Outlook 2010 Will Not Connect to Exchange 2007 on SBS 2008 Server

Good Morning,
I have a user who cannot connect to the exchange server on SBS 2008 with outlook 2010. When they start outlook, it shows disconnected and will not connect for a minimum of 20 minutes to an hour. Any suggestions on how to fix this would be appreciated.
I have rebuilt their profile, but that does not fix the issue.
Thank you,
Lee F.
Lee Feldman SMB Consultant

Hi,
Thanks for posting in the forum.
Regarding the current issue, since you have recreated the user profile without any issue, I suspect that it’s mainly caused by the network issue. At this time, please first check the TCP/IP
configurations as Larry mentioned. Then, please also refer to the article below for details about how to troubleshoot Outlook connectivity issue.
Troubleshooting Microsoft Exchange: Outlook Connectivity Issues
http://blogs.technet.com/b/mspfe/archive/2011/04/12/troubleshooting_2d00_microsoft_2d00_exchange_2d00_outlook_2d00_connectivity_2d00_issues.aspx
Hope this helps.
Best Regards,
Andy Qi
TechNet Subscriber Support
If you are
TechNet Subscription user and have any feedback on our support quality, please send your feedback
here.
Andy Qi
TechNet Community Support

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Hi,
It’s really a common issue.
This issue occurs if the following conditions are true:
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The
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This may differ from the host name that is used in the FQDN of the replacement certificate. For example, the replacement certificate
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URL:
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Hi,
According to your description, I understand that Outlook client cannot connect to Exchange server 2013 while one member of DAG failed.
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I want to double confirm whether all account store in MBX1 experience this issue, users in MBX2 works fine.
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Transition
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Removing SBS 2008 – Step 2:
ADCS
Removing
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It's recommended to download and install
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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
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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.
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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.
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The certificate passed all validation requirements.
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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
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Validating the certificate name.
The certificate name was validated successfully.
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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.
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Analyzing the certificate chains for compatibility problems with versions of Windows.
Potential compatibility problems were identified with some versions of Windows.
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Testing the certificate date to confirm the certificate is valid.
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Checking the IIS configuration for client certificate authentication.
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Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
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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.
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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.
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 2010 Profiles Not Creating with Exchange 2010 Backend

In an enterprise environment. Issue has been replicated on multiple Windows Terminal Servers, with multiple accounts.
With multiple accounts have recreated the user profiles from scratch, and launched outlook 2010. The profile does not autocreate, it was working in production about a week ago. Windows Updates were applied for December 2014.
Does anyone know if a Local Windows Client side patch would cause Outlook 2010 not to resolve a profile correctly. Could this be the outlook mapi rpc issue that was part of RU8. Have searched several hundred artciles on this on google and twitter
in the last weeks time frame and cannot find anywhere online that lists excatly what a user experiences when RU8 fails. Have not heard back from the Exchange administrator if RU8 was deployed. There are also multiple Windows Updates for December
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http://exchangetips.us/2014/12/exchange-users-unable-to-connect-with-outlook-2010/
Microsoft did pull/release a version #2 of an exchange patch in December which might be the root cause.
https://nakedsecurity.sophos.com/2014/12/12/microsoft-pulls-patch-tuesday-fix-outlook-cant-connect-to-exchange/
not sure if we are we running “Exchange Server 2010 SP3 Update Rollup 8”
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http://blogs.technet.com/b/exchange/archive/2014/12/09/exchange-releases-december-2014.aspx
https://social.technet.microsoft.com/Forums/en-US/1f77b07b-8330-453c-bc4e-4322d21d1aa3/outlook-error-code-0x800040050x800040050x000501?forum=exchangesvrclientslegacy
http://www.anywherexchange.com/2014/12/mapi-http-support-now-available-for.html
http://blogs.technet.com/b/exchange/archive/2014/05/09/outlook-connectivity-with-mapi-over-http.aspx
http://windowsitpro.com/blog/exchange-2010-sp3-ru8-withdrawn-due-bug-mapi-rpc-layer
http://www.reddit.com/r/sysadmin/comments/2oxfdf/microsoft_exchange_2010_sp3_ru8_breaks_outlook/?utm_medium=twitter&utm_source=twitterfeed
http://blogs.technet.com/b/exchange/archive/2014/12/09/exchange-releases-december-2014.aspx
https://social.technet.microsoft.com/Forums/en-US/1be9b816-b0ab-40ea-a43a-446239f8eae3/outlook-client-issues-following-exchange-2010-rollup-8?forum=exchange2010
https://social.technet.microsoft.com/Forums/en-US/8a66406b-2047-4108-bd5a-9a178114c424/exchange-2010-sp3-rollup-8-and-rollup-7?forum=smallbusinessserver2011essentials

There are known issues with Outlook connections if you are using Exchange 2010 SP3 UR8 (as you have found). You can check which update you are running by going to
Control Panel/Uninstall a Program, then click the
View Installed Updates selection (upper left). Your
Exchange Server 2010 - Software Updates will show a definite difference between UR8 and UR8V2. To be safe, I'd fully remove UR8 and install UR8V2 after a system restart.

Outlook 2010 will not sync at all

I have a Iphone 3Gs and Ipad 2 both on IOS 5. Using Windows 7 and Outlook 2010. I have stopped using iCLoud and now Outlook will not sync at all. I turned off iCloud on the devices. While working with Steve from Apple customer care we restored the Ipad 2 to New, and I have uninstalled the downloaded MIcrosoft office version and reinstalled it using the CD. It still will not sync any information. Could the problem be due to the iCloud section still shows in Outlook but I get a "The set of folders can not be opened The information source can not be opened" error" Im not sure where to go from here? I dont understand why restoring to New would not work.
I have not done anything with the phone (other than stopping icloud sync contacs & calendar on phone) until I get I find a solution that works.

Hi,
I got the same problems with win7 and outlook 2007.
My iphone 4 does the sync (supposedly) actions but there is no iPhone Calendar items. on Outlook's Calendar and vice versa, no Outlook Calendar items on iPhone calendar. The Contacts sync gives the same results.
The same thing happens with iPad syncing to the same computer's Outlook.
But the strange things are still to come: When I do the iPhone sync to Outlook, then the iPad, I find iPhone items on the iPad; then I do the iPhone sync again, iPad's items are synced to the iPhone.
It looks like there are hidden Outlook Calendar and Contact files that are synced wiith the iPhone & iPad!
I too get the same error message, Outlook Sync Client has stopped working.

Outlook 2010 Will Not Connect to Exchange 2007 on SBS 2008 Server

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