Entourage 2008 – New Features (Part II)

Now let's talk about features which are exclusive to Entourage 2008 users in an Exchange organization where they are working with other Outlook users. Some of them, like Calendar features below may also apply to non-Exchange users as well.

Calendar Features
Entourage 2008 contains several new features and improvements in the area of event & calendar management. They are:

Accept, Tentative & Decline Buttons on Meeting (screenshot) - After a single instance or recurring meeting is accepted or tentatively added to the calendar (like by 'Calendar Assistant' in Exchange 2007), Entourage 2008 users are now able to act on the resulting event from the event itself. This is essentially the same as acting on a meeting request when it arrives in user's Inbox. This feature can also be used to decline a previously accepted meeting request later when user's plan changes.

Event Deletion Update (screenshot) - If an Entourage user (as a meeting attendee) deletes a previously accepted single instance or recurring meeting (or a single instance of a recurring meeting), the user is prompted to send a response to meeting organizer.

Time Zone Mismatch Warning (screenshot) - Outlook for Windows handles time zones differently when sending recurring vs. single instance meeting invites. In the recurring case, Outlook stamps the invite with sender's time zone and thus they are received & displayed appropriately in Entourage. On single instance meeting invites, Outlook does not stamp sender's time zone and thus Exchange Server stamps its own time zone on the invite. When Entourage receives such an invite, it uses the time zone stamped by Exchange to calculate start and end times. Some issues may occur if Exchange server is in a different time zone than the Entourage user (see KB 925376). Entourage 2008 displays better event status text related to event and local computer's time zones to handle this situation.

Processing of Incoming New Meeting Requests - Entourage 2008 behaves like Outlook and moves invites to 'Deleted Items' folder after they are processed in the Inbox by user. Invites having attachments with them are still left in the Inbox so that user can access them later when needed. Entourage 2008 does not support having attachments with events placed on Calendar.

Conflict Status (screenshot) - When an invite arrives, Entourage now compares it to the contextually related primary calendar (like Exchange Calendar) to determine if the invite conflicts with an existing event or not. If any portion of the time span of the invite intersects or overlaps with an existing event, an appropriate status text to that effect is displayed on the incoming new meeting request.

Adjacent Status (screenshot) – Same determination as above is made for detecting new invite being adjacent to an existing invite and if the beginning and/or end of the new invite's time span equals an existing event's time span, an appropriate status text to that effect is displayed on the incoming invite.

New Events Are Always Added to December - When the Mac OS X 'International Language' preference is set to Portuguese or Spanish, all new events created using Entourage 2004 appear in December of the respective year, though it preserves the day and date of event. This issue has been resolved in Entourage 2008 through adding support for 'Textual Separators' (like 'de') which is used to separate day, month and year in Portuguese, Spanish & some other languages.

To Do List (screenshot)
Entourage 2008 does not support synching with 'Tasks' folder in an Exchange mailbox but it does support the new 'To Do' based tasks feature (also in Outlook 2007 & Exchange 2007 OWA Premium) which lacks tasks assignment and progress tracking. This feature allows users to easily create and view their daily action items as well as provide a consistent experience with Outlook. Though 'To Do List' appears with the local 'Tasks' folder in Entourage, 'To Dos' are synchronized to the Exchange server and users will find consistent experience working with their 'To Do' items no matter which client they are using at a particular instant, be it Outlook 2007, Entourage 2008 or Exchange 2007 OWA Premium. The 'To Do List' can also be printed which provides a handy resource for users who are mostly in and out of meetings.

Out of Office Assistant (screenshot)
Using 'OOF Assistant' feature in Entourage 2008 users can set their out of office (OOF) status along with an OOF message when connecting to an Exchange Server. The feature is supported for Exchange 2000 or higher versions. This feature requires 'Outlook Web Access' to be functional on Exchange Server (2000 & 2003). Its implementation is based upon the 'OOF Assistant' available in OWA (2000 & 2003) and thus provides equivalent feature-set. It does not provide support for 'OOF Rules' which is available in Outlook for Windows. Support for separate internal and external OOF messages is only available for Entourage 2008 users connecting to a mailbox on Exchange 2007 Server. Such users can also set the OOF period (i.e. start and end date & times) and they can also send rich text or HTML based OOF messages. Entourage 2008 utilizes 'Exchange Web Services' and 'autodiscover' on Exchange 2007 for this feature.

Kerberos Authentication (screenshot)
Entourage 2008 supports Kerberos for authentication only for Exchange and LDAP (used for GAL access in Exchange organizations) accounts. It is not supported for all other types of accounts which you can configure in Entourage, like POP/SMTP, IMAP, Hotmail & News (NNTP) accounts. Mac OS X (Tiger and later) includes built-in support for Microsoft Kerberos (MSK) authentication and Active Directory authentication policies, such as password changes, expiration and forced password changes. By leveraging the OS's Kerberos service, Entourage provides better password handling and a cleaner setup experience. Kerberos authentication will mainly work only inside the corpnet environments as obtaining a Kerberos ticket (first step before you can use Kerberos authentication in Entourage) requires access to a Kerberos ticket or 'Key Distribution Center' (KDC), which generally in a Microsoft Windows Active Directory based environment is a 'Domain Controller' or a DC serving in Global Catalog Server (GC) role. Exchange Servers that are internally accessible are primarily the ones serving in back-end mailbox server roles, they support Kerberos authentication thus they can be used for connecting to Exchange mailboxes by Entourage users using Kerberos. Front-end or Client Access Servers (CAS) do not support Kerberos authentication for mailbox connectivity (by default) for users thus users will have to use three-tier domain credentials (i.e. username, domain & password for Windows Integrated/NTLM or Basic Authentication with SSL) to connect to their mailboxes. If Entourage is configured to use Kerberos authentication with Exchange account and user tries to assign delegation rights to another user on his own mailbox, then Entourage may try to establish a MAPI connection with user's mailbox server (see KB 909269 for more info) and it does not use Kerberos authentication for that purpose. MAPI library code which is used for delegation does not support Kerberos authentication. MAPI connection is established by Entourage for delegation rights assignment if mailbox server is running Exchange 2007 RTM or lower, like Exchange 2003 or 2000 (any version or build). For MAPI connectivity to user's mailbox server Entourage uses NTLM v2 authentication and thus it prompts the user with domain credentials dialog, asking user to enter username, password and domain.

Interoperability with Exchange 2007
Exchange 2007 introduced a whole new set of 'Web Services' which can be utilized thru SOAP (which is based on XML, another widely used protocol) based programming to interact with users' mailboxes and most of the other major components of Exchange. Entourage 2008 utilizes some of those features provided by 'Exchange Web Services' (EWS) thru SOAP based calls which are sent directly to CAS (Client Access Server) as EWS (and 'autodiscover') virtual directory is hosted only on a CAS server. The new features in Entourage 2008 which utilize 'Exchange Web Services' on server side are: 'Out of Office Assistant' (discussed above), 'Free/Busy Info Pull-up' & 'Delegate Rights Management'. Another new feature that's available on Exchange 2007 Server and supported in Entourage 2008 is working with 'Managed Folders'. This comes under the area of 'Messaging Records Management' which has been emphasized in Exchange 2007 (see demo here).

Free/Busy Info Pull-up - In Exchange environment when an Entourage user tries to schedule meetings with other users, the classic way to pull up their free/busy information is to send a WebDAV based query (Get /public/?Cmd=freebusy) to Public Folder server configured in Entourage (Exchange Account Settings : Advanced tab). Entourage 2004 still works in this way while Entourage 2008 can also utilize 'Exchange Web Services' (available only on Exchange 2007 Server) for this purpose. If Entourage 2008 is connecting to a CAS server for mailbox connectivity (Entourage : Exchange Account Settings), then it utilizes the 'autodiscover' & web services (EWS) running on CAS for querying free/busy information for Exchange users. On initial connection Entourage always requests the 'autodiscover' service on CAS to provide the contents of 'autodiscover.xml' file, that file contains URL information for EWS and related services which are used by Entourage for OOF assistant, F/B info pull-up and delegation. There is an 'Availability Service' (AS) also there offered by EWS, using the URL for AS (which is there in 'autodiscover.xml') called as 'ASURL', Entourage can pull up F/B info for attendees of a meeting. If Entourage is connecting directly to a mailbox server (back-end) for mailbox contents (Entourage : Exchange Account Settings), then a call to retrieve the contents of 'autodiscover.xml' fails as 'autodiscover' and EWS only run on a CAS server thus in that case, even if you point Entourage to a CAS server for Public Folder access (Entourage : Exchange Account Settings : Advanced tab), it can't use ASURL to pull up F/B info, and thus it falls back to classic mechanism described above, i.e. send a WebDAV based query to Public Folder server.

Delegate Rights Management - In Exchange 2007 Service Pack 1, a new web service is included for delegate management. Entourage 2008 uses that for delegate management if it is available on server side, i.e. if SP1 is installed on Exchange 2007 server. Again it works thru CAS server only because it's a web service and EWS is only available thru CAS as described above. If Entourage is connecting to Exchange 2007 RTM build or earlier versions like Exchange 2003 or 2000, then it falls back to classic delegate rights assignment procedure which uses a direct MAPI connection to mailbox server of Entourage user (discussed above). The best part of using the web service for delegate management on server side is that it can work thru a pure HTTPS connection, no need to have a direct connection to mailbox server and thus it's location independent as CAS servers in enterprise environments are published to Internet for OWA access. Entourage feature-set in this regard has not changed, meaning the options available for delegate rights management process (i.e. add/remove delegate, set desired permissions, etc.) are still the same but now it can use delegate management web service if its available on server side to assign delegate rights, which is great new for remote users.

Support For Managed Folders (screenshot) - Exchange 2007 has a new feature known as 'Managed Folders' as part of Microsoft's effort to help our customers with 'Messaging Records Management'. Using managed folders Exchange administrators can provide their users with extra folders in their mailboxes to be used for archiving and journaling (or any other use) which are managed by them on server side thru custom policies configured for retention and size quota. Users interact with them like they do with any other folder in their mailboxes, the limited control makes sure that they are not able to delete the top level managed folder created and provided by their administrators, but they sure can create subfolders of any type under it and manage them as they desire. The same policies (size or quota mainly) apply to all subfolders created under a managed folder. Entourage 2008 provides identical experience to Outlook & OWA 2007 when working with managed folders on Exchange 2007 server. It syncs the contents of managed folders just like it syncs the contents of all other folders in a user's mailbox. With every managed folder administrator can also have some policy statement text which describes what that folder's purpose is and any other related information, Entourage displays that on top of the items list view where it lists all items in that folder. The size quota is also mentioned in terms of percentage used & available and the actual size in megabytes. If user exceeds the quota, an appropriate warning is displayed for user's information.

Support For Message Classification (screenshot) - Exchange 2007 also has a new feature using which users can classify a message based on administrator's provided message classifications, which can be defined and set on server side and are then available for use in different Exchange clients like OWA & Outlook 2007. This feature can be used for company wide distribution and exchange of important documents and information thru e-mail. Examples include legal documents, contract information, classified or confidential information, etc. All such classified messages usually display some text informing user what kind of information they contain and if any corporate or company policy applies with regards to the provision or exchange of such info. Entourage 2008 supports the display of those text labels at the top of such messages for its users' information.

Interoperability with Outlook 2007
Entourage 2008 also has some features which improves its interoperability with Outlook 2007. This increases the feature parity between Outlook and Entourage. Some limitations of Entourage 2008 are also mentioned below for the purpose of full disclosure.

Free/Busy Permissions (screenshot) - Outlook 2007 has added a new set of permissions for 'Free/Busy' (F/B) data for users having mailboxes on Exchange 2007 server. Users can now determine what level of free/busy information should be available and visible to other users who are trying to schedule meetings with them. These levels are: None (no F/B data is visible), Free/Busy time (only F/B time is visible in the graphic form, new permission level), Free/Busy time, subject, location (meeting time, subject and location is visible, new permission level) & Full Details (all meeting information is visible, i.e. equal to Reviewer permission). These new F/B permission levels however are not available in Entourage 2008. Using Entourage 2004 a user cannot retrieve this level of information even if he has required permissions assigned to him. Entourage 2008 though works identically to Outlook 2007 and shows appropriate F/B info to its users according to assigned permissions. Entourage uses the new 'Availability Service' provided by 'Exchange Web Services' running on an Exchange 2007 'CAS' Server for this feature. The F/B info is displayed via a tooltip above a particular free/busy block when Entourage user views F/B info for other attendees in a meeting request being composed.

Payload Calendars (screenshot) - In Outlook 2007, a user can send another person a partial or full copy of his calendar by e-mail, including free/busy information with or without details and attachments (if there are any with events). All details are included in that e-mail within an '.ics' file along with an HTML representation of sender's calendar. If recipient is an Entourage 2004 user then opening the '.ics' file launches Apple's iCal application and Entourage does not handle it itself. HTML representation of the senders calendar though appears fine in that e-mail. Even if the user changes the association of '.ics' file to Entourage, user can only see one event, not multiple events if that file contains multiple events. Now in Entourage 2008 when such an '.ics' file is opened from a mail attachment, Entourage handles the file even if another application is the registered '.ics' file handler at Mac OS level. It also handles an '.ics' file containing multiple events and the collection of individual events including their free/busy information is automatically added to default calendar in Entourage. Attachments with any events in this case will not show up with events after they are imported to Calendar in Entourage.

Flagging & To Do Tasks - Outlook 2007 users can flag a mail item or contact and create a 'To Do' task. Entourage 2008 also includes the same feature which works identically (discussed above).

Electronic Business Card (screenshot) - Outlook 2007 contact items have a new 'Business Card' area as well as a built-in editor. A 'Send as Business Card' option allows users to exchange contacts (vCard format including images and formatting) via e-mail. Outlook users can also insert their own business cards as signatures at the end of e-mail messages. Both Entourage 2004 & 2008 display the HTML representation of incoming 'Business Card' correctly in-line in the message. Using the attached 'vcf' file that contact can also be opened and added into default 'Contacts' folder in Entourage. If that contact also has a picture embedded in it, that's also imported into Entourage when that contact is added thru its corresponding 'vcf' file. Keep in mind that Entourage 2008 does not sync the associated pictures in contacts added thru Outlook 2007, when user connects to the same Exchange mailbox using Entourage.

Meeting Updates (screenshot) - Meeting updates in Outlook 2007 now have an improved status description of any changes from preceding invite(s). The original invite data (i.e. time, location, etc.) is shown in the status area with a strikethrough directly next to the current or new value. Both Entourage 2004 & 2008 show a standard message in info bar which says: 'This is an update to an existing event'.

Sharing Messages (screenshot) - Outlook 2007 has a new method of quickly sharing calendar and contacts folders via e-mail. Using this option results in reviewer rights for the recipient as well as a request for the recipient to share the same folder. Entourage 2004 and 2008 both do not support this feature, the sharing message displays fine but has no effect on Entourage.

Delegate Changes - Outlook 2007 has added a new meeting requests forwarding option, i.e. 'My delegates only, but send a copy of meeting requests and responses to me (recommended)'. This option sends the original meeting request to the delegate, while the principal receives an informational message with the details of the invite. Entourage 2004 & 2008 users in principal roles still receive original meeting request with Accept/Decline buttons, so there is no change in Entourage's behavior due to this new feature in Outlook.

Categories - Outlook 2007 has improved its category feature which is also very identical to Entourage but Entourage still does not sync category information to & from Exchange Server thus if a user is using multiple clients to connect to his mailbox, and uses categories in Entourage, that information is still kept local in Entourage database and is not synched back to server.

RSS, InfoPath & SharePoint Integration (screenshot) - Outlook 2007 has added support for RSS feeds, improved InfoPath integration and Windows SharePoint support. These features are not supported in Entourage 2008. Only RSS Feeds folder is accessible thru Entourage if a user is also using Outlook 2007 to connect to the same mailbox. Any RSS feed to which user has subscribed thru Outlook are also synchronized by Entourage to its local database so that user can access them.