Enable Logging SSL handshake failure(Audit purpose logs) only on Tomcat 8+ with Java

Question

I need to log if a SSL handshake fails while a REST client tries to connect to my application. The application is build using Spring Boot and Java 8 and deployed on Tomcat 8.

Answer 1

Unfortunately, it is not possible likely. And it is not related to Tomcat. Logging of SSL it is not part of standard logging in your application. You could try reduce output with following option:

-Djava.net.debug=handshake

Some others:

• record - Print a trace of each SSL record (at the SSL protocol level).
• handshake - Print each handshake message as it is received
• keygen - Print key generation data for the secret key exchange.
• session - Print SSL session activity.
• defaultctx - Print the default SSL initialization information.
• sslctx - Print information about the SSL context.
• sessioncache - Print information about the SSL session cache.
• keymanager - Print information about calls to the key manager.
• trustmanager - Print information about calls to the trust manager.
• data - For handshake tracing, print out a hex dump of each message.
• verbose - For handshake tracing, print out verbose information.
• plaintext - For record tracing, print out a hex dump of the record.

See docs.

If you really need this and performance is critical for your application, you could instrument SSLSocket (in docs you could read about handshake process) with ASM/Btrace /etc and check the state of handshake inside it. But in that case you wouldn't have debug information - only true/false.

See also Tomcat docs with all available settings. There you can read that there is JSSEImplementation class, which is used in Tomcat. And it is wrapper for JSSE.

Answer 2

I had same issue many times and i cracked it as following way. i had my project setup in intelliJ.

1. set Debug level of the VM option : -Djavax.net.debug=all (Edit Configurations->VM Options) save and apply.
2. Run project(App) in debug mode and check the calls between server and client. you will find there will be additional CertificateRequest call from the server to client in console as below for instance.

*** CertificateRequest Cert Types: RSA, DSS, ECDSA Supported Signature Algorithms: SHA512withRSA, Unknown (hash:0x6, signature:0x2), SHA512withECDSA, SHA384withRSA, Unknown (hash:0x5, signature:0x2), SHA384withECDSA, SHA256withRSA, Unknown (hash:0x4, signature:0x2), SHA256withECDSA, SHA224withRSA, Unknown (hash:0x3, signature:0x2), SHA224withECDSA, SHA1withRSA, SHA1withDSA, SHA1withECDSA Cert Authorities:

CN=Symantec Public Class 3, O=Symantec Corporation, C=US

CN=Symantec Class 3 Manage, OU=Symantec Trusted Network, O=Symantec, C=US

[read] MD5 and SHA1 hashes: len = 302

3. If you can see certificate request with "CN" as above that means you are missing these certs in cacert keystore.

Solution : add missing certs (for our example two certs CN=Symantec Public Class 3 and CN=Symantec Class 3 Manage).

we have to understand the calls between server and client by the SSL Protocol, please check the following link to get more information how server and client communicate.

https://docs.oracle.com/javase/6/docs/technotes/guides/security/jsse/JSSERefGuide.html#InstallProbs

I will give youtube video demo if someone have issue.

I hope this solution will help someone.

Thank You.