diff --git a/lib/docs_compressor.rb b/lib/docs_compressor.rb
index 0fad71f..38a398a 100644
--- a/lib/docs_compressor.rb
+++ b/lib/docs_compressor.rb
@@ -2,12 +2,14 @@
 require 'fileutils'
 require 'shellwords'
 require 'logging'
+require 'running'
 
 # Compresses HTML, JavaScript, and CSS under the given directory, recursively.
 #
 # We do this to leverage gzip_static in nginx.
 class DocsCompressor
   include Logging
+  include Running
 
   EXTENSIONS = %w(.js .html .css)
 
@@ -40,7 +42,7 @@ def compress_file(file)
     orig = Shellwords.shellescape(file)
     dest = Shellwords.shellescape(gzname(file))
 
-    system %(gzip -c -9 #{orig} > #{dest})
+    log_and_system %(gzip -c -9 #{orig} > #{dest})
   end
 
   def compress_file?(file)
diff --git a/lib/generators/base.rb b/lib/generators/base.rb
index c59da8c..5b0cf20 100644
--- a/lib/generators/base.rb
+++ b/lib/generators/base.rb
@@ -74,7 +74,13 @@ def env_as_assigns(env)
     def run(command, env={})
       command = "rvm #{ruby_version} do #{command} >/dev/null"
       log "#{env_as_assigns(env)} #{command}"
-      system(env, command)
+
+      if system(env, command)
+        true
+      else
+        log "\"#{command}\" failed to execute"
+        abort
+      end
     end
 
     # Runs `bundle exec rake` with the appropriate Bundler and Ruby versions.
diff --git a/lib/git_manager.rb b/lib/git_manager.rb
index 0184bc1..9ef3f95 100644
--- a/lib/git_manager.rb
+++ b/lib/git_manager.rb
@@ -1,8 +1,10 @@
 require 'logging'
+require 'running'
 
 # Lightweight wrapper over Git, shells out everything.
 class GitManager
   include Logging
+  include Running
 
   attr_reader :basedir
 
@@ -18,7 +20,7 @@ def update_master
     Dir.chdir(basedir) do
       unless Dir.exist?('master')
         log "cloning master into #{basedir}/master"
-        system "git clone -q #{remote_rails_url} master"
+        log_and_system "git clone -q #{remote_rails_url} master"
       end
 
       Dir.chdir('master') do
@@ -28,8 +30,8 @@ def update_master
         # git pull from succeeding. Starting with Bundler 1.10, if Gemfile.lock
         # does not change BUNDLED WITH is left as is, even if versions differ,
         # but since docs generation is automated better play safe.
-        system 'git checkout Gemfile.lock'
-        system 'git pull -q'
+        log_and_system 'git checkout Gemfile.lock'
+        log_and_system 'git pull -q'
       end
     end
   end
@@ -37,10 +39,10 @@ def update_master
   def checkout(tag)
     Dir.chdir(basedir) do
       log "checking out tag #{tag}"
-      system "git clone -q #{remote_rails_url} #{tag}"
+      log_and_system "git clone -q #{remote_rails_url} #{tag}"
 
       Dir.chdir(tag) do
-        system "git checkout -q #{tag}"
+        log_and_system "git checkout -q #{tag}"
       end
     end
   end
diff --git a/lib/running.rb b/lib/running.rb
new file mode 100644
index 0000000..b8ddb3f
--- /dev/null
+++ b/lib/running.rb
@@ -0,0 +1,8 @@
+module Running
+  include Logging
+
+  def log_and_system(*args)
+    log(args.map(&:to_s).join(' '))
+    system(*args).tap { log "Done" }
+  end
+end