No matter how many times you check the Remember Password box, Outlook/Outlook Express will refuse to save passwords for your account(s). To fix:
1. Go to Start>> Run. Type in: regedit [Enter]
2. Navigate to: HKEY_CURRENT_USER\Software\Microsoft\Protected Storage System Provider
3. Right-click the Protected Storage System Provider key, and from the menu choose Permissions
4. In the Security window, press the Advanced button
5. With the Permissions tab selected, place a check mark in the check box titled: "Replace permission entries on all child objects with entries shown here that apply to child objects". Click Apply, and then click Yes on the Security warning dialog
6. In the Name column, ensure that the user currently logged on has Full Control access. Click OK. The following message appears:
Do you want to replace the permission on all existing subkeys within Protected Storage System Provider?
7. Click Yes
8. Double-click the Protected Storage System Provider key to expand the key, click the user subkey folder that is directly below the Protected Storage System Provider key, click Delete on the Edit menu, and then click Yes in the warning message dialog box
The user subkey folder looks similar to the following example:
S-1-5-21-789336058-2025429265-1801674531-1003
Note: For every identity that you have, there may be a subkey under the Protected Storage System Provider key. To resolve this issue in all of your identities, you must delete all of the user subkeys folders under the Protected Storage System Provider key.
9. Close the registry editor
10. Log restart Windows for the changes to take effect
The next time you start your e-mail program, enter the password when prompted and select Remember Password. This should now be retained.