Net:HTTP SSL negotiation timeout on Ubuntu 14.04 - ruby

Question

After a long day I managed to get to the bottom of what I believe is a SSL/TLS cipher negotiation issue with a server that doesn't support the latest and greatest versions.
Stack:
Ubuntu 14.04 fully patched
OpenSSL 1.0.1f 6 Jan 2014
irb 0.9.6(09/06/30)
ruby 2.2.2p95 (2015-04-13 revision 50295) [x86_64-linux] (using rbenv)
After 60 seconds the snippet below gives me an error:
require 'net/http'
require 'openssl'
uri = URI.parse('https://some_old_server/my/path')
http = Net::HTTP.new('some_old_server', 443)
http.verify_mode = OpenSSL::SSL::VERIFY_NONE
http.use_ssl = true
response = http.request(Net::HTTP::Get.new(uri.request_uri))
Errno::ECONNRESET: Connection reset by peer - SSL_connect
If I add this to the code, it works:
(...)
http.ciphers = ['AES128-SHA']
(...)
=> #<Net::HTTPOK 200 OK readbody=true>
This isn't a ruby-specific issue but ideally there's a ruby solution. I can't lock the ciphers to 'AES128-SHA' because the same code handles a number of sites that may or may not support this cipher.
Has anyone ever come across this and found a generic solution?
EDIT: this seems to be caused by the "TLS hang bug" and was fixed in openssl 1.0.1g.
New question: is there a work-around that can be implemented on the ruby side?
More information.
A Gentoo server running OpenSSL 1.0.1j 15 Oct 2014 doesn't have this issue. I tried installing 1.0.1j on the Ubuntu 14.04 server, recompiling ruby (rbenv install 2.2.2) and the error was still present.
I've tried to monkey patch ext/openssl but that didn't work.
Using the whole cipher list from the link above doesn't work. However, using a small subset does work:
require 'net/http'
require 'openssl'
uri = URI.parse('https://some_old_server/my/path')
http = Net::HTTP.new('some_old_server', 443)
http.verify_mode = OpenSSL::SSL::VERIFY_NONE
http.use_ssl = true
http.ciphers = %w{
AES128-GCM-SHA256
AES256-GCM-SHA384
AES128-SHA256
AES256-SHA256
AES128-SHA
AES256-SHA
ECDHE-ECDSA-RC4-SHA
ECDHE-RSA-RC4-SHA
RC4-SHA
}.join(":")
response = http.request(Net::HTTP::Get.new(uri.request_uri))
Openssl agrees with ruby (as it should). Running these, on the same system, replicates the issue as I see them in ruby:
openssl s_client -connect some_old_server:443
CONNECTED(00000003)
(...)
write:errno=104
---
no peer certificate available
---
No client certificate CA names sent
---
SSL handshake has read 0 bytes and written 295 bytes
---
New, (NONE), Cipher is (NONE)
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
---
Passing the cipher:
openssl s_client -cipher AES128-SHA -connect some_old_server:443
CONNECTED(00000003)
(...)
---
No client certificate CA names sent
---
SSL handshake has read 2721 bytes and written 425 bytes
---
New, TLSv1/SSLv3, Cipher is AES128-SHA
Server public key is 2048 bit
Secure Renegotiation IS NOT supported
Compression: NONE
Expansion: NONE
SSL-Session:
Protocol : TLSv1
Cipher : AES128-SHA
Session-ID: removed
Session-ID-ctx:
Master-Key: removed
Key-Arg : None
PSK identity: None
PSK identity hint: None
SRP username: None
Start Time: 1454394952
Timeout : 300 (sec)
Verify return code: 20 (unable to get local issuer certificate)
---
I read somewhere to use
http.ssl_options = OpenSSL::SSL::OP_ALL
but ssl_options isn't available in Net::HTTP on ruby 2.2.2.

Answer 1

After spending more time on this than I'd care to admit, my solution was to upgrade from Ubuntu 14.04 to 15.10 which comes with OpenSSL 1.0.2d 9 Jul 2015.
While the TLS negotiation still hangs using the openssl CLI, in Ruby it does not:
require 'net/http'
require 'openssl'
require 'pp'
uri = URI.parse('https://broken_server/my/path')
http = Net::HTTP.new('broken_server', 443)
http.instance_eval {
#ssl_context = OpenSSL::SSL::SSLContext.new
#ssl_context.set_params({:options=>OpenSSL::SSL::OP_ALL})
}
http.verify_mode = OpenSSL::SSL::VERIFY_NONE
http.use_ssl = true
pp response = http.request(Net::HTTP::Get.new(uri.request_uri))
SSL context code above courtesy of #vinhboy.
The CLI equivalent of the above is turned-on with the -bugs option:
openssl s_client -bugs -connect broken_server:443