diff --git a/lib/inspec/plugin/v2/installer.rb b/lib/inspec/plugin/v2/installer.rb
index f29fed705..3ff363611 100644
--- a/lib/inspec/plugin/v2/installer.rb
+++ b/lib/inspec/plugin/v2/installer.rb
@@ -248,10 +248,10 @@ module Inspec::Plugin::V2
     end
 
     def install_from_gem_file(requested_plugin_name, opts)
-      plugin_dependency = Gem::Dependency.new(requested_plugin_name)
-
       # Make Set that encompasses just the gemfile that was provided
       plugin_local_source = Gem::Source::SpecificFile.new(opts[:gem_file])
+
+      plugin_dependency = Gem::Dependency.new(requested_plugin_name, plugin_local_source.spec.version)
       requested_local_gem_set = Gem::Resolver::InstallerSet.new(:both) # :both means local and remote; allow satisfying our gemfile's deps from rubygems.org
       requested_local_gem_set.add_local(plugin_dependency.name, plugin_local_source.spec, plugin_local_source)
 
@@ -264,7 +264,7 @@ module Inspec::Plugin::V2
       install_gem_to_plugins_dir(plugin_dependency, [Gem::Resolver::BestSet.new], opts[:update_mode])
     end
 
-    def install_gem_to_plugins_dir(new_plugin_dependency, extra_request_sets = [], update_mode = false)
+    def install_gem_to_plugins_dir(new_plugin_dependency, extra_request_sets = [], update_mode = false) # rubocop: disable Metrics/AbcSize
       # Get a list of all the gems available to us.
       gem_to_force_update = update_mode ? new_plugin_dependency.name : nil
       set_available_for_resolution = build_gem_request_universe(extra_request_sets, gem_to_force_update)
@@ -272,7 +272,7 @@ module Inspec::Plugin::V2
       # Solve the dependency (that is, find a way to install the new plugin and anything it needs)
       request_set = Gem::RequestSet.new(new_plugin_dependency)
       begin
-        request_set.resolve(set_available_for_resolution)
+        solution = request_set.resolve(set_available_for_resolution)
       rescue Gem::UnsatisfiableDependencyError => gem_ex
         # TODO: use search facility to determine if the requested gem exists at all, vs if the constraints are impossible
         ex = Inspec::Plugin::V2::InstallError.new(gem_ex.message)
@@ -280,6 +280,29 @@ module Inspec::Plugin::V2
         raise ex
       end
 
+      # Activate all current plugins before trying to activate the new one
+      loader.list_managed_gems.each do |spec|
+        next if spec.name == new_plugin_dependency.name && update_mode
+        spec.activate
+      end
+
+      # Make sure we remove any previously loaded gem on update
+      Gem.loaded_specs.delete(new_plugin_dependency.name) if update_mode
+
+      # Test activating the solution. This makes sure we do not try to load two different versions
+      # of the same gem on the stack or a malformed dependency.
+      begin
+        solution.each do |activation_request|
+          unless activation_request.full_spec.activated?
+            activation_request.full_spec.activate
+          end
+        end
+      rescue Gem::LoadError => gem_ex
+        ex = Inspec::Plugin::V2::InstallError.new(gem_ex.message)
+        ex.plugin_name = new_plugin_dependency.name
+        raise ex
+      end
+
       # OK, perform the installation.
       # Ignore deps here, because any needed deps should already be baked into new_plugin_dependency
       request_set.install_into(gem_path, true, ignore_dependencies: true)
@@ -358,6 +381,18 @@ module Inspec::Plugin::V2
     #                        Utilities
     #===================================================================#
 
+    # This class alows us to build a Vendor set with the gems that are
+    # already included either with Ruby or with the InSpec install
+    class InstalledVendorSet < Gem::Resolver::VendorSet
+      def initialize
+        super
+        Gem::Specification.find_all do |spec|
+          @specs[spec.name] = spec
+          @directories[spec] = spec.gem_dir
+        end
+      end
+    end
+
     # Provides a RequestSet (a set of gems representing the gems that are available to
     # solve a dependency request) that represents a combination of:
     # * the gems included in the system
@@ -374,7 +409,7 @@ module Inspec::Plugin::V2
       # Combine the Sets, so the resolver has one composite place to look
       Gem::Resolver.compose_sets(
         installed_plugins_gem_set,     # The gems that are in the plugin gem path directory tree
-        Gem::Resolver::CurrentSet.new, # The gems that are already included either with Ruby or with the InSpec install
+        InstalledVendorSet.new,
         *extra_request_sets,           # Anything else our caller wanted to include
       )
     end
diff --git a/test/unit/plugin/v2/installer_test.rb b/test/unit/plugin/v2/installer_test.rb
index 80f97e8fe..e4ae1264e 100644
--- a/test/unit/plugin/v2/installer_test.rb
+++ b/test/unit/plugin/v2/installer_test.rb
@@ -54,6 +54,9 @@ module InstallerTestHelpers
       end
     end
 
+    # Clean up any activated gems
+    Gem.loaded_specs.delete('inspec-test-fixture')
+
     # TODO: may need to edit the $LOAD_PATH, if it turns out that we need to "deactivate" gems after installation
   end
 end
@@ -117,9 +120,9 @@ class PluginInstallerInstallationTests < MiniTest::Test
     installed_gem_base = File.join(@installer.gem_path, 'gems', 'inspec-test-fixture-0.1.0')
     assert Dir.exist?(installed_gem_base), 'After installation from a gem file, the gem tree should be installed to the gem path'
 
-    # Installation != gem activation
-    spec = Gem::Specification.load(spec_path)
-    refute spec.activated?, 'Installing a gem should not cause the gem to activate'
+    # Installation = gem activation
+    spec = Gem.loaded_specs['inspec-test-fixture']
+    assert spec.activated?, 'Installing a gem should cause the gem to activate'
   end
 
   def test_install_a_gem_from_missing_local_file
@@ -171,8 +174,8 @@ class PluginInstallerInstallationTests < MiniTest::Test
     assert Dir.exist?(installed_gem_base), 'After installation from a gem file, the gem tree should be installed to the gem path'
 
     # Installation != gem activation
-    spec = Gem::Specification.load(spec_path)
-    refute spec.activated?, 'Installing a gem should not cause the gem to activate'
+    spec = Gem.loaded_specs['inspec-test-fixture']
+    assert spec.activated?, 'Installing a gem should cause the gem to activate'
   end
 
   def test_handle_no_such_gem
@@ -198,7 +201,25 @@ class PluginInstallerInstallationTests < MiniTest::Test
     entry = plugin_json_data['plugins'].detect { |e| e["name"] == 'inspec-test-fixture'}
     assert_includes entry.keys, 'version', 'plugins.json should include version pinning key'
     assert_equal '= 0.1.0', entry['version'], 'plugins.json should include version pinning value'
- end
+  end
+
+  def test_install_a_gem_with_conflicting_depends_from_rubygems_org
+    ENV['INSPEC_CONFIG_DIR'] = File.join(@config_dir_path, 'empty')
+
+    ex = assert_raises(Inspec::Plugin::V2::InstallError) do
+      @installer.install('inspec-test-fixture', version: '= 0.1.1')
+    end
+    assert_includes ex.message, "can't activate rake-0.4.8, already activated rake-"
+  end
+
+  def test_install_a_gem_with_invalid_depends_from_rubygems_org
+    ENV['INSPEC_CONFIG_DIR'] = File.join(@config_dir_path, 'empty')
+
+    ex = assert_raises(Inspec::Plugin::V2::InstallError) do
+      @installer.install('inspec-test-fixture', version: '= 0.1.2')
+    end
+    assert_includes ex.message, "Could not find 'fake_plugin_dependency' (>= 0)"
+  end
 
   def test_install_a_plugin_from_a_path
     ENV['INSPEC_CONFIG_DIR'] = File.join(@config_dir_path, 'empty')