Instagram X-twitter
TL-Logo-small
Github X-twitter Linkedin

Outlook Anywhere – Message: The underlying connection was closed: The connection was closed unexpectedly.

Recent Visitor 32

I ran into this problem a while back and thought Iā€™d share my troubleshooting steps with the other professionals out there.

When trying to configure Outlook Anywhere at Some Company and using the https://www.testexchangeconnectivity.com/ to test, I kept getting the following error:

clip_image002[14]

Testing Http Authentication Methods for URL https://mail.domain.ca/rpc/rpcproxy.dll

Http Authentication Test failed

clip_image003[48]

Additional Details

Exception Details:
Message: The underlying connection was closed: The connection was closed unexpectedly.
Type: System.Net.WebException
Stack Trace:
at System.Net.HttpWebRequest.GetResponse()
at Microsoft.Exchange.Tools.ExRca.Tests.HttpAuthMethodsTest.GetSupportedHttpAuthMethods()
at Microsoft.Exchange.Tools.ExRca.Tests.HttpAuthMethodsTest.PerformTestReally()

Hereā€™s the detailed test results:

clip_image005[4]

Connectivity Test Failed

Test Details

clip_image002[15]

Testing RPC/HTTP connectivity

RPC/HTTP test failed

clip_image003[49]

Test Steps

clip_image007[12]

Attempting to test Autodiscover for mailto:tluk@domain.ca

Successfully tested Autodiscover

clip_image003[50]

Test Steps

clip_image007[13]

Attempting each method of contacting the AutoDiscover Service

The AutoDiscover Service was successfully tested.

clip_image003[51]

Test Steps

clip_image002[16]

Attempting to test potential AutoDiscover URL https://domain.ca/AutoDiscover/AutoDiscover.xml

Failed testing this potential AutoDiscover URL

clip_image003[52]

Test Steps

clip_image009[30]

Attempting to resolve the host name domain.ca in DNS.

Host successfully resolved

clip_image003[53]

Additional Details

IP(s) returned: 99.999.999.99

clip_image009[31]

Testing TCP Port 443 on host domain.ca to ensure it is listening and open.

The port was opened successfully.

clip_image002[17]

Testing SSL Certificate for validity.

The SSL Certificate failed one or more certificate validation checks.

clip_image003[54]

Test Steps

clip_image002[18]

Validating certificate name

Certificate name validation failed

clip_image010[4] Tell me more about this issue and how to resolve it

clip_image003[55]

Additional Details

Host name domain.ca does not match any name found on the server certificate CN=webmail.domain.ca, OU=Domain Control Validated, O=webmail.domain.ca

clip_image007[14]

Attempting to test potential AutoDiscover URL https://autodiscover.domain.ca/AutoDiscover/AutoDiscover.xml

Testing AutoDiscover URL succeeded

clip_image003[56]

Test Steps

clip_image009[32]

Attempting to resolve the host name autodiscover.domain.ca in DNS.

Host successfully resolved

clip_image003[57]

Additional Details

IP(s) returned: 99.999.999.99

clip_image009[33]

Testing TCP Port 443 on host autodiscover.domain.ca to ensure it is listening and open.

The port was opened successfully.

clip_image007[15]

Testing SSL Certificate for validity.

The certificate passed all validation requirements.

clip_image003[58]

Test Steps

clip_image009[34]

Validating certificate name

Successfully validated the certificate name

clip_image003[59]

Additional Details

Found hostname autodiscover.domain.ca in Certificate Subject Alternative Name entry

clip_image012[6]

Validating certificate trust

The test passed with some warnings encountered. Please expand additional details.

clip_image003[60]

Additional Details

Only able to build certificate chain when using the Root Certificate Update functionality from Windows Update. Your server may not be properly configured to send down the required intermediate certificates to complete the chain. Consult the certificate installation instructions or FAQ’s from your Certificate Authority for more information.

clip_image009[35]

Testing certificate date to ensure validity

Date Validation passed. The certificate is not expired.

clip_image003[61]

Additional Details

Certificate is valid: NotBefore = 5/6/2010 3:34:15 PM, NotAfter = 5/6/2013 3:34:15 PM”

clip_image009[36]

Attempting to send AutoDiscover POST request to potential autodiscover URLs.

Successfully Retrieved AutoDiscover Settings by sending AutoDiscover POST.

clip_image003[62]

Test Steps

clip_image009[37]

Attempting to Retrieve XML AutoDiscover Response from url https://autodiscover.domain.ca/AutoDiscover/AutoDiscover.xml for user mailto:tluk@domain.ca

Successfully Retrieved AutoDiscover XML Response

clip_image003[63]

Additional Details

AutoDiscover Account Settings
XML Response:
<?xml version=”1.0″?>
<Autodiscover xmlns:xsi=”http://www.w3.org/2001/XMLSchema-instance” xmlns:xsd=”http://www.w3.org/2001/XMLSchema” xmlns=”http://schemas.microsoft.com/exchange/autodiscover/responseschema/2006“>
<Response xmlns=”http://schemas.microsoft.com/exchange/autodiscover/outlook/responseschema/2006a“>
<User>
<DisplayName>Terence Luk</DisplayName>
<LegacyDN>/o=domain/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=TLuk</LegacyDN>
<DeploymentId>86ca6927-bc9f-43d0-8d7a-2b694bd93d75</DeploymentId>
</User>
<Account>
<AccountType>email</AccountType>
<Action>settings</Action>
<Protocol>
<Type>EXCH</Type>
<Server>hq-exch1.domain.local</Server>
<ServerDN>/o=Domain/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=HQ-EXCH1</ServerDN>
<ServerVersion>720280B0</ServerVersion>
<MdbDN>/o=Domain/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=HQ-EXCH1/cn=Microsoft Private MDB</MdbDN>
<ASUrl>https://hq-exch1.domain.local/EWS/Exchange.asmx%3c/ASUrl>
<OOFUrl>https://hq-exch1.domain.local/EWS/Exchange.asmx%3c/OOFUrl>
<OABUrl>http://hq-exch1.domain.local/OAB/0fa5be65-3c78-4ad4-826d-0775ea7cbc91/%3c/OABUrl>
<UMUrl>https://hq-exch1.domain.local/UnifiedMessaging/Service.asmx%3c/UMUrl>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<PublicFolderServer>hq-exch1.domain.local</PublicFolderServer>
<AD>hq-dc2.domain.local</AD>
<EwsUrl>https://hq-exch1.domain.local/EWS/Exchange.asmx%3c/EwsUrl>
</Protocol>
<Protocol>
<Type>EXPR</Type>
<Server>mail.domain.ca</Server>
<OABUrl>https://mail.domain.ca/OAB/0fa5be65-3c78-4ad4-826d-0775ea7cbc91/%3c/OABUrl>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<SSL>On</SSL>
<AuthPackage>Basic</AuthPackage>
</Protocol>
<Protocol>
<Type>WEB</Type>
<Port>0</Port>
<DirectoryPort>0</DirectoryPort>
<ReferralPort>0</ReferralPort>
<External>
<OWAUrl AuthenticationMethod=”Fba”>https://webmail.domain.com/owa%3c/OWAUrl>
<OWAUrl AuthenticationMethod=”Fba”>https://webmail.domain.ca/owa%3c/OWAUrl>
</External>
<Internal>
<OWAUrl AuthenticationMethod=”Basic, Fba”>https://hq-exch1.domain.local/owa%3c/OWAUrl>
<OWAUrl AuthenticationMethod=”Basic, Fba”>https://hq-exchange1.domain.local/owa%3c/OWAUrl>
<Protocol>
<Type>EXCH</Type>
<ASUrl>https://hq-exch1.domain.local/EWS/Exchange.asmx%3c/ASUrl>
</Protocol>
</Internal>
</Protocol>
</Account>
</Response>
</Autodiscover>

clip_image009[38]

Validating Autodiscover Settings for Outlook Anywhere

Outlook Anywhere Autodiscover Settings validated

clip_image009[39]

Attempting to resolve the host name mail.domain.ca in DNS.

Host successfully resolved

clip_image003[64]

Additional Details

IP(s) returned: 99.999.999.99

clip_image009[40]

Testing TCP Port 443 on host mail.domain.ca to ensure it is listening and open.

The port was opened successfully.

clip_image007[16]

Testing SSL Certificate for validity.

The certificate passed all validation requirements.

clip_image003[65]

Test Steps

clip_image009[41]

Validating certificate name

Successfully validated the certificate name

clip_image003[66]

Additional Details

Found hostname mail.domain.ca in Certificate Subject Alternative Name entry

clip_image012[7]

Validating certificate trust

The test passed with some warnings encountered. Please expand additional details.

clip_image003[67]

Additional Details

Only able to build certificate chain when using the Root Certificate Update functionality from Windows Update. Your server may not be properly configured to send down the required intermediate certificates to complete the chain. Consult the certificate installation instructions or FAQ’s from your Certificate Authority for more information.

clip_image009[42]

Testing certificate date to ensure validity

Date Validation passed. The certificate is not expired.

clip_image003[68]

Additional Details

Certificate is valid: NotBefore = 5/6/2010 3:34:15 PM, NotAfter = 5/6/2013 3:34:15 PM”

clip_image002[19]

Testing Http Authentication Methods for URL https://mail.domain.ca/rpc/rpcproxy.dll

Http Authentication Test failed

clip_image003[69]

Additional Details

Exception Details:
Message: The underlying connection was closed: The connection was closed unexpectedly.
Type: System.Net.WebException
Stack Trace:
at System.Net.HttpWebRequest.GetResponse()
at Microsoft.Exchange.Tools.ExRca.Tests.HttpAuthMethodsTest.GetSupportedHttpAuthMethods()
at Microsoft.Exchange.Tools.ExRca.Tests.HttpAuthMethodsTest.PerformTestReally()

As it turns out, when the RPC Windows component is installed, ā€œEnable anonymous accessā€ is enabled. The correct setting should be ā€œIntegrated Windows authenticationā€ and ā€œBasic authenticationā€.

clip_image014[4]

Once the proper settings were checked and iisreset was ran, the test ran correctly with:

clip_image009[43]

Testing Http Authentication Methods for URL https://mail.domain.ca/rpc/rpcproxy.dll

Http Authentication Methods are correct

clip_image003[70]

Additional Details

Found all expected authentication methods and no disallowed methods. Methods Found: Basic, Negotiate, NTLM

Back to Blogs

Hello! My name is Terence Luk and welcome to my blog.

About me

Follow me:

Github X-twitter Linkedin

Categories

Related Posts

10 Responses

  1. Thank you very much for this information. I recently worked on an active sync issue which was resolved after installing sp2 for exchange 2003. Unfortunately this broke RPCoverHTTP. I had searched several webistes prior to with no success. Your permissions on the RPC directory was spot on!

  3. Just helped me out as well. Much appreciated Terence. I had ripped out IIS and client access and reinstalled them, and set up virtual directories again. RPC over HTTP had defaulted to anonymous after reinstalling just like you said.

    Thanks for posting!

  4. Thank you for taking the time to post this.

    I had already checked a bunch of IIS settings (including this one) from the excellent article at http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_1798-Exchange-2003-Activesync-Connection-Problems-FAQ.html. The settings was right, and after a reboot the problem persisted. I wouldn't have checked the settings again except for you having the exact cause listed here. I checked again and sure enough anonymous was set! It's as though the change was made but the UI didn't update until a restart. In any event unticking it fixed the issue.

  6. Greatly appreciated! Worked for me as well. Exchange 2003 on Windows 2003 Server Standard Edition SP2.

  10. Thank you so much for leaving this topic live on your blog. It just saved my bacon. You da man!

Subscribe to the mailing list to receive posts updates!

Sign up for my newsletter to see new photos, tips, and blog posts. Do not worry, we will never spam you.

Dive deep into the world of cloud computing with expert insights, tips, and tutorials tailored specifically for architects, engineers, and developers.

Github X-twitter Linkedin

Categories

Recent Posts

  • 2024 Terence Luk. All rights reserved.