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Switch from Apple Mail to Entourage

Contributed by Michel Bintener, Microsoft MVP

Preliminary information

This article focuses on Mail 3 (part of Mac OS X 10.5 "Leopard") and Entourage 2008. Most statements made in this article are true for Mail 2 and Entourage 2004, but some newer features are only available in the latest versions of both applications.

Moving from Mail to Entourage

E-mail

To import your mail messages from Mail into Entourage, see these links: Import/Export from other e-mail applications and Import information into Entourage

Contacts

You can set up Entourage to sync its contacts with the contacts that are in Address Book. (Note Apple stores it's contacts in a separate application (Address Book) where Entourage stores both messages and contacts in Entourage.) To find out how, read this article on how to use Sync Services in Entourage to import. More info can be found on Mactopia: Import information into Entourage

Alternatively, you can also import your contacts. To do so, open Address Book, select all your contacts and drag them to the desktop. A .vcf file will be created, which you can then simply drag into Entourage's contact list. See Importing/Exporting Contacts for help importing your contacts.

General behavior

Mail stores its messages in individual files in folders inside ~/Library/Mail, where “~” represents the name of your user account. Entourage stores all its data inside a single monolithic database in ~/Documents/Microsoft User Data/Office 2008 Identities/[name of your identity]. To find out more about Entourage’s database and get tips on how to perform backups, read this article.

Preferences

In this section, we will be looking at the various settings that can be made in Mail’s preferences (Mail>Preferences, or Command + , ) and see where some of these settings can be found in Entourage. Keep in mind that each application contains features that the other does not, so some options in Mail will not be available in Entourage and vice-versa.

General

In Mail’s General section, you can define the default e-mail reader for your Mac. This setting makes sure that when you click on an e-mail address in Safari, for instance, the appropriate application launches and a new message is created. Since Mail offers you a dropdown list of applications, you can use this setting to define Entourage as your default e-mail application. Alternatively, you can hit the button “Set Entourage to be my default e-mail client” button in Entourage 2008’s preferences (Entourage>Preferences, General). Note that Entourage needs to be set as the default e-mail client for some advanced functionality in Microsoft Word, most notably e-mail merge and sending documents as HTML attachments.

Another option is the interval at which Mail checks for new incoming messages. In Entourage, this setting has a proper name, Schedule, and it can be found in Tools>Run Schedule>Edit Schedules. The Schedules window contains all your schedules, including those that are created by default when you first launch Entourage, and they are more flexible than the single option provided by Mail. To create a new schedule, click on the plus button, and you will be able to define when the schedule is supposed to be run, and also the actions that take place when the schedule runs. You can for instance set up different schedules for different accounts, or you can also create schedules to empty the Deleted Items folder. Furthermore, schedules can also launch aliases or run AppleScripts, which makes them a very powerful feature.

Sounds can be set in the Notifications section of Entourage’s preferences, whereas the search options are set in the Spotlight section.

Accounts

The settings included in Mail’s Accounts section can be found under Tools>Accounts. The options that are given are very similar, and the settings that can/need to be applied depend on the type of e-mail account you are using, which is why we are not going to go into great detail. Some options are quite difficult to find in Entourage, so be sure to click on the “Click here for advanced receiving/sending options” buttons (in the Account Settings section) and the Options and Advanced tabs in Entourage’s Edit Accounts window. More info on setting up accounts here.

RSS

RSS feeds are not supported in Entourage 2008. NetNewsWire (freeware) is a popular Mac RSS reader.

Junk Mail

Entourage uses a junk mail filtering system that is quite different from the one used in Mail. Mail uses Bayesian spam filtering; to find out more about this type of spam filtering, read the corresponding Wikipedia article. One of the advantages of this method is that the user can help improve the filter by telling it which messages are junk and which ones are not. Entourage uses a more mechanical approach by relying on internal lists that are updated by Microsoft at irregular intervals. Both methods have their advantages and disadvantages, some of which are also discussed in the article referred to above.

To access Entourage’s junk mail options, in the menu bar click on Tools>Junk E-mail Protection. You can access a number of options in the window that shows up; you can specify the desired level of junk e-mail protection, and you can also specify safe domains as well as blocked senders. Junk E-mail Protection also offers a few more “under the hood” options; you can find out more by reading some of the articles posted on this page.

Fonts & Colors

The options in Mail’s Font & Colors section are split up into two different sections in Entourage’s preferences, Fonts and View. The options are mostly self-explanatory, so go ahead and customise Entourage’s appearance to your personal preferences. One useful detail that ought to be mentioned is that Entourage distinguishes between plain text font when viewed on screen and when printed, meaning that you can have two different settings for plain text font.

Viewing

Once again, the options presented in this section are split up into two different sections in Entourage. The options relating to the display of messages can be found in the View section; security-related options, such as “Display remote images in HTML messages”, can be found in the Security section. Please note that Smart Addresses and message highlighting are not supported in Entourage, which is why it does not offer these options. Also, the online status of your contacts is displayed automatically, both in the e-mail message list (the tiny MSN symbol next to a contact’s name in a message window) and in the contact list. This online status display only works in combination with Microsoft Messenger and MSN, whereas Mail’s buddy feature requires an AIM or MobileMe account with iChat. It is currently not possible to integrate iChat with Entourage or Microsoft Messenger with Mail.

Composing

Most options found in this section can be found in the Compose and Reply & Forward sections. The default message format can be set in the Compose section. Since Entourage is also a newsgroup reader (which Mail is not), you can set a default format for newsgroup messages as well. Regardless of the format set in the preferences, you can always switch between plain text messages and HTML messages when writing a message by clicking on the small button labelled “ab/ab”, which you can find below the Attachments section of a new mail message window, on the left side.

:Mail format.png

Spell checking options are set in the Spelling section. While typing a new message, you can also change languages by clicking on Tools>Spelling Languages. Note that you can also access Word’s AutoCorrect settings in Entourage by clicking on Tools>AutoCorrect. This is also the right place if you want to switch off some of Entourage’s automatic behavior, such as capitalising the first letter of sentences or the automatic creation of lists, which has the potential to become very annoying if you do not know how to disable it.

The account which is used when hitting the New Mail Message button is determined by your default account; this setting is made in Tools>Accounts (select the account, then click the button which reads “Make the selected account the default one”).

The options found in Mail’s Responding section can be found in the Reply & Forward section.

Signatures

Signatures can be created by clicking on Tools>Signatures. These signatures can then be associated with a particular account by going to Tools>Accounts, double-clicking the account and switching to the Options tab. A signature can also be applied on a per case basis by clicking the Signature button in a new compose window. The placement of signatures is determined in the Reply & Forward section of Entourage’s preferences (Mail Attribution). A more detailed breakdown of the different options can be found here. More info on creating signatures with images.

Rules

In Entourage, rules are created in Tools>Rules. Entourage offers a series of powerful options when it comes to rules, so try to use this to your advantage. As a result, rules are handled differently from Mail and can be quite complex to create and organise. First of all, whereas Mail offers rules that apply to any type of account, Entourage differentiates between different types of rules, based on the account to which they apply (POP, IMAP, HTML, Exchange, and News). Entourage also allows you to create rules for outgoing messages.

You will therefore need to know which type of account you are using before you can create a rule for incoming messages sent to that particular account. Once you know which type of rule you want to create, you are given quite a few options. The principles remain the same between Mail and Entourage; if you know how to create a rule in Mail, you should have no problems creating one in Entourage. As is the case in Mail, rules are applied based on the order in which they appear in the list, which means that you can determine the order in which they are run by sorting them manually. Also, make sure that the option “Do not apply other rules to messages that meet these criteria” is not checked for messages that need to be processed by other rules as well.

A particularly useful type of rule is the previously mentioned outgoing rule. This type of rule applies to messages you send; for instance, you can instruct Entourage to categorise and move messages that fit a number of criteria. Again, it is up to you to make this feature as useful as possible. Since this particular type of rule cannot be found in Mail, it may take some time getting used to it.

Rules can also be run manually by selecting one or more messages, ctrl-/right-clicking it and selecting Apply Rule from the contextual menu. Entourage is more useful in that regard than Mail, as it allows you to apply specific rules only, whereas Mail insists on applying all the rules. To find out more about rules, check this page.

Lastly, Entourage also offers a feature called Mailing List Manager. This particular type of feature is actually a collection of rules that allow users to deal with mailing list messages more easily. If you are not subscribed to mailing list, you will never have to use this feature; if you participate in one or more mailing lists, however, its usefulness should soon become obvious. You can find this feature by clicking on Tools>Mailing List Manager.

One of the most common mistakes users make is accidentally creating a MLM rule when marking a message as junk. Since MLM rules run first all your messages will start going to the wrong folder. Simple delete the MLM rule to fix.

See Frequently Asked Questions for help with the transition from Mail and Entourage.