Problem

JIRA is running behind the proxy which is configured with SSL. JIRA is throwing the following SSL handshake_failure error. 

The following appears in the atlassian-jira.log

2018-01-10 18:09:55,431 http-nio-8080-exec-5 ERROR      [c.a.g.r.internal.http.HttpClientFetcher] Unable to perform a request to: https://<jira-hostname/rest/gadgets/1.0/g/messagebundle/und/gadget.common%2Cgadget.activity.stream
javax.net.ssl.SSLHandshakeException: Received fatal alert: handshake_failure
    at sun.security.ssl.Alerts.getSSLException(Alerts.java:192)
    at sun.security.ssl.Alerts.getSSLException(Alerts.java:154)
    at sun.security.ssl.SSLSocketImpl.recvAlert(SSLSocketImpl.java:2023)
    at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:1125)
    at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1375)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1403)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1387)

Same problem is reproducible with HttpClientTest

Diagnosis

Proxy

• Nginx has been configured with the following strong ciphers:

  ssl_ciphers ECDHE-RSA-AES256-GCM-SHA512:DHE-RSA-AES256-GCM-SHA512:ECDHE-RSA-AES256-GCM-SHA384:DHE-RSA-AES256-GCM-SHA384:ECDHE-RSA-AES256-SHA384:ECDHE-RSA-AES256-SHA:DHE-RSA-AES256-SHA;

• Nmap output shows the same: 

  [root@jira ~]# nmap --script ssl-enum-ciphers -p 443 <jira-hostname>
  
  Starting Nmap 6.40 ( http://nmap.org ) at 2018-01-10 18:14 CET
  Nmap scan report for <base-hostname> (IP.IP.IP.IP)
  Host is up (-1600s latency).
  PORT    STATE SERVICE
  443/tcp open  https
  | ssl-enum-ciphers:
  ...
  |   TLSv1.2:
  |     ciphers:
  |       TLS_DHE_RSA_WITH_AES_256_CBC_SHA - strong
  |       TLS_DHE_RSA_WITH_AES_256_GCM_SHA384 - strong
  |       TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA - strong
  |       TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384 - strong
  |       TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384 - strong

   Execute the following command to return the output: 

  nmap --script ssl-enum-ciphers -p 443 <jira-hostname>

JAVA DEBUG

• Enable SSL DEBUG, add the following option to JVM parameters:

  -Djavax.net.debug=ssl:handshake:verbose

• In catalina.out you will get detailed logging, this snippet shows cipher suites which JAVA is not going to use. These ciphers are unavailable due to restrictions: 

  Ignoring unavailable cipher suite: TLS_DHE_DSS_WITH_AES_256_GCM_SHA384
  Ignoring unavailable cipher suite: TLS_RSA_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_DHE_RSA_WITH_AES_256_GCM_SHA384
  Ignoring unavailable cipher suite: TLS_ECDH_ECDSA_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384
  Ignoring unavailable cipher suite: TLS_RSA_WITH_AES_256_CBC_SHA256
  Ignoring unavailable cipher suite: TLS_DHE_DSS_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_ECDH_ECDSA_WITH_AES_256_GCM_SHA384
  Ignoring unavailable cipher suite: TLS_ECDH_RSA_WITH_AES_256_CBC_SHA384
  Ignoring unavailable cipher suite: TLS_RSA_WITH_AES_256_GCM_SHA384
  Ignoring unavailable cipher suite: TLS_ECDH_ECDSA_WITH_AES_256_CBC_SHA384
  Ignoring unavailable cipher suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384
  Ignoring unavailable cipher suite: TLS_ECDH_RSA_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_ECDH_RSA_WITH_AES_256_GCM_SHA384
  Ignoring unavailable cipher suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384
  Ignoring unavailable cipher suite: TLS_DHE_RSA_WITH_AES_256_CBC_SHA256
  Ignoring unavailable cipher suite: TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_DHE_DSS_WITH_AES_256_CBC_SHA256
  Ignoring unavailable cipher suite: TLS_DHE_RSA_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA
  Ignoring unavailable cipher suite: TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384

• Also you can see logging for TLS handshake:

  *** ClientHello, TLSv1.2
  RandomCookie:  GMT: 1515604257 bytes = { 167, 25, 54, 55, 56, 23, 147, 10, 79, 186, 46, 41, 32, 220, 5, 179, 169, 6, 109, 111, 30, 179, 70, 123, 93, 141, 30, 47 }
  Session ID:  {}
  Cipher Suites: [TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256, TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256, TLS_RSA_WITH_AES_128_CBC_SHA256, TLS_ECDH_ECDSA_WITH_AES_128_CBC_SHA256, TLS_ECDH_RSA_WITH_AES_128_CBC_SHA256, TLS_DHE_RSA_WITH_AES_128_CBC_SHA256, TLS_DHE_DSS_WITH_AES_128_CBC_SHA256, TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA, TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA, TLS_RSA_WITH_AES_128_CBC_SHA, TLS_ECDH_ECDSA_WITH_AES_128_CBC_SHA, TLS_ECDH_RSA_WITH_AES_128_CBC_SHA, TLS_DHE_RSA_WITH_AES_128_CBC_SHA, TLS_DHE_DSS_WITH_AES_128_CBC_SHA, TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256, TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256, TLS_RSA_WITH_AES_128_GCM_SHA256, TLS_ECDH_ECDSA_WITH_AES_128_GCM_SHA256, TLS_ECDH_RSA_WITH_AES_128_GCM_SHA256, TLS_DHE_RSA_WITH_AES_128_GCM_SHA256, TLS_DHE_DSS_WITH_AES_128_GCM_SHA256, TLS_ECDHE_ECDSA_WITH_3DES_EDE_CBC_SHA, TLS_ECDHE_RSA_WITH_3DES_EDE_CBC_SHA, SSL_RSA_WITH_3DES_EDE_CBC_SHA, TLS_ECDH_ECDSA_WITH_3DES_EDE_CBC_SHA, TLS_ECDH_RSA_WITH_3DES_EDE_CBC_SHA, SSL_DHE_RSA_WITH_3DES_EDE_CBC_SHA, SSL_DHE_DSS_WITH_3DES_EDE_CBC_SHA, TLS_EMPTY_RENEGOTIATION_INFO_SCSV]
  Compression Methods:  { 0 }
  Extension elliptic_curves, curve names: {secp256r1, sect163k1, sect163r2, secp192r1, secp224r1, sect233k1, sect233r1, sect283k1, sect283r1, secp384r1, sect409k1, sect409r1, secp521r1, sect571k1, sect571r1, secp160k1, secp160r1, secp160r2, sect163r1, secp192k1, sect193r1, sect193r2, secp224k1, sect239k1, secp256k1}
  Extension ec_point_formats, formats: [uncompressed]
  Extension signature_algorithms, signature_algorithms: SHA512withECDSA, SHA512withRSA, SHA384withECDSA, SHA384withRSA, SHA256withECDSA, SHA256withRSA, SHA256withDSA, SHA224withECDSA, SHA224withRSA, SHA224withDSA, SHA1withECDSA, SHA1withRSA, SHA1withDSA
  Extension server_name, server_name: [type=host_name (0), value=jira.company.com]
  ***
  HealthCheck:thread-4, WRITE: TLSv1.2 Handshake, length = 221
  HealthCheck:thread-4, READ: TLSv1.2 Alert, length = 2
  HealthCheck:thread-4, RECV TLSv1.2 ALERT:  fatal, handshake_failure
  HealthCheck:thread-4, called closeSocket()
  HealthCheck:thread-4, handling exception: javax.net.ssl.SSLHandshakeException: Received fatal alert: handshake_failure

• Note that list of Cipher Suites section. Ciphers advertised by JAVA doesn't have overlap with the list from Nginx. 

Cause

• Java doesn't support 256-bit encryption w/o JCE, quote from Security - SunProviders - importlimits 
  • If stronger algorithms are needed (for example, AES with 256-bit keys), the JCE Unlimited Strength Jurisdiction Policy Files must be obtained and installed in the JDK/JRE
• Since these ciphers are using 256-bit encryption, Java will not support them by default (up to 8u161, see below), so there is no overlap with the list from Nginx. That leads to handshake_failure
  • Starting from Java 8u161 Unlimited cryptography enabled by default, see Java 8u161 relnotes

Resolution

• One of the options could be low the encryption at proxy, eg: set TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256
• If stronger algorithms are needed (for example, AES with 256-bit keys), the JCE Unlimited Strength Jurisdiction Policy files must be obtained and installed in the JDK/JRE.

1. 1. Download the Java Cryptography Extension (JCE) Unlimited Strength Jurisdiction Policy Files 8 Download
   2. Extract the jce\local_policy.jar and jce\US_export_policy.jar files from the archive to the JAVA_HOME directory that JIRA is currently using for eg.  /opt/atlassian/jira/jre/lib/security
   3. Restart JIRA