# Serverspec and Chef 11

**URL:** <https://discourse.chef.io/t/serverspec-and-chef-11/7501>\
**Category:** Chef Infra (archive)\
**Created:** [December 22, 2015, 12:42am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501 "2015-12-22T00:42:49Z")\
**Posts on this page:** 6\
**Page:** 1

<div class="post-metadata">

**Author:** ![coderanger](https://sea2.discourse-cdn.com/flex016/user_avatar/discourse.chef.io/coderanger/32/5_2.png) [@coderanger](https://discourse.chef.io/u/coderanger)\
**Post date:** [December 22, 2015, 12:42am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501/1 "2015-12-22T00:42:49Z")

</div>

A quick blog post because this keeps coming up, how to fix Chef 11 with Test Kitchen and Serverspec: [https://coderanger.net/serverspec-chef-11/](https://coderanger.net/serverspec-chef-11/)

If you are hitting issues with net-ssh, that is how to fix them. Or you could upgrade to Chef 12 and/or InSpec 🙂

---

<div class="post-metadata">

**Author:** ![christian.clarke](https://sea2.discourse-cdn.com/flex016/user_avatar/discourse.chef.io/christian.clarke/32/1200_2.png) [@christian.clarke](https://discourse.chef.io/u/christian.clarke)\
**Post date:** [December 22, 2015, 9:35am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501/2 "2015-12-22T09:35:52Z")

</div>

Hello.

I’ve found that this solution works for Linux. But not for Windows. I’m using ChefDK 0.6.0 with Chef-Client 11.18.6. Using Chef-Client 12 of course works fine.

Below is the output of a kitchen verify -l debug output. I noticed that the log is complaining about an SSL Cert problem. I found this site and verified the .pem file it refered to was already in on my system

([https://gist.github.com/luislavena/f064211759ee0f806c88](https://gist.github.com/luislavena/f064211759ee0f806c88))

```auto
C:\chef-repo\cookbooks\nvm_win2012>kitchen verify -l debug
-----> Starting Kitchen (v1.4.0)
D [Vagrant command] BEGIN (vagrant --version)
D [Vagrant command] END (0m0.00s)
D [Vagrant command] BEGIN (vagrant plugin list)
D [Vagrant command] END (0m0.00s)
D Berksfile found at C:/chef-repo/cookbooks/nvm_win2012/Berksfile, loading Berkshelf
C:/opscode/chefdk/embedded/lib/ruby/gems/2.1.0/gems/httpclient-2.6.0.1/lib/httpclient/webagent-cookie.rb:458: warning: already initialized constant HTTPClient::CookieManager
C:/opscode/chefdk/embedded/lib/ruby/gems/2.1.0/gems/httpclient-2.6.0.1/lib/httpclient/cookie.rb:8: warning: previous definition of CookieManager was here
D Berkshelf 4.0.1 library loaded
D Winrm Transport requested, loading WinRM::Transport gem (~> 1.0)
D WinRM::Transport 1.0.3 library loaded
-----> Setting up <default-Windows2012>...
       Finished setting up <default-Windows2012> (0m0.00s).
-----> Verifying <default-Windows2012>...
       Preparing files for transfer
D Creating local sandbox in C:/Users/CHRIST~1.CLA/AppData/Local/Temp/default-Windows2012-sandbox-20151222-18400-19kcl80
D [WinRM] plaintext::http://127.0.0.1:5985/wsman<{:disable_sspi=>true, :basic_auth_only=>true, :user=>"vagrant", :pass=>"vagrant"}> (
$env:BUSSER_ROOT = "$env:TEMP\verifier"
$env:GEM_HOME = "$env:TEMP\verifier\gems"
$env:GEM_PATH = "$env:TEMP\verifier\gems"
$env:GEM_CACHE = "$env:TEMP\verifier\gems\cache"
$ruby = "$env:systemdrive\opscode\chef\embedded\bin\ruby.exe"
$gem = "$env:systemdrive\opscode\chef\embedded\bin\gem"
$version = "busser"
$gem_install_args = "busser --no-rdoc --no-ri"
$busser = "$env:TEMP\verifier\bin\busser.bat"
$plugins = "busser-serverspec"

if ((& "$ruby" "$gem" list busser -i) -ne "true") {
  Write-Host "-----> Installing Busser ($version)`n"
  & "$ruby" "$gem" install $gem_install_args.Split() 2>&1
} else {
  Write-Host "-----> Busser installation detected ($version)`n"
}

if (-Not (Test-Path "$busser")) {
  $gem_bindir = & "$ruby" -rrubygems -e "puts Gem.bindir.dup.gsub('/', '\\')"
  & "$ruby" "$gem_bindir\busser" setup --type bat 2>&1
}

Write-Host " Installing Busser plugins: $plugins`n"
& "$busser" plugin install $plugins.Split() 2>&1
)
D [WinRM] opening remote shell on plaintext::http://127.0.0.1:5985/wsman<{:disable_sspi=>true, :basic_auth_only=>true, :user=>"vagrant", :pass=>"vagrant"}>
D [WinRM] remote shell 6AFB19F0-0228-4E1B-B604-F9823402B4F1 is open on plaintext::http://127.0.0.1:5985/wsman<{:disable_sspi=>true, :basic_auth_only=>true, :user=>"vagrant", :pass=>"vagrant"}>
-----> Installing Busser (busser)
       Successfully installed thor-0.19.0
       Successfully installed busser-0.7.1
       2 gems installed
-----> Setting up Busser
       Creating BUSSER_ROOT in C:\Users\vagrant\AppData\Local\Temp\verifier
       Creating busser binstub
       Installing Busser plugins: busser-serverspec
       Plugin serverspec installed (version 0.5.7)
-----> Running postinstall for serverspec plugin
D [WinRM] plaintext::http://127.0.0.1:5985/wsman<{:disable_sspi=>true, :basic_auth_only=>true, :user=>"vagrant", :pass=>"vagrant"}> (
$env:BUSSER_ROOT = "$env:TEMP\verifier"
$env:GEM_HOME = "$env:TEMP\verifier\gems"
$env:GEM_PATH = "$env:TEMP\verifier\gems"
$env:GEM_CACHE = "$env:TEMP\verifier\gems\cache"

& $env:TEMP\verifier\bin\busser.bat suite cleanup
)
       Suite path directory C:/Users/vagrant/AppData/Local/Temp/verifier/suites does not exist, skipping.
       Transferring files to <default-Windows2012>
D [TmpZip::C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip] Populating files
D [TmpZip::C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip] +++ Adding suites/serverspec/Gemfile
D [TmpZip::C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip] +++ Adding suites/serverspec/registry_spec.rb
D [TmpZip::C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip] +++ Adding suites/serverspec/spec_helper.rb
D [TmpZip::C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip] +++ Adding suites/serverspec/sysinternals_spec.rb
D [TmpZip::C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip] === All files added.
D [FileTransporter] Running check_files.ps1
D [FileTransporter] @{
D [FileTransporter] "$env:TEMP\tmpzip-acc0d28e254656318730bc9b93273a3a.zip" = "acc0d28e254656318730bc9b93273a3a"
D [FileTransporter] }
D [FileTransporter] Uploading C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip to encoded tmpfile $env:TEMP\b64-acc0d28e254656318730bc9b93273a3a.txt
D [FileTransporter] Finished uploading C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip to encoded tmpfile $env:TEMP\b64-acc0d28e254656318730bc9b93273a3a.txt (1.764 KB ov
er 1 chunks) in (0m0.13s)
D [FileTransporter] Running decode_files.ps1
D [FileTransporter] @{
D [FileTransporter] "$env:TEMP\b64-acc0d28e254656318730bc9b93273a3a.txt" = @{
D [FileTransporter] "dst" = "$env:TEMP\verifier";
D [FileTransporter] "tmpzip" = "$env:TEMP\tmpzip-acc0d28e254656318730bc9b93273a3a.zip"
D [FileTransporter] }
D [FileTransporter] }
D [FileTransporter] Cleaned up src_zip C:/Users/CHRIST~1.CLA/AppData/Local/Temp/tmpzip-20151222-18400-m0n9lq.zip
D [FileTransporter] Uploaded 1 items in (0m2.10s)
D Transfer complete
D [WinRM] plaintext::http://127.0.0.1:5985/wsman<{:disable_sspi=>true, :basic_auth_only=>true, :user=>"vagrant", :pass=>"vagrant"}> (
$env:BUSSER_ROOT = "$env:TEMP\verifier"
$env:GEM_HOME = "$env:TEMP\verifier\gems"
$env:GEM_PATH = "$env:TEMP\verifier\gems"
$env:GEM_CACHE = "$env:TEMP\verifier\gems\cache"

& $env:TEMP\verifier\bin\busser.bat test
)
-----> Running serverspec test suite
-----> Bundle Installing..
         run C:/opscode/chef/embedded/bin/ruby C:/Users/vagrant/AppData/Local/Temp/verifier/gems/bin/bundle install --gemfile C:/Users/vagrant/AppData/Local/Temp/verifier/suites/serverspec/Gemfile --
local || C:/opscode/chef/embedded/bin/ruby C:/Users/vagrant/AppData/Local/Temp/verifier/gems/bin/bundle install --gemfile C:/Users/vagrant/AppData/Local/Temp/verifier/suites/serverspec/Gemfile from ".
"
       Could not find gem 'specinfra (= 2.44.7) x86-mingw32' in any of the gem sources
       listed in your Gemfile or available on this machine.
       Fetching gem metadata from https://rubygems.org/.......
       Fetching version metadata from https://rubygems.org/..
       Resolving dependencies...
       Rubygems 1.8.28 is not threadsafe, so your gems will be installed one at a time. Upgrade to Rubygems 2.1.0 or higher to enable parallel gem installation.

       Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://rubygems.org/gems/diff-lcs-1.2.5.gem)

       Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://rubygems.org/gems/multi_json-1.11.2.gem)

       Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://rubygems.org/gems/net-ssh-2.9.2.gem)

       Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://rubygems.org/gems/net-telnet-0.1.1.gem)

       Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://rubygems.org/gems/rspec-support-3.4.1.gem)

       Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (https://rubygems.org/gems/sfl-2.2.gem)
       Using bundler 1.11.2
       An error occurred while installing diff-lcs (1.2.5), and Bundler cannot
       continue.
       Make sure that `gem install diff-lcs -v '1.2.5'` succeeds before bundling.
-----> Installing Serverspec..
$$$$$$ C:/opscode/chef/embedded/lib/ruby/site_ruby/1.9.1/rubygems/installer.rb:388:in `ensure_required_ruby_version_met': net-ssh requires Ruby version >= 2.0. (Gem::InstallError)
$$$$$$ from C:/opscode/chef/embedded/lib/ruby/site_ruby/1.9.1/rubygems/installer.rb:156:in `install'
$$$$$$ from C:/opscode/chef/embedded/lib/ruby/site_ruby/1.9.1/rubygems/dependency_installer.rb:297:in `block in install'
$$$$$$ from C:/opscode/chef/embedded/lib/ruby/site_ruby/1.9.1/rubygems/dependency_installer.rb:270:in `each'
$$$$$$ from C:/opscode/chef/embedded/lib/ruby/site_ruby/1.9.1/rubygems/dependency_installer.rb:270:in `each_with_index'
$$$$$$ from C:/opscode/chef/embedded/lib/ruby/site_ruby/1.9.1/rubygems/dependency_installer.rb:270:in `install'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-0.7.1/lib/busser/rubygems.rb:44:in `install_gem'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-0.7.1/lib/busser/helpers.rb:57:in `install_gem'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-serverspec-0.5.7/lib/busser/runner_plugin/serverspec.rb:60:in `install_serverspec'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-serverspec-0.5.7/lib/busser/runner_plugin/serverspec.rb:33:in `test'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/command.rb:27:in `run'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:126:in `invoke_command'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `block in invoke_all'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `each'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `map'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `invoke_all'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/group.rb:232:in `dispatch'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:115:in `invoke'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-0.7.1/lib/busser/command/test.rb:43:in `block in perform'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-0.7.1/lib/busser/command/test.rb:35:in `each'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-0.7.1/lib/busser/command/test.rb:35:in `perform'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/command.rb:27:in `run'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:126:in `invoke_command'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `block in invoke_all'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `each'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `map'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:133:in `invoke_all'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/group.rb:232:in `dispatch'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:115:in `invoke'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor.rb:40:in `block in register'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/command.rb:27:in `run'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/invocation.rb:126:in `invoke_command'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor.rb:359:in `dispatch'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/thor-0.19.0/lib/thor/base.rb:440:in `start'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/gems/busser-0.7.1/bin/busser:8:in `<top (required)>'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/bin/busser:23:in `load'
$$$$$$ from C:/Users/vagrant/AppData/Local/Temp/verifier/gems/bin/busser:23:in `<main>'
D Cleaning up local sandbox in C:/Users/CHRIST~1.CLA/AppData/Local/Temp/default-Windows2012-sandbox-20151222-18400-19kcl80
>>>>>> Verify failed on instance <default-Windows2012>.
>>>>>> Please see .kitchen/logs/default-Windows2012.log for more details
>>>>>> ------Exception-------
>>>>>> Class: Kitchen::ActionFailed
>>>>>> Message: WinRM exited (1) for command: [
$env:BUSSER_ROOT = "$env:TEMP\verifier"
$env:GEM_HOME = "$env:TEMP\verifier\gems"
$env:GEM_PATH = "$env:TEMP\verifier\gems"
$env:GEM_CACHE = "$env:TEMP\verifier\gems\cache"

& $env:TEMP\verifier\bin\busser.bat test
]
>>>>>> ----------------------
D Verify failed on instance <default-Windows2012>.
D ------Exception-------
D Class: Kitchen::InstanceFailure
D Message: Verify failed on instance <default-Windows2012>. Please see .kitchen/logs/default-Windows2012.log for more details
D ---Nested Exception---
D Class: Kitchen::ActionFailed
D Message: WinRM exited (1) for command: [
$env:BUSSER_ROOT = "$env:TEMP\verifier"
$env:GEM_HOME = "$env:TEMP\verifier\gems"
$env:GEM_PATH = "$env:TEMP\verifier\gems"
$env:GEM_CACHE = "$env:TEMP\verifier\gems\cache"

& $env:TEMP\verifier\bin\busser.bat test
]
D ------Backtrace-------
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/verifier/base.rb:79:in `rescue in call'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/verifier/base.rb:82:in `call'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:398:in `block in verify_action'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:488:in `call'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:488:in `synchronize_or_call'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:453:in `block in action'
D C:/opscode/chefdk/embedded/lib/ruby/2.1.0/benchmark.rb:279:in `measure'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:452:in `action'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:394:in `verify_action'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:341:in `block in transition_to'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:340:in `each'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:340:in `transition_to'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/instance.rb:160:in `verify'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/command.rb:176:in `public_send'
D C:/opscode/chefdk/embedded/apps/test-kitchen/lib/kitchen/command.rb:176:in `block (2 levels) in run_action'
D C:/Users/christian.clarke/.chefdk/gem/ruby/2.1.0/gems/logging-2.0.0/lib/logging/diagnostic_context.rb:448:in `call'
D C:/Users/christian.clarke/.chefdk/gem/ruby/2.1.0/gems/logging-2.0.0/lib/logging/diagnostic_context.rb:448:in `block in create_with_logging_context'
D ----------------------
D [CommandExecutor] closing remote shell 6AFB19F0-0228-4E1B-B604-F9823402B4F1 on plaintext::http://127.0.0.1:5985/wsman<{:disable_sspi=>true, :basic_auth_only=>true, :user=>"vagrant", :pass=>"vag
rant"}>
D [CommandExecutor] remote shell 6AFB19F0-0228-4E1B-B604-F9823402B4F1 closed

```

---

<div class="post-metadata">

**Author:** ![coderanger](https://sea2.discourse-cdn.com/flex016/user_avatar/discourse.chef.io/coderanger/32/5_2.png) [@coderanger](https://discourse.chef.io/u/coderanger)\
**Post date:** [December 22, 2015, 9:46am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501/3 "2015-12-22T09:46:03Z")

</div>

The relevant bit is toward the middle:

> [@christian.clarke](#):
>
> Gem::RemoteFetcher::FetchError: SSL\_connect returned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed ([https://rubygems.org/gems/diff-lcs-1.2.5.gem](https://rubygems.org/gems/diff-lcs-1.2.5.gem))

Bundler isn't able to verify the TLS cert for [rubygems.org](http://rubygems.org). I've got no idea how to fix that, but it should give you something to work towards at least. Do you have a MITM-ing corporate proxy perhaps?

---

<div class="post-metadata">

**Author:** ![christian.clarke](https://sea2.discourse-cdn.com/flex016/user_avatar/discourse.chef.io/christian.clarke/32/1200_2.png) [@christian.clarke](https://discourse.chef.io/u/christian.clarke)\
**Post date:** [December 22, 2015, 10:40am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501/4 "2015-12-22T10:40:02Z")

</div>

Hello.

No there is no Man-In-The-Middle proxy. It’s going directly to rubygems. I did find this site

> <https://gist.github.com/luislavena/f064211759ee0f806c88>

But the .pem file that it’s refering to is already deployed on my system in this directory.

Directory of C:\opscode\chefdk\embedded\lib\ruby\site\_ruby\2.1.0\rubygems\ssl\_certs

16/09/2015 10:04 .  
16/09/2015 10:04 …  
15/05/2015 02:29 1,521 AddTrustExternalCARoot-2048.pem  
15/05/2015 02:29 1,952 AddTrustExternalCARoot.pem  
15/05/2015 02:29 834 Class3PublicPrimaryCertificationAuthority.pem  
15/05/2015 02:29 1,367 DigiCertHighAssuranceEVRootCA.pem  
15/05/2015 02:29 1,740 EntrustnetSecureServerCertificationAuthority.pem  
15/05/2015 02:29 1,216 GeoTrustGlobalCA.pem

---

<div class="post-metadata">

**Author:** ![coderanger](https://sea2.discourse-cdn.com/flex016/user_avatar/discourse.chef.io/coderanger/32/5_2.png) [@coderanger](https://discourse.chef.io/u/coderanger)\
**Post date:** [December 22, 2015, 10:59am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501/5 "2015-12-22T10:59:42Z")

</div>

Try running [https://raw.githubusercontent.com/mislav/ssl-tools/8b3dec4bedcc725a142fa9bc297610f8d09f5d9d/doctor.rb](https://raw.githubusercontent.com/mislav/ssl-tools/8b3dec4bedcc725a142fa9bc297610f8d09f5d9d/doctor.rb) using Chef’s Ruby. That should give you some visibility into what OpenSSL thinks it is doing. With luck there will be some more Windows-knowledgeable people around in the morning.

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<div class="post-metadata">

**Author:** ![christian.clarke](https://sea2.discourse-cdn.com/flex016/user_avatar/discourse.chef.io/christian.clarke/32/1200_2.png) [@christian.clarke](https://discourse.chef.io/u/christian.clarke)\
**Post date:** [December 22, 2015, 11:11am UTC](https://discourse.chef.io/t/serverspec-and-chef-11/7501/6 "2015-12-22T11:11:23Z")

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Thanks coderanger! I’m looking into this now. As a temporary work-around for anyone else in the community that has this same problem was change the gem source in the Gemfile.

source ‘[http://rubygems.org](http://rubygems.org)’

Instead of Https