We have an issue with all of our Windows 7 remote users where they cannot connect to our hosted exchange server while connected VPN (PPTP or SSTP). Our email is hosted at Rackspace.com. Users connect to the exchange server using RPC over HTTPS. All of that works great over the Internet. If the a Windows 7 user connects to our VPN (Windows routing and remote access server in our corp. office) first and then tries to get into Outlook, it continually prompts for the password and never connects. If you disconnect from the VPN, email connects up and works great. If you get into email first and then connect to VPN, some users work fine. Others say it works for a while and then it prompts for password. Same results using the VPN property "use remote default gateway" or not. We usually uncheck for the user so they can use their own Internet. We have no problems with Windows XP users. Email works fine with VPN in any order on XP. This is a new issue since we started issuing Windows 7 laptops. Wondering if you have come across anything like this? Sorry if this is in the wrong area but since its related to so many things (exchange, network, dns, windows 7) I thought I would start here. autodiscover resolves to Rackspace Rackspace says they have not heard of this problem. Thanks Bill

Thanks for the reply but it's really not an Exchange issue. Its a routing and DNS issue. We have found that my statement above "Use Remote Default Gateway" was wrong. If we do leave it checked, the VPN uses our internal DNS and all works fine. Because we used the same domain for both internal and external DNS, this caused the confusion. Thanks

Hi, I would like to suggest you check your Mail setting to see what the result is: 1. In the Mail dialog box, click your Outlook profile, and then click Properties. 2. Click E-mail Accounts, and then click Change. 3. In the Change E-mail Account dialog box, click More Settings. 4. In the Microsoft Exchange dialog box, click the Security tab. 5. Uncheck “Always prompt for logon credentials”. 6. In the Logon network security list, click Password Authentication (NTLM), and then click OK. 7. Click Next, click Finish, and then click Close two times. Meanwhile, it seems this is related to the Exchange, it is also recommended to post in Exchange forum for further help: Exchange Server Forum Alex ZhaoPlease remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.

Thanks for the reply but it's really not an Exchange issue. Its a routing and DNS issue. We have found that my statement above "Use Remote Default Gateway" was wrong. If we do leave it checked, the VPN uses our internal DNS and all works fine. Because we used the same domain for both internal and external DNS, this caused the confusion. Thanks