NullPointerException in SSLContext#createSSLEngine with net-imap 0.5.x on JRuby 10

[limmet]

Summary

On JRuby 10.0.2.0 + Java 21, establishing an IMAPS connection using net-imap 0.5.12 crashes with:

java.lang.NullPointerException: Cannot invoke "org.jruby.ext.openssl.SSLContext$InternalContext.getSSLContext()" because "this.internalContext" is null

The exception occurs in org/jruby/ext/openssl/SSLContext.java:784 during createSSLEngine, called via SSLSocket#connect_nonblock.

This works on MRI Ruby (same host/service), and also works on JRuby with older net-imap versions (0.3.x).

Environment

• OS: Windows (mswin32)
• JRuby: jruby 10.0.2.0 (3.4.2) 2025-08-07 cba6031bd0 OpenJDK 64-Bit Server VM 21.0.7+6-LTS on 21.0.7+6-LTS +indy +jit [x86_64-mswin32]
• Java: OpenJDK 21.0.7+6-LTS
• net-imap: 0.5.12
• jruby-openssl: 0.15.5-java (also reproduced with 0.15.3-java)
• Target: outlook.office365.com:993 (IMAPS)

Reproduction

Gemfile

source "https://rubygems.org"

platform :jruby do
 gem "net-imap", "0.5.12"
end

Script

gem "net-imap", "0.5.12"
require "net/imap"
require "openssl"

imap = Net::IMAP.new("outlook.office365.com", 993, true, nil, false)
# or more modern
# imap = Net::IMAP.new("outlook.office365.com", port: 993, ssl: true)

puts imap.capability
imap.logout
imap.disconnect

Actual result

Unhandled Java exception:

Unhandled Java exception: java.lang.NullPointerException: Cannot invoke
"org.jruby.ext.openssl.SSLContext$InternalContext.getSSLContext()"
because "this.internalContext" is null
 createSSLEngine at org/jruby/ext/openssl/SSLContext.java:784
 ...

Expected result

IMAPS connection should succeed or raise a Ruby-level exception, not crash with a JVM-level NPE.

Notes

• Connectivity verified with: openssl s_client -connect outlook.office365.com:993 -crlf
• JRuby 9.4.7.0 works with net-imap 0.3.x against the same server, but fails with net-imap 0.5.x (NPE).
• This appears to be an initialization/ordering bug where SSLContext.internalContext is not set before SSLSocket creates an SSLEngine.