In some cases Outlook doesn’t remember your password, even if you enable the option to remember the password. This error is caused by a malfunctioning of the Protected Storage Space from Windows. To solve this problem, run the registry editor and navigate to the key HKEY_CURRENT_USER\Software\Microsoft\Protected Storage System Provider. You will find a key with a long name starting with S-1-5-21 which you have to delete. In most cases the problem is solved and next time the passwords will be saved.

Note: by doing this you will lose all stored passwords in Internet Explorer, Windows Live Messenger and other Microsoft applications. It’s advisable to recover and backup all types of saved passwords using Password Recovery Bundle.

If you are not allowed to delete that key, there is probably a problem with the permissions of your user account. Select the key Protected Storage System Provider, right click on it and choose  Permissions button and then click Advanced button. Make sure that your user account has Full Control for this key and subkeys. Activate the option Reset permissions on all child objects and enable propagation of inheritable permissions, click OK and repeat the earlier mentioned procedure. If needed, check the Microsoft KB files (http://support.microsoft.com/kb/290684). Here you will find out why Outlook can’t remember password and solutions to fix this problem.