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Autodiscover not working with Outlook 2003 and Exchange 2010 and it keeps asking for username and password

Posted on 2010-11-18
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Last Modified: 2012-08-14
Hi

I have 4 exchange servers (Exch 2010 on Win 2008 Ent)

2 for MBX/HT and 2 for CAS Array. I have configured DAG and CAS Array

Im trying to connect to Exch 2010 account with Outlook 2003 and it keeps popping up login box asking for username and password. On outlook I have checked box under "security tab" that reads "encrypt data between outlook and exchange". Also upgrade to SP1 on all exchange servers. Please advice

Outlook was connecting ok before i configured CAS array. I have also ran command Set-ClientAccessArray to point to my CAS array
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Question by:MANGO247
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Accepted Solution

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rr1968 earned 500 total points
ID: 34163999
Autodiscover is not supported on Outlook 2003.
You need to manually enter server settings in outlook 2003
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Expert Comment

by:rr1968
ID: 34164034
remember SP1 doesn't have RPC encrytion enabled by default.
Try this and post the result:
Get-RPCClientAccess | fl name, encryptionrequired

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Author Comment

by:MANGO247
ID: 34164036
Ok, thanks for the info.

Could you also advice why it keeps asking for login details and never lets me configure a user account on outlook 2003. I can ping my cas array by name from the PC.

I have not made any changes to my CAS apart from changing internal and external url which i believe should not make any difference with Outlooki MAPI conneciton

I can however access mail box on OWA and its working fine there
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Author Comment

by:MANGO247
ID: 34164053
Here we go... Thx

[PS] C:\Windows\system32>Get-RPCClientAccess | fl name, encryptionrequired


Name               : RpcClientAccess
EncryptionRequired : True

Name               : RpcClientAccess
EncryptionRequired : True

Name               : RpcClientAccess
EncryptionRequired : True

Name               : RpcClientAccess
EncryptionRequired : True

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Expert Comment

by:rr1968
ID: 34164298
Looks like authentication issue...
Did you try re-profiling the outlook 2003 by specifying a single CAS name instead of the array name?
What is the service pack level on office 2003?

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Author Comment

by:MANGO247
ID: 34164612
I have Outlook SP3 and i have tried pointing to individual servers in my cas array but it keeps popping up same login box and doesnt let me do it
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Expert Comment

by:rr1968
ID: 34164997
run Get-WebServicesVirtualDirectory | fl cmdlet on the CAS server and post the result. I am interested in authentication methods
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Author Comment

by:MANGO247
ID: 34165070
I have run the command but for security reasons i cant upload it. Hope you will understand. Could you  advice me to locate any info for you?
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Expert Comment

by:rr1968
ID: 34165202
I am only interested in the following parameters:

InternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated}
ExternalAuthenticationMethods : {Basic, Ntlm, WindowsIntegrated}
BasicAuthentication           : True
DigestAuthentication          : False
WindowsAuthentication         : True
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Author Comment

by:MANGO247
ID: 34165397
I have following values for both of my CAS array servers

InternalAuthenticationMethods   : {Ntlm, WindowsIntegrated, WSSecurity}
ExternalAuthenticationMethods   : {Ntlm, WindowsIntegrated, WSSecurity}
BasicAuthentication             : False
DigestAuthentication            : False
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Author Comment

by:MANGO247
ID: 34165443
WindowsAuthentication           : True

sorry,
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Expert Comment

by:rr1968
ID: 34165696
On the outlook clients:he page where you sepcify the RPC encryption settings, what is the "Logon Network Security"?
Make sure you un-check "User Identification" (Always prompt for username and password)
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Expert Comment

by:rr1968
ID: 34165755
IS there a reason why you enabled WSSecurity?
I am not sure if that's causing this issue..
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Author Comment

by:MANGO247
ID: 34165758
Logon network security is "Kerberos/NTLM Password Authentication"

Under User Identification "Alway prompt for user....." is un-checked
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Author Comment

by:MANGO247
ID: 34166415
i have tested this with outlook 2007 and it runs autodiscover and then pops up message "The connection to Microsoft Exchange server is unavailable. Outlook must be online or connected to complete this action"

Also i typed https://casarray.domain/rpc and it kept asking for login details. I have checked rpc on IIS and it has problems with authorization when you run test on it. What configuration changes we should make here or it is configured automatically?
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Expert Comment

by:rr1968
ID: 34166491
show me the result of get-ClientAccessServer |fl
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Author Comment

by:MANGO247
ID: 34166652
I have changed domain name to "mydomain.co.uk" and Exch org to "myexchorg"
EBEXH03 and EBEXH04 are 2 of my CAS Servers

Please advice
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Expert Comment

by:rr1968
ID: 34167077
can you show me the Get-ClientAccessServer | fl >c:\cas.txt (The result will be saved in C drive and you can mask the sensitive info and post the results here)
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Author Comment

by:MANGO247
ID: 34167719
sorry i didnt attach file last time. I will do it tomorrow morning thx
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LVL 8

Expert Comment

by:rr1968
ID: 34167758
no worries!!!
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Author Comment

by:MANGO247
ID: 34171317
Please find attached now
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Author Comment

by:MANGO247
ID: 34171351
[PS] C:\Windows\system32>get-ClientAccessServer |fl


RunspaceId                           : a2db9a7b-9114-4c31-9b1a-2fa493819c5b
Name                                 : EBEXH03
Fqdn                                 : EBEXH03.mydomain.co.uk
OutlookAnywhereEnabled               : False
AutoDiscoverServiceCN                : EBEXH03
AutoDiscoverServiceClassName         : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri       : https://ebexh03.mydomain.co.uk/Autodiscover/Autodiscover.xml
AutoDiscoverServiceGuid              : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope                : {Default-First-Site-Name}
AlternateServiceAccountConfiguration :
IrmLogEnabled                        : True
IrmLogMaxAge                         : 30.00:00:00
IrmLogMaxDirectorySize               : 250 MB (262,144,000 bytes)
IrmLogMaxFileSize                    : 10 MB (10,485,760 bytes)
IrmLogPath                           : C:\Program Files\Microsoft\Exchange Server\V14\Logging\IRMLogs
MigrationLogLoggingLevel             : Information
MigrationLogFilePath                 :
MigrationLogMaxAge                   : 180.00:00:00
MigrationLogMaxDirectorySize         : 10 GB (10,737,418,240 bytes)
MigrationLogMaxFileSize              : 100 MB (104,857,600 bytes)
IsValid                              : True
ExchangeVersion                      : 0.1 (8.0.535.0)
DistinguishedName                    : CN=EBEXH03,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Admi
                                       nistrative Groups,CN=MyExchOrg,CN=Microsoft Exchange,CN=Services,CN=Configuration
                                       ,DC=mydomain,DC=co,DC=uk
Identity                             : EBEXH03
Guid                                 : 9eb4ae1a-8b13-488a-b5c5-c97f411c6b74
ObjectCategory                       : mydomain.co.uk/Configuration/Schema/ms-Exch-Exchange-Server
ObjectClass                          : {top, server, msExchExchangeServer}
WhenChanged                          : 18/11/2010 12:50:08
WhenCreated                          : 15/11/2010 16:33:21
WhenChangedUTC                       : 18/11/2010 12:50:08
WhenCreatedUTC                       : 15/11/2010 16:33:21
OrganizationId                       :
OriginatingServer                    : EBDMC01.mydomain.co.uk

RunspaceId                           : a2db9a7b-9114-4c31-9b1a-2fa493819c5b
Name                                 : EBEXH04
Fqdn                                 : EBEXH04.mydomain.co.uk
OutlookAnywhereEnabled               : False
AutoDiscoverServiceCN                : EBEXH04
AutoDiscoverServiceClassName         : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri       : https://ebexh04.mydomain.co.uk/Autodiscover/Autodiscover.xml
AutoDiscoverServiceGuid              : 77378f46-2c66-4aa9-a6a6-3e7a48b19596
AutoDiscoverSiteScope                : {Default-First-Site-Name}
AlternateServiceAccountConfiguration :
IrmLogEnabled                        : True
IrmLogMaxAge                         : 30.00:00:00
IrmLogMaxDirectorySize               : 250 MB (262,144,000 bytes)
IrmLogMaxFileSize                    : 10 MB (10,485,760 bytes)
IrmLogPath                           : C:\Program Files\Microsoft\Exchange Server\V14\Logging\IRMLogs
MigrationLogLoggingLevel             : Information
MigrationLogFilePath                 :
MigrationLogMaxAge                   : 180.00:00:00
MigrationLogMaxDirectorySize         : 10 GB (10,737,418,240 bytes)
MigrationLogMaxFileSize              : 100 MB (104,857,600 bytes)
IsValid                              : True
ExchangeVersion                      : 0.1 (8.0.535.0)
DistinguishedName                    : CN=EBEXH04,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Admi
                                       nistrative Groups,CN=MyExchOrg,CN=Microsoft Exchange,CN=Services,CN=Configuration
                                       ,DC=mydomain,DC=co,DC=uk
Identity                             : EBEXH04
Guid                                 : a5ffab12-b6cb-436d-914a-b30b915846f3
ObjectCategory                       : mydomain.co.uk/Configuration/Schema/ms-Exch-Exchange-Server
ObjectClass                          : {top, server, msExchExchangeServer}
WhenChanged                          : 18/11/2010 13:07:43
WhenCreated                          : 17/11/2010 14:26:43
WhenChangedUTC                       : 18/11/2010 13:07:43
WhenCreatedUTC                       : 17/11/2010 14:26:43
OrganizationId                       :
OriginatingServer                    : EBDMC01.mydomain.co.uk

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Author Comment

by:MANGO247
ID: 34174676
i have now reinstalled my cas server but its doing exactly same. ie. keeps asking for login name and password. When i enter my cas array in the server box while configuring email account on outlook it resolves name of my user but then it keeps asking for username and password
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Expert Comment

by:rr1968
ID: 34175045
Sorry I was in meetings all day.
Is the outlook on cache mode or online mode?
What is the Exchange server 2010 update level, are you using RTM?
What is the OS Service Pack level on CAS servers?
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LVL 8

Expert Comment

by:rr1968
ID: 34175236
Since you have reinstalled CAS, can you please run Get-WebServicesVirtualDirectory | fl  and post the result by removing the sensitive info.
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Author Comment

by:MANGO247
ID: 34180429
Reinstallation seems to have done the trick. I tried in couple of hours on a different pc and it all worked fine. Thx
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Author Closing Comment

by:MANGO247
ID: 34180430
problem resolved auto
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