Outlook prompting for password in cache mode

Try clearing the cache on the workstation, open up outlook, go into account settings, take the check mark of out exchange cache mode, close outlook, navigate to the outlook folder containing the .ost file, create a junk folder, move everything but the .ost file into the junk folder, re-open outlook, re-enable exchange cache mode, close outlook again and re-open.

Also clear managed passwords, open up the run command, type: control userpasswords2, click the advanced tab and then managed passwords, clear the passwords in there.

This is a known problem, please see my guide here on how to resolve this: https://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_2300-Outlook-continually-prompting-for-username-and-password.html

Try the service pack first then the Kernel Mode Authentication settings.

I followed all the steps, but i'm still being prompted for password when I start outlook in cache mode.  it didn't ask for it when i opened it with the cache mode unchecked. when i checked it, closed it and reopened it the prompt for password showed up again.

Does it do this for all users or just one or two?

All users that are using cache mode.

Are you using a public dns server on your client machines or a local dns server ?

Both ?

If both, which is listed first ?

demazter, I update the server to sp3, but still having the same problem.  I wanted to try the Kernel authentication Mode but i cant seem to locate the Authentication Icon you're talking about in IIS.

In turn highlight each of these virtual directories and double click the Authentication icon on the right hand side. Right click on Windows Authentication and select Advanced Settings. Place a check box in the box for Enable kernel-mode authentication. Do this for each virtual directory listed above.

I'm using a local dns.  I am, however using a smart host on the send connector.

Demazter, it seems your Kernel authentication mode suggestion only applies to server 2008, but i'm using server 2003.

Ahh, yes it does only apply to 2008.

What is SSL set to on your default website?

Do you mean the website tab under the Default Web Site Properties? if so it is set to port# 443

Under the Secure Communications box, is select the Require secure channel checked or not? What other settings do you have here?

it is checked.  here's a screen shot
IISDefault.png

Can you uncheck the require 128bit encryption and then run IISRESET from a command prompt.

Does it make any difference?

No that didn't help.  what if i checked Intergrated Windows Authentication and uncheck enable anonymous access?

I found out what the problem was.  we still have an old server that has exchange 2003 on it.  it serves as the recipient update server and target bridgehead for two connectors.  i'll have to assign these roles to the new server before i disable the services of the old server.