Entourage 2008 – New Features (Part I)

Since the release of Entourage 2008 for Mac, I have been watching the newsgroups, blogs and forums and I see one request more than any other which is to have a comprehensive list of features in Entourage 2008. In this blog I will try to provide exactly what our customers and Entourage users are looking for. As my expertise mainly lies with Entourage's interaction with Exchange Server thus I will also highlight the features important to Exchange users. This blog provides a list of features and a brief description of them, later I will blog on those specific features in detail from users' and administrators' perspectives.

Let's start with features which are common for all Entourage 2008 users irrespective of the type of mail server they are connecting to (Part I). In Part II I will talk about those features which are exclusive to Entourage 2008 users in an Exchange organization where they are working with other Outlook users

Application Shell (screenshot)
The main user interface of Entourage 2008 has been redesigned to provide a modern and compelling user experience that demonstrates to its users that Entourage is a premium messaging application and an integrated part of Office for Mac suite. It consists of 4 main areas, i.e. Toolbar (on top), Folder List (on left hand side), Item List (in the middle) & Preview Pane (on right hand side). There is a new 'View Switcher' panel (top left hand corner) to switch to different available modules, i.e. Mail, Address Book, Calendar, Notes, Tasks & Projects. The new 'MiniCal' (bottom left hand corner) can now be displayed in all folder views and it can be turned on or off using the toggle button.

Customizable Toolbars (screenshot)
Every toolbar you find in Entourage 2008 is now customizable, i.e. toolbar for every folder view, item view & composition window. Users can customize it by right clicking on it and choosing the option 'Customize Toolbar' or use the same option under 'View' menu.

Favorites Bar (screenshot)
This is a new addition in Entourage 2008 and provides feature parity with Outlook for Windows. Its located just below the toolbar in the main UI. Users can drag and drop any folder (or saved search) in their 'Folder List' to 'Favorites' bar and that creates a shortcut (or alias) for that folder which can then be used by the user to quickly get to that folder from any view in Entourage. 'Favorites' bar remains visible and accessible from all views in Entourage 2008 just like the main toolbar on top. Some really cool features of 'Favorites' bar are: it displays the number of unread items right beside the folder name, drag & drop folders to add/remove & re-organize them, drag and drop items to move them from one folder to another, etc.

Folder List (screenshot)
In the new 'Folder List' the folders related to the default mail account are displayed on the top and then rest are displayed according to alphabetical order with respect to the account names. Local folders (related to 'On My Computer') show up after all the other accounts if they are not associated with a default POP mail account. The first level children folders have been shifted to the left and start at the same position as their parent folder.

To Dos (in Item List) (screenshot)
Working thru 'Item List', users can now quickly toggle the state of flag for an item and use the contextual menu to take more precise actions to create 'To Dos'. This new feature provides more consistency with Outlook for Windows. These flags are also synched back to user's mailbox on Exchange server and thus also reflect in Outlook for Windows & OWA (Premium only, not Basic), similarly if user flags an item as a 'To Do' item using Outlook or OWA Premium, its also reflected in Entourage.

Preview Pane (screenshot)
Entourage 2008 also displays the e-mail sender's picture in 'Preview Pane' if user receives an e-mail from a contact with a picture saved in contacts folder. The pictures associated with contacts are not synchronized with Exchange server or the one saved thru Outlook for Windows will not be available in Entourage either. All pictures are saved with associated contacts in local database only. The message headers also display the category color in their background when viewed in preview pane. A new effect known as 'Glass' can be experienced in the message header area, where background color (reflects category) has two distinct shades. This effect is also available in Calendar when viewing appointments and meetings in any view.

New Calendar Experience (screenshot)
All calendar views have been redesigned to provide more solid look and feel which enhances end user experience. There is a new 'Today' button which brings a user back to the current day in any view. 'To Do List' (discussed later in Part II) can be displayed on the right hand side of all calendar views. It lists all 'to do' tasks (created by flagging items in Inbox) & tasks (from local Tasks folder which is not synchronized with Exchange server). The new 'All Day Events Area' is designed to display events that transpire over a full day or set of dates. All events have tile like appearance when they are placed on calendar, they inherit the category color and exhibit glass effect as well. They are composed of many elements like free/busy indicator, meeting title/subject, meeting location, travel time indicator & several different status icons. For users who create events on their calendars very frequently, Entourage provides a way to create them quickly by dragging the mouse from start to end time (works in both directions, up or down) and then populating the event title and location by typing inline inside the event tile.

My Day (screenshot)
'My Day' is a new application included with Entourage 2008 which provides its users with an easy and quick way to access their calendar, to do list & tasks without running the full Entourage application. It interacts with the database directly to pull up related information rather than going thru Entourage, thus you don't need to run Entourage to use 'My Day'. It enables users to easily manage their daily activities and with the help of robust preferences they can customize their access to data and their interaction behavior. Users can also create tasks quickly thru 'My Day' but cannot create events in Calendar. It can also print a quick snapshot of the day for you.

Reminders (screenshot)
Office Reminders is the new application in Entourage 2008 which is replacing 'Office Notifications' in Entourage 2004. Reminders is often the most frequently used application with regards to Outlook & Entourage, thus a redesign is expected to improve end user experience. It also supports reminders for 'To Do' items and thus provides a new way to interact with them.

WebKit Integration (screenshot)
Entourage 2004 uses Tasman engine (from Internet Explorer for Mac) to render complex HTML mail messages. Tasman Engine has now been replaced by Apple's WebKit in Entourage 2008. WebKit is the HTML rendition engine which is used by Apple's Safari web browser and thus Entourage using the same engine is now better integrated with Mac OS and Safari. Entourage 2008 still does not support the composition of complex HTML mail messages (with tables, embedded hyperlinks, etc.) like Outlook for Windows does.

Integrated Spotlight Search (screenshot)
Spotlight is the search feature by Apple which was introduced in Mac OS 10.4 (Tiger). It provides users with a single entry point for searching the entire contents of their computer. Support for Spotlight was first introduced in Update 11.2.3 for Entourage 2004, but it was not integrated into the application. Entourage 2008 now has integrated Spotlight based search feature. Spotlight based searches are really fast in Entourage and it provides an integrated UI for building queries, which can be saved as well for later use. Users can now also run search against the contents of attachments with mail items in their databases. If an e-mail contains an attachment of a file type which has been designated as 'un-safe' in Office 2008 for Mac then that is not available for searching. Encrypted messages are also not indexed for Spotlight based search as they were encrypted to keep the content secure.

Zip Compression Support (screenshot)
Entourage 2004 provides compression feature when a user sends attachments with message or meeting invite. It uses Stuffit software by Aladdin Systems to compress those attachments. The compression option is available by default if Stuffit software is already installed on user's Mac OS system. Apple used to provide Stuffit libraries by default when you install Mac OS but they have stopped doing so with Tiger (Mac OS 10.4). Thus now users (using Mac OS 10.4) have to download and install Stuffit directly from the vendor's site (a free version is available) to use the compression feature inside Entourage. Entourage 2008 uses a new mechanism to compress attachments which has replaced Stuffit with Zip compression. As of Panther (Mac OS 10.3), Zip compression is also supported in Mac OS. This makes zip the most cross-platform compatible compression method for Windows and Mac users exchanging files. It also improves interoperability with Windows users. Windows and Mac users can now extract a zip file without any help from a 3rd party software as underlying operating systems provide required support, this reduces the need of installing any additional software to be able to work with zip files. Entourage 2008 uses 'Ditto' from Mac OS X to provide Zip compression feature. Ditto is a shell command that supports Zip compression while retaining resource forks. It is available in Mac OS X out of the box and is used by Entourage 2008 for compressing outgoing folders and files. Ditto is used and preferred over 'zip' shell command which is also available in Mac OS X because 'zip' command does not preserve resource forks.

Digital Signing & Encryption (S/MIME) (screenshot)
Entourage 2008 provides support for newer industry standard hash algorithms for digitally signing and encrypting mail messages. The use of old and weak encryption algorithms has been deprecated. Support for AES (Advanced Encryption Standard) based encryption and decryption has also been added. On top of this support for SHA-256, 384 and 512 with RSA keys ('SHA' stands for 'Secure Hash Algorithm & 'RSA' is another such algorithm named after their inventors) has been added for digitally signing and verifying e-mail messages. Entourage supports RSA & DSA (Digital Signature Algorithm) for signing and/or encrypting messages in any key length. It also warns users when RSA or DSA key size is less than 1024 bits in length. All these new features require Mac OS 10.4 (Tiger) or higher.

Unsafe Attachment Blocking (screenshot)
Entourage 2008 has built-in mechanisms to prevent its user from sending and opening unsafe file types as e-mail attachments. As Entourage is widely used as an Exchange client thus in enterprise environments administrators may want to modify or override the default attachment blocking policies, thus a procedure is available here for them to be able to do so and deploy that to their users. This provision makes it an evident fact that this feature is not to stop users from sending unsafe attachments through e-mail, but to help them avoid accidentally forwarding unsafe attachments to other users and then as a result of that spreading virus (if unsafe attachments are infected with some virus). Since unsafe attachments can be used to hide viruses thus its important to provide a mechanism to try to prevent that and make the whole user experience more secure and better. User education is another most important part of this effort. The list of file types which are blocked by default is available here. Attachment security mechanism is applied at two different levels, one is to block direct user access to unsafe attachments from being opened through Entourage, and second is to help user make proper decisions about sending unsafe attachments through Entourage. The blocked attachments are never deleted from incoming messages, they are just blocked from being accessed inside Entourage.

Junk E-mail Enhancements (screenshot)
In Entourage 2008, when a message is moved to 'Junk E-mail' folder, it is marked by an open red envelope (under 'Priority' field) signifying that it is a junk e-mail message. A warning also appears in the info-bar section of the message which warns about using the hyperlinks in the message. This warning is there on all junk e-mail messages whether they contain any links or not. The headers area also reflects a darker shade of gray for junk mail messages. Entourage 2004 had a 'Safe Domains' list and now Entourage 2008 has a new list named as 'Blocked Senders' list. It can contain e-mail addresses and domains which Entourage user wants to block as senders of junk e-mail. Both 'Safe Domains' & 'Blocked Senders' lists are stored in the Entourage database on a per identity basis. Users can also right click on 'Junk E-mail' folder and click on 'Empty Junk E-mail' option to permanently delete all junk messages in the folder (rather than delete them first and then empty 'Deleted Items' folder). It works like emptying your 'Deleted Items' folder. The algorithm used for processing incoming e-mail to identify junk mail has also been improved which reduces the number of false positives.

Anti-Phishing (screenshot)
Entourage 2008 also sports some new built-in anti-phishing features, which help users in detecting phishing messages and also aide users in making proper choices when dealing with such messages. Below are some of the anti-phishing features in Entourage 2008:

  1. When a user hovers mouse pointer over links in an e-mail message in Junk E-mail folder, a pop-up tooltip with the full URL of the link is displayed

  2. User is always warned when clicking on a link from a message in the 'Junk E-mail' Folder

  3. User is always warned when clicking on links in HTML messages in Inbox (or Junk E-mail) folder which have mismatched text or domains (i.e. the visible hyperlink text is different than the embedded link text)

  4. User is always warned when clicking on links in HTML messages in Inbox folder which have mismatched protocols (like http & ftp)

  5. User is always warned when clicking on links in HTML messages in Inbox folder which have non-standard URLs, like consisting IP addresses, hexadecimal, octal or DWORD representations, etc.

  6. User is always warned when clicking on links in HTML messages in Inbox folder which have login information embedded within the URL

  7. Pictures thru embedded links are never downloaded automatically for messages in Inbox (or Junk E-mail) folder, regardless of 'Download pictures' settings under 'Security' in Entourage preferences, a message is displayed in info-bar letting the user know that pictures were not downloaded to protect user's privacy as they are used as 'beacons' (a common phishing practice), picture attachments with such messages which can be rendered inline are also not rendered

Smart Card Support
Entourage 2004 Service Pack 2 had very limited support for 'Smart Card' for specific purposes. Apple laid the ground work in their Mac OS X (10.4) and Entourage built support for Smart Cards on top of that. It was mainly on the request of US Department of Defense (and related military organizations like US Military) and only CAC (Common Access Cards) Smart Cards are supported at this point which are issued by DoD/US Military to its employees. Entourage 2008 has some enhancements in this area. Apple has also released a guide on its website for these customers. This article provides the manual for the 'Apple Federal Smart Card Package Installation and Setup Guide' in PDF format.

Online Help (screenshot)
The new 'Online Help' feature aligns with the Microsoft-wide help initiative, which incorporates a mixture of offline and online help, like in Office 2007 for Windows. The Microsoft online help system allows for future help topics in Mac Office to be easily & quickly incorporated and current content to be continuously updated. Microsoft Assistance Platform is a company-wide platform for assistance or help content. It encompasses authoring, publishing, hosting and analysis which are the basic components of continuous publishing. Continuous publishing is achieved thru publishing new and updated content on the Internet on an ongoing basis. A goal of continuous publishing is to respond to customers needs and desires in a timely fashion based on real data (like from support) & customer feedback. Office 2008 for Mac 'Help Viewer' is integrated into Entourage 2008 as well and provides assistance to its users which is consistent with the help provided for other applications in Office for Mac suite. It also offers 'Online Courses' & 'Quick Walk-Thrus' for several features in Entourage 2008.

Toolbox (screenshot)
Entourage 2008 now has Toolbox which is mainly composed of three tools, i.e. Scrapbook (was there in Entourage 2004 as well), Reference Tools & Object Palette (both are new to Entourage 2008). Reference Tools include the following tools for Entourage 2008 users: Thesaurus. Encarta Encyclopedia, Dictionary, Bilingual Dictionary, Translation & Web Search. Object Palette allows users to quickly find and insert images into your e-mail messages. It is designed to provide quick access to commonly used objects, like Shapes, Clip Art, Symbols & Photos. Users can also add photos from their iPhoto library or a folder. Read more about it over here. As a result of adding support for 'Reference Tools' in Entourage 2008, the link for 'Tools on the Web' & 'Dictionary' feature under 'Tools' menu (in Entourage 2004) have been removed.

Database Rebuild
With Entourage 2008 (using Microsoft Database Utility, see KB 268322) if you rebuild your database, you don't lose meta data, like categories, links, linked projects, flags, pictures saved with contacts & mail data cached in local database for different types of mail accounts (Exchange, IMAP, etc.).

Comments (6)
  1. Anonymous says:

    Microsoft’s Amir Haque has a great summary of the new features in Entourage 2008– it’s in two parts here and here. IMHO part 2 is more interesting because it focuses on Exchange integration. In fact, until I read this I…

  2. Anonymous says:

    A ton of things have been happening in the Exchange world that I’ve not been keeping up with very well, but I did come across two items that were of particular interest to me that I thought I’d share. …

  3. Anonymous says:

    Microsoft Entourage:mac News Microsoft Office 2004 for Mac 114 update released Tuesday, February 12,

  4. Anonymous says:

    Be sure to check out Amir Haque’s blog posts for helpful info on Office 2008. Part I describes features for all users. In Part II, Amir describes features which are exclusive to Entourage 2008 users in an Exchange organization where they are working with

  5. Anonymous says:

    Entourage 2008 has shipped and my customers are asking questions. What’s new? How can deploying Entourage

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