Entourage 2008 for Mac: Entourage for Mac: “Mail Could not be sent” - Error 17099

SUPPORT SOLUTION:
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 error message details may state “syntax error,” followed by the number. Some other error messages that maybe be part of this error: Error - Requested action not taken: mailbox unavailable or not localError: Transaction failed: Rejected by content filterError Invalid sender addressError 5.5.0 <vcxczvb> domain name requiredError: Could not relay messageError: 4.4.5 Too many connections to this listener5.7.1 Message content rejectedError - Domain name xxx.com does not resolve or mail not configured5.1.3 Bad recipient address syntax 5.5.2 Syntax error Error 5.5.1 - disapproved since there is a violation on policy4.3.0 Mail server temporarily rejected message.Important: Most email providers have sending limits for the TO, CC and BCC fields as well as a limit in how much email can be sent in a 24 hour period. This is likely the case if you were able to send before and now cannot in the last 12-24 hours. .Step 1: Check the Outbox
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A message in the Outbox that is corrupted causing this problem. Entourage keeps trying  to send this corrupt email but failing. Or, the problem could be a corrupted message that is incoming.Hold down the SHIFT key when you start Entourage. When you start Entourage with the SHIFT key pressed, the send and receive schedule at startup is disabled. You will have to re-create the message. The best thing to do is to delete the message from the Outbox. After the message is deleted, exit Entourage, and then restart it as usual (without the SHIFT key pressed).If the problem continues to occur, go to the next step. .Step 2: Rebuild the Entourage preferences
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To resolve this problem, you have to restore the preferences file for Entourage to its default settings. To do this, follow these steps: Exit all Microsoft Office programs. On the Go menu, select Home.Open the Library folder.Open the Preferences folder.Look for the following files:com.microsoft.entourage.plistcom.microsoft.entourage.database_daemon.plistcom.microsoft.entourage.database_utility.plistcom.microsoft.entourage.office_reminders.plistcom.microsoft.entourage.syncservices12.plist

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.Test Microsoft Entourage. If the problem is still occurring, exit Microsoft Entourage. Put the file or files back in the 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. After you test each time, exit Entourage before you move the next file. When you isolate the file that is causing the problem, move that file to the trash.Exit all Microsoft Office programs.On the Go menu, select Home.Open the Library folder.Open the Preferences folder.Open the Microsoft Folder.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.If you move a file to the desktop, test Microsoft Entourage. If the problem still occurs, exit 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.Exit all Microsoft Office programs.On the Go menu, select Home.Open the Library folder.Open the Preferences folder.Open the Microsoft Folder.Open the Office 2008 or Office 2004 folder. Look for the following files:Entourage Preferences

Office Sync Prefs

23If 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. Test Microsoft Entourage. If the problem is still occurring, exit Microsoft Entourage. Move the file or files back to the original location, and then continue with the steps. If the issue seems to be resolved, move the files one at a time back into the folder. Test Entourage after you move each file. After each test, exit Entourage before you move the next file. When you isolate the file that is causing the problem, move that file to the trash. Step 3: Review ALL POP and SMTP settings.1.      Start Entourage.2.      Click Tools, click Accounts.3.      Double-click the account you have set up in Entourage. 4.      Review the settings so they are correct. If in the past, you were able to send email just fine, see Important section in this article, below the Resolution. 5.      Clear your Outbox. If this error is being experienced while sending to a group, break down a group into smaller group and then try sending again.     .Step 4: Create NewUser Account
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ometimes, a user’s specific information may be corrupted which can cause problems with applications starting, installing, or using. To determine if this is the case, you can log on as a new user or create a new user account, and then test an application. For steps and instructions on how to create a new user account, click the following article number to view the article in the Microsoft Knowledge Base: 2439218
(http://support.microsoft.com/kb/2439218)
 Testing your user account to troubleshoot Office for Mac applications .

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