autodiscover outlook error - encrypted connection to your mail server is not available
3 Exchange 2010sp1, CA, Hub, Mail (DAG), Windows 2008R2 TMG 2010sp1 with Edge server role Remote Connectivity Analyzer for Autodiscover and Outlook Anywhere says "Connectivity Test Successful" but when trying to setup a profile in Outlook 2007 & 2010 (entering name, email address, and password) I get an error "An encrypted connection to your mail server is not available." Does anyone have ideas what's going wrong and how to troubleshoot this further? Thanks in advance for any help.
April 11th, 2011 5:04pm

Just noticed there was an "Test Email AutoConfiguration" tool in Outlook 2010. I'll see if I can decipher the log results to help further troubleshoot this problem.
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April 11th, 2011 10:41pm

Hi pmatsune, From your description, I understand that when you setup a profile in Outlook 2007 & Outlook 2010 (entering name, email address, and password) you get the error “An encrypted connection to your mail server is not available”. For this issue, I want to clarify the following information: 1. What is the method that clients connect to Exchange Server, MAPI or Outlook Anywhere? 2. How about setup profile on a computer (in the domain). 3. Is there any related information in your event log? Here is a similar thread for you, hope it help: Outlook to EX 2010 Issue - an encrypted connection is not available http://social.technet.microsoft.com/Forums/en-US/exchange2010/thread/98b24066-ba32-4d48-949e-86f1d862427c Thanks, Evan Liu TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.com Please remember to click “Mark as Answer” on the post that helps you, and to click “Unmark as Answer” if a marked post does not actually answer your question. This can be beneficial to other community members read
April 12th, 2011 11:39am

1. Outlook Anywhere 2. I can setup a profile manually on a computer. 3. I don't see anything in the event log. When I run the "Test E-mail AutoConfiguration" in Outlook 2010 I see: When testing external email address: Autodiscover to https://autodiscover.external.name/autodiscover/autodiscover.xml starting Autodiscover request completed with http status code 500 Autodiscover to https://autodiscover.external.name/autodiscover/autodiscover.xml Failed (0x8004005) When testing internal email address: Autodiscover to https://autodiscover.internal.name/autodiscover/autodiscover.xml starting Autodiscover internet timeout against URL https://autodiscover.internal.name/autodiscover/autodiscover.xml Autodiscover internet timeout against URL https://autodiscover.internal.name/autodiscover/autodiscover.xml Autodiscover to https://autodiscover.internal.name/autodiscover/autodiscover.xml Failed (0x800C8203)
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April 13th, 2011 4:19pm

Hi pmatsune, What happen if you try that URL in a browser? Please run test-Outlookwebservices |fl command in EMS, and post the result in your next post. For error “http status code 500” I suggest you follow these steps to check on IIS: 1) Open IIS 2) Expend Default web site 3) Select Autodiscover 4) Select Content View 5) Locate Web.config file 6) Right click on Web.config file and select Edit Permission for "authenticated users" and "System" 7) Now select Security 8) Uncheck any all the boxes showing under Deny 9) Also make sure Read & Execute and Read permissions should be allowed for "authenticated users" and "System" Thanks, Evan Liu TechNet Subscriber Support in forum If you have any feedback on our support, please contact tngfb@microsoft.com Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.
April 17th, 2011 4:05am

In a web browser using the public domain name, I get a FBA login page from our TMG. After I login with username and password I get an errorcode 600 response ( which I believe is the expected response). From a browser using autodiscover.internal.domain/autodiscover/autodiscover.xml I get a 403 "forbidden" error. If I use https://servername.internal.domain/autodiscover/autodiscover.xml I get prompted with a "windows security" login box for username and password, I enter my credentials and get the same error code 600 response. Checked web.config permissions and they looked okay. Here's the output from the test-OutlookWebServices command: RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1019 Type : Information Message : A valid Autodiscover service connection point was found. The Autodiscover URL on this object is https://EX CHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1006 Type : Information Message : Contacted the Autodiscover service at https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1016 Type : Information Message : [EXCH] The AS is configured for this user in the Autodiscover response received from https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1015 Type : Information Message : [EXCH] The OAB is configured for this user in the Autodiscover response received from https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1014 Type : Information Message : [EXCH] The UM is configured for this user in the Autodiscover response received from https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1016 Type : Warning Message : [EXPR] The AS is not configured for this user in the AutoDiscover response received from https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1015 Type : Warning Message : [EXPR] The OAB is not configured for this user in the AutoDiscover response received from https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1014 Type : Warning Message : [EXPR] The UM is not configured for this user in the AutoDiscover response received from https://EXCHX1.internal.domain/Autodiscover/Autodiscover.xml. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1022 Type : Success Message : Autodiscover was tested successfully. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1021 Type : Information Message : The following web services generated errors: As,Oab,UM in EXPR. Use the previous output to diagnose and correct the errors. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1024 Type : Success Message : [EXCH] Successfully contacted the AS service at https://exchx1.internal.domain/EWS/Exchange.asmx. The elapsed time was 46 milliseconds. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1026 Type : Success Message : [EXCH] Successfully contacted the UM service at https://exchx1.internal.domain/EWS/Exchange.asmx. The elapsed time was 0 milliseconds. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1124 Type : Success Message : [Server] Successfully contacted the AS service at https://exchx1.internal.domain/ews/exchange.asmx. The elapsed time was 546 milliseconds. RunspaceId : 56d1849c-baff-4b08-a801-3b5614dfee29 Id : 1126 Type : Success Message : [Server] Successfully contacted the UM service at https://exchx1.internal.domain/ews/exchange.asmx. The elapsed ti me was 0 milliseconds.
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April 18th, 2011 3:22pm

Hi, Can you please elaborate on this a bit more? Do you mean to create a separate publishing rule specifically for autodiscover and then set the following: 1. Authentication Delegation - No delegation, but client may authenticate directly. 2. Users - Set to All Users? If you can please clarify the above I would appreciate it. I am having the same issue with Exchange autodiscover through TMG. Thanks.
April 12th, 2012 5:06pm

Yes, they had me create a separate publishing rule specifically for autodiscover. 1. No delegation, but client may authenticate directly 2. Users - Set to All Users.
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April 12th, 2012 6:01pm

3 Exchange 2010sp1, CA, Hub, Mail (DAG), Windows 2008R2 TMG 2010sp1 with Edge server role Remote Connectivity Analyzer for Autodiscover and Outlook Anywhere says "Connectivity Test Successful" but when trying to setup a profile in Outlook 2007 & 2010 (entering name, email address, and password) I get an error "An encrypted connection to your mail server is not available." Does anyone have ideas what's going wrong and how to troubleshoot this further? Thanks in advance for any help. Is this tools is helpful for send encrypted mail with any errors? I used to use it and I think this is the simplest solution for me. Visit http://www.encryptomatic.com/ for details of Email encryption without any errors
August 16th, 2012 12:35pm

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