diff --git a/Dockerfile b/Dockerfile
index 4d832e74bd4..a8f75c052d5 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -98,21 +98,37 @@ RUN mkdir -p /tmp/ruby-install \
  && rm -rf /var/lib/gems/*/cache/* \
  && rm -rf /tmp/ruby-install
 
-### PYTHON
 
+### PYTHON
+COPY --chown=dependabot:dependabot python/helpers /opt/python/helpers
 # Install Python with pyenv.
+USER root
 ENV PYENV_ROOT=/usr/local/.pyenv \
   PATH="/usr/local/.pyenv/bin:$PATH"
 RUN mkdir -p "$PYENV_ROOT" && chown dependabot:dependabot "$PYENV_ROOT"
 USER dependabot
+ENV DEPENDABOT_NATIVE_HELPERS_PATH="/opt"
 RUN git -c advice.detachedHead=false clone https://github.com/pyenv/pyenv.git --branch v2.3.6 --single-branch --depth=1 /usr/local/.pyenv \
   # This is the version of CPython that gets installed
   && pyenv install 3.11.0 \
   && pyenv global 3.11.0 \
-  && rm -Rf /tmp/python-build*
-USER root
-
+  && pyenv install 3.10.8 \
+  && pyenv install 3.9.15 \
+  && pyenv install 3.8.15 \
+  && pyenv install 3.7.15 \
+  && rm -Rf /tmp/python-build* \
+  && bash /opt/python/helpers/build \
+  && cd /usr/local/.pyenv \
+  && tar czf 3.10.tar.gz versions/3.10.8 \
+  && tar czf 3.9.tar.gz versions/3.9.15 \
+  && tar czf 3.8.tar.gz versions/3.8.15 \
+  && tar czf 3.7.tar.gz versions/3.7.15 \
+  && rm -Rf versions/3.10.8 \
+  && rm -Rf versions/3.9.15 \
+  && rm -Rf versions/3.8.15 \
+  && rm -Rf versions/3.7.15
 
+USER root
 ### JAVASCRIPT
 
 # Install Node and npm
@@ -303,9 +319,6 @@ RUN bash /opt/npm_and_yarn/helpers/build
 # 3.2.3.
 RUN corepack prepare yarn@3.2.3 --activate
 
-COPY --chown=dependabot:dependabot python/helpers /opt/python/helpers
-RUN bash /opt/python/helpers/build
-
 COPY --chown=dependabot:dependabot terraform/helpers /opt/terraform/helpers
 RUN bash /opt/terraform/helpers/build
 
diff --git a/python/helpers/build b/python/helpers/build
index d28e0d92962..f47502610e9 100755
--- a/python/helpers/build
+++ b/python/helpers/build
@@ -19,3 +19,7 @@ cp -r \
 
 cd "$install_dir"
 PYENV_VERSION=3.11.0 pyenv exec pip --disable-pip-version-check install --use-pep517 -r "requirements.txt"
+PYENV_VERSION=3.10.8 pyenv exec pip --disable-pip-version-check install --use-pep517 -r "requirements.txt"
+PYENV_VERSION=3.9.15 pyenv exec pip --disable-pip-version-check install --use-pep517 -r "requirements.txt"
+PYENV_VERSION=3.8.15 pyenv exec pip --disable-pip-version-check install --use-pep517 -r "requirements.txt"
+PYENV_VERSION=3.7.15 pyenv exec pip --disable-pip-version-check install --use-pep517 -r "requirements.txt"
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 0dcd0767733..ddde890c99a 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
@@ -168,7 +168,7 @@ def handle_pip_errors(stdout, command, time_taken, exit_value)
         end
 
         def run_pip_compile_command(command, allow_unsafe_shell_command: false)
-          run_command("pyenv local #{python_version}")
+          run_command("pyenv local #{Helpers.python_major_minor(python_version)}")
           run_command(
             command,
             allow_unsafe_shell_command: allow_unsafe_shell_command
diff --git a/python/lib/dependabot/python/file_updater/pipfile_file_updater.rb b/python/lib/dependabot/python/file_updater/pipfile_file_updater.rb
index ba179a226a0..c3304b7ca7c 100644
--- a/python/lib/dependabot/python/file_updater/pipfile_file_updater.rb
+++ b/python/lib/dependabot/python/file_updater/pipfile_file_updater.rb
@@ -133,6 +133,7 @@ def prepared_pipfile_content
           content = freeze_other_dependencies(content)
           content = freeze_dependencies_being_updated(content)
           content = add_private_sources(content)
+          content = update_python_requirement(content)
           content
         end
 
@@ -142,6 +143,12 @@ def freeze_other_dependencies(pipfile_content)
             freeze_top_level_dependencies_except(dependencies)
         end
 
+        def update_python_requirement(pipfile_content)
+          PipfilePreparer.
+            new(pipfile_content: pipfile_content).
+            update_python_requirement(Helpers.python_major_minor(python_version))
+        end
+
         # rubocop:disable Metrics/PerceivedComplexity
         def freeze_dependencies_being_updated(pipfile_content)
           pipfile_object = TomlRB.parse(pipfile_content)
@@ -264,7 +271,7 @@ def run_command(command, env: {})
         end
 
         def run_pipenv_command(command, env: pipenv_env_variables)
-          run_command("pyenv local #{python_version}")
+          run_command("pyenv local #{Helpers.python_major_minor(python_version)}")
           run_command(command, env: env)
         end
 
@@ -276,7 +283,7 @@ def write_temporary_dependency_files(pipfile_content)
           end
 
           # Overwrite the .python-version with updated content
-          File.write(".python-version", python_version)
+          File.write(".python-version", Helpers.python_major_minor(python_version))
 
           setup_files.each do |file|
             path = file.name
diff --git a/python/lib/dependabot/python/file_updater/pipfile_preparer.rb b/python/lib/dependabot/python/file_updater/pipfile_preparer.rb
index fc19b4716d7..6f16e6af34a 100644
--- a/python/lib/dependabot/python/file_updater/pipfile_preparer.rb
+++ b/python/lib/dependabot/python/file_updater/pipfile_preparer.rb
@@ -70,10 +70,12 @@ def update_python_requirement(requirement)
           pipfile_object = TomlRB.parse(pipfile_content)
 
           pipfile_object["requires"] ||= {}
-          pipfile_object["requires"].delete("python_full_version")
-          pipfile_object["requires"].delete("python_version")
-          pipfile_object["requires"]["python_full_version"] = requirement
-
+          if pipfile_object.dig("requires", "python_full_version") && pipfile_object.dig("requires", "python_version")
+            pipfile_object["requires"].delete("python_full_version")
+          elsif pipfile_object.dig("requires", "python_full_version")
+            pipfile_object["requires"].delete("python_full_version")
+            pipfile_object["requires"]["python_version"] = requirement
+          end
           TomlRB.dump(pipfile_object)
         end
 
diff --git a/python/lib/dependabot/python/helpers.rb b/python/lib/dependabot/python/helpers.rb
index baa49f30f1d..9689573bfe0 100644
--- a/python/lib/dependabot/python/helpers.rb
+++ b/python/lib/dependabot/python/helpers.rb
@@ -1,19 +1,36 @@
 # frozen_string_literal: true
 
 require "dependabot/logger"
+require "dependabot/python/version"
 
 module Dependabot
   module Python
     module Helpers
       def self.install_required_python(python_version)
         # The leading space is important in the version check
-        return if SharedHelpers.run_shell_command("pyenv versions").include?(" #{python_version}")
+        return if SharedHelpers.run_shell_command("pyenv versions").include?(" #{python_major_minor(python_version)}.")
+
+        if File.exist?("/usr/local/.pyenv/#{python_major_minor(python_version)}.tar.gz")
+          SharedHelpers.run_shell_command(
+            "tar xzf /usr/local/.pyenv/#{python_major_minor(python_version)}.tar.gz -C /usr/local/.pyenv/"
+          )
+          return if SharedHelpers.run_shell_command("pyenv versions").
+                    include?(" #{python_major_minor(python_version)}.")
+        end
 
         Dependabot.logger.info("Installing required Python #{python_version}.")
+        start = Time.now
         SharedHelpers.run_shell_command("pyenv install -s #{python_version}")
         SharedHelpers.run_shell_command("pyenv exec pip install --upgrade pip")
         SharedHelpers.run_shell_command("pyenv exec pip install -r" \
                                         "#{NativeHelpers.python_requirements_path}")
+        time_taken = Time.now - start
+        Dependabot.logger.info("Installing Python #{python_version} took #{time_taken}s.")
+      end
+
+      def self.python_major_minor(python_version)
+        python = Python::Version.new(python_version)
+        "#{python.segments[0]}.#{python.segments[1]}"
       end
     end
   end
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 f3e5983a135..cbbd95d8e25 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
@@ -254,7 +254,7 @@ def pip_compile_index_options
         end
 
         def run_pip_compile_command(command)
-          run_command("pyenv local #{python_version}")
+          run_command("pyenv local #{Helpers.python_major_minor(python_version)}")
           run_command(command)
         end
 
diff --git a/python/lib/dependabot/python/update_checker/pipenv_version_resolver.rb b/python/lib/dependabot/python/update_checker/pipenv_version_resolver.rb
index c5bb2f9848a..88944c79a05 100644
--- a/python/lib/dependabot/python/update_checker/pipenv_version_resolver.rb
+++ b/python/lib/dependabot/python/update_checker/pipenv_version_resolver.rb
@@ -290,7 +290,7 @@ def write_temporary_dependency_files(updated_req: nil,
           end
 
           # Overwrite the .python-version with updated content
-          File.write(".python-version", python_version)
+          File.write(".python-version", Helpers.python_major_minor(python_version))
 
           setup_files.each do |file|
             path = file.name
@@ -341,6 +341,7 @@ def pipfile_content(updated_requirement:)
           content = freeze_other_dependencies(content)
           content = set_target_dependency_req(content, updated_requirement)
           content = add_private_sources(content)
+          content = update_python_requirement(content)
           content
         end
 
@@ -350,6 +351,12 @@ def freeze_other_dependencies(pipfile_content)
             freeze_top_level_dependencies_except([dependency])
         end
 
+        def update_python_requirement(pipfile_content)
+          Python::FileUpdater::PipfilePreparer.
+            new(pipfile_content: pipfile_content).
+            update_python_requirement(Helpers.python_major_minor(python_version))
+        end
+
         # rubocop:disable Metrics/PerceivedComplexity
         def set_target_dependency_req(pipfile_content, updated_requirement)
           return pipfile_content unless updated_requirement
@@ -461,7 +468,7 @@ def run_command(command, env: {})
         end
 
         def run_pipenv_command(command, env: pipenv_env_variables)
-          run_command("pyenv local #{python_version}")
+          run_command("pyenv local #{Helpers.python_major_minor(python_version)}")
           run_command(command, env: env)
         end
 
diff --git a/python/spec/dependabot/python/file_updater/pipfile_file_updater_spec.rb b/python/spec/dependabot/python/file_updater/pipfile_file_updater_spec.rb
index 345d2120886..3076c64cd30 100644
--- a/python/spec/dependabot/python/file_updater/pipfile_file_updater_spec.rb
+++ b/python/spec/dependabot/python/file_updater/pipfile_file_updater_spec.rb
@@ -133,7 +133,7 @@
         )
       end
 
-      it "updates both files correctly", :slow do
+      it "updates both files correctly" do
         expect(updated_files.map(&:name)).to eq(%w(Pipfile Pipfile.lock))
 
         updated_lockfile = updated_files.find { |f| f.name == "Pipfile.lock" }