IIS

A quick way to troubleshoot SSL chain issues using OpenSSL

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You can use OpenSSL and run this command:

openssl.exe s_client -connect www.mysite.com:443

which will use a generic SSL/TLS client to connect to your site and give you a ton of diagnostic info.  You can see your entire SSL cert chain, the SSL handshake, SSL session info, etc.  Here’s a full list of switches you can use with it:  http://www.openssl.org/docs/apps/s_client.html

And here’s a great online tool to graphically verify your SSL chain is intact:  http://www.sslshopper.com/ssl-checker.html

About Jason Samuel

Jason Samuel lives in Houston, TX with a primary focus on strategic advisory and architecture of end-user computing, security, enterprise mobility, virtualization, and cloud technologies from Citrix, Microsoft, & VMware. He also has an extensive background in web architecture and networking over his 20+ year career in IT. He is an Author, Speaker, and Local User Group Community Leader. He is certified in several technologies and is 1 of 63 people globally that is a recipient of the prestigious Citrix Technology Professional (CTP) award. He is 1 of 42 people in the world that has been awarded as a VMware EUC Champion and VMware vExpert. He is a featured author on DABCC which provides the latest IT Community News on Cloud, Data Center, Desktop, Mobility, Security, Storage, & Virtualization. In his spare time Jason enjoys writing how-to articles and evangelizing the technologies he works with. Disclaimer: The content and opinions expressed in articles and posts are his own and are by no means associated with his employer.

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