Please can you provide some more details as to how this happens?

In net/http/persistent there is a reference to OpenSSL after the autoload statement that should always trigger an autoload. It will fail if OpenSSL is not in the lib path, e.g. if somehow openssl was in a non-bundled gem.

Can you at minimum expand on "some Rubies" ?

I wish I had a better answer, I found this solution in rubygems/bundler#3107. As stated in issue #36 SSL autoloading was not working. My Ruby version on the machine in question is 2.2.2p95. This can be seen with the following code:

irb(main):001:0> autoload :OpenSSL, 'openssl'
=> nil
irb(main):002:0> defined? OpenSSL::SSL
=> nil
irb(main):003:0> require 'openssl'
=> true
irb(main):004:0> defined? OpenSSL::SSL
=> "constant"

On other versions of Ruby on different machines (even some running 2.2.2p95) autoloading works as intended:

:001 > autoload :OpenSSL, 'openssl'
 => nil 
 :002 > defined? OpenSSL::SSL
 => "constant" 

I know this is an edge case, that probably isn't very easy to reproduce, but it was an issue fixed by forcing the loading of OpenSSL.

Has this been reported to net/http/persistent ?

On Tue, Jul 28, 2015, 7:52 PM Don Reilly [email protected] wrote:

I wish I had a better answer, I found this solution in
rubygems/bundler#3107 rubygems/bundler#3107. As
stated in issue #36
#36 SSL autoloading
was not working. My Ruby version on the machine in question is 2.2.2p95.
This can be seen with the following code:

irb(main):001:0> autoload :OpenSSL, 'openssl'
=> nil
irb(main):002:0> defined? OpenSSL::SSL
=> nil
irb(main):003:0> require 'openssl'
=> true
irb(main):004:0> defined? OpenSSL::SSL
=> "constant"

On other versions of Ruby on different machines (even some running
2.2.2p95) autoloading works as intended:

:001 > autoload :OpenSSL, 'openssl'
=> nil
:002 > defined? OpenSSL::SSL
=> "constant"

I know this is an edge case, that probably isn't very easy to reproduce,
but it was an issue fixed by forcing the loading of OpenSSL.

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#37 (comment)
.

I opened a ticket with them drbrain/net-http-persistent#70

The mentioned issue was recently closed.