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How to: Debug SSL certificate problems from the shell prompt

Posted by Vivek on Thursday October 18, 07 @6:46 pm

OpenSSL is a cryptography toolkit implementing the Secure Sockets Layer (SSL v2/v3) and Transport Layer Security (TLS v1) network protocols and related cryptography standards required by them.

It also includes the openssl command, which provides a rich variety of commands You can use the same command to debug problems with SSL certificates.

To test the secure connections to a server, type the following command at a shell prompt:
openssl s_client -connect ssl.servername.com:443
Where,

For example connect to www.cyberciti.biz at port 443, enter:
openssl s_client -connect www.cyberciti.biz:443
Output:

CONNECTED(00000003)
depth=0 /C=IN/ST=Berkshire/L=Newbury/O=My Company Ltd/CN=*.cyberciti.biz/emailAddress=vivek@nixcraft.com
verify error:num=18:self signed certificate
verify return:1
depth=0 /C=IN/ST=Berkshire/L=Newbury/O=My Company Ltd/CN=*.cyberciti.biz/emailAddress=vivek@nixcraft.com
verify return:1
---
Certificate chain
 0 s:/C=IN/ST=Berkshire/L=Newbury/O=My Company Ltd/CN=*.cyberciti.biz/emailAddress=vivek@nixcraft.com
   i:/C=IN/ST=Berkshire/L=Newbury/O=My Company Ltd/CN=*.cyberciti.biz/emailAddress=vivek@nixcraft.com
---
Server certificate
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----
subject=/C=IN/ST=Berkshire/L=Newbury/O=My Company Ltd/CN=*.cyberciti.biz/emailAddress=vivek@nixcraft.com
issuer=/C=IN/ST=Berkshire/L=Newbury/O=My Company Ltd/CN=*.cyberciti.biz/emailAddress=vivek@nixcraft.com
---
No client certificate CA names sent
---
SSL handshake has read 1066 bytes and written 316 bytes
---
New, TLSv1/SSLv3, Cipher is AES256-SHA
Server public key is 1024 bit
Compression: NONE
Expansion: NONE
SSL-Session:
    Protocol  : TLSv1
    Cipher    : AES256-SHA
    Session-ID: 989C62FBF87884C9F6904DD216A9A36189BE660059F419DAA16711AF2A7F42D4
    Session-ID-ctx:
    Master-Key: 9A01374F14D7300E8DD02BE2AA3C3567F26E1BB00267D5AB0156C6C11A10EB0D8424FBD06D3B15013B4FBA0F121EC99D
    Key-Arg   : None
    Start Time: 1192732059
    Timeout   : 300 (sec)
    Verify return code: 18 (self signed certificate)
---

Using grep you can see the SSL and TLS connection handshaking, security negotiate, public keys and transfer of digital certificates and key information to the client:
$ openssl s_client -state -nbio -connect www.cyberciti.biz:443 2>&1 | grep "^SSL"
Output:

SSL_connect:before/connect initialization
SSL_connect:SSLv2/v3 write client hello A
SSL_connect:error in SSLv2/v3 read server hello A
SSL_connect:SSLv3 read server hello A
SSL_connect:SSLv3 read server certificate A
SSL_connect:SSLv3 read server done A
SSL_connect:SSLv3 write client key exchange A
SSL_connect:SSLv3 write change cipher spec A
SSL_connect:SSLv3 write finished A
SSL_connect:SSLv3 flush data
SSL_connect:error in SSLv3 read finished A
SSL_connect:error in SSLv3 read finished A
SSL_connect:SSLv3 read finished A
SSL handshake has read 1066 bytes and written 316 bytes
SSL-Session:

Further readings:

=> OpenSSL man pages and documentation.

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