diff --git a/lib/bundler/rubygems_ext.rb b/lib/bundler/rubygems_ext.rb
index 79bea01e6e..481587df86 100644
--- a/lib/bundler/rubygems_ext.rb
+++ b/lib/bundler/rubygems_ext.rb
@@ -407,4 +407,23 @@ module Gem
       end
     end
   end
+
+  unless Gem.rubygems_version >= Gem::Version.new("3.5.19")
+    class Resolver::ActivationRequest
+      remove_method :installed?
+
+      def installed?
+        case @spec
+        when Gem::Resolver::VendorSpecification then
+          true
+        else
+          this_spec = full_spec
+
+          Gem::Specification.any? do |s|
+            s == this_spec && s.base_dir == this_spec.base_dir
+          end
+        end
+      end
+    end
+  end
 end
diff --git a/lib/rubygems/resolver/activation_request.rb b/lib/rubygems/resolver/activation_request.rb
index fc9ff58f57..5c722001b1 100644
--- a/lib/rubygems/resolver/activation_request.rb
+++ b/lib/rubygems/resolver/activation_request.rb
@@ -106,7 +106,7 @@ class Gem::Resolver::ActivationRequest
       this_spec = full_spec
 
       Gem::Specification.any? do |s|
-        s == this_spec
+        s == this_spec && s.base_dir == this_spec.base_dir
       end
     end
   end
diff --git a/spec/bundler/runtime/gem_tasks_spec.rb b/spec/bundler/runtime/gem_tasks_spec.rb
index 1dffbd5c92..046300391b 100644
--- a/spec/bundler/runtime/gem_tasks_spec.rb
+++ b/spec/bundler/runtime/gem_tasks_spec.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
 
 RSpec.describe "require 'bundler/gem_tasks'" do
-  before :each do
+  let(:define_local_gem_using_gem_tasks) do
     bundled_app("foo.gemspec").open("w") do |f|
       f.write <<-GEMSPEC
         Gem::Specification.new do |s|
@@ -26,7 +26,46 @@ RSpec.describe "require 'bundler/gem_tasks'" do
     G
   end
 
+  let(:define_local_gem_with_extensions_using_gem_tasks_and_gemspec_dsl) do
+    bundled_app("foo.gemspec").open("w") do |f|
+      f.write <<-GEMSPEC
+        Gem::Specification.new do |s|
+          s.name = "foo"
+          s.version = "1.0"
+          s.summary = "dummy"
+          s.author = "Perry Mason"
+          s.extensions = "ext/extconf.rb"
+        end
+      GEMSPEC
+    end
+
+    bundled_app("Rakefile").open("w") do |f|
+      f.write <<-RAKEFILE
+        require "bundler/gem_tasks"
+      RAKEFILE
+    end
+
+    Dir.mkdir bundled_app("ext")
+
+    bundled_app("ext/extconf.rb").open("w") do |f|
+      f.write <<-EXTCONF
+        require "mkmf"
+        File.write("Makefile", dummy_makefile($srcdir).join)
+      EXTCONF
+    end
+
+    install_gemfile <<-G
+      source "https://gem.repo1"
+
+      gemspec
+
+      gem "rake"
+    G
+  end
+
   it "includes the relevant tasks" do
+    define_local_gem_using_gem_tasks
+
     with_gem_path_as(base_system_gem_path.to_s) do
       sys_exec "#{rake} -T", env: { "GEM_HOME" => system_gem_path.to_s }
     end
@@ -44,6 +83,8 @@ RSpec.describe "require 'bundler/gem_tasks'" do
   end
 
   it "defines a working `rake install` task", :ruby_repo do
+    define_local_gem_using_gem_tasks
+
     with_gem_path_as(base_system_gem_path.to_s) do
       sys_exec "#{rake} install", env: { "GEM_HOME" => system_gem_path.to_s }
     end
@@ -55,8 +96,18 @@ RSpec.describe "require 'bundler/gem_tasks'" do
     expect(err).to be_empty
   end
 
+  it "defines a working `rake install` task for local gems with extensions", :ruby_repo do
+    define_local_gem_with_extensions_using_gem_tasks_and_gemspec_dsl
+
+    bundle "exec rake install"
+
+    expect(err).to be_empty
+  end
+
   context "rake build when path has spaces", :ruby_repo do
     before do
+      define_local_gem_using_gem_tasks
+
       spaced_bundled_app = tmp("bundled app")
       FileUtils.cp_r bundled_app, spaced_bundled_app
       bundle "exec rake build", dir: spaced_bundled_app
@@ -69,6 +120,8 @@ RSpec.describe "require 'bundler/gem_tasks'" do
 
   context "rake build when path has brackets", :ruby_repo do
     before do
+      define_local_gem_using_gem_tasks
+
       bracketed_bundled_app = tmp("bundled[app")
       FileUtils.cp_r bundled_app, bracketed_bundled_app
       bundle "exec rake build", dir: bracketed_bundled_app
@@ -81,6 +134,8 @@ RSpec.describe "require 'bundler/gem_tasks'" do
 
   context "bundle path configured locally" do
     before do
+      define_local_gem_using_gem_tasks
+
       bundle "config set path vendor/bundle"
     end
 
@@ -98,6 +153,8 @@ RSpec.describe "require 'bundler/gem_tasks'" do
   end
 
   it "adds 'pkg' to rake/clean's CLOBBER" do
+    define_local_gem_using_gem_tasks
+
     with_gem_path_as(base_system_gem_path.to_s) do
       sys_exec %(#{rake} -e 'load "Rakefile"; puts CLOBBER.inspect'), env: { "GEM_HOME" => system_gem_path.to_s }
     end