This article was previously published under Q290051
We strongly recommend that all users upgrade to Microsoft Internet Information Services (IIS) version 7.0 running on Microsoft Windows Server 2008. IIS 7.0 significantly increases Web infrastructure security. For more information about IIS security-related topics, visit the following Microsoft Web site:
This step-by-step article describes how to determine if Secure Sockets Layer (SSL) connectivity is not working on the Web server or on a intermediate device that is on the path from the client to the Web server.
After you install a Secure Sockets Layer (SSL) certificate on a computer that is running Internet Information Server (IIS) or Internet Information Services (IIS), you may find that you cannot connect to the computer across the Internet. When you try to connect, you may receive the following error messages in the browser:
To isolate this as a possible cause, first make sure that an SSL request to the server on the server is successful. After you install the SSL certificate, you can make an SSL request to the server by using the browser on the server (that is, connect to https://www.commonnameonthecertificate.com by using the browser on the Web server).
If you can connect to the server, follow these steps to confirm that an intermediate device is blocking the SSL traffic:
On the Web server, open a command prompt and use the Microsoft TCP/IP Tracert utility to connect to a known Web server on the Internet that has an SSL certificate installed (such as www.microsoft.com). This shows all of the "hops" between the Web server and the destination server.
The -d switch tells Tracert not to map IP addresses to host names.
tracert www.microsoft.com -d 1 20 ms 10 ms 10 ms 188.8.131.52 2 <10 ms 10 ms 10 ms 184.108.40.206 3 <10 ms 10 ms <10 ms 220.127.116.11 4 <10 ms 10 ms 10 ms 18.104.22.168 5 20 ms 20 ms 20 ms 22.214.171.124 6 20 ms 20 ms 20 ms 126.96.36.199 7 20 ms 20 ms 20 ms 188.8.131.52 8 40 ms 30 ms 30 ms 184.108.40.206 9 40 ms 30 ms 40 ms 220.127.116.11 10 40 ms 30 ms 30 ms 18.104.22.168 11 80 ms 71 ms 70 ms 22.214.171.124 12 70 ms 70 ms 70 ms 126.96.36.199
When you have obtained this information, use the Microsoft TCP/IP Telnet utility to determine which router is blocking the SSL traffic. First, try to telnet to port 443 on the first hop that is reported from the Tracert output.
For example, telnet to each hop that is listed in the Tracert output:
telnet 188.8.131.52 443
When a connection is made to a listening SSL port, the telnet session shows a blank flashing cursor, as if the server is waiting for input. After several seconds, or if you press any keys, the telnet client displays the following:
Connection to host lost.
A connection to a server that is not listening on SSL immediately returns the following message:
Could not open a connection to host on port 443 : Connect failed
Continue this process for each item on the Tracert list until you have determined the first intermediate device that is blocking SSL connections. After you find that device, work with the administrator of that device to correct this issue, and then try to connect to the site from the Internet.