I'm having an issue with accessing any of the sites under the SBS Web Applications site (owa, remote, etc.) from outside the local network (tried from multiple external sources with same result). All internal access works, from both domain & non-domain hsots. The SBS 08 was recently migrated from SBS 03 without issue. All sites were up and running fine from both internal & external until I attempted to add a trusted certificate from GoDaddy. I followed the instructions here to install both certificates: http://sbs.seandaniel.com/2009/02/installing-godaddy-standard-ssl.html The specific issue is that navigating to any of the SBS Web Application sites return the same error conditions. When accessing any of these sites: https://remote.<mydomain>.com https://remote.<mydomain>.com/remote https://remote.<mydomain>.com/owa https://remote.<mydomain>.com/exchange https://<SBS WAN IP>/remote https://<SBS WAN IP>/owa https://<SBS WAN IP>/exchange These errors are returned: In IE: Certificate error is displayed & when the option to "Continue to this website (not recommended)" is selected, the error "Internet Explorer cannot display the webpage" is returned. In Firefox: "This Connection is Untrusted" error is displayed & when an exception is added, a blank, white page is displayed & "Done" is displayed on the status bar. When the Technical Details is expanded, the following is displayed: "remote.<mydomain>.com uses an invalid security certificate. The certificate is not trusted because it is self-signed. The certificate is only valid for ccvv The certificate expired on 12/2/2006 1:26 PM. (Error code: sec_error_expired_issuer_certificate)" In attempting to resolve the issue, I have done the following: Updated all SBS apps & OS with most recent available updates Ran SBS BPA & resolved all minor issue (no critical issues found) Verified all required SBS internet DNS settings are correct using nslookup & other tools Verified all SBS ports are forwarded from router to SBS (80, 443, 25, 987) Verified the correct certificate is selected through IIS Manager Verified the certificate being presented to all internal hosts matches the one selected through IIS, and is not expired Reverted back to self-signed certificate & ran IAMW with same results & error conditions Verified permissions on physical paths to all virtual directories Rebooted or reset IIS during each step of the process Moved internet DNS settings to another freshly installed test SBS on a completely seperate network & ran IAMW to use same exact settings, which worked fine (narrowing the issue to the SBS) Verified all IIS settings are set to default when compared to freshly installed test SBS Here are my thoughts on the issue: Based on the information presented by FireFox, it would appear that the certificate being presented by the site is not the same certificate that is configured through IIS. I have exhausted all resources available to me to find out how to troubleshoot this probable issue. Any ideas?