"Mail Could not be sent" error message when you try to send email in Entourage 2008 for Mac

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SYMPTOMS

When you try to send email in Entourage 2008, you receive an error message that resembles the following message:
Explanation: Mail could not be sent.
Error 17099
The message text may state "syntax error" before the error number. The message text may also include any of the following information:
  • Error - Requested action not taken: mailbox unavailable or not local
  • Error: Transaction failed: Rejected by content filter
  • Error Invalid sender address
  • Error 5.5.0 <vcxczvb> domain name required
  • Error: Could not relay message
  • Error: 4.4.5 Too many connections to this listener
  • 5.7.1 Message content rejected
  • Error - Domain name xxx.com does not resolve or mail not configured
  • 5.1.3 Bad recipient address syntax
  • 5.5.2 Syntax error
  • Error 5.5.1 - disapproved since there is a violation on policy
  • 4.3.0 Mail server temporarily rejected message

RESOLUTION

Important: Most email providers enforce a limit on the number of entries that you can put into the TO, CC, and BCC fields. They might also limit how many messages you can send in a 24-hour period. This is likely the cause of the problem if you could prior to 24 hours ago but you could not send email within the past 12 to 24 hours.

Step 1: Check the Outbox

This problem may occur because Entourage is trying to receive a corrupted email message. This problem may also occur because the Outbox contains a corrupted message. Because the outgoing message is corrupted, Entourage continuously fails to successfully send the message.

To resolve this problem, press and hold the Shift key when you start Entourage. When you do this, the send and receive operations are disabled at startup. Then, delete the message in the Outbox, exit Entourage, and restart the program as usual (without pressing the Shift key). You will have to re-create the message.

If the problem continues to occur, go to the next step.

Step 2: Rebuild the Entourage preferences

To restore the Entourage preferences file to its default settings, follow these steps:
  1. Quit all Microsoft Office programs.
  2. On the Go menu, select Home.
  3. Open Library.
    Note The Library folder is hidden in MAC OS X Lion. To display this folder, hold down the OPTION key while you click the Go menu.
  4. Open the Preferences folder.
  5. Look for the following files:
    • com.microsoft.entourage.plist
    • com.microsoft.entourage.database_daemon.plist
    • com.microsoft.entourage.database_utility.plist
    • com.microsoft.entourage.office_reminders.plist
    • com.microsoft.entourage.syncservices12.plist
  6. Move any of these files that you find to the desktop. If you do not find these files, this means that the program is not using any information that differs from the default preferences.
  7. Test Microsoft Entourage. If the problem still occurs, quit Microsoft Entourage. Restore the file or files to their original location, and then continue with the steps. If the problem seems to be resolved, move the files one at a time back into the folder. Test Entourage after you move each file, and quit Entourage before you move the next file. If you isolate the file that is causing the problem, move that file to the trash.
  8. Quit all Microsoft Office programs.
  9. On the Go menu, click Home.
  10. Open Library.
    Note The Library folder is hidden in MAC OS X Lion. To display this folder, hold down the OPTION key while you click the Go menu.
  11. Open the Preferences folder.
  12. Open the Microsoft Folder.
  13. Look for the file com.microsoft.Entourage.prefs.plist. If you find the file, move it to the desktop. If you do not find the file, this means that the program is not using any information that differs from the default set of preferences.
  14. If you move a file to the desktop, test Microsoft Entourage. If the problem still occurs, quit Microsoft Entourage, and then move the file back to the original location. Continue with the steps. If the issue seems to be resolved, the file can be moved to the trash.
  15. Quit all Microsoft Office programs.
  16. On the Go menu, click Home.
  17. Open Library.
    Note The Library folder is hidden in MAC OS X Lion. To display this folder, hold down the OPTION key while you click the Go menu.
  18. Open the Preferences folder.
  19. Open the Microsoft Folder.
  20. Open the Office 2008 or Office 2004 folder.
  21. Look for the following files:
    • Entourage Preferences
    • Office Sync Prefs 23
    If you find these files, move them to the desktop. If you do not find these files, this means that the program is not using any information that differs from the default preferences.
  22. Test Microsoft Entourage. If the problem still occurs, quit Microsoft Entourage. Return the file or files to the original location, and then continue with the steps. If the issue seems to be resolved, restore the files one at a time to the folder. Test Entourage after you move each file, and quit Entourage before you move the next file. If you isolate the file that is causing the problem, move that file to the trash.

Step 3: Review all POP and SMTP settings

To review all POP and SMTP settings, follow these steps:
  1. Start Entourage.
  2. Click Tools, and then click Accounts.
  3. Double-click the account that you have set up in Entourage.
  4. Review the settings to make sure that they are correct. If you previously could send email without errors, see the "Important" note at the beginning of the "Resolution" section.
  5. Clear the Outbox.
If you experience this error when you send a message to a group, divide the group into smaller groups, and then try to send separate messages to each group.

Step 4: Create a new user account

Sometimes, specific user information is corrupted. This problem can prevent a program from installing, starting, or running correctly. To determine whether this is the case, you can log on as a new user or create a new user account, and then test the program. For more information about how to create a new user account, click the following article number to view the article in the Microsoft Knowledge Base:

2439218 Testing your user account to troubleshoot Office for Mac applications

Properties

Article ID: 2279080 - Last Review: September 8, 2011 - Revision: 12.0
APPLIES TO
  • Microsoft Entourage 2008 for Mac
Keywords: 
dftsdahomeportal KB2279080

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