diff --git a/python/helpers/requirements.txt b/python/helpers/requirements.txt
index 4aad2ff2eb..f69bc62261 100644
--- a/python/helpers/requirements.txt
+++ b/python/helpers/requirements.txt
@@ -7,6 +7,7 @@ plette==2.1.0
 poetry==1.8.3
 # TODO: Replace 3p package `toml` with 3.11's new stdlib `tomllib` once we drop support for Python 3.10.
 toml==0.10.2
+uv==0.4.9
 
 # Some dependencies will only install if Cython is present
 Cython==3.0.10
diff --git a/python/lib/dependabot/python/file_updater/pip_compile_file_updater.rb b/python/lib/dependabot/python/file_updater/pip_compile_file_updater.rb
index 67f2121475..89d2d46f69 100644
--- a/python/lib/dependabot/python/file_updater/pip_compile_file_updater.rb
+++ b/python/lib/dependabot/python/file_updater/pip_compile_file_updater.rb
@@ -96,13 +96,14 @@ def compile_new_requirement_files
         def compile_file(filename)
           # Shell out to pip-compile, generate a new set of requirements.
           # This is slow, as pip-compile needs to do installs.
-          options = pip_compile_options(filename)
+
+          options, command = pip_compile_options(filename)
           options_fingerprint = pip_compile_options_fingerprint(options)
 
-          name_part = "pyenv exec pip-compile " \
+          name_part = "#{command} " \
                       "#{options} -P " \
                       "#{dependency.name}"
-          fingerprint_name_part = "pyenv exec pip-compile " \
+          fingerprint_name_part = "#{command} " \
                                   "#{options_fingerprint} -P " \
                                   "<dependency_name>"
 
@@ -453,10 +454,16 @@ def pip_compile_options(filename)
           options += pip_compile_index_options
 
           if (requirements_file = compiled_file_for_filename(filename))
-            options += pip_compile_options_from_compiled_file(requirements_file)
+            if requirements_file.content.include?("uv pip compile")
+              options += uv_pip_compile_options_from_compiled_file(requirements_file)
+              command = "pyenv exec uv pip compile"
+            else
+              options += pip_compile_options_from_compiled_file(requirements_file)
+              command = "pyenv exec pip-compile"
+            end
           end
 
-          options.join(" ")
+          [options.join(" "), command]
         end
 
         def pip_compile_options_from_compiled_file(requirements_file)
@@ -483,6 +490,32 @@ def pip_compile_options_from_compiled_file(requirements_file)
           options
         end
 
+        def uv_pip_compile_options_from_compiled_file(requirements_file)
+          options = ["--output-file=#{requirements_file.name}"]
+
+          options << "--no-emit-index-url" unless requirements_file.content.include?("index-url http")
+
+          options << "--generate-hashes" if requirements_file.content.include?("--hash=sha")
+
+          options << "--no-annotate" unless requirements_file.content.include?("# via ")
+
+          options << "--pre" if requirements_file.content.include?("--pre")
+
+          options << "--no-strip-extras" if requirements_file.content.include?("--no-strip-extras")
+
+          if requirements_file.content.include?("--no-binary") || requirements_file.content.include?("--only-binary")
+            options << "--emit-build-options"
+          end
+
+          if (resolver = RESOLVER_REGEX.match(requirements_file.content))
+            options << "--resolver=#{resolver}"
+          end
+
+          options << "--universal" if requirements_file.content.include?("--universal")
+
+          options
+        end
+
         def pip_compile_index_options
           credentials
             .select { |cred| cred["type"] == "python_index" }
diff --git a/python/lib/dependabot/python/update_checker/pip_compile_version_resolver.rb b/python/lib/dependabot/python/update_checker/pip_compile_version_resolver.rb
index 1b8accb8af..3c78b99601 100644
--- a/python/lib/dependabot/python/update_checker/pip_compile_version_resolver.rb
+++ b/python/lib/dependabot/python/update_checker/pip_compile_version_resolver.rb
@@ -91,12 +91,12 @@ def fetch_latest_resolvable_version_string(requirement:)
         def compile_file(filename)
           # Shell out to pip-compile.
           # This is slow, as pip-compile needs to do installs.
-          options = pip_compile_options(filename)
+          options, command = pip_compile_options(filename)
           options_fingerprint = pip_compile_options_fingerprint(options)
 
           run_pip_compile_command(
-            "pyenv exec pip-compile -v #{options} -P #{dependency.name} #{filename}",
-            fingerprint: "pyenv exec pip-compile -v #{options_fingerprint} -P <dependency_name> <filename>"
+            "#{command} -v #{options} -P #{dependency.name} #{filename}",
+            fingerprint: "#{command} -v #{options_fingerprint} -P <dependency_name> <filename>"
           )
 
           return true if dependency.top_level?
@@ -110,8 +110,8 @@ def compile_file(filename)
           # update_not_possible.
           write_original_manifest_files
           run_pip_compile_command(
-            "pyenv exec pip-compile #{options} #{filename}",
-            fingerprint: "pyenv exec pip-compile #{options_fingerprint} <filename>"
+            "#{command} #{options} #{filename}",
+            fingerprint: "#{command} #{options_fingerprint} <filename>"
           )
 
           true
@@ -201,12 +201,12 @@ def check_original_requirements_resolvable
               write_temporary_dependency_files(update_requirement: false)
 
               filenames_to_compile.each do |filename|
-                options = pip_compile_options(filename)
+                options, command = pip_compile_options(filename)
                 options_fingerprint = pip_compile_options_fingerprint(options)
 
                 run_pip_compile_command(
-                  "pyenv exec pip-compile #{options} #{filename}",
-                  fingerprint: "pyenv exec pip-compile #{options_fingerprint} <filename>"
+                  "#{command} #{options} #{filename}",
+                  fingerprint: "#{command} #{options_fingerprint} <filename>"
                 )
               end
 
@@ -251,7 +251,16 @@ def pip_compile_options(filename)
             options << "--output-file=#{requirements_file.name}"
           end
 
-          options.join(" ")
+          if (requirements_file = compiled_file_for_filename(filename))
+            if requirements_file.content.include?("uv pip compile")
+              options += uv_pip_compile_options_from_compiled_file(requirements_file)
+              command = "pyenv exec uv pip compile"
+            else
+              command = "pyenv exec pip-compile"
+            end
+          end
+
+          [options.join(" "), command]
         end
 
         def pip_compile_index_options
@@ -277,6 +286,32 @@ def run_pip_compile_command(command, fingerprint:)
           run_command(command, fingerprint: fingerprint)
         end
 
+        def uv_pip_compile_options_from_compiled_file(requirements_file)
+          options = ["--output-file=#{requirements_file.name}"]
+
+          options << "--no-emit-index-url" unless requirements_file.content.include?("index-url http")
+
+          options << "--generate-hashes" if requirements_file.content.include?("--hash=sha")
+
+          options << "--no-annotate" unless requirements_file.content.include?("# via ")
+
+          options << "--pre" if requirements_file.content.include?("--pre")
+
+          options << "--no-strip-extras" if requirements_file.content.include?("--no-strip-extras")
+
+          if requirements_file.content.include?("--no-binary") || requirements_file.content.include?("--only-binary")
+            options << "--emit-build-options"
+          end
+
+          if (resolver = RESOLVER_REGEX.match(requirements_file.content))
+            options << "--resolver=#{resolver}"
+          end
+
+          options << "--universal" if requirements_file.content.include?("--universal")
+
+          options
+        end
+
         def python_env
           env = {}
 
diff --git a/python/spec/dependabot/python/file_updater/pip_compile_file_updater_v2_spec.rb b/python/spec/dependabot/python/file_updater/pip_compile_file_updater_v2_spec.rb
new file mode 100644
index 0000000000..4ad1f17dce
--- /dev/null
+++ b/python/spec/dependabot/python/file_updater/pip_compile_file_updater_v2_spec.rb
@@ -0,0 +1,568 @@
+# typed: false
+# frozen_string_literal: true
+
+require "spec_helper"
+require "dependabot/dependency"
+require "dependabot/dependency_file"
+require "dependabot/python/file_updater/pip_compile_file_updater"
+require "dependabot/shared_helpers"
+
+RSpec.describe Dependabot::Python::FileUpdater::PipCompileFileUpdater do
+  let(:updater) do
+    described_class.new(
+      dependency_files: dependency_files,
+      dependencies: [dependency],
+      credentials: credentials
+    )
+  end
+  let(:dependency_files) { [manifest_file, generated_file] }
+  let(:manifest_file) do
+    Dependabot::DependencyFile.new(
+      name: "requirements/test.in",
+      content: fixture("pip_compile_files", manifest_fixture_name)
+    )
+  end
+  let(:generated_file) do
+    Dependabot::DependencyFile.new(
+      name: "requirements/test.txt",
+      content: fixture("requirements", generated_fixture_name)
+    )
+  end
+  let(:manifest_fixture_name) { "unpinned.in" }
+  let(:generated_fixture_name) { "uv_pip_compile_unpinned.txt" }
+  let(:dependency) do
+    Dependabot::Dependency.new(
+      name: dependency_name,
+      version: dependency_version,
+      previous_version: dependency_previous_version,
+      requirements: dependency_requirements,
+      previous_requirements: dependency_previous_requirements,
+      package_manager: "pip"
+    )
+  end
+  let(:dependency_name) { "attrs" }
+  let(:dependency_version) { "18.1.0" }
+  let(:dependency_previous_version) { "17.3.0" }
+  let(:dependency_requirements) do
+    [{
+      file: "requirements/test.in",
+      requirement: nil,
+      groups: [],
+      source: nil
+    }]
+  end
+  let(:dependency_previous_requirements) do
+    [{
+      file: "requirements/test.in",
+      requirement: nil,
+      groups: [],
+      source: nil
+    }]
+  end
+  let(:credentials) do
+    [Dependabot::Credential.new({
+      "type" => "git_source",
+      "host" => "github.com",
+      "username" => "x-access-token",
+      "password" => "token"
+    })]
+  end
+  let(:tmp_path) { Dependabot::Utils::BUMP_TMP_DIR_PATH }
+
+  before { FileUtils.mkdir_p(tmp_path) }
+
+  describe "#updated_dependency_files" do
+    subject(:updated_files) { updater.updated_dependency_files }
+
+    it "updates the requirements.txt" do
+      expect(updated_files.count).to eq(1)
+      expect(updated_files.first.content).to include("attrs==18.1.0")
+      expect(updated_files.first.content)
+        .to include("pbr==4.0.2\n    # via mock")
+      expect(updated_files.first.content).to include("# This file was autogenerated by uv")
+      expect(updated_files.first.content).not_to include("--hash=sha")
+    end
+
+    context "with a mismatch in filename" do
+      let(:generated_fixture_name) { "uv_pip_compile_unpinned_renamed.txt" }
+      let(:generated_file) do
+        Dependabot::DependencyFile.new(
+          name: "requirements/test-funky.txt",
+          content: fixture("requirements", generated_fixture_name)
+        )
+      end
+
+      it "updates the requirements.txt" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==18.1.0")
+        expect(updated_files.first.content)
+          .to include("pbr==4.0.2\n    # via mock")
+        expect(updated_files.first.content).to include("# This file was autogenerated by uv")
+        expect(updated_files.first.content).not_to include("--hash=sha")
+      end
+    end
+
+    context "with uv header" do
+      let(:manifest_fixture_name) { "unpinned.in" }
+      let(:generated_fixture_name) { "uv_pip_compile.txt" }
+
+      it "upgrades attrs to latest" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==18.1.0")
+        expect(updated_files.first.content).to include("This file was autogenerated by uv")
+        expect(updated_files.first.content).to include("uv pip compile")
+      end
+    end
+
+    context "with a no-binary flag" do
+      let(:manifest_fixture_name) { "no_binary_uv.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_no_binary.txt" }
+      let(:dependency_name) { "psycopg2" }
+      let(:dependency_version) { "2.7.6" }
+      let(:dependency_previous_version) { "2.7.4" }
+
+      it "updates the requirements.txt correctly" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("psycopg2==2.7.6")
+        expect(updated_files.first.content).to include("--no-binary psycopg2")
+        expect(updated_files.first.content)
+          .not_to include("--no-binary psycopg2==")
+      end
+    end
+
+    context "with hashes" do
+      let(:generated_fixture_name) { "uv_pip_compile_hashes.txt" }
+
+      it "updates the requirements.txt, keeping the hashes" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==18.1.0")
+        expect(updated_files.first.content).to include("4b90b09eeeb9b88c35bc64")
+        expect(updated_files.first.content).to include("# This file was autogenerated by uv")
+      end
+
+      context "when needing an augmented hashin" do
+        let(:manifest_fixture_name) { "extra_hashes.in" }
+        let(:generated_fixture_name) { "uv_pip_compile_extra_hashes.txt" }
+        let(:dependency_name) { "pyasn1-modules" }
+        let(:dependency_version) { "0.1.5" }
+        let(:dependency_previous_version) { "0.1.4" }
+
+        it "updates the requirements.txt, keeping all the hashes" do
+          expect(updated_files.count).to eq(1)
+          expect(updated_files.first.content)
+            .to include("# This file was autogenerated by uv")
+          expect(updated_files.first.content)
+            .to include("pyasn1-modules==0.1.5 \\\n    --hash=sha256:01")
+          expect(updated_files.first.content)
+            .to include("--hash=sha256:b437be576bdf440fc0e930")
+          expect(updated_files.first.content)
+            .to include("pyasn1==0.3.7 \\\n    --hash=sha256:16")
+          expect(updated_files.first.content)
+            .to include("--hash=sha256:bb6f5d5507621e0298794b")
+          expect(updated_files.first.content)
+            .to include("# via pyasn1-modules")
+          expect(updated_files.first.content).not_to include("WARNING")
+        end
+      end
+    end
+
+    context "with another dependency with an unmet marker" do
+      let(:manifest_fixture_name) { "unmet_marker.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_unmet_marker.txt" }
+
+      it "updates the requirements.txt, keeping the unmet dep out of it" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==18.1.0")
+        expect(updated_files.first.content).not_to include("flaky")
+      end
+    end
+
+    context "with an unsafe dependency" do
+      let(:manifest_fixture_name) { "unsafe.in" }
+      let(:dependency_name) { "flake8" }
+      let(:dependency_version) { "3.6.0" }
+      let(:dependency_previous_version) { "3.5.0" }
+
+      context "when not including in the lockfile" do
+        let(:generated_fixture_name) { "uv_pip_compile_safe.txt" }
+
+        it "does not include the unsafe dependency" do
+          expect(updated_files.count).to eq(1)
+          expect(updated_files.first.content).to include("flake8==3.6.0")
+          # Distinct from pip-compile, which will not include setuptools as it is considered unsafe dependency
+          # UV's default will include it by default. Future major pip-tools version will do the same.
+          expect(updated_files.first.content).to include("setuptools")
+          expect(updated_files.first.content).to end_with("via flake8\n")
+        end
+      end
+
+      context "when including in the lockfile" do
+        let(:generated_fixture_name) { "uv_pip_compile_unsafe.txt" }
+
+        it "includes the unsafe dependency" do
+          expect(updated_files.count).to eq(1)
+          expect(updated_files.first.content).to include("flake8==3.6.0")
+          expect(updated_files.first.content).to include("setuptools")
+        end
+      end
+    end
+
+    context "with an import of the setup.py" do
+      let(:dependency_files) do
+        [manifest_file, generated_file, setup_file, pyproject]
+      end
+      let(:setup_file) do
+        Dependabot::DependencyFile.new(
+          name: "setup.py",
+          content: fixture("setup_files", setup_fixture_name)
+        )
+      end
+      let(:pyproject) do
+        Dependabot::DependencyFile.new(
+          name: "pyproject.toml",
+          content: fixture("pyproject_files", "black_configuration.toml")
+        )
+      end
+      let(:manifest_fixture_name) { "imports_setup.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_imports_setup.txt" }
+      let(:setup_fixture_name) { "small.py" }
+
+      it "updates the requirements.txt", :slow do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==18.1.0")
+        expect(updated_files.first.content)
+          .to include("-e file:///Users/greysteil/code/python-test")
+        expect(updated_files.first.content).not_to include("tmp/dependabot")
+        expect(updated_files.first.content)
+          .to include("pbr==4.0.2\n    # via mock")
+        expect(updated_files.first.content).to include("# This file was autogenerated by uv")
+        expect(updated_files.first.content).not_to include("--hash=sha")
+      end
+
+      context "when needing sanitization", :slow do
+        let(:setup_fixture_name) { "small_needs_sanitizing.py" }
+
+        it "updates the requirements.txt" do
+          expect(updated_files.count).to eq(1)
+          expect(updated_files.first.content).to include("attrs==18.1.0")
+        end
+      end
+    end
+
+    context "with vcs url dependencies" do
+      let(:manifest_fixture_name) { "vcs_url.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_vcs_url.txt" }
+
+      it "updates the requirements.txt" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==18.1.0")
+        expect(updated_files.first.content)
+          .to include("mock @ git+https://github.com/testing-cabal/mock.git@286792b2")
+      end
+    end
+
+    context "with a subdependency" do
+      let(:dependency_name) { "pbr" }
+      let(:dependency_version) { "4.2.0" }
+      let(:dependency_previous_version) { "4.0.2" }
+      let(:dependency_requirements) { [] }
+      let(:dependency_previous_requirements) { [] }
+
+      it "updates the requirements.txt" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content)
+          .to include("pbr==4.2.0\n    # via mock")
+      end
+    end
+
+    context "when targeting a non-latest version" do
+      let(:dependency_version) { "17.4.0" }
+
+      it "updates the requirements.txt" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("attrs==17.4.0")
+        expect(updated_files.first.content)
+          .to include("pbr==4.0.2\n    # via mock")
+        expect(updated_files.first.content).to include("# This file was autogenerated by uv")
+        expect(updated_files.first.content).not_to include("--hash=sha")
+      end
+    end
+
+    context "when the requirement.in file needs to be updated" do
+      let(:manifest_fixture_name) { "bounded.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_bounded.txt" }
+
+      let(:dependency_requirements) do
+        [{
+          file: "requirements/test.in",
+          requirement: "<=18.1.0",
+          groups: [],
+          source: nil
+        }]
+      end
+      let(:dependency_previous_requirements) do
+        [{
+          file: "requirements/test.in",
+          requirement: "<=17.4.0",
+          groups: [],
+          source: nil
+        }]
+      end
+
+      it "updates the requirements.txt and the requirements.in" do
+        expect(updated_files.count).to eq(2)
+        expect(updated_files.first.content).to include("Attrs<=18.1.0")
+        expect(updated_files.last.content).to include("attrs==18.1.0")
+        expect(updated_files.last.content).not_to include("# via mock")
+      end
+
+      context "with an additional requirements.txt" do
+        let(:dependency_files) { [manifest_file, generated_file, other_txt] }
+        let(:other_txt) do
+          Dependabot::DependencyFile.new(
+            name: "requirements.txt",
+            content:
+              fixture("requirements", "uv_pip_compile_unpinned.txt")
+          )
+        end
+
+        let(:dependency_requirements) do
+          [{
+            file: "requirements/test.in",
+            requirement: "<=18.1.0",
+            groups: [],
+            source: nil
+          }, {
+            file: "requirements.txt",
+            requirement: "==18.1.0",
+            groups: [],
+            source: nil
+          }]
+        end
+        let(:dependency_previous_requirements) do
+          [{
+            file: "requirements/test.in",
+            requirement: "<=17.4.0",
+            groups: [],
+            source: nil
+          }, {
+            file: "requirements.txt",
+            requirement: "==17.3.0",
+            groups: [],
+            source: nil
+          }]
+        end
+
+        it "updates the other requirements.txt, too" do
+          expect(updated_files.count).to eq(3)
+          expect(updated_files.first.content).to include("Attrs<=18.1.0")
+          expect(updated_files[1].content).to include("attrs==18.1.0")
+          expect(updated_files.last.content).to include("attrs==18.1.0")
+        end
+      end
+
+      context "with multiple requirement.in files" do
+        let(:dependency_files) do
+          [
+            manifest_file, manifest_file2, manifest_file3, manifest_file4,
+            generated_file, generated_file2, generated_file3, generated_file4
+          ]
+        end
+
+        let(:manifest_file2) do
+          Dependabot::DependencyFile.new(
+            name: "requirements/dev.in",
+            content:
+              fixture("pip_compile_files", manifest_fixture_name)
+          )
+        end
+        let(:generated_file2) do
+          Dependabot::DependencyFile.new(
+            name: "requirements/dev.txt",
+            content: fixture("requirements", generated_fixture_name)
+          )
+        end
+
+        let(:manifest_file3) do
+          Dependabot::DependencyFile.new(
+            name: "requirements/mirror2.in",
+            content:
+              fixture("pip_compile_files", "imports_mirror.in")
+          )
+        end
+        let(:generated_file3) do
+          Dependabot::DependencyFile.new(
+            name: "requirements/mirror2.txt",
+            content: fixture("requirements", generated_fixture_name)
+          )
+        end
+
+        let(:manifest_file4) do
+          Dependabot::DependencyFile.new(
+            name: "requirements/mirror.in",
+            content:
+              fixture("pip_compile_files", "imports_dev.in")
+          )
+        end
+        let(:generated_file4) do
+          Dependabot::DependencyFile.new(
+            name: "requirements/mirror.txt",
+            content: fixture("requirements", generated_fixture_name)
+          )
+        end
+
+        let(:dependency_requirements) do
+          [{
+            file: "requirements/test.in",
+            requirement: "<=18.1.0",
+            groups: [],
+            source: nil
+          }, {
+            file: "requirements/dev.in",
+            requirement: "<=18.1.0",
+            groups: [],
+            source: nil
+          }]
+        end
+        let(:dependency_previous_requirements) do
+          [{
+            file: "requirements/test.in",
+            requirement: "<=17.4.0",
+            groups: [],
+            source: nil
+          }, {
+            file: "requirements/dev.in",
+            requirement: "<=17.4.0",
+            groups: [],
+            source: nil
+          }]
+        end
+
+        it "updates the other manifest file, too" do
+          expect(updated_files.count).to eq(6)
+          expect(updated_files[0].name).to eq("requirements/test.in")
+          expect(updated_files[1].name).to eq("requirements/dev.in")
+          expect(updated_files[2].name).to eq("requirements/test.txt")
+          expect(updated_files[3].name).to eq("requirements/dev.txt")
+          expect(updated_files[4].name).to eq("requirements/mirror2.txt")
+          expect(updated_files[5].name).to eq("requirements/mirror.txt")
+          expect(updated_files[0].content).to include("Attrs<=18.1.0")
+          expect(updated_files[1].content).to include("Attrs<=18.1.0")
+          expect(updated_files[2].content).to include("attrs==18.1.0")
+          expect(updated_files[3].content).to include("attrs==18.1.0")
+          expect(updated_files[4].content).to include("attrs==18.1.0")
+          expect(updated_files[5].content).to include("attrs==18.1.0")
+        end
+      end
+    end
+
+    context "with stripped extras" do
+      let(:manifest_fixture_name) { "strip_extras.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_strip_extras.txt" }
+      let(:dependency_name) { "cachecontrol" }
+      let(:dependency_version) { "0.12.10" }
+      let(:dependency_previous_version) { "0.12.9" }
+
+      it "doesn't add an extras annotation on cachecontrol" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("cachecontrol==0.12.10")
+        expect(updated_files.first.content)
+          .not_to include("cachecontrol[filecache]==")
+      end
+    end
+
+    context "with no stripped extras" do
+      let(:manifest_fixture_name) { "strip_extras.in" }
+      let(:generated_fixture_name) { "uv_pip_compile_no_strip_extras.txt" }
+      let(:dependency_name) { "cachecontrol" }
+      let(:dependency_version) { "0.12.10" }
+      let(:dependency_previous_version) { "0.12.9" }
+
+      it "adds an extras annotation on cachecontrol" do
+        expect(updated_files.count).to eq(1)
+        expect(updated_files.first.content).to include("cachecontrol[filecache]==0.12.10")
+      end
+    end
+  end
+
+  describe "#package_hashes_for" do
+    let(:name) { "package_name" }
+    let(:version) { "1.0.0" }
+    let(:algorithm) { "sha256" }
+
+    context "when index_urls is not set" do
+      let(:updater) do
+        described_class.new(
+          dependencies: [],
+          dependency_files: [],
+          credentials: []
+        )
+      end
+
+      before do
+        allow(Dependabot::SharedHelpers).to receive(:run_helper_subprocess).and_return([{ "hash" => "123abc" }])
+      end
+
+      it "returns hash" do
+        result = updater.send(:package_hashes_for, name: name, version: version, algorithm: algorithm)
+        expect(result).to eq(["--hash=sha256:123abc"])
+      end
+    end
+
+    context "when multiple index_urls are set" do
+      let(:updater) do
+        described_class.new(
+          dependencies: [],
+          dependency_files: [],
+          credentials: [],
+          index_urls: [nil, "http://example.com"]
+        )
+      end
+
+      before do
+        allow(Dependabot::SharedHelpers).to receive(:run_helper_subprocess)
+          .and_return([{ "hash" => "123abc" }], [{ "hash" => "312cba" }])
+      end
+
+      it "returns returns two hashes" do
+        result = updater.send(:package_hashes_for, name: name, version: version, algorithm: algorithm)
+        expect(result).to eq(%w(--hash=sha256:123abc --hash=sha256:312cba))
+      end
+    end
+
+    context "when multiple index_urls are set but package does not exist in PyPI" do
+      let(:updater) do
+        described_class.new(
+          dependencies: [],
+          dependency_files: [],
+          credentials: [],
+          index_urls: [nil, "http://example.com"]
+        )
+      end
+
+      before do
+        allow(Dependabot::SharedHelpers).to receive(:run_helper_subprocess).with({
+          args: %w(package_name 1.0.0 sha256),
+          command: "pyenv exec python3 /opt/python/run.py",
+          function: "get_dependency_hash"
+        }).and_raise(
+          Dependabot::SharedHelpers::HelperSubprocessFailed.new(
+            message: "Error message", error_context: {}, error_class: "PackageNotFoundError"
+          )
+        )
+
+        allow(Dependabot::SharedHelpers).to receive(:run_helper_subprocess)
+          .with({
+            args: %w(package_name 1.0.0 sha256 http://example.com),
+            command: "pyenv exec python3 /opt/python/run.py",
+            function: "get_dependency_hash"
+          }).and_return([{ "hash" => "123abc" }])
+      end
+
+      it "returns returns two hashes" do
+        result = updater.send(:package_hashes_for, name: name, version: version, algorithm: algorithm)
+        expect(result).to eq(["--hash=sha256:123abc"])
+      end
+    end
+  end
+end
diff --git a/python/spec/fixtures/pip_compile_files/no_binary_uv.in b/python/spec/fixtures/pip_compile_files/no_binary_uv.in
new file mode 100644
index 0000000000..08018c1cdc
--- /dev/null
+++ b/python/spec/fixtures/pip_compile_files/no_binary_uv.in
@@ -0,0 +1,2 @@
+psycopg2
+--no-binary psycopg2
diff --git a/python/spec/fixtures/pip_compile_files/vcs_url.in b/python/spec/fixtures/pip_compile_files/vcs_url.in
new file mode 100644
index 0000000000..cf1ae99c61
--- /dev/null
+++ b/python/spec/fixtures/pip_compile_files/vcs_url.in
@@ -0,0 +1,2 @@
+git+https://github.com/testing-cabal/mock.git@2.0.0
+Attrs
diff --git a/python/spec/fixtures/requirements/uv_pip_compile.txt b/python/spec/fixtures/requirements/uv_pip_compile.txt
new file mode 100644
index 0000000000..e47dcb2a67
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile.txt
@@ -0,0 +1,22 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file uv_pip_compile.txt unpinned_uv.in
+attrs==18.1.0
+    # via -r unpinned_uv.in
+execnet==2.1.1
+    # via pytest-xdist
+flaky==3.8.1
+    # via -r unpinned_uv.in
+iniconfig==2.0.0
+    # via pytest
+mock==5.1.0
+    # via -r unpinned_uv.in
+packaging==24.1
+    # via pytest
+pluggy==1.5.0
+    # via pytest
+pytest==8.2.2
+    # via
+    #   -r unpinned_uv.in
+    #   pytest-xdist
+pytest-xdist==3.6.1
+    # via -r unpinned_uv.in
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_bounded.txt b/python/spec/fixtures/requirements/uv_pip_compile_bounded.txt
new file mode 100644
index 0000000000..a35bb7f8e3
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_bounded.txt
@@ -0,0 +1,15 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --no-annotate --output-file requirements/text.txt requirements/test.in
+apipkg==1.4
+attrs==17.3.0
+execnet==1.5.0
+flaky==3.4.0
+mock==2.0.0
+more-itertools==4.1.0
+pbr==4.0.3
+pluggy==0.6.0
+py==1.5.3
+pytest-forked==0.2
+pytest-xdist==1.22.2
+pytest==3.5.1
+six==1.11.0
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_extra_hashes.txt b/python/spec/fixtures/requirements/uv_pip_compile_extra_hashes.txt
new file mode 100644
index 0000000000..e0b36be5e2
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_extra_hashes.txt
@@ -0,0 +1,43 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --generate-hashes --output-file req.txt req.in
+atomicwrites==1.2.1 \
+    --hash=sha256:0312ad34fcad8fac3704d441f7b317e50af620823353ec657a53e981f92920c0 \
+    --hash=sha256:ec9ae8adaae229e4f8446952d204a3e4b5fdd2d099f9be3aaf556120135fb3ee \
+    # via pytest
+attrs==18.2.0 \
+    --hash=sha256:10cbf6e27dbce8c30807caf056c8eb50917e0eaafe86347671b57254006c3e69 \
+    --hash=sha256:ca4be454458f9dec299268d472aaa5a11f67a4ff70093396e1ceae9c76cf4bbb \
+    # via pytest
+more-itertools==5.0.0 \
+    --hash=sha256:38a936c0a6d98a38bcc2d03fdaaedaba9f412879461dd2ceff8d37564d6522e4 \
+    --hash=sha256:c0a5785b1109a6bd7fac76d6837fd1feca158e54e521ccd2ae8bfe393cc9d4fc \
+    --hash=sha256:fe7a7cae1ccb57d33952113ff4fa1bc5f879963600ed74918f1236e212ee50b9 \
+    # via pytest
+pluggy==0.8.0 \
+    --hash=sha256:447ba94990e8014ee25ec853339faf7b0fc8050cdc3289d4d71f7f410fb90095 \
+    --hash=sha256:bde19360a8ec4dfd8a20dcb811780a30998101f078fc7ded6162f0076f50508f \
+    # via pytest
+py==1.7.0 \
+    --hash=sha256:bf92637198836372b520efcba9e020c330123be8ce527e535d185ed4b6f45694 \
+    --hash=sha256:e76826342cefe3c3d5f7e8ee4316b80d1dd8a300781612ddbc765c17ba25a6c6 \
+    # via pytest
+pyasn1-modules==0.1.4 \
+    --hash=sha256:2e39aead1602e4e5aa8b796260848f9383e51bea278edf7d2b4fb686944425fa \
+    --hash=sha256:34e1d014608ca4f8a0cc3164a5add93f4b8a04a3871b96d31a028ff36a6fe924 \
+    --hash=sha256:529d5d509562c22877a53771c5b394d8102c98cd62f33bb5af23b475879ea6d5 \
+    --hash=sha256:641cc18cf56d4a60679804aa8ae8cbc7359b3fa2d5559df064ecfaca27d15b10 \
+    --hash=sha256:6ad0e6772af4b74bd63c78c0102ece7b6a775f764e395137968af575c20bbfc9 \
+    --hash=sha256:7411e837c83ea4cb6088aa3bf63691d348454fcd9bb3d9cc342859282419bfcf \
+    --hash=sha256:7930d0f6109a47f78e5fb88a4f7ed2bfa1073ec9ddb2657deffa92f0805568fb \
+    --hash=sha256:a24f5118f41af33f13fa0c7e8419fc7380dfe2d2f2dc0f554d928141c842f924 \
+    --hash=sha256:ab7e23e45f32f0515e5a084eecaff22653bb6277d0d4229cb7369117abf33baa \
+    --hash=sha256:b07c17bdb34d6f64aafea6269f2e8fb306a57473f0f38d9a6ca389d6ab30ac4a \
+    --hash=sha256:beb3d344fee1fa68ddf36471c5d9120665ba049900d7fccbffa50c77036581de \
+    --hash=sha256:ca3cdc5d8ecc97f78a202009512254bd7aeef77069405e9e834b45c48a26a4db
+pytest==4.0.2 \
+    --hash=sha256:f689bf2fc18c4585403348dd56f47d87780bf217c53ed9ae7a3e2d7faa45f8e9 \
+    --hash=sha256:f812ea39a0153566be53d88f8de94839db1e8a05352ed8a49525d7d7f37861e9
+six==1.12.0 \
+    --hash=sha256:3350809f0555b11f552448330d0b52d5f24c91a322ea4a15ef22629740f3761c \
+    --hash=sha256:d16a0141ec1a18405cd4ce8b4613101da75da0e9a7aec5bdd4fa804d0e0eba73 \
+    # via more-itertools, pytest
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_hashes.txt b/python/spec/fixtures/requirements/uv_pip_compile_hashes.txt
new file mode 100644
index 0000000000..147d25f15a
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_hashes.txt
@@ -0,0 +1,51 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --generate-hashes --output-file req.txt req.in
+apipkg==1.4 \
+    --hash=sha256:2e38399dbe842891fe85392601aab8f40a8f4cc5a9053c326de35a1cc0297ac6 \
+    --hash=sha256:65d2aa68b28e7d31233bb2ba8eb31cda40e4671f8ac2d6b241e358c9652a74b9 \
+    # via execnet
+attrs==17.3.0 \
+    --hash=sha256:1c7960ccfd6a005cd9f7ba884e6316b5e430a3f1a6c37c5f87d8b43f83b54ec9 \
+    --hash=sha256:a17a9573a6f475c99b551c0e0a812707ddda1ec9653bed04c13841404ed6f450
+execnet==1.5.0 \
+    --hash=sha256:a7a84d5fa07a089186a329528f127c9d73b9de57f1a1131b82bb5320ee651f6a \
+    --hash=sha256:fc155a6b553c66c838d1a22dba1dc9f5f505c43285a878c6f74a79c024750b83 \
+    # via pytest-xdist
+flaky==3.4.0 \
+    --hash=sha256:4ad7880aef8c35a34ddb394d4fa33047765bca1e3d67d182bf6eba9c8eabf3a2 \
+    --hash=sha256:d0533f473a46b916e6db6e84e20b06d8a70656600a0c14e819b0760b63f70226
+mock==2.0.0 \
+    --hash=sha256:5ce3c71c5545b472da17b72268978914d0252980348636840bd34a00b5cc96c1 \
+    --hash=sha256:b158b6df76edd239b8208d481dc46b6afd45a846b7812ff0ce58971cf5bc8bba
+more-itertools==4.1.0 \
+    --hash=sha256:0dd8f72eeab0d2c3bd489025bb2f6a1b8342f9b198f6fc37b52d15cfa4531fea \
+    --hash=sha256:11a625025954c20145b37ff6309cd54e39ca94f72f6bb9576d1195db6fa2442e \
+    --hash=sha256:c9ce7eccdcb901a2c75d326ea134e0886abfbea5f93e91cc95de9507c0816c44 \
+    # via pytest
+pbr==4.0.3 \
+    --hash=sha256:680bf5ba9b28dd56e08eb7c267991a37c7a5f90a92c2e07108829931a50ff80a \
+    --hash=sha256:6874feb22334a1e9a515193cba797664e940b763440c88115009ec323a7f2df5 \
+    # via mock
+pluggy==0.6.0 \
+    --hash=sha256:7f8ae7f5bdf75671a718d2daf0a64b7885f74510bcd98b1a0bb420eb9a9d0cff \
+    --hash=sha256:d345c8fe681115900d6da8d048ba67c25df42973bda370783cd58826442dcd7c \
+    --hash=sha256:e160a7fcf25762bb60efc7e171d4497ff1d8d2d75a3d0df7a21b76821ecbf5c5 \
+    # via pytest
+py==1.5.3 \
+    --hash=sha256:29c9fab495d7528e80ba1e343b958684f4ace687327e6f789a94bf3d1915f881 \
+    --hash=sha256:983f77f3331356039fdd792e9220b7b8ee1aa6bd2b25f567a963ff1de5a64f6a \
+    # via pytest
+pytest-forked==0.2 \
+    --hash=sha256:e4500cd0509ec4a26535f7d4112a8cc0f17d3a41c29ffd4eab479d2a55b30805 \
+    --hash=sha256:f275cb48a73fc61a6710726348e1da6d68a978f0ec0c54ece5a5fae5977e5a08 \
+    # via pytest-xdist
+pytest-xdist==1.22.2 \
+    --hash=sha256:be2662264b035920ba740ed6efb1c816a83c8a22253df7766d129f6a7bfdbd35 \
+    --hash=sha256:e8f5744acc270b3e7d915bdb4d5f471670f049b6fbd163d4cbd52203b075d30f
+pytest==3.5.1 \
+    --hash=sha256:54713b26c97538db6ff0703a12b19aeaeb60b5e599de542e7fca0ec83b9038e8 \
+    --hash=sha256:829230122facf05a5f81a6d4dfe6454a04978ea3746853b2b84567ecf8e5c526
+six==1.11.0 \
+    --hash=sha256:70e8a77beed4562e7f14fe23a786b54f6296e34344c23bc42f07b15018ff98e9 \
+    --hash=sha256:832dc0e10feb1aa2c68dcc57dbb658f1c7e65b9b61af69048abc87a2db00a0eb \
+    # via mock, more-itertools, pytest
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_imports_setup.txt b/python/spec/fixtures/requirements/uv_pip_compile_imports_setup.txt
new file mode 100644
index 0000000000..48b89a0277
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_imports_setup.txt
@@ -0,0 +1,19 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file something.txt something.in
+-e file:///Users/greysteil/code/python-test
+apipkg==1.5               # via execnet
+atomicwrites==1.2.1       # via pytest
+attrs==18.2.0
+contextlib2==0.5.5        # via raven
+execnet==1.5.0            # via pytest-xdist
+flaky==3.4.0
+mock==2.0.0
+more-itertools==4.3.0     # via pytest
+pbr==4.0.2                # via mock
+pluggy==0.7.1             # via pytest
+py==1.6.0                 # via pytest
+pytest-forked==0.2        # via pytest-xdist
+pytest-xdist==1.23.0
+pytest==3.7.4
+raven==5.32.0
+six==1.11.0               # via mock, more-itertools, pytest, pytest-xdist
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_no_binary.txt b/python/spec/fixtures/requirements/uv_pip_compile_no_binary.txt
new file mode 100644
index 0000000000..258ce1fdfa
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_no_binary.txt
@@ -0,0 +1,5 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file requirements.txt requirements.in
+--no-binary psycopg2
+
+psycopg2==2.7.4
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_no_strip_extras.txt b/python/spec/fixtures/requirements/uv_pip_compile_no_strip_extras.txt
new file mode 100644
index 0000000000..e26439ba89
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_no_strip_extras.txt
@@ -0,0 +1,18 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --no-strip-extras --output-file=constraints.txt constraints.in
+cachecontrol==0.12.10
+    # via -r constraints.in
+certifi==2021.10.8
+    # via requests
+charset-normalizer==2.0.7
+    # via requests
+idna==3.3
+    # via requests
+lockfile==0.12.2
+    # via cachecontrol
+msgpack==1.0.2
+    # via cachecontrol
+requests==2.26.0
+    # via cachecontrol
+urllib3==1.26.7
+    # via requests
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_safe.txt b/python/spec/fixtures/requirements/uv_pip_compile_safe.txt
new file mode 100644
index 0000000000..5151446181
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_safe.txt
@@ -0,0 +1,6 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file dev-requirements.txt dev-requirements.in
+flake8==3.5.0
+mccabe==0.6.1             # via flake8
+pycodestyle==2.4.0        # via flake8
+pyflakes==2.0.0           # via flake8
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_strip_extras.txt b/python/spec/fixtures/requirements/uv_pip_compile_strip_extras.txt
new file mode 100644
index 0000000000..7c21fe5e45
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_strip_extras.txt
@@ -0,0 +1,18 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file=constraints.txt constraints.in
+cachecontrol==0.12.10
+    # via -r constraints.in
+certifi==2021.10.8
+    # via requests
+charset-normalizer==2.0.7
+    # via requests
+idna==3.3
+    # via requests
+lockfile==0.12.2
+    # via cachecontrol
+msgpack==1.0.2
+    # via cachecontrol
+requests==2.26.0
+    # via cachecontrol
+urllib3==1.26.7
+    # via requests
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_unmet_marker.txt b/python/spec/fixtures/requirements/uv_pip_compile_unmet_marker.txt
new file mode 100644
index 0000000000..cd2d87df5f
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_unmet_marker.txt
@@ -0,0 +1,15 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file=requirements.txt requirements.in
+apipkg==1.5               # via execnet
+atomicwrites==1.1.5       # via pytest
+attrs==17.3.0
+execnet==1.5.0            # via pytest-xdist
+mock==2.0.0
+more-itertools==4.3.0     # via pytest
+pbr==4.2.0                # via mock
+pluggy==0.7.1             # via pytest
+py==1.5.4                 # via pytest
+pytest-forked==0.2        # via pytest-xdist
+pytest-xdist==1.22.5
+pytest==3.7.2
+six==1.11.0               # via mock, more-itertools, pytest, pytest-xdist
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_unpinned.txt b/python/spec/fixtures/requirements/uv_pip_compile_unpinned.txt
new file mode 100644
index 0000000000..a776c74089
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_unpinned.txt
@@ -0,0 +1,15 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file=requirements/test.txt requirements/test.in
+apipkg==1.4               # via execnet
+attrs==17.3.0
+execnet==1.5.0            # via pytest-xdist
+flaky==3.4.0
+mock==2.0.0
+more-itertools==4.1.0     # via pytest
+pbr==4.0.2                # via mock
+pluggy==0.6.0             # via pytest
+py==1.5.3                 # via pytest
+pytest-forked==0.2        # via pytest-xdist
+pytest-xdist==1.22.2
+pytest==3.5.1
+six==1.11.0               # via mock, more-itertools, pytest
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_unpinned_renamed.txt b/python/spec/fixtures/requirements/uv_pip_compile_unpinned_renamed.txt
new file mode 100644
index 0000000000..5c455cda2c
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_unpinned_renamed.txt
@@ -0,0 +1,15 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file=requirements/test-funky.txt requirements/test.in
+apipkg==1.4               # via execnet
+attrs==17.3.0
+execnet==1.5.0            # via pytest-xdist
+flaky==3.4.0
+mock==2.0.0
+more-itertools==4.1.0     # via pytest
+pbr==4.0.2                # via mock
+pluggy==0.6.0             # via pytest
+py==1.5.3                 # via pytest
+pytest-forked==0.2        # via pytest-xdist
+pytest-xdist==1.22.2
+pytest==3.5.1
+six==1.11.0               # via mock, more-itertools, pytest
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_unsafe.txt b/python/spec/fixtures/requirements/uv_pip_compile_unsafe.txt
new file mode 100644
index 0000000000..c037e652c0
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_unsafe.txt
@@ -0,0 +1,10 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file dev-requirements.txt dev-requirements.in
+
+flake8==3.5.0
+mccabe==0.6.1             # via flake8
+pycodestyle==2.4.0        # via flake8
+pyflakes==2.0.0           # via flake8
+
+# The following packages are considered to be unsafe by pip-compile by default, but not by uv, in a requirements file:
+setuptools==40.4.3        # via flake8
diff --git a/python/spec/fixtures/requirements/uv_pip_compile_vcs_url.txt b/python/spec/fixtures/requirements/uv_pip_compile_vcs_url.txt
new file mode 100644
index 0000000000..3a0ace2a81
--- /dev/null
+++ b/python/spec/fixtures/requirements/uv_pip_compile_vcs_url.txt
@@ -0,0 +1,6 @@
+# This file was autogenerated by uv via the following command:
+#    uv pip compile --output-file req.txt req.in
+mock @ git+https://github.com/testing-cabal/mock.git@286792b2cd5b5baa8338260538ed207391280e34
+attrs==17.3.0
+pbr==5.1.1
+six==1.12.0