Automatic Login
Outlook Password Retention
and Related Troubleshooting
Outlook may continue to prompt for your password each time you start it, even though you've checked the box that you want Outlook to retain the password. The following steps will normally enable Outlook to retain the password correctly.
It is actually your Internet Options settings that allow automatic login. Adjust them as follows.
Open Internet Options through Control Panel or from within Internt Explorer. Use the search box in Control Panel or in IE, Tools menu, Internet Options.
Once you're in the Internet Options go to the Security tab, Local Intranet, Sites, Advanced. The dialog shown below will appear.
Add the Outlook Anywhere URL to the Local Intranet zone. See screen shot below. The URL to add here is https://mail.webville.net While you're here, if you have SharePoint and you'd like to make that login easier, add your SharePoint URL here as well.

Click the Close button and Ok button to return to the security tab. While on the Security tab, select Local Intranet zone and click Custom level. The dialog shown below will appear. Scroll to the bottom and verify that your computer is set to allow Automatic logon in the Intranet zone. That's the default setting, you probably won't need to change it. See screen shot below.

Click Ok to close the Local Intranet Zone security settings dialog. Choose the Advanced tab of the main Internet Options dialog. Look near the bottom of the settings list under Security for Integrated Windows Authentication, it should be enabled. See screen shot below.

The above is normally all that's required. If you still have problems after doing all that, continue to these additional steps.
In Outlook 2007, find Account Settings on the Tools menu. In Outlook 2010, find Account Settings on the File tab. Select the Exchange account and click the Change button, then More Settings. Look on the Security tab for the Always Prompt for logon credentials checkbox. This checkbox must be cleared.
Verify the credentials are saved in the Windows user account. Scroll to the bottom of this page for Windows XP steps. In Vista or Windows 7, type Credential in the Start search field. Find the server address and click it to expand it. Edit or add mail.webville.net if necessary.
LmCompatibilityLevel in your registry must be set to 3.
- Click Start, click Run, type regedit in the Open box, and then press ENTER.
- Locate and then click the following registry subkey:
HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Lsa\
- In the right pane, double-click lmcompatibilitylevel.
- In the Value data box, type a value of 3 and then click OK.
- Quit Registry Editor.
- Restart your computer.
Save your password.
- Open the Windows Stored User Names and Passwords dialog.
- In Windows Vista, Control Panel (Classic View), click on User Accounts icon, click on Manage your network passwords.
- In Windows XP, Control Panel (Classic View), click on User Accounts icon, click on Advanced tab page, click on Manage Passwords button.
- Click the Add button.
- If there is no Add button, see below.
- Enter *.webville.net
- Enter your logon name, example username@domain.com
- Enter your mailbox password, click ok and close.
- Launch Outlook and when prompted for your password, click Remember Password.
- Close Outlook after login is complete.
- Launch Outlook again and it should have retained your password.
The Add button may not be available in Windows XP Media Center Edition. Online forums indicate this may be a feature that is not available in Media Center Edition. We don't have definite confirmation of that.
The Add button may not be available in Windows XP Professional or Home editions depending on a registry setting. You can change this registry setting if necessary.
HKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\Lsa\
Value Name: disabledomaincreds
Value Type: REG_DWORD
Values: 0 = allow domain credentials to be stored
1 = do not store domain credentials
Reference http://technet.microsoft.com/en-us/library/cc743443.aspx regarding the disabledomaincreds registry setting.
Reference http://support.microsoft.com/kb/820281 for more details.