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HTML Newsletters, Messages & Signatures

Using Entourage to send HTML newsletters (not spam)

Entourage's HTML layout capabilities are extremely limited. Office 2004 offers one relatively easy way of creating more complex layouts through Word 2004. Please note, Word's HTML is not exactly W3C compatible. This can result in discrepancies between the original Word document and the resulting Entourage E-mail.

Now that you understand Entourage limited capabilities, check out the following options for creating and sending your newsletter.

Tip: Don't trust styles in the head of the document to be read or used by all HTML mail clients: inline is probably the most reliable. My recommendation is to email good, snappy TEXT-ONLY content, inviting them to click an included link to get the full info and formatting.


Create your newsletter using Word. Options for sending from Word are "Send to Mail Recipient (HTML)" and 'mail merge to email'. For more info see Word 2004 Help: Distribute merged form letters as e-mail messages.

Other options:

Send Complex HTML with Inline Files 2004 by Rob Buckley. This script will take an arbitrary HTML file and embed it in an outgoing Entourage message; will parse the HTML for links to files (images, etc), isolating duplicates; attach the file to the message with base64 encoding (using UNIX magic to guess the MIME type); then rewrite the HTML to reference the attachment rather than the local file.

"Send Complex HTML" by Paul Berkowitz. This script allows you to send complex HTML via Entourage. It gets the source of the HTML from either a saved HTML file or from the front browser window of Internet Explorer.

A good article to read if you plan on using a program like GoLive or Dreamweaver to create your HTML email is "Adobe GoLive & HTML Email."

Other software that has been recommended by users for this purpose:


Splitting recipients into smaller groups:

Entourage does not set a limit on the number of recipients. This is done by your ISP and the number is usually 50. You should contact your mail provider to ascertain the maximum number of recipients per message and note it.

There is a script, Split Recipients X, that will split your contacts into smaller groups so that you can send from Entourage. This script will replicate messages into the number of copies needed to comply with an ISP's maximum number of recipients allowed per outgoing message.

You can also create your newsletter in Word, and use the 'mail merge to email' function to send out a personalized copy of it to each recipient in the Office/Entourage address book.


Creating complex HTML Signatures

There is currently no way of inserting a live hyperlink into an Entourage signature, at least no convenient or straightforward way. You can always insert the URL, with the http:// prefix, and most e-mail clients should automatically convert them to active hyperlinks. Enclose the URL with < and > viz: <http://www.office.mvps.org/> so that if the URL wraps over more than one line, it will still work when it gets there.

An alternative, if you are using Entourage 2004, would be to use Word 2004 to compose your e-mail message, since you can easily create hyperlinks in that program (select some text, then hit Cmd+K). If Entourage is configured as your default e-mail client, you can, when you're done, go to File>Send To>Mail Recipient (as HTML) (this is still in Word, by the way). The downside to this method is that once the document has been passed on to Entourage, you can no longer modify it, or add attachments.

Mactopia has some great templates for creating HTML Signatures. Entourage Signatures and Backgrounds. Use these as a starting point to design your own signatures. Here is an example of a signature I created using a template.

Yet another alternative would be to use Paul Berkowitz's free AppleScript Make Hyperlinks X. (broken in Entourge 2008)


Including complex HTML into messages:

Entourage does not include the ability to send complex HTML. As noted above, Word 2004 does offer the ability to create HTML. Directions for creating newsletters also apply to HTML messages.


Frequently Asked Questions: HTML Messages

  1. Send multipart/alternative email
  2. Send auto-replies in HTML rather than text
  3. Embed HTML coding created in an outside application
  4. Crash when trying to open Complex HTML Messages
  5. Show pictures inline in HTML message
  6. Turn off curly quotes
  7. PC Mail displays incorrectly
  8. Red X
  9. Forward complex HTML msg preserving formatting & add comments
    1. Retaining HTML formating while forwarding an email
  10. Keyboard commands for page up and page down not work in HTML messages
  11. Turn HTML formatting OFF for selected email addresses
  12. Forward HTML with graphics
  13. Messages are failing to display inline images
    1. Entourage does display images in spam
  14. Compose HTML in Word and send with Entourage
  15. Include graphics in signature

1) Is there any way to configure Entourage so it can send multipart/alternative emails? I want to send html emails with html content that pulls its graphics from a website, but also want to send a text only equivalent for those who can't read html mail.

Entourage does not offer this option. Send Complex HTML with Inline Files 2004 by Rob Buckley can do that: as well as embedding HTML into a message, it will use the existing content as the plain text alternative for email readers that can't read HTML.

Other Options:

IntelliMerge X

Direct Mail

MaxBulk Mailer X


2) Can I configure Entourage to send my auto-replies in HTML rather than text?

Yes. Download Paul Berkowitz's free "Auto-Reply in HTML" script.

A Read Me is included with the script, which gives detailed instructions on usage. The script has you create a signature formatted with HTML as the auto-reply. You then create a rule and set up the script appropriately to have the signature used as an auto-reply.


3) How can I embed HTML coding created in an outside application into an outgoing Entourage e-mail message?

This feature has not been built into Entourage, however, there are two scripts that can do this.

Send Complex HTML with Inline Files 2004 by Rob Buckley

"Send Complex HTML" is a free download. Make sure you download the right version! http://homepage.mac.com/berkowit28/


4) Entourage X crashes when trying to open Complex HTML Messages.

Drag Macintosh HD/Users/<Problematic User>/Library/Preferences/com.apple.internetconfig.plist and com.microsoft.explorer.plist to the Desktop. Re-launch Entourage, open a complex HTML message, and see if you experience another crash. If you do crash, move the Internet Preferences files back. If you don't, you can trash the Internet Preferences files.


5) I want my pictures to show up inline in an HTML message. How do I do this?

Entourage X and 2004: From the Menu bar select Message: Insert picture. Note you need to use the HTML format for the message. This attachment MAY be displayed in the message window of your recipients, depending on their mail client and preference settings.

More info

You can also paste an image from the clipboard into an HTML message, or drag a graphic file from a finder window to a HTML draft message window - note that in this case the image will be inserted at the cursor location, not the location at which you drop the image!

Entourage 2001: This option is not available for 2001.

Get the script Send Complex HTML. It allows you to insert images inline, but requires a full-blown standalone HTML editor to create the source of the message body.


6) Is there any way to turn off curly quotes (aka smart quotes) when typing text in HTML mode? The curly quotes turn out to be commas (,) when the email msg is displayed on non-Mac users in our office.

Entourage X and 2004: Tools/AutoCorrect/AutoFormat/ Replace smart quotes with straight quotes.

Entourage 2001: Tools>AutoCorrect>AutoFormat As You Type>Replace as you type> and uncheck 'Straight quotes' with 'Smart quotes'.


7) If I send an HTML message to an Outlook (PC) user and that user replies to my message, several punctuation characters in my original message display incorrectly in Entourage X: apostrophe appears as comma, start quote appears as a double comma, end quote appears as percent, hyphen appears as tilde.

From the Format menu, choose Character set; Western European (Windows).

You can set a mail rule to set this character set on incoming mail for regular correspondents. See Rule#10 for an example. This rule will also help with small fonts seen from PC users.


8) My HTML messages are not displaying -or- I see a graphic in the preview window but not when I open the message -or- I see little red circles with x's in the middle. What's going on?

Entourage 2001:

You may need to increase Entourage 2001's memory. Navigate to the Entourage icon in the finder and click on it once to select it. Hit Command (Apple key) and the letter I (a.k.a., Get Info). Toggle to the Memory dialog box and raise the Preferred memory setting to 20000K. Leave the Minimum setting alone. Also, in Edit -> Preferences -> Mail and News, make sure 'Display complex HTML in messages' and 'Allow network access when displaying complex HTML' are checked. Make sure File -> Work Offline is unchecked.

In Entourage 2001 and X:

Most newsletter (& spam) images are not embedded within the message, but are stored remotely, on a web server. You will not be able to view these images if this option is turned off or if you are working offline. You need to turn on the option to allow network access when displaying complex HTML (Edit>Preferences>Mail & News>View). Also check to see that you have not set Entourage to work offline.

Note: Entourage doesn't like to email CMYK pictures, only RGB. So whenever you save and send a file, make sure it is in RGB mode.

In Entourage 2004, check the new Security Preferences:


9) How can I forward a complex HTML message preserving the formatting as well as being able to add comments?

Option 1:

  • Create a new message window first, and place it so that you can see it behind the Entourage Main Window.
  • Select the message you want to forward, and drag it into the composition area of the blank message window.
  • Click on the Attachment options box (starting with Encode for...). Change Encoding to Any Computer, Compression must be off, and attachments should be sent to CC/BCC recipients.
    • If you are sending to Windows users, be on the safe side and append Windows file extensions (though not necessary).
  • Create a subject, address your message, add any comments, and send.

Option 2:

  • Drag the message to the desktop then attach to new message.
  • Change Encoding using directions in Option 1.
9b) How do I forward HTML emails? I receive most of my mail in HTML format. I notice that when I try to forward these types of messages, the formatting is gone and I end up forwarding the raw html source instead.

Use "Forward as Attachment" or "Redirect " under Message in the Menu bar . Entourage's editor doesn't allow composition of complex HTML documents such as those containing tables, so it converts the formatting to simple HTML when forwarding or replying.


10) Why do the keyboard commands for page up and page down not work in HTML emails?

This is fixed in Entourage 2004. If you are using an earlier version...

This has to do with the fact that complex HTML messages are interpreted by the Internet Explorer rendering engine rather than by Entourage. Many commands that work with normal messages don't with complex HTML messages - it's essentially because it's displaying a web page in the Preview Pane.


11) Is there a way to turn HTML formatting OFF in Entourage for selected email addresses? As far as I can tell, HTML formatting is fully ON or fully OFF with no way to select particular addresses.

It's suggested to leave it off, and enable the Preference to reply to messages in the format in which they were received. That way, you'll use HTML in response to people who send HTML to you, but not to people who use plain text (who may not want it).

To turn HTML on or off for just the message you're writing, click the abab button on the left of your message's HTML toolbar.

To make sure that toolbar is always there, check "Show HTML Formatting Toolbar in the Message Composition window" in Mail & News preferences / Compose.


12) I have never been able to forward an HTML message that has graphics in it and have the message remain intact. It changes to all text.

You can either forward it as an attachment or redirect it. Entourage's editor doesn't allow composition of complex HTML documents such as those containing tables, so it converts the formatting to simple HTML when forwarding or replying.


13) I've just installed the new Entourage and suddenly my emails are failing to display inline images. I've checked the Preferences to insure that this is turn on and have tried turning it off and then back on. Doesn't work. Has anyone else seen this?

Entourage 2004 handles email images differently from Entourage X. In Entourage X, you had two choices: all images on, all images off. Entourage 2004 has these options:

  1. all images off
  2. images only on from people in your Address Book and Mailing Lists.

For very good security reasons, there is no longer an option to allow all images.

On-line content (including images) will not be displayed unless the sender is in your address book (a new security measure), and only then IF you have that preference set in the security pane of the preferences.

However, you can display the content by clicking the link in the yellow "info bar" at the top of the message.

A huge amount of requests were made for the old preference to block access to on-line content to be made available on a message by message basis, since people didn't want spam messages reporting back to base, but did want the pictures etc in subscribed newsletters. This was probably one of the 'most requested features', and MS listened.

13a) Entourage, however, fails to protect my privacy for most of the spam that has embedded images. In other words, Entourage does display images in nearly all of my incoming spam that has images. How does Entourage 'decide' whether or not to display embedded images?

If the images are enclosed within the message they will be displayed (unless you have unchecked 'show attached pictures...' in the 'view' pane of the preferences). However, if the images are stored on a remote web server and are only linked to in the message, they will not be displayed.


14) One of the big differences I am trying to get used to in Entourage is that, unlike Outlook, it does not use Word to compose E-mail messages--or if it does, I do not know how to configure my system to do it.

You can actually use Word to compose your HTML e-mails, and you can create real tables, even formatted ones; however, you will need to have Office 2004 to do this, and Entourage has to be set up as your default e-mail client.

Open Word 2004, compose your e-mail with all the tools available in Word, and when you're done, click on File>Send To>Mail Recipient (as HTML), and Word will send your current document to Entourage.

The one big drawback to this method is that you cannot attach files to it later on, and you cannot modify the text any longer, so if you need to make additional changes, you will have to open the Word document again and repeat the "Send to" procedure after you're done.