There have been documented cases of Entourage 2004 and 2008 continually prompting for passwords and rejecting logins for users when the same logins work in Outlook or Outlook Web Access. Although we have worked with Microsoft on this issue, currently there is no known permanent fix for that issue. Below are suggestions from both Microsoft and Apple on how to resolve the issues when they appear. We have listed them in the order of how successful we have found them to be in resolving the problems.

1. Change your login information. Instead of using the information provided in HostPilot, try one of the two authentication methods below: 

Domain: [Leave blank]
Account ID: Type your primary email address.
Password: Type your mailbox password.


Domain: [Leave blank]
Account ID*: EXCHXXX\Mailbox Username
Password: Type your mailbox password. 

*Note: To create your account ID for this login workaround, you need to use your EXCH0XX Domain and your mailbox username. To find this, navigate to HostPilot > Services > Exchange Mailboxes > click on Action button next to a user > choose Edit user info.

2. Delete any email with garbled text or “odd-looking" character sets.

3. Remove any daily calendar reminders (turn off the reminders or remove or archive old appointments).

4. Empty your Deleted Items and Junk E-mail folders.

5. Remove stored passwords from the keychain. For instructions, see one of the following Apple articles for your OS version:

6. Clear your font cache.

Quit Entourage, open the following folder on your computer, and delete the two files listed below:


- Tasman Browser.cache 

  1. Go to your Applications folder and launch Font Book.
  2. Select all fonts by holding down Command as you click on them.
  3. Go to File > Validate Fonts to open the Font Validation window.
  4. If you see a checkbox next to a font, it means the font is OK.
    If you see a yellow warning sign, there may be a problem, and if you see a red “X” the font is corrupted.
    Remove any corrupted fonts by checking the boxes next to them and clicking Remove Checked at the bottom of the window. 

7. Try logging in to Outlook Web Access first. To do this, close Entourage. Launch a browser and log in to OWA (select “Private” to keep the session active longer). Once logged in to OWA, open Entourage and log in. When the OWA session times out, see if the password prompt returns.