Issue 1 (Error message when connecting)

ISSUE: Users may receive the following error when connecting to Smarsh Hosted Services Exchange servers using Entourage 2008:

 “Unable to establish a secure connection to the “” because server name or IP address does not match the name or IP address on the server's certificate.” 

CAUSE: This is an issue with the Entourage 2008 application and will have to be resolved by Microsoft.

WORKAROUND: If you click the OK button on this error message Entourage 2008 will open and function normally.

Issue 2  (Meeting request replies not recognized)


ISSUE: If there is a rule configured in Outlook Web Access (OWA) or Outlook to move messages from specific users to an Inbox subfolder, then meeting requests show up in Entourage as not accepted from this user until you open OWA or Outlook, although the acceptance is received.  

CAUSE: Entourage does not recognize the meeting request that is filtered to an Inbox sub-folder. This is an issue with the Entourage 2008 application and will have to be resolved by Microsoft.

WORKAROUND: There is no known workaround at this time. Removing the rule that filters the messages will resolve the issue.

Issue 3 (Entourage loses connection to email account)

ISSUE: Microsoft Entourage 2008 for Mac may lose the connection to your email account on an Exchange Server. You do not receive an error message when this problem occurs. Additionally, you do not receive new email messages.  

CAUSE: This problem occurs because Entourage 2008 for Mac does not automatically re-subscribe to your email account when it loses the connection, if the email account is configured to use an Exchange Server back-end cluster node or a Network Load Balancing Server (NLBS) front-end node and a server failover occurs.

A server failover occurs when the primary node of an Exchange Server cluster fails and the cluster switches to another node and makes that node the primary node. When this occurs, Entourage 2008 for Mac will lose its connection to the server.

WORKAROUND: To work around this problem, use one of the following methods.

Method 1: Restart Entourage

You can reestablish the connection to the Exchange Server. To do this, exit Entourage 2008 for Mac, and then reopen the program. Entourage 2008 for Mac will connect to the new primary node on the Exchange Server and download any new email messages that are on the server.

Method 2: Open another folder

You can force Entourage 2008 for Mac to reconnect to the Exchange Server. To do this, select the Address Book folder or the Calendar folder for the Exchange email account. By opening the Address Book or Calendar folder, Entourage 2008 for Mac will log on again to the Exchange Server and download new email messages.

Method 3: Send a new message


On the File menu, point to New, and then click New Message.


Address the message to your own email address.


Click Send.


In the navigation pane, click the Outbox folder.


When the message leaves the Outbox folder and moves to the Sent Items folder, click the Inbox folder.

Entourage 2008 for Mac can now download new messages from the server.



Issue 4 (Certificate bug) 

There is an Entourage bug which affects users in an Exchange environment where users must import an SSL server root certificate into their Mac OS X keychain. The error reported by Entourage is that the root certificate is not correct. A valid certificate appears in the Keychain Access utility as trusted and unexpired.



Whereas Mac OS X 10.4 users could acquire the server certificate and import it into their x509Anchors, Mac OS X 10.5 users can now import the certificates into the user’s login keychain and the system will trust it. Entourage, however, is not trusting the server.



Although Apple released the Login & Keychain Update 1.0 (, it does not address the certificate issue.





Issue 5 (Notes and Tasks do not synchronize)

Entourage versions prior to EWS do not synchronize Notes and Tasks with Exchange. The ability to synchronize Notes and Tasks is available in the Exchange Web Services (EWS) Edition of Entourage.

You can also refer to Microsoft's Help and Support page: Entourage 2008 for Mac may lose the connection to your e-mail account on an Exchange Server