Mail address lookup in shared hosting with multiple address lists setup

Question

Hi, we have an Exchange 2013 environment for hosting purposes.
One client uses two seperate company names (and domain names). These companies are seperated in Exchange and use seperate address lists. This client uses mail between the two domains.
Let's say the domains are yin.com and yang.com. The users use Outlook Webmail and the Mac OSX builtin mailclient
The problem is that when [email protected] sends email to [email protected], Bob is able to receieve the mail, but the email-address from Kevin is not included in the mail. It is just listed as Kevin, without any property.
When Bob replies to the message from the OSX Mail client, it apparently tries to make up an address and generates something to the effect of this:
Kevin </o=Hosting Company/ou=Exchange Administrative Group /cn=Recipients/cn=*longnumber*>
This address is not correct and when sent, the email is bounced back with a NDR-report.
When Bob replies to the message from OWA, the address is simply the name with no email-address. This also results in an NDR report.
What can we do to make OWA or Mac mail keep the correct emailaddresses?

Answer 1

Hi Nithyanandham,
1. The cached addresses were removed, had no effect.
2. Typing the address manually ([email protected]) works.
3. Sending mail to an additional smtp address also works.
4. Originally Kevin has one smtp address on his mailbox. There are no errors in them.
5. This happens for all users who are sending mail between these two companies/address lists.
6. Output of this command is as follows (replaced usersnames and domainnames to protect the innocent)
[PS] C:\Windows\system32>get-mailbox -identity "Kevin"|fl
RunspaceId : 2407ca9f-7e5a-466e-9230-d55c8e804380
Database : MailBoxDB001
Location :
UseDatabaseRetentionDefaults : True
RetainDeletedItemsUntilBackup : False
DeliverToMailboxAndForward : False
IsExcludedFromServingHierarchy : False
LitigationHoldEnabled : False
SingleItemRecoveryEnabled : False
RetentionHoldEnabled : False
EndDateForRetentionHold :
StartDateForRetentionHold :
RetentionComment :
RetentionUrl :
LitigationHoldDate :
LitigationHoldOwner :
LitigationHoldDuration : Unlimited
ManagedFolderMailboxPolicy :
RetentionPolicy :
AddressBookPolicy : yin_ABP
CalendarRepairDisabled : False
ExchangeGuid : 23d17a76-cc3d-40db-ada7-5d72aa14384a
MailboxContainerGuid :
AggregatedMailboxGuids : {}
ExchangeSecurityDescriptor : System.Security.AccessControl.RawSecurityDescriptor
ExchangeUserAccountControl : None
AdminDisplayVersion : Version 15.0 (Build 847.32)
MessageTrackingReadStatusEnabled : True
ExternalOofOptions : External
ForwardingAddress :
ForwardingSmtpAddress :
RetainDeletedItemsFor : 14.00:00:00
IsMailboxEnabled : True
Languages : {nl-NL}
OfflineAddressBook :
ProhibitSendQuota : Unlimited
ProhibitSendReceiveQuota : Unlimited
RecoverableItemsQuota : 30 GB (32,212,254,720 bytes)
RecoverableItemsWarningQuota : 20 GB (21,474,836,480 bytes)
CalendarLoggingQuota : 6 GB (6,442,450,944 bytes)
DowngradeHighPriorityMessagesEnabled : False
ProtocolSettings : {MAPI§1§§§§§§§, IMAP4§1§§§§§§§§§§§§, HTTP§1§1§§§§§§, OWA§1, POP3§1§§§§§§§§§§§§
RecipientLimits : Unlimited
ImListMigrationCompleted : False
IsResource : False
IsLinked : False
IsShared : False
IsRootPublicFolderMailbox : False
LinkedMasterAccount :
ResetPasswordOnNextLogon : False
ResourceCapacity :
ResourceCustom : {}
ResourceType :
RoomMailboxAccountEnabled :
SamAccountName : YIN-KBN
SCLDeleteThreshold :
SCLDeleteEnabled :
SCLRejectThreshold :
SCLRejectEnabled :
SCLQuarantineThreshold :
SCLQuarantineEnabled :
SCLJunkThreshold :
SCLJunkEnabled :
AntispamBypassEnabled : False
ServerLegacyDN : /o=Tao Hosting Services/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)
/cn=Configuration/cn=Servers/cn=PHSSV1-005
ServerName : phssv1-005
UseDatabaseQuotaDefaults : False
IssueWarningQuota : Unlimited
RulesQuota : 64 KB (65,536 bytes)
Office :
UserPrincipalName : [email protected]
UMEnabled : False
MaxSafeSenders :
MaxBlockedSenders :
NetID :
ReconciliationId :
WindowsLiveID :
MicrosoftOnlineServicesID :
ThrottlingPolicy :
RoleAssignmentPolicy : Default Role Assignment Policy
DefaultPublicFolderMailbox :
SharingPolicy : Default Sharing Policy
RemoteAccountPolicy :
MailboxPlan :
ArchiveDatabase :
ArchiveGuid : 00000000-0000-0000-0000-000000000000
ArchiveName : {}
JournalArchiveAddress :
ArchiveQuota : 100 GB (107,374,182,400 bytes)
ArchiveWarningQuota : 90 GB (96,636,764,160 bytes)
ArchiveDomain :
ArchiveStatus : None
ArchiveState : None
RemoteRecipientType : None
DisabledArchiveDatabase :
DisabledArchiveGuid : 00000000-0000-0000-0000-000000000000
QueryBaseDN :
QueryBaseDNRestrictionEnabled : False
MailboxMoveTargetMDB :
MailboxMoveSourceMDB :
MailboxMoveFlags : None
MailboxMoveRemoteHostName :
MailboxMoveBatchName :
MailboxMoveStatus : None
MailboxRelease :
ArchiveRelease :
IsPersonToPersonTextMessagingEnabled : True
IsMachineToPersonTextMessagingEnabled : True
UserSMimeCertificate : {}
UserCertificate : {}
CalendarVersionStoreDisabled : False
ImmutableId :
PersistedCapabilities : {}
SKUAssigned :
AuditEnabled : False
AuditLogAgeLimit : 90.00:00:00
AuditAdmin : {Update, Move, MoveToDeletedItems, SoftDelete, HardDelete, FolderBind, SendAs,
SendOnBehalf, Create}
AuditDelegate : {Update, SoftDelete, HardDelete, SendAs, Create}
AuditOwner : {}
WhenMailboxCreated : 22-1-2014 10:12:00
SourceAnchor :
UsageLocation :
IsSoftDeletedByRemove : False
IsSoftDeletedByDisable : False
IsInactiveMailbox : False
IncludeInGarbageCollection : False
WhenSoftDeleted :
InPlaceHolds : {}
Extensions : {}
HasPicture : False
HasSpokenName : False
AcceptMessagesOnlyFrom : {}
AcceptMessagesOnlyFromDLMembers : {}
AcceptMessagesOnlyFromSendersOrMembers : {}
AddressListMembership : {\yin_GAL, \yin_AL, \Mailboxes(VLV), \All Mailboxes(VLV), \All Recipient
s(VLV), \Default Global Address List}
Alias : kevin_yin.com
ArbitrationMailbox :
BypassModerationFromSendersOrMembers : {}
OrganizationalUnit : phs.local/Hosting/yin
CustomAttribute1 :
CustomAttribute10 :
CustomAttribute11 :
CustomAttribute12 :
CustomAttribute13 :
CustomAttribute14 :
CustomAttribute15 :
CustomAttribute2 : yin
CustomAttribute3 :
CustomAttribute4 :
CustomAttribute5 :
CustomAttribute6 :
CustomAttribute7 :
CustomAttribute8 :
CustomAttribute9 :
ExtensionCustomAttribute1 : {}
ExtensionCustomAttribute2 : {}
ExtensionCustomAttribute3 : {}
ExtensionCustomAttribute4 : {}
ExtensionCustomAttribute5 : {}
DisplayName : Kevin
EmailAddresses : {X500:/O=TAO HOSTING SERVICES/OU=EXCHANGE ADMINISTRATIVE GROUP /CN=RECIPIE
NTS/CN=665EE4639A4D47ABAB470761E386AF05, SMTP:[email protected]}
GrantSendOnBehalfTo : {}
ExternalDirectoryObjectId :
HiddenFromAddressListsEnabled : False
LastExchangeChangedTime :
LegacyExchangeDN : /o=Tao Hosting Services/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)
/cn=Recipients/cn=665ee4639a4d47abab470761e386af05
MaxSendSize : Unlimited
MaxReceiveSize : Unlimited
ModeratedBy : {}
ModerationEnabled : False
PoliciesIncluded : {}
PoliciesExcluded : {{26491cfc-9e50-4857-861b-0cb8df22b5d7}}
EmailAddressPolicyEnabled : False
PrimarySmtpAddress : [email protected]
RecipientType : UserMailbox
RecipientTypeDetails : UserMailbox
RejectMessagesFrom : {}
RejectMessagesFromDLMembers : {}
RejectMessagesFromSendersOrMembers : {}
RequireSenderAuthenticationEnabled : False
SimpleDisplayName :
SendModerationNotifications : Always
UMDtmfMap : {reversedPhone:63900611613+, lastNameFirstName:8262522337367653, firstNameLast
Name:7653826252233736, emailAddress:7653}
WindowsEmailAddress : [email protected]
MailTip :
MailTipTranslations : {}
Identity : phs.local/Hosting/yin/Kevin
IsValid : True
ExchangeVersion : 0.20 (15.0.0.0)
Name : Kevin
DistinguishedName : CN=Kevin,OU=yin,OU=Hosting,DC=phs,DC=local
Guid : f9ac1bfa-e174-4922-86a9-7698f30ac54e
ObjectCategory : phs.local/Configuration/Schema/Person
ObjectClass : {top, person, organizationalPerson, user}
WhenChanged : 20-11-2014 12:42:16
WhenCreated : 14-1-2014 13:05:03
WhenChangedUTC : 20-11-2014 11:42:16
WhenCreatedUTC : 14-1-2014 12:05:03
OrganizationId :
OriginatingServer : PHSSV1-001.phs.local
ObjectState : Unchanged
[PS] C:\Windows\system32>