Exchange - Constantly asking for credentials

Question

I have a problem with the Exchange server. The "Exchange Active Sync" test performed with Microsoft Remote Connectivity Analyzer exits successfully. The Outlook Connectivity test fails. Outlook (in various versions 2007-2010) keeps asking for credentials, therefore there are synchronization problems. After providing the credentials, the window returns again. OWA works correctly.

Exchange Server Version: Exchange Server 2010 SP3 (14.03.0496.000)

konstantinospassadis · Answer

HelloIs this happening to all users ? Can you perform the RCA test in English and re -post please ?What is the last configuration change that lead to this problem ?We can help if we get some more info 🙂

sergey kluzner · Answer

mateusz710 · Answer

Sergey Kluzner&nbsp;KonstantinosPassadis&nbsp;Screen on English language in attachments. I am sending the log below.&nbsp;[PS] C:\ProgramData\Microsoft\Windows\Start Menu\Programs\Microsoft Exchange Server 2010&gt;Get-ActiveSyncVirtualDirectory | fl
RunspaceId                                 : 07206f30-6958-496c-b970-1442e294512e
MobileClientFlags                          : BadItemReportingEnabled, SendWatsonReport
MobileClientCertificateProvisioningEnabled : False
BadItemReportingEnabled                    : True
SendWatsonReport                           : True
MobileClientCertificateAuthorityURL        :
MobileClientCertTemplateName               :
ActiveSyncServer                           : https://remote.SERVER.org/Microsoft-Server-ActiveSync
RemoteDocumentsActionForUnknownServers     : Allow
RemoteDocumentsAllowedServers              : {}
RemoteDocumentsBlockedServers              : {}
RemoteDocumentsInternalDomainSuffixList    : {}
MetabasePath                               : IIS://SERVER.SERVER.local/W3SVC/1/ROOT/Microsoft-Server-ActiveSync
BasicAuthEnabled                           : True
WindowsAuthEnabled                         : False
CompressionEnabled                         : True
ClientCertAuth                             : Ignore
WebsiteName                                : Default Web Site
WebSiteSSLEnabled                          : True
VirtualDirectoryName                       : Microsoft-Server-ActiveSync
Path                                       :
ExtendedProtectionTokenChecking            : None
ExtendedProtectionFlags                    : {}
ExtendedProtectionSPNList                  : {}
Server                                     : SERVER
InternalUrl                                : https://remote.SERVER.org/Microsoft-Server-ActiveSync
InternalAuthenticationMethods              : {}
ExternalUrl                                : https://remote.SERVER.org/Microsoft-Server-ActiveSync
ExternalAuthenticationMethods              : {}
AdminDisplayName                           :
ExchangeVersion                            : 0.10 (14.0.100.0)
Name                                       : Microsoft-Server-ActiveSync (Default Web Site)
DistinguishedName                          : CN=Microsoft-Server-ActiveSync (Default Web Site),CN=HTTP,CN=Protocols,CN=
                                             SERVER,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Ad
                                             ministrative Groups,CN=First Organization,CN=Microsoft Exchange,CN=Service
                                             s,CN=Configuration,DC=SERVER,DC=local
Identity                                   : SERVER\Microsoft-Server-ActiveSync (Default Web Site)
Guid                                       : 788bdc06-162b-41a9-aea6-0b1cb09ada60
ObjectCategory                             : SERVER.local/Configuration/Schema/ms-Exch-Mobile-Virtual-Directory
ObjectClass                                : {top, msExchVirtualDirectory, msExchMobileVirtualDirectory}
WhenChanged                                : 2020-07-07 01:13:23
WhenCreated                                : 2020-07-07 01:04:37
WhenChangedUTC                             : 2020-07-06 23:13:23
WhenCreatedUTC                             : 2020-07-06 23:04:37
OrganizationId                             :
OriginatingServer                          : SERVER.SERVER.local
IsValid                                    : True

[PS] C:\ProgramData\Microsoft\Windows\Start Menu\Programs\Microsoft Exchange Server 2010&gt;Get-OutlookAnywhere | fl
RunspaceId                      : 07206f30-6958-496c-b970-1442e294512e
ServerName                      : SERVER
SSLOffloading                   : False
ExternalHostname                : remote.SERVER.org
ClientAuthenticationMethod      : Basic
IISAuthenticationMethods        : {Basic, Ntlm}
XropUrl                         :
MetabasePath                    : IIS://SERVER.SERVER.local/W3SVC/1/ROOT/Rpc
Path                            : C:\Windows\System32\RpcProxy
ExtendedProtectionTokenChecking : None
ExtendedProtectionFlags         : {}
ExtendedProtectionSPNList       : {}
Server                          : SERVER
AdminDisplayName                :
ExchangeVersion                 : 0.10 (14.0.100.0)
Name                            : Rpc (Default Web Site)
DistinguishedName               : CN=Rpc (Default Web Site),CN=HTTP,CN=Protocols,CN=SERVER,CN=Servers,CN=Exchange Admin
                                  istrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=First Organization,CN=M
                                  icrosoft Exchange,CN=Services,CN=Configuration,DC=SERVER,DC=local
Identity                        : SERVER\Rpc (Default Web Site)
Guid                            : e5f24032-8406-4b5f-9f14-e8aa9ea0dd57
ObjectCategory                  : SERVER.local/Configuration/Schema/ms-Exch-Rpc-Http-Virtual-Directory
ObjectClass                     : {top, msExchVirtualDirectory, msExchRpcHttpVirtualDirectory}
WhenChanged                     : 2018-11-01 21:10:32
WhenCreated                     : 2018-11-01 21:10:32
WhenChangedUTC                  : 2018-11-01 20:10:32
WhenCreatedUTC                  : 2018-11-01 20:10:32
OrganizationId                  :
OriginatingServer               : SERVER.SERVER.local
IsValid                         : True

[PS] C:\ProgramData\Microsoft\Windows\Start Menu\Programs\Microsoft Exchange Server 2010&gt;Get-ExchangeCertificate | fl
AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule}
CertificateDomains : {SERVER.SERVER.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=SERVER-SERVER-CA
NotAfter           : 2021-07-10 16:11:11
NotBefore          : 2020-07-10 16:11:11
PublicKeySize      : 2048
RootCAType         : Registry
Services           : None
Status             : Valid
Subject            : CN=SERVER.SERVER.local
Thumbprint         : C4014A6E4302363FD4B9B1E6F0DA6EBB3FEBFCBD

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {SERVER.org, *.SERVER.org}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=Let's Encrypt Authority X3, O=Let's Encrypt, C=US
NotAfter           : 2020-08-30 12:35:06
NotBefore          : 2020-06-01 12:35:06
PublicKeySize      : 2048
RootCAType         : ThirdParty
Services           : IMAP, POP, IIS, SMTP
Status             : Valid
Subject            : CN=SERVER.org
Thumbprint         : 3CEB14E4C403D11DD8AD57A7F6859C98B9658D73

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {remote.SERVER.org, SERVER.org, SERVER.SERVER.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=SERVER-SERVER-CA
NotAfter           : 2020-10-31 20:58:54
NotBefore          : 2018-11-01 20:58:54
PublicKeySize      : 2048
RootCAType         : Registry
Services           : IMAP, POP, IIS, SMTP
Status             : Valid
Subject            : CN=remote.SERVER.org
Thumbprint         : 23471E44C52A43A53A42B3D910C692EFE9DB7BCD

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {*.SERVER.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=SERVER-SERVER-CA
NotAfter           : 2020-10-03 04:47:49
NotBefore          : 2018-10-04 04:47:49
PublicKeySize      : 2048
RootCAType         : Registry
Services           : None
Status             : Valid
Subject            : CN=*.SERVER.local, OU=IT, O=SERVER, L=Warszawa, S=Mazowieskie, C=PL
Thumbprint         : 46B8CDBEB02177C7B49F7DF1D804B461E5F4C4A5

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {SERVER-SERVER-CA}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=SERVER-SERVER-CA
NotAfter           : 2023-10-04 10:38:03
NotBefore          : 2018-10-03 10:28:03
PublicKeySize      : 2048
RootCAType         : Registry
Services           : SMTP
Status             : Valid
Subject            : CN=SERVER-SERVER-CA
Thumbprint         : 55871FB434CF5B5495FF5535D81DE4E7031C3B56

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {WMSvc-SERVER}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=WMSvc-SERVER
NotAfter           : 2022-05-21 23:38:53
NotBefore          : 2012-05-23 23:38:53
PublicKeySize      : 2048
RootCAType         : Registry
Services           : None
Status             : Valid
Subject            : CN=WMSvc-SERVER
Thumbprint         : 5E3076011AA656C04BD639210A294704279508C7

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule}
CertificateDomains : {SERVER-SERVER-CA}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=SERVER-SERVER-CA
NotAfter           : 2016-06-13 13:51:58
NotBefore          : 2011-06-13 13:41:58
PublicKeySize      : 2048
RootCAType         : Unknown
Services           : None
Status             : Invalid
Subject            : CN=SERVER-SERVER-CA
Thumbprint         : AEBD93FA03B1B9992A6EE631B459B770FCB16DC7

[PS] C:\ProgramData\Microsoft\Windows\Start Menu\Programs\Microsoft Exchange Server 2010&gt;Get-ClientAccessServer | fl
RunspaceId                           : 07206f30-6958-496c-b970-1442e294512e
Name                                 : SERVER
Fqdn                                 : SERVER.SERVER.local
OutlookAnywhereEnabled               : True
AutoDiscoverServiceCN                : SERVER
AutoDiscoverServiceClassName         : ms-Exchange-AutoDiscover-Service
AutoDiscoverServiceInternalUri       : https://remote.SERVER.org/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
IsOutOfService                       : False
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=SERVER,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Admin
                                       istrative Groups,CN=First Organization,CN=Microsoft Exchange,CN=Services,CN=Conf
                                       iguration,DC=SERVER,DC=local
Identity                             : SERVER
Guid                                 : ac17ac4c-c5a2-40f5-a1be-1368f6616c96
ObjectCategory                       : SERVER.local/Configuration/Schema/ms-Exch-Exchange-Server
ObjectClass                          : {top, server, msExchExchangeServer}
WhenChanged                          : 2020-06-01 13:40:37
WhenCreated                          : 2011-06-13 14:02:03
WhenChangedUTC                       : 2020-06-01 11:40:37
WhenCreatedUTC                       : 2011-06-13 12:02:03
OrganizationId                       :
OriginatingServer                    : SERVER.SERVER.local&nbsp;

mateusz710 · Answer

Sergey Kluzner&nbsp;KonstantinosPassadis&nbsp;&nbsp;Screen in English in the attachments.&nbsp;I am sending the log below.&nbsp;[PS] C:\ProgramData\Microsoft\Windows\Start Menu\Programs\Microsoft Exchange Server 2010&gt;Get-ActiveSyncVirtualDirectory | fl
RunspaceId                                 : 07206f30-6958-496c-b970-1442e294512e
MobileClientFlags                          : BadItemReportingEnabled, SendWatsonReport
MobileClientCertificateProvisioningEnabled : False
BadItemReportingEnabled                    : True
SendWatsonReport                           : True
MobileClientCertificateAuthorityURL        :
MobileClientCertTemplateName               :
ActiveSyncServer                           : https://remote.SERVER.org/Microsoft-Server-ActiveSync
RemoteDocumentsActionForUnknownServers     : Allow
RemoteDocumentsAllowedServers              : {}
RemoteDocumentsBlockedServers              : {}
RemoteDocumentsInternalDomainSuffixList    : {}
MetabasePath                               : IIS://SERVER.SERVER.local/W3SVC/1/ROOT/Microsoft-Server-ActiveSync
BasicAuthEnabled                           : True
WindowsAuthEnabled                         : False
CompressionEnabled                         : True
ClientCertAuth                             : Ignore
WebsiteName                                : Default Web Site
WebSiteSSLEnabled                          : True
VirtualDirectoryName                       : Microsoft-Server-ActiveSync
Path                                       :
ExtendedProtectionTokenChecking            : None
ExtendedProtectionFlags                    : {}
ExtendedProtectionSPNList                  : {}
Server                                     : SERVER
InternalUrl                                : https://remote.SERVER.org/Microsoft-Server-ActiveSync
InternalAuthenticationMethods              : {}
ExternalUrl                                : https://remote.SERVER.org/Microsoft-Server-ActiveSync
ExternalAuthenticationMethods              : {}
AdminDisplayName                           :
ExchangeVersion                            : 0.10 (14.0.100.0)
Name                                       : Microsoft-Server-ActiveSync (Default Web Site)
DistinguishedName                          : CN=Microsoft-Server-ActiveSync (Default Web Site),CN=HTTP,CN=Protocols,CN=
                                             SERVER,CN=Servers,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Ad
                                             ministrative Groups,CN=First Organization,CN=Microsoft Exchange,CN=Service
                                             s,CN=Configuration,DC=SERVER,DC=local
Identity                                   : SERVER\Microsoft-Server-ActiveSync (Default Web Site)
Guid                                       : 788bdc06-162b-41a9-aea6-0b1cb09ada60
ObjectCategory                             : SERVER.local/Configuration/Schema/ms-Exch-Mobile-Virtual-Directory
ObjectClass                                : {top, msExchVirtualDirectory, msExchMobileVirtualDirectory}
WhenChanged                                : 2020-07-07 01:13:23
WhenCreated                                : 2020-07-07 01:04:37
WhenChangedUTC                             : 2020-07-06 23:13:23
WhenCreatedUTC                             : 2020-07-06 23:04:37
OrganizationId                             :
OriginatingServer                          : SERVER.SERVER.local
IsValid                                    : True