Entourage 2008/2004 for Mac “An operation on the server timed out. Error 3259” when sending email.

This problem occurs because an incorrect port number is set for the outgoing connection.

Step 1: Verify that you can connect to the Internet

First, test to see you can sign in using the web based application. For example, if its a Gmail account, visit gmail.com and Sign in. If you were able to sign in then proceed to the next step. If you are not able to sign in, contact your email client to obtain correct user name and password.

Step 2: Change the SMTP port to 587

Entourage 2008

  1. Start Entourage 2008.
  2. Click Tools, and then click Accounts.
  3. Double-click the account you want to set up for Entourage.
  4. In the Sending mail section, click Click here for advanced sending options.
  5. Click to select the Override default SMTP port check box, and then change the port value 587.
  6. Clear the Outbox, and try to send a test email message.

If the issue continues to occur, create a new user account and try again with the original email settings.

Entourage 2004

  1. Start Entourage.
  2. On the Tools menu, click Accounts.
  3. Select your email account.
  4. Click Edit.
  5. Click the Account Settings tab.
  6. In the Sending mail section, type the following text in the SMTP serverfield:
    mail.your-domain-name.com
  7. Click Click here for advanced sending options.
  8. Click to select the Override default SMTP port check box, and then change the port value 587.
  9. Click the small box in the upper-left corner to close the Edit Account window.
  10. Click OK to save the changes and to close the Accounts window.
If that doesn’t work, try to create a new user account

Step 3: Create a new user account