SQL Server JDBC Error on Java 8: The driver could not establish a secure connection to SQL Server by using Secure Sockets Layer (SSL) encryption

I turned on SSL logging in the Java 8 JVM on a Linux instance which reproduces the problem. SSL logging is turned on using -Djavax.net.debug=ssl:handshake:verbose. This revealed some useful information.

The workaround that we are using in production and has proven to work for us is to set this parameter on the JVM:

 -Djdk.tls.client.protocols=TLSv1

If you want more details, please read on.

On a server where the problem can be reproduced (again, only 5-10% of the time), I observed the following:

*** ClientHello, TLSv1.2
--- 8<-- SNIP -----
main, WRITE: TLSv1.2 Handshake, length = 195
main, READ: TLSv1.2 Handshake, length = 1130
*** ServerHello, TLSv1.2
--- 8<-- SNIP -----
%% Initialized:  [Session-79, TLS_DHE_RSA_WITH_AES_128_GCM_SHA256]
** TLS_DHE_RSA_WITH_AES_128_GCM_SHA256
--- 8<-- SNIP -----
Algorithm: [SHA1withRSA]
--- 8<-- SNIP -----
*** Diffie-Hellman ServerKeyExchange
--- 8<-- SNIP -----
*** ServerHelloDone
*** ClientKeyExchange, DH
--- 8<-- SNIP -----
main, WRITE: TLSv1.2 Handshake, length = 133
--- 8<-- SNIP -----
main, WRITE: TLSv1.2 Change Cipher Spec, length = 1
*** Finished
verify_data:  { 108, 116, 29, 115, 13, 26, 154, 198, 17, 125, 114, 166 }
***
main, WRITE: TLSv1.2 Handshake, length = 40
main, called close()
main, called closeInternal(true)
main, SEND TLSv1.2 ALERT:  warning, description = close_notify
main, WRITE: TLSv1.2 Alert, length = 26
main, called closeSocket(true)
main, waiting for close_notify or alert: state 5
main, received EOFException: ignored
main, called closeInternal(false)
main, close invoked again; state = 5
main, handling exception: java.io.IOException: SQL Server returned an incomplete response. The connection has been closed. ClientConnectionId:12a722b3-d61d-4ce4-8319-af049a0a4415

Notice that TLSv1.2 is selected by the database server and used in this exchange. I've observed that, when connections fail from the problematic linux service, TLSv1.2 is ALWAYS the level which was selected. However, connections do not ALWAYS fail when TLSv1.2 is used. They only fail 5-10% of the time.

Now here is an exchange from a server that does NOT have the problem. Everything else is equal. I.e., connecting to the same database, same version of the JVM (Java 1.8.0_60), same JDBC driver, etc. Notice that, here, TLSv1 is selected by the database server instead of TLSv1.2 as in the faulty server's case.

*** ClientHello, TLSv1.2
--- 8<-- SNIP -----
main, WRITE: TLSv1.2 Handshake, length = 207
main, READ: TLSv1 Handshake, length = 604
*** ServerHello, TLSv1
--- 8<-- SNIP -----
Cipher Suite: TLS_RSA_WITH_AES_128_CBC_SHA
--- 8<-- SNIP -----
%% Initialized:  [Session-79, TLS_RSA_WITH_AES_128_CBC_SHA]
** TLS_RSA_WITH_AES_128_CBC_SHA
--- 8<-- SNIP -----
Algorithm: [SHA1withRSA]
--- 8<-- SNIP -----
***
*** ServerHelloDone
*** ClientKeyExchange, RSA PreMasterSecret, TLSv1
--- 8<-- SNIP -----
main, WRITE: TLSv1 Handshake, length = 134
main, WRITE: TLSv1 Change Cipher Spec, length = 1
*** Finished
verify_data:  { 26, 155, 166, 89, 229, 193, 126, 39, 103, 206, 126, 21 }
***
main, WRITE: TLSv1 Handshake, length = 48
main, READ: TLSv1 Change Cipher Spec, length = 1
main, READ: TLSv1 Handshake, length = 48
*** Finished

So, when TLSv1 is negotiated between the Linux JVM and the SQL Server, connections are ALWAYS successful. When TLSv1.2 is negotiated, we get sporadic connection failures.

(Note: Java 7 (1.7.0_51) always negotiates TLSv1, which is why the problem never occurred for us with a Java 7 JVM.)

The open questions we still have are:

WHY is that the same Java 8 JVM run from 2 different Linux servers will always negotiate TLSv1, but when connecting from another Linux server it always negotiates TLSv1.2.
And also why are TLSv1.2 negotiated connections successful most, but not all, of the time on that server?

Update 6/10/2017: This posting from Microsoft describes the problem and their proposed solution.

Resources:

http://www.infoworld.com/article/2849292/operating-systems/more-patch-problems-reported-with-the-ms14-066-kb-2992611-winshock-mess.html

http://blogs.msdn.com/b/jdbcteam/archive/2008/09/09/the-driver-could-not-establish-a-secure-connection-to-sql-server-by-using-secure-sockets-layer-ssl-encryption.aspx

Java 8 , JCE Unlimited Strength Policy and SSL Handshake over TLS

http://blogs.msdn.com/b/saponsqlserver/archive/2013/05/10/analyzing-jdbc-connection-issues.aspx

https://docs.oracle.com/javase/8/docs/technotes/guides/security/jsse/JSSERefGuide.html#descPhase2

https://blogs.oracle.com/java-platform-group/entry/java_8_will_use_tls

Before you upgrade SQL JDBC Driver, check the compatibility first:

Sqljdbc.jar requires a JRE of 5 and supports the JDBC 3.0 API
Sqljdbc4.jar requires a JRE of 6 and supports the JDBC 4.0 API
Sqljdbc41.jar requires a JRE of 7 and supports the JDBC 4.1 API
Sqljdbc42.jar requires a JRE of 8 and supports the JDBC 4.2 API

Source: https://www.microsoft.com/en-us/download/details.aspx?id=11774

This appears to have been fixed in version 4.2 of the MS SQL JDBC driver. I created a program where I connected to the server 1000 times, pausing 100ms between each attempt. With version 4.1 I was able to reproduce the problem every time, although it happened only sporadically. With version 4.2 I was unable to reproduce the problem.

SQL Server JDBC Error on Java 8: The driver could not establish a secure connection to SQL Server by using Secure Sockets Layer (SSL) encryption

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