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FAQs: Attachments

  1. .pif, .exe, .bat, .scr
  2. Size doubles
  3. Print
  4. Crash
  5. Open in a different application
  6. .vcf file
  7. winmail.dat files
  8. Combine and decode
  9. Include attachments when I forward
  10. Does deleting a message also delete its attachment?
  11. Sending attachment fails - error 5421 "server is busy"
  12. Animated GIFs
  13. Corrupted Attachments sent with Entourage 2004
  14. Do I really need Stuffit to add attachment to Entourage?
  15. Remove attachments from exchange server
  16. Attachments over 400KB (Entourage 2008)
  17. Opening attachments keeps adding numbers
  18. AOL sends multiple .JPG files as .mim extension

Help with Compression

Entourage can only remove attachments from messages that are "on the computer". For "online" accounts (IMAP, HTTP, Exchange), Entourage only removes the attachment from the local copy of the message; the message on the server still contains the attachment(s).

Remove Attachments Script This script removes all attachments from the currently selected messages in Entourage. The script allows you to optionally extract removed attachments to a folder named "Removed Attachments" on disk, and also optionally adds notes and links to affected messages.


1) I frequently receive attachments in various Windows file formats (.pif, .exe, .bat, .scr, etc.) from unknown senders. What's going on?

Windows file formats like these are commonly used to distribute PC viruses. You cannot be infected by them on a Mac but you should never try to open an attachment from an unverified source regardless. And, by all means, don't forward these to your PC friends!


2) I sent myself a photo in .gif format. It left at 172K in size and arrived back at 226K. How do you account for that?

The size display in Entourage is the total size of the source of the message. This means that any encoding is included, together with headers, body text etc. That would account for your 172k image blowing up to 226 without any problem.

The next problem arises with Entourage's rounding. It switches from kb to mb at 512kb. It then rounds everything to the nearest mb, so a 600k message will show as a 1mb message, as would a 1500kb message.

As a final thought, when sending images its always worth stripping out the preview, custom icons and other resource info. This can often amount to 150-200kb on it's own. GraphicConverter has a 'save web ready' option for this, and also a 'strip resource fork' conversion mode for trimming down individual files or batches of files.


3) How can I configure Entourage to print messages with an attachments list at the bottom if necessary?

Get Paul Berkowitz's free Print Message w/Attach script.

That will include the filename of the attachments below the printed e-mail to signify that attachments are present in the e-mail.


4) Entourage crashes when trying to open attachments. What do I do to fix this?

Quit Entourage, go into your Microsoft User Data folder, delete the Entourage Temp folder, then restart. See if that helps. That is where Entourage is trying to save the file before it opens.


5) I want an attachment or file to open in a different application than the one that currently opens automatically. Every time I get .jpg file as an attachment, when I click to open it, Classic tries to start and use the Classic QuickTime. If I click on any .jpg not in Entourage, OSX Preview opens the file (which is what I want). I've gone through all the settings in E'rage that I could find. How do I change this?

In Entourage X and 2004:

To set the default application for files (in this case JPEGs) try the following:

  1. Save a sample file that has a type & creator code assigned to it, to the Desktop
  2. If the file does not have a file extension, add it.
  3. Select the file and "Get Info" from the "File" menu.
  4. In the "Open With" section, select the app you wish to make the default and click "Change All".
  5. Remove the file extension from the filename and repeat steps 3 and 4.

Type and creator codes are still used in OS X to determine the application that will open a file AND they are considered with a higher priority than file extension. Step 5 above ensures that you set the default for a specific file type as well as by extension.

You might have noticed that when you clicked "Change All" in step 4, that you are prompted to confirm that you wish to change the default app for all files ending in ".jpg" (or whatever extension you used). In step 5 you are, instead, asked to comfirm that you wish to change the default app for all files of type "JPEG" (or whatever type the file has).

--Remo Del Bello, Entourage Talk member

In Entourage 2001:

Apple Menu -> Control Panels -> Internet / Advanced tab > File Mapping. Scroll down the list of file extensions to find the one you're looking for. Select it and click Change. When the Change Mapping window appears, scroll to the application you want, select it and click Change. Close out of the Internet Control Panel and click Save if prompted.


6) How can I make Entourage v X make a new contact when I double-click a .vcf file sent to me as an attachment?

Here's the correct sequence:

  1. As a one-time only drill, drag or save any .vcf attachment from the Entourage X message window to the Desktop.
  2. Control-click (or right-click) on the .vcf file on the Desktop.
  3. Choose "Get Info" ("Show Info" if you use OS X 10.0-10.1)
  4. Click the "Open With" button (in OS X 10.0-10.1, select Open with Application from pop down menu).
  5. Choose Entourage X from menu
  6. Click "Change All"

7) What are winmail.dat files?

Winmail.dat and/or application/ms-tnef files are sent by Windows users of Outlook or Exchange who have their mail clients set up to use 'RTF' instead of plain text or HTML.

Usually they only contain a styled text version of the message you have just read in plain text, but they can contain encoded attachments that you can't usually get to.

TNEF's Enough, by Josh Jacob, allows you to extract and read these files and attachments.

Better still, contact your correspondent and ask them to reset their mail format from the (MS proprietary) "Rich Text" to either "Plain Text" or "HTML. If they have you in their Outlook Address Book they can make a setting to always send you Plain Text automatically.

See also Microsoft KB: How to Prevent the Winmail.dat File from Being Sent to Internet Users


8) How do you combine and decode attachments?

You can't do it in Entourage. There are a number of other newsreaders that have this function, many of which can be found here: http://www.newsreaders.com/mac/clients.html A favorite free one is MT-NewsWatcher.


9) I'd like Entourage to include attachments when I forward a message to someone. How do I do this?

In E2004, attachments are automatically included when you Forward, and there is no preference to NOT include them!

There is a preference you can set for CC and BCC recipients to receive attachments. When you have an attachment, click on the "Encode..." option bar below the attachment window. At the bottom is the preference checkbox.

You might also want to check out the 'forward as attachment' command in the 2004 Message menu.


10) Does deleting a message also delete its attachment?

Yes! You can use a script to remove attachments and a note is placed in the message that points to the attachment. See Favorite Scripts Attachments- Friendlier Claris It!


11) I am unable to send an attachment (including MS documents) when using Entourage X. I get error 5421 "server is busy". Plain e-mail without attachments go OK. I'm using Verizon DSL and they say everthing is OK on their end (of course). I've already set the account information correctly - checked and checked and checked again - in Entourage Account settings. Any assistance would be greatly appreciated.

Two Solutions:

1) Many people have reported such problems if they have a DSL connection that uses PPPoE - especially when using Airport. I often have this problem and solve it by setting the MTU via the following command in the Terminal:

 sudo ifconfig en1 mtu 1364

Which value (e.g. 1364) is good is something that can be determined by experiment. (Max is 1500, so start there and decrease it untill it works.)"

2) Update Router Firmware. For full details read user experience.


12) Does Entourage enable us to use animated gifs in our email?

Entourage will not animate embedded gifs in simple HTML (or as attachments to plain text messages). It will, however, animate gifs in complex HTML messages as the rendering there is done by the IE engine.


13) Corrupted Attachments sent with Entourage 2004

Change the preferences in Entourage so that attachments are set to be encoded "... For any computer (AppleDouble); no compression; Windows file name extension" instead of "Windows Mime/Base 64".

User reported this tip: Do you have LittleSnitch installed? If so, update to the latest version. It specifically had problems with corrupting attachments in Entourage. The latest version fixes that.


14) Do I really need Stuffit to add attachments to Entourage?

A folder cannot be sent without being compressed. You can use the Mac OS archive function to zip a file or use a third party application like Stuffit. Compression will only be 'required' by Entourage when you are trying to attach a folder _OR_ an application bundle (which is just a folder in disguise).

If you archive a single item, the archived file has the name of the original item with a ".zip" extension. If you archive multiple items at once, the archived file is called Archive.zip.

Entourage 2004 was originally designed with a much older version of Stuffit than the one available now. The Stuffit engine name (or location?) changed in an update and broke Entourage's ability to use it.

As an alternative, use Barry Wainwright's script "Attach Zip".


15) Remove attachments from exchange server

The only way to remove the attachment on the server is to move the message to a local folder (one under the 'on my computer' hierarchy), remove the attachment then copy the message back to the exchange server.


16) Attachments over 400KB do not show in messages.

Entourage 2008 will not show jpgs on the message if they are over 400kb.


17) Opening attachments keeps adding numbers

When you open an attachment in Entourage without saving it, Entourage makes a copy of it in the Saved Attachments folder in the Microsoft User Data folder. If you open the same attachment (or another with the same name) during the same Entourage session, Entourage will append a number to the name.

Quitting Entourage will delete the attachments from the Saved Attachments folder. So to get rid of them, just quit Entourage.