel.net in DNS.
The host name resolved successfully.
Additional Details
IP addresses returned: 208.74.124.130, 208.74.124.133, 208.74.125.50, 208.74.125.51, 208.74.123.82
Elapsed Time: 109 ms.
Testing TCP port 443 on host cpanelemaildiscovery.cpanel.net to ensure it's listening and open.
The port was opened successfully.
Additional Details
Elapsed Time: 135 ms.
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
Additional Details
Elapsed Time: 358 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server cpanelemaildiscovery.cpanel.net on port 443.
The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
Additional Details
Remote Certificate Subject: CN=*.cpanel.net, OU=Domain Control Validated, O=*.cpanel.net, Issuer: SERIALNUMBER=07969287, CN=Go Daddy Secure Certification Authority, OU=http://certificates.godaddy.com/repository, O="GoDaddy.com, Inc.", L=Scottsdale, S=Arizona,
C=US.
Elapsed Time: 278 ms.
Validating the certificate name.
The certificate name was validated successfully.
Additional Details
The host name that was found, cpanelemaildiscovery.cpanel.net, is a wildcard certificate match for common name *.cpanel.net.
Elapsed Time: 0 ms.
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
Test Steps
The Microsoft Connectivity Analyzer is attempting to build certificate chains for certificate CN=*.cpanel.net, OU=Domain Control Validated, O=*.cpanel.net.
One or more certificate chains were constructed successfully.
Additional Details
A total of 2 chains were built. The highest quality chain ends in root certificate OU=Go Daddy Class 2 Certification Authority, O="The Go Daddy Group, Inc.", C=US.
Elapsed Time: 30 ms.
Analyzing the certificate chains for compatibility problems with versions of Windows.
No Windows compatibility problems were identified.
Additional Details
The certificate chain has been validated up to a trusted root. Root =
[email protected], CN=http://www.valicert.com/, OU=ValiCert Class 2 Policy Validation Authority, O="ValiCert, Inc.", L=ValiCert Validation Network.
Elapsed Time: 4 ms.
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 = 8/18/2011 6:11:10 PM, NotAfter = 10/18/2016 5:19:12 AM
Elapsed Time: 0 ms.
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
Additional Details
Accept/Require Client Certificates isn't configured.
Elapsed Time: 349 ms.
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
The Microsoft Connectivity Analyzer successfully retrieved Autodiscover settings by sending an Autodiscover POST.
Additional Details
Elapsed Time: 509 ms.
Test Steps
The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL
https://cpanelemaildiscovery.cpanel.net/autodiscover/autodiscover.xml for user
[email protected].
The Autodiscover XML response was successfully retrieved.
Additional Details
Autodiscover Account Settings XML response: <?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>[email protected]</DisplayName> </User> <Account> <AccountType>email</AccountType> <Action>settings</Action> <Protocol> <Type>IMAP</Type> <Server>have02b.have1.com</Server>
<Port>993</Port> <DirectoryPort>0</DirectoryPort> <ReferralPort>0</ReferralPort> <SSL>on</SSL> <DomainRequired>off</DomainRequired> <SPA>off</SPA> <AuthRequired>on</AuthRequired>
<LoginName>[email protected]</LoginName> </Protocol> <Protocol> <Type>SMTP</Type> <Server>have02b.have1.com</Server> <Port>465</Port> <DirectoryPort>0</DirectoryPort> <ReferralPort>0</ReferralPort>
<SSL>on</SSL> <DomainRequired>off</DomainRequired> <SPA>off</SPA> <AuthRequired>on</AuthRequired> <LoginName>[email protected]</LoginName> </Protocol> </Account> </Response>
</Autodiscover> HTTP Response Headers: Keep-Alive: timeout=5, max=100 Connection: Keep-Alive Content-Length: 1362 Content-Type: text/xml Date: Fri, 28 Feb 2014 01:49:02 GMT Server: Apache/2.2.17 (Unix) mod_ssl/2.2.17 OpenSSL/0.9.8e-fips-rhel5 mod_perl/2.0.5
Perl/v5.8.8
Elapsed Time: 509 ms.
Autodiscover settings for Outlook Anywhere are being validated.
The Microsoft Connectivity Analyzer wasn't able to validate Outlook Anywhere Autodiscover settings.
Tell me more about this issue and how to resolve it
Additional Details
The EXCH provider section is missing from the Autodiscover response.
Elapsed Time: 0 ms.

Outlook 2011 won't connect offsite

we are using Exchange 2007 and i can't get my email to work off site using outlook for mac 2011. It work on site but when i try from my house it dose not work. I have it working on IPhone and IPad's but can't get it working on the macbook pro at all. I can't us the mail app or out look. I know we use OWA to connect to outlook. I can use it on my PC at home and my pc laptop. All the mac laptop that use 2011 outlook can't connect to exchange sever at home. The URL is Https://myserver.edu/owa

I've been using Outlook with Gmail ever since Outlook replaced Entourage and have never encountered any problems.
Your incoming and outgoing server names are correct, but I'm use port 993 for imap.gmail.com and port 465 for smtp.gmail.com. I'm also using SSL on both ports and have Authentication set for username and password (using the "Advanced" button in Account setup) for the smtp server.
Good luck - I think that you just have a port problem...
Clinton

Outlook 2007 doesn't connect hub server automatically

We have exchange 2010 installed for our organization. We have two HUB transport mail servers in our system for load balancing purpose. When we configure Microsoft outlook in a workstation then it connect with hub02 even if we select hub01 manually.
what can i do now?
Setu Bandhan Saha

Hi,
To understand more about this issue, I’d like to ask How you manually selected the HUB01.
Because if there are multiple HUB roles in one site, by default, the HUB roles are always load balanced, and we don’t need to manually point the dedicated server.
If you have any question, please feel free to let me know.
Thanks,
Angela Shi
When we configure outlook, then we select the email server manually, in there we put the server name of the server.
Setu Bandhan Saha

Outlook 2003 won't connect with gmail

I use Outlook 2003 SP3 on my Windows 7 laptop and it will not always pull my gmail down using the Verizon hotspot. My AT&T hotspot works fine, and a direct wifi connection works fine.
I get the server not available message.
However, in the Options setup, I can test and receive the gmail just fine, including the test message.
Some research indicates this might be an issue with IPv6 verses IPv4.
Other than updating to Outlook 2010 which does not appear to have the same issue, any suggestions?

Hey there skyking4ar. That certainly is odd. If you're able to get gmail sometimes you certainly should be able to all of the time, especially if a competitors device is always able to bring it up.
Do you have any issues with any other websites? Which mobile hotspot device do you have? Are the server settings set up correctly?
Please provide additional details skyking4ar and we will continue to troubleshoot. I am confident we can resolve the issue.
NickB_VZW
VZWSupport
Follow us on Twitter @VZWSupport

Outlook 2007 won't connect / Autodiscover issues

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