diff --git a/bin/vagrant b/bin/vagrant
index ba7e40076..c019f30ff 100755
--- a/bin/vagrant
+++ b/bin/vagrant
@@ -23,9 +23,9 @@ if idx = argv.index("--")
   argv = argv.slice(0, idx)
 end
 
+require_relative "../lib/vagrant/version"
 # Fast path the version of Vagrant
 if argv.include?("-v") || argv.include?("--version")
-  require_relative "../lib/vagrant/version"
   puts "Vagrant #{Vagrant::VERSION}"
   exit 0
 end
@@ -82,6 +82,29 @@ end
 $stdout.sync = true
 $stderr.sync = true
 
+# Before we start activate all our dependencies
+# so we can provide correct resolutions later
+builtin_specs = []
+
+vagrant_spec = Gem::Specification.find_all_by_name("vagrant").detect do |spec|
+  spec.version == Gem::Version.new(Vagrant::VERSION)
+end
+
+dep_activator = proc do |spec|
+  spec.runtime_dependencies.each do |dep|
+    gem(dep.name, *dep.requirement.as_list)
+    dep_spec = Gem::Specification.find_all_by_name(dep.name).detect(&:activated?)
+    if dep_spec
+      builtin_specs << dep_spec
+      dep_activator.call(dep_spec)
+    end
+  end
+end
+
+if vagrant_spec
+  dep_activator.call(vagrant_spec)
+end
+
 env = nil
 begin
   require 'log4r'
@@ -91,6 +114,9 @@ begin
   require 'vagrant/util/platform'
   require 'vagrant/util/experimental'
 
+  # Set our list of builtin specs
+  Vagrant::Bundler.instance.builtin_specs = builtin_specs
+
   # Schedule the cleanup of things
   at_exit(&Vagrant::Bundler.instance.method(:deinit))
 
diff --git a/lib/vagrant.rb b/lib/vagrant.rb
index d696bdff8..f3dcba0bc 100644
--- a/lib/vagrant.rb
+++ b/lib/vagrant.rb
@@ -81,7 +81,7 @@ if ENV["VAGRANT_LOG"] && ENV["VAGRANT_LOG"] != ""
     # See https://github.com/rest-client/rest-client/issues/34#issuecomment-290858
     # for more information
     class VagrantLogger < Log4r::Logger
-      def << (msg)
+      def << msg
         debug(msg.strip)
       end
     end
diff --git a/lib/vagrant/bundler.rb b/lib/vagrant/bundler.rb
index 7abc01a97..1165fdf2a 100644
--- a/lib/vagrant/bundler.rb
+++ b/lib/vagrant/bundler.rb
@@ -189,8 +189,11 @@ module Vagrant
     attr_reader :env_plugin_gem_path
     # @return [Pathname] Vagrant environment data path
     attr_reader :environment_data_path
+    # @return [Array<Gem::Specification>, nil] List of builtin specs
+    attr_accessor :builtin_specs
 
     def initialize
+      @builtin_specs = []
       @plugin_gem_path = Vagrant.user_data_path.join("gems", RUBY_VERSION).freeze
       @logger = Log4r::Logger.new("vagrant::bundler")
     end
@@ -287,7 +290,6 @@ module Vagrant
         # Never allow dependencies to be remotely satisfied during init
         request_set.remote = false
 
-        repair_result = nil
         begin
           @logger.debug("resolving solution from available specification set")
           # Resolve the request set to ensure proper activation order
@@ -647,7 +649,6 @@ module Vagrant
         self_spec.activate
         @logger.info("Activated vagrant specification version - #{self_spec.version}")
       end
-      self_spec.runtime_dependencies.each { |d| gem d.name, *d.requirement.as_list }
       # discover all the gems we have available
       list = {}
       if Gem.respond_to?(:default_specifications_dir)
@@ -656,10 +657,16 @@ module Vagrant
         spec_dir = Gem::Specification.default_specifications_dir
       end
       directories = [spec_dir]
-      Gem::Specification.find_all{true}.each do |spec|
-        list[spec.full_name] = spec
+      if Vagrant.in_bundler?
+        Gem::Specification.find_all{true}.each do |spec|
+          list[spec.full_name] = spec
+        end
+      else
+        builtin_specs.each do |spec|
+          list[spec.full_name] = spec
+        end
       end
-      if(!Object.const_defined?(:Bundler))
+      if Vagrant.in_installer?
         directories += Gem::Specification.dirs.find_all do |path|
           !path.start_with?(Gem.user_dir)
         end
diff --git a/lib/vagrant/errors.rb b/lib/vagrant/errors.rb
index 782615bc4..5cb861c06 100644
--- a/lib/vagrant/errors.rb
+++ b/lib/vagrant/errors.rb
@@ -636,6 +636,18 @@ module Vagrant
       error_key(:provisioner_winrm_unsupported)
     end
 
+    class PluginNeedsDeveloperTools < VagrantError
+      error_key(:plugin_needs_developer_tools)
+    end
+
+    class PluginMissingLibrary < VagrantError
+      error_key(:plugin_missing_library)
+    end
+
+    class PluginMissingRubyDev < VagrantError
+      error_key(:plugin_missing_ruby_dev)
+    end
+
     class PluginGemNotFound < VagrantError
       error_key(:plugin_gem_not_found)
     end
diff --git a/lib/vagrant/plugin/manager.rb b/lib/vagrant/plugin/manager.rb
index 9058e68b3..b73f07f9c 100644
--- a/lib/vagrant/plugin/manager.rb
+++ b/lib/vagrant/plugin/manager.rb
@@ -179,8 +179,26 @@ module Vagrant
         result
       rescue Gem::GemNotFoundException
         raise Errors::PluginGemNotFound, name: name
-      rescue Gem::Exception => e
-        raise Errors::BundlerError, message: e.to_s
+      rescue Gem::Exception => err
+        @logger.warn("Failed to install plugin: #{err}")
+        @logger.debug("#{err.class}: #{err}\n#{err.backtrace.join("\n")}")
+        # Try and determine a cause for the failure
+        case err.message
+        when /install development tools first/
+          raise Errors::PluginNeedsDeveloperTools
+        when /library not found in default locations/
+          lib = err.message.match(/(\w+) library not found in default locations/)
+          if lib.nil?
+            raise Errors::BundlerError, message: err.message
+          end
+          raise Errors::PluginMissingLibrary,
+            library: lib.captures.first,
+            name: name
+        when /find header files for ruby/
+          raise Errors::PluginMissingRubyDev
+        else
+          raise Errors::BundlerError, message: err.message
+        end
       end
 
       # Uninstalls the plugin with the given name.
diff --git a/templates/locales/en.yml b/templates/locales/en.yml
index 782904f49..edae9b477 100644
--- a/templates/locales/en.yml
+++ b/templates/locales/en.yml
@@ -794,9 +794,9 @@ en:
         matching this provider. For example, if you're using VirtualBox,
         the clone environment must also be using VirtualBox.
       cloud_init_not_found: |-
-        cloud-init is not found. Please ensure that cloud-init is installed and 
+        cloud-init is not found. Please ensure that cloud-init is installed and
         available on path for guest '%{guest_name}'.
-      cloud_init_command_failed: |- 
+      cloud_init_command_failed: |-
         cloud init command '%{cmd}' failed on guest '%{guest_name}'.
       command_deprecated: |-
         The command 'vagrant %{name}' has been deprecated and is no longer functional
@@ -1238,6 +1238,23 @@ en:
         following command:
 
           vagrant plugin install --local
+      plugin_needs_developer_tools: |-
+        Vagrant failed to install the requested plugin because development tools
+        are required for installation but are not currently installed on this
+        machine. Please install development tools and then try this command
+        again.
+      plugin_missing_library: |-
+        Vagrant failed to install the requested plugin because it depends
+        on a library which is not currently installed on this system. The
+        following library is required by the '%{name}' plugin:
+
+          %{library}
+
+        Please install the library and then run the command again.
+      plugin_missing_ruby_dev: |-
+        Vagrant failed to install the requested plugin because the Ruby header
+        files could not be found. Install the ruby development package for your
+        system and then run this command again.
       powershell_not_found: |-
         Failed to locate the powershell executable on the available PATH. Please
         ensure powershell is installed and available on the local PATH, then
@@ -2998,7 +3015,7 @@ en:
     pushes:
       file:
         no_destination: "File destination must be specified."
-    
+
     autocomplete:
       installed: |-
         Autocomplete installed at paths:
diff --git a/test/unit/bin/vagrant_test.rb b/test/unit/bin/vagrant_test.rb
index bc11309aa..dbbd52112 100644
--- a/test/unit/bin/vagrant_test.rb
+++ b/test/unit/bin/vagrant_test.rb
@@ -30,6 +30,7 @@ describe "vagrant bin" do
     allow(Kernel).to receive(:exit)
     allow(Vagrant::Environment).to receive(:new).and_return(env)
     allow(Vagrant).to receive(:in_installer?).and_return(true)
+    allow(self).to receive(:require_relative)
   end
 
   after { expect(run_vagrant).to eq(exit_code) }
diff --git a/test/unit/vagrant/bundler_test.rb b/test/unit/vagrant/bundler_test.rb
index 00cedc021..69f425c66 100644
--- a/test/unit/vagrant/bundler_test.rb
+++ b/test/unit/vagrant/bundler_test.rb
@@ -778,42 +778,46 @@ describe Vagrant::Bundler do
       end
     end
 
-    context "when run time dependencies are defined" do
-      let(:vagrant_dep_specs) { [double("spec", name: "vagrant-dep", requirement: double("spec-req", as_list: []))] }
-
-      it "should call #gem to activate the dependencies" do
-        expect(subject).to receive(:gem).with("vagrant-dep", any_args)
-        subject.send(:vagrant_internal_specs)
-      end
-    end
-
     context "when bundler is not defined" do
-      before { expect(Object).to receive(:const_defined?).with(:Bundler).and_return(false) }
+      before { expect(Vagrant).to receive(:in_bundler?).and_return(false) }
 
-      it "should load gem specification directories" do
-        expect(Gem::Specification).to receive(:dirs).and_return(spec_dirs)
-        subject.send(:vagrant_internal_specs)
-      end
+      context "when running inside the installer" do
+        before { expect(Vagrant).to receive(:in_installer?).and_return(true) }
 
-      context "when checking paths" do
-        let(:spec_dirs) { [double("spec-dir", start_with?: in_user_dir)] }
-        let(:in_user_dir) { true }
-        let(:user_dir) { double("user-dir") }
-
-        before { allow(Gem).to receive(:user_dir).and_return(user_dir) }
-
-        it "should check if path is within local user directory" do
-          expect(spec_dirs.first).to receive(:start_with?).with(user_dir).and_return(false)
+        it "should load gem specification directories" do
+          expect(Gem::Specification).to receive(:dirs).and_return(spec_dirs)
           subject.send(:vagrant_internal_specs)
         end
 
-        context "when path is not within user directory" do
-          let(:in_user_dir) { false }
+        context "when checking paths" do
+          let(:spec_dirs) { [double("spec-dir", start_with?: in_user_dir)] }
+          let(:in_user_dir) { true }
+          let(:user_dir) { double("user-dir") }
 
-          it "should use path when loading specs" do
-            expect(Gem::Specification).to receive(:each_spec) { |arg| expect(arg).to include(spec_dirs.first) }
+          before { allow(Gem).to receive(:user_dir).and_return(user_dir) }
+
+          it "should check if path is within local user directory" do
+            expect(spec_dirs.first).to receive(:start_with?).with(user_dir).and_return(false)
             subject.send(:vagrant_internal_specs)
           end
+
+          context "when path is not within user directory" do
+            let(:in_user_dir) { false }
+
+            it "should use path when loading specs" do
+              expect(Gem::Specification).to receive(:each_spec) { |arg| expect(arg).to include(spec_dirs.first) }
+              subject.send(:vagrant_internal_specs)
+            end
+          end
+        end
+      end
+
+      context "when running outside the installer" do
+        before { expect(Vagrant).to receive(:in_installer?).and_return(false) }
+
+        it "should not load gem specification directories" do
+          expect(Gem::Specification).not_to receive(:dirs)
+          subject.send(:vagrant_internal_specs)
         end
       end
     end