diff --git a/CHANGELOG.md b/CHANGELOG.md
index de7befb1..02e856b3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,9 @@
 master
 ===
 
+* Remove 'upgrade' and 'install' CLI commands.
+* Gemfile may be in a parent directory of your Middleman project root (where 'config.rb' is).
+* All dependencies for your Middleman project must be expressed in `Gemfile` - Bundler is no longer optional.
 * Asciidoc information now available with the `asciidoc` local, which is a normal hash.
 * Remove `page` template local. Use `current_resource` instead.
 * Dropped support for providing a block to `page` & `proxy`.
diff --git a/Gemfile b/Gemfile
index 83cd68cc..6b365575 100644
--- a/Gemfile
+++ b/Gemfile
@@ -24,7 +24,6 @@ platforms :ruby do
   gem 'therubyracer'
   gem 'redcarpet', '~> 3.1'
   gem 'pry', :require => false, :group => :development
-  gem 'pry-debugger', :require => false, :group => :development
 end
 
 platforms :jruby do
diff --git a/middleman-cli/lib/middleman-cli.rb b/middleman-cli/lib/middleman-cli.rb
index ee02429d..48fb1b2d 100644
--- a/middleman-cli/lib/middleman-cli.rb
+++ b/middleman-cli/lib/middleman-cli.rb
@@ -88,7 +88,6 @@ end
 
 # Include the core CLI items
 require 'middleman-cli/init'
-require 'middleman-cli/bundler'
 require 'middleman-cli/extension'
 require 'middleman-cli/server'
 require 'middleman-cli/build'
diff --git a/middleman-cli/lib/middleman-cli/bundler.rb b/middleman-cli/lib/middleman-cli/bundler.rb
deleted file mode 100644
index 43a0d862..00000000
--- a/middleman-cli/lib/middleman-cli/bundler.rb
+++ /dev/null
@@ -1,40 +0,0 @@
-# CLI Module
-module Middleman::Cli
-
-  # A initializing Bundler
-  class Bundle < Thor
-    include Thor::Actions
-    check_unknown_options!
-
-    namespace :bundle
-
-    desc 'bundle', 'Setup initial bundle', :hide => true
-
-    # The setup task
-    def bundle
-      run('bundle install')#, :capture => true)
-    end
-  end
-
-  # A upgrading Bundler
-  class Upgrade < Thor
-    include Thor::Actions
-    check_unknown_options!
-
-    namespace :upgrade
-
-    desc 'upgrade', 'Upgrade installed bundle'
-
-    # The upgrade task
-    def upgrade
-      inside(ENV['MM_ROOT']) do
-        run('bundle update')#, :capture => true)
-      end
-    end
-  end
-
-  # Map "u" to "upgrade"
-  Base.map({
-    'u' => 'upgrade'
-  })
-end
diff --git a/middleman-core/lib/middleman-core/load_paths.rb b/middleman-core/lib/middleman-core/load_paths.rb
index 673563f6..968e61ec 100644
--- a/middleman-core/lib/middleman-core/load_paths.rb
+++ b/middleman-core/lib/middleman-core/load_paths.rb
@@ -8,35 +8,16 @@ module Middleman
       @_is_setup ||= begin
 
         # Only look for config.rb if MM_ROOT isn't set
-        if !ENV['MM_ROOT'] && found_path = locate_root
+        if !ENV['MM_ROOT'] && (found_path = findup('config.rb'))
           ENV['MM_ROOT'] = found_path
         end
 
-        is_bundler_setup = false
-
         # If we've found the root, try to setup Bundler
         if ENV['MM_ROOT']
-
-          root_gemfile = File.expand_path('Gemfile', ENV['MM_ROOT'])
-          ENV['BUNDLE_GEMFILE'] ||= root_gemfile
-
-          if !File.exists?(ENV['BUNDLE_GEMFILE'])
-            git_gemfile = Pathname.new(__FILE__).expand_path.parent.parent.parent + 'Gemfile'
-            ENV['BUNDLE_GEMFILE'] = git_gemfile.to_s
-          end
-
-          if File.exists?(ENV['BUNDLE_GEMFILE'])
-            is_bundler_setup = true
-            require 'bundler/setup'
-          end
-        end
-
-        # Automatically discover extensions in RubyGems
-        require 'middleman-core/extensions'
-
-        if is_bundler_setup
-          Bundler.require
+          setup_bundler
         else
+          # Automatically discover extensions in RubyGems
+          require 'middleman-core/extensions'
           ::Middleman.load_extensions_in_path
         end
 
@@ -44,11 +25,29 @@ module Middleman
       end
     end
 
-    # Recursive method to find config.rb
-    def locate_root(cwd = Pathname.new(Dir.pwd))
-      return cwd.to_s if (cwd + 'config.rb').exist?
+    private
+
+    # Set BUNDLE_GEMFILE and run Bundler setup. Raises an exception if there is no Gemfile
+    def setup_bundler
+      ENV['BUNDLE_GEMFILE'] ||= findup('Gemfile', ENV['MM_ROOT'])
+
+      if !File.exists?(ENV['BUNDLE_GEMFILE'])
+        ENV['BUNDLE_GEMFILE'] = File.expand_path('../../../../Gemfile', __FILE__)
+      end
+
+      if File.exists?(ENV['BUNDLE_GEMFILE'])
+        require 'bundler/setup'
+        Bundler.require
+      else
+        raise "Couldn't find your Gemfile. Middleman projects require a Gemfile for specifying dependencies."
+      end
+    end
+
+    # Recursive method to find a file in parent directories
+    def findup(filename, cwd = Pathname.new(Dir.pwd))
+      return cwd.to_s if (cwd + filename).exist?
       return false if cwd.root?
-      locate_root(cwd.parent)
+      findup(filename, cwd.parent)
     end
 
   end