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Certificate Verify Failed During Gem Update

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I pull the Git commits from the origin of this blog to Git Bash on M$ Win*. The Gemfile has changed due to commit fbc3c0b.


I ran bundle install according to the official documentation, and got an unexpected error.1

Owner@OWNER-PC /c/github/ (source)
$ bundle install
DL is deprecated, please use Fiddle
Fetching gem metadata from
Resolving dependencies...
Bundler could not find compatible versions for gem "sass":
  In snapshot (Gemfile.lock):
    sass (3.2.19)

  In Gemfile:
    compass (~> 1.0.1) x64-mingw32 depends on
      sass (< 3.5, >= 3.3.13) x64-mingw32

Running `bundle update` will rebuild your snapshot from scratch, using only
the gems in your Gemfile, which may resolve the conflict.

Without updated gems, even though everything in the source folder is correct, one can’t generate an Octopress blog. How can one get the gems updated?

I then tried to follow the suggestion, but received another error.

Owner@OWNER-PC /c/github/ (source)
Owner@OWNER-PC /c/github/ (source)
$ bundle update
DL is deprecated, please use Fiddle
Fetching gem metadata from
Resolving dependencies...

Gem::RemoteFetcher::FetchError: SSL_connect returned=1 errno=0 state=SSLv3 read
server certificate B: certificate verify failed (
An error occurred while installing rake (10.4.2), and Bundler cannot continue.
Make sure that `gem install rake -v '10.4.2'` succeeds before bundling.

I ran the command in bold in the above message, and got similar messages.

Owner@OWNER-PC /c/github/ (source)
$ gem install rake -v '10.4.2'
ERROR:  Could not find a valid gem 'rake' (= 10.4.2), here is why:
          Unable to download data from - SSL_connect retur
ned=1 errno=0 state=SSLv3 read server certificate B: certificate verify failed (


I googled “windows unable to download data from https // - ssl_connect returned=1”, and clicked on the first Stack Overflow question that I saw. I quickly skimmed through the first answer of this question, and read the last section “Windows note”, which referred interested readers to two places:

  1. RubyInstaller issue 249 on GitHub,
  2. The second answer of this question.

I clicked the first webpage, and quickly jumped to Luis Lavena’s response to the issue. Unlike the previous webpages, I read every word from the beginning to the third section this time, and read the Stack Overflow question again, before deciding what to be done.

I followed the instructions in the third section, instead of manually downloading and inserting the PEM file back to the folder which the command gem which rubygems returned.

Owner@OWNER-PC /c/github/ (source)
$ gem install --local ~/Downloads/rubygems-update-2.0.15.gem
Successfully installed rubygems-update-2.0.15
Parsing documentation for rubygems-update-2.0.15
Installing ri documentation for rubygems-update-2.0.15
1 gem installed

Owner@OWNER-PC /c/github/ (source)
$ update_rubygems --no-ri --no-rdoc
RubyGems 2.0.15 installed

=== 2.0.14 / 2013-11-12

Bug fixes:

* Restore concurrent requires following the fix for ruby bug #8374.  Pull
  request #637 and issue #640 by Charles Nutter.
* Gem::Specification::remove_spec no longer checks for existence of the spec
  to be removed.  Issue #698 by Tiago Macedo.
* Restored wildcard handling when installing gems.  Issue #697 by Chuck Remes.
* Added DigiCert High Assurance EV Root CA certificate for the
  certificate change.
* The Gem::RemoteFetcher tests now choose the test server port more reliably.
  Pull Request #706 by akr.


RubyGems installed the following executables:

Owner@OWNER-PC /c/github/ (source)
$ gem uninstall rubygems-update -x
Removing update_rubygems
Successfully uninstalled rubygems-update-2.0.15

Then I ran bundle install again, and I still got the same error shown at the very beginning of the post. However, I could update the gems.

Owner@OWNER-PC /c/github/ (source)
$ bundle update
DL is deprecated, please use Fiddle
Fetching gem metadata from
Resolving dependencies...
Installing rake 10.4.2 (was 10.3.2)
Using RedCloth 4.2.9
Using blankslate
Installing hitimes 1.2.2
Installing timers 4.0.1 (was 1.1.0)
Installing celluloid 0.16.0 (was 0.15.2)
Installing chunky_png 1.3.3 (was 1.3.1)
Using fast-stemmer 1.0.2
Installing classifier-reborn 2.0.3 (was 2.0.1)
Using coffee-script-source 1.8.0
Installing execjs 2.2.2 (was 2.2.1)
Using coffee-script 2.3.0
Using colorator 0.1
Installing multi_json 1.10.1
Installing sass 3.4.9 (was 3.2.19)
Installing compass-core 1.0.1
Installing compass-import-once 1.0.5
Using rb-fsevent 0.9.4
Installing ffi 1.9.6 (was 1.9.3)
Using rb-inotify 0.9.5
Installing compass 1.0.1 (was 0.12.7)
Using tilt 1.4.1
Installing haml 4.0.6 (was 4.0.5)
Installing jekyll-coffeescript 1.0.1 (was 1.0.0)
Using jekyll-gist 1.1.0
Installing jekyll-paginate 1.1.0 (was 1.0.0)
Installing jekyll-sass-converter 1.3.0 (was 1.2.0)
Installing listen 2.8.4 (was 2.7.9)
Installing jekyll-watch 1.2.0 (was 1.1.0)
Installing kramdown 1.5.0 (was 1.4.1)
Using liquid 2.6.1
Installing mercenary 0.3.5 (was 0.3.4)
Using posix-spawn 0.3.9
Using yajl-ruby 1.1.0
Using pygments.rb 0.6.0
Installing redcarpet 3.2.2 (was 3.1.2)
Installing safe_yaml 1.0.4 (was 1.0.3)
Using parslet 1.5.0
Installing toml 0.1.2 (was 0.1.1)
Installing jekyll 2.5.3 (was 2.3.0)
Installing jekyll-sitemap 0.7.0 (was 0.5.1)
Installing octopress-hooks 2.2.3 (was 2.2.1)
Installing octopress-date-format 2.0.2 (was 2.0.1)
Installing rack 1.6.0 (was 1.5.2)
Using rack-protection 1.5.3
Using rubypants 0.2.0
Using sass-globbing 1.0.0
Using sinatra 1.4.5
Using stringex 1.4.0
Using wdm 0.1.0
Using bundler 1.7.2
Your bundle is updated!

Lessons learnt

To save space in the hard disk, I removed the old versions of gems with a short and simple command.

Owner@OWNER-PC /c/github/ (source)
$ gem cleanup
Cleaning up installed gems...
Attempting to uninstall rake-10.3.2
Successfully uninstalled rake-10.3.2
Attempting to uninstall rack-1.5.2
Successfully uninstalled rack-1.5.2
Attempting to uninstall octopress-date-format-2.0.1
Successfully uninstalled octopress-date-format-2.0.1
Attempting to uninstall octopress-hooks-2.2.1
Successfully uninstalled octopress-hooks-2.2.1
Attempting to uninstall jekyll-sitemap-0.5.1
Successfully uninstalled jekyll-sitemap-0.5.1
Attempting to uninstall jekyll-2.3.0
Successfully uninstalled jekyll-2.3.0
Attempting to uninstall jekyll-watch-1.1.0
Successfully uninstalled jekyll-watch-1.1.0
Attempting to uninstall listen-2.7.9
Successfully uninstalled listen-2.7.9
Attempting to uninstall jekyll-sass-converter-1.2.0
Successfully uninstalled jekyll-sass-converter-1.2.0
Attempting to uninstall jekyll-coffeescript-1.0.0
Successfully uninstalled jekyll-coffeescript-1.0.0
Attempting to uninstall jekyll-paginate-1.0.0
Successfully uninstalled jekyll-paginate-1.0.0
Attempting to uninstall toml-0.1.1
Successfully uninstalled toml-0.1.1
Attempting to uninstall redcarpet-3.1.2
Successfully uninstalled redcarpet-3.1.2
Attempting to uninstall safe_yaml-1.0.3
Successfully uninstalled safe_yaml-1.0.3
Attempting to uninstall mercenary-0.3.4
Successfully uninstalled mercenary-0.3.4
Attempting to uninstall kramdown-1.4.1
Successfully uninstalled kramdown-1.4.1
Attempting to uninstall haml-4.0.5
Successfully uninstalled haml-4.0.5
Attempting to uninstall ffi-1.9.3-x64-mingw32
Successfully uninstalled ffi-1.9.3-x64-mingw32
Attempting to uninstall execjs-2.2.1
Successfully uninstalled execjs-2.2.1
Attempting to uninstall compass-0.12.7
Successfully uninstalled compass-0.12.7
Attempting to uninstall classifier-reborn-2.0.1
Successfully uninstalled classifier-reborn-2.0.1
Attempting to uninstall chunky_png-1.3.1
Successfully uninstalled chunky_png-1.3.1
Attempting to uninstall celluloid-0.15.2
Successfully uninstalled celluloid-0.15.2
Attempting to uninstall timers-1.1.0
Successfully uninstalled timers-1.1.0
Attempting to uninstall sass-3.2.19
Successfully uninstalled sass-3.2.19
Clean Up Complete

  1. Updating Octopress in Octopress Documentation