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

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

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

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

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?

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

run Get-WebServicesVirtualDirectory | fl cmdlet on the CAS server and post the result. I am interested in authentication methods

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?

I am only interested in the following parameters:

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

I have following values for both of my CAS array servers

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

WindowsAuthentication           : True

sorry,

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)

IS there a reason why you enabled WSSecurity?
I am not sure if that's causing this issue..

Logon network security is "Kerberos/NTLM Password Authentication"

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

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?

show me the result of get-ClientAccessServer |fl

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

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)

sorry i didnt attach file last time. I will do it tomorrow morning thx

no worries!!!

Please find attached now

[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

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

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?

Since you have reinstalled CAS, can you please run Get-WebServicesVirtualDirectory | fl  and post the result by removing the sensitive info.

Reinstallation seems to have done the trick. I tried in couple of hours on a different pc and it all worked fine. Thx

problem resolved auto