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TypeError: nil is not a string when trying to write smime. #4585

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mungler opened this issue May 2, 2017 · 4 comments
Closed

TypeError: nil is not a string when trying to write smime. #4585

mungler opened this issue May 2, 2017 · 4 comments
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Invalid or Duplicate

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@mungler
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mungler commented May 2, 2017

Environment

Re: https://twitter.com/headius/status/859532672611356672

macOS Sierra 10.12.3 on iMac 27'' 5K

Darwin Eddie.mungler.home 16.4.0 Darwin Kernel Version 16.4.0: Thu Dec 22 22:53:21 PST 2016; root:xnu-3789.41.3~3/RELEASE_X86_64 x86_64

jruby 9.1.8.0 (2.3.1) 2017-03-06 90fc7ab Java HotSpot(TM) 64-Bit Server VM 25.40-b23 on 1.8.0_40-ea-b20 +jit [darwin-x86_64]
JRUBY_OPTS=-J-Xmn512m -J-Xms4096m -J-Xmx4096m -J-server

Gems included by the bundle:

  • activesupport (3.0.0)
  • asw-cache (0.2.0)
  • asw-services (0.0.55 399297c)
  • asw_database (1.0.1)
  • asw_models (0.2.10 5f042c2)
  • bond (0.5.1)
  • bundler (1.14.6)
  • chronic (0.10.2)
  • commander (4.4.3)
  • concurrent-ruby (1.0.5)
  • diff-lcs (1.3)
  • dry-configurable (0.7.0)
  • dry-container (0.6.0)
  • dry-core (0.2.4)
  • dry-equalizer (0.2.0)
  • dry-logic (0.4.1)
  • dry-struct (0.2.1)
  • dry-types (0.10.2)
  • faraday (0.12.1)
  • fotc (0.2.1)
  • gcm (0.1.1)
  • grocer (0.7.1)
  • highline (1.7.8)
  • httparty (0.14.0)
  • ice_nine (0.11.2)
  • inflecto (0.0.2)
  • jdbc-mysql (5.1.40)
  • jedis_rb (2.7.2)
  • jruby-openssl (0.9.20)
  • json (2.1.0)
  • msgpack (1.1.0)
  • multi_xml (0.6.0)
  • multipart-post (2.0.0)
  • nelson-rpc (0.0.24)
  • passbook (0.4.4)
  • puma (3.8.2)
  • rack (1.6.5)
  • rack-test (0.6.3)
  • rake (10.5.0)
  • require_all (1.4.0)
  • ripl (0.7.1)
  • ripl-color_error (0.1.1)
  • ripl-color_streams (0.1.2)
  • ripl-ripper (0.1.0)
  • rspec (3.5.0)
  • rspec-core (3.5.4)
  • rspec-expectations (3.5.0)
  • rspec-mocks (3.5.0)
  • rspec-support (3.5.0)
  • rubyzip (1.2.1)
  • sequel (4.46.0)
  • sequel_polymorphic_asw (0.2.3)
  • terminal-table (1.7.3)
  • unicode-display_width (1.1.3)
  • whenever (0.9.7)
>> p12 = OpenSSL::PKCS12.new File.read(certificate), password
=> #<OpenSSL::PKCS12:0x2e62e227 @key=#<OpenSSL::PKey::RSA:0x5ebe903a>, @ca_certs=[], @der="0\x82\x19\x18\x02\x01\x030\x82\x18\xDF\x06\t*\x86H\x86\xF7\r\x01\a\x01\xA0\x82\x18\xD0\x04\x82\x18\xCC0\x82\x18\xC80\x82\r\xFF\x06\t*\x86H\x86\xF7\r\x01\a\x06\xA0\x82\r\xF00\x82\r\xEC\x02\x01\x000\x82\r\xE5\x06\t..... etc etc 

>> p12.key.to_s
=> "-----BEGIN RSA PRIVATE KEY-----\nMIIEdqpn1xRuIJyx\n6oklTnT4y8pDPhlnqX8BBJmURik8VUSF\ntFeKzfLRIh8GxoO6Yfdki2ESffh6ynxmv+c8PuMrhHd3zKow6eeSgXmFqjCIQu3okiVUkB8owBvJr9r/QZkKa3ZGlQiZz/XVTdzpaUSh7YzeZuzlI9ipj9lElrtsb\n0n7RFED50uW0SxTFtxTFGv4Y/uSxvvd6/uPw5TfxINfr5JDDsqQ9zqg8KxBZxHJsaqKN5RtmzhmYu6wXKk/TT4B8sMr\npGss6A...... snip ......9kZahyvHVKd/5bahPiwGuBXEcbfaGNL8sjPr3eRP3KDJf\n-----END RSA PRIVATE KEY-----\n"

>> p12.certificate.to_s
=> "-----BEGIN CERTIFICATE-----\nMIYxCzAJBgNV\nBAYTAlVTMRMwEQYDVQQKDApBcHBsZSBJbmMuMSwwKgYDVQQLDCNBcHBsZSBXb3Js\nZHdpZGUgRGV2ZWxvcGVyIFJlbGF0aW9uczFEMEIGA1UEAww7QXBwbGUgV29ybGR3\na..... snip .....EmZD1K5TM=\n-----END CERTIFICATE-----\n"
>> 

>> wwdc  = OpenSSL::X509::Certificate.new File.read(wwdc)
=> #<OpenSSL::X509::Certificate:0x5d2e65bd subject=/C=US/O=Apple Inc./OU=Apple Worldwide Developer Relations/CN=Apple Worldwide Developer Relations Certification Authority, issuer=/C=US/O=Apple Inc./OU=Apple Certification Authority/CN=Apple Root CA, serial=134752589830791184, not_before=2013-02-07 21:48:47 UTC, not_after=2023-02-07 21:48:47 UTC>

>> data = 'foobarbaz'
=> "foobarbaz"
>> key_hash = {}
=> {}
>> key_hash[:cert] = p12.certificate
=> #<OpenSSL::X509::Certificate:0x75663443 subject=/userId=pass.com.asmallworld.events.ticket/CN=Pass Type ID: pass.com.asmallworld.events.ticket/OU=QY8279AAHT/O=aSmallworld.net/C=US, issuer=/C=US/O=Apple Inc./OU=Apple Worldwide Developer Relations/CN=Apple Worldwide Developer Relations Certification Authority, serial=534939252856400662, not_before=2017-04-26 12:37:42 UTC, not_after=2018-04-26 12:37:42 UTC>
>> key_hash[:key] = p12.key
=> #<OpenSSL::PKey::RSA:0x7cbe3a05>
>>
>> pk7   = OpenSSL::PKCS7.sign key_hash[:cert], key_hash[:key], data.to_s, [wwdc], OpenSSL::PKCS7::BINARY | OpenSSL::PKCS7::DETACHED
=> #<OpenSSL::PKCS7:0x7aa63f50 @data="foobarbaz">

>> data  = OpenSSL::PKCS7.write_smime pk7
TypeError: nil is not a string
    org/jruby/ext/openssl/PKCS7.java:197:in `write_smime'
    (ripl):28:in `<eval>'
    org/jruby/RubyKernel.java:1000:in `eval'
>>

Sorry, had to throw this together quickly as its late, but wanted to get it logged asap.
@mungler
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mungler commented May 3, 2017

@headius FYI :)

@kares
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kares commented May 3, 2017

seems like a JRuby-OpenSSL issue ... preferably move it to https://github.com/jruby/jruby-openssl/issues

@kares
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kares commented May 3, 2017

also if we're to have a small reproducable (self-contained) script it would sure help resolve the issue faster.

@mungler
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mungler commented May 3, 2017

@kares ok thanks, will move it. Will try to put together something to reproduce.

@mungler mungler closed this as completed May 3, 2017
@enebo enebo added this to the Invalid or Duplicate milestone May 11, 2017
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