diff --git a/python/helpers/requirements.txt b/python/helpers/requirements.txt
index 1501bbb76c2..179a0244695 100644
--- a/python/helpers/requirements.txt
+++ b/python/helpers/requirements.txt
@@ -1,5 +1,5 @@
-pip>=21.3.1  # Allow earlier versions to retain python 3.6 support
-pip-tools>=6.4.0  # Allow earlier versions to retain python 3.6 support
+pip>=21.3.1,<=22.1.1  # Allow earlier versions to retain python 3.6 support
+pip-tools>=6.4.0,<=6.6.2  # Allow earlier versions to retain python 3.6 support
 flake8==4.0.1
 hashin==0.17.0
 pipenv==2022.4.8
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 e02e9ec65e5..02bc234a08d 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
@@ -223,6 +223,7 @@ def install_required_python
           return if run_command("pyenv versions").include?("#{python_version}\n")
 
           run_command("pyenv install -s #{python_version}")
+          run_command("pyenv exec pip install --upgrade pip")
           run_command("pyenv exec pip install -r "\
                       "#{NativeHelpers.python_requirements_path}")
         end
diff --git a/python/lib/dependabot/python/file_updater/poetry_file_updater.rb b/python/lib/dependabot/python/file_updater/poetry_file_updater.rb
index cacfdc55a34..bebbd53f360 100644
--- a/python/lib/dependabot/python/file_updater/poetry_file_updater.rb
+++ b/python/lib/dependabot/python/file_updater/poetry_file_updater.rb
@@ -178,6 +178,7 @@ def updated_lockfile_content_for(pyproject_content)
 
               if python_version && !pre_installed_python?(python_version)
                 run_poetry_command("pyenv install -s #{python_version}")
+                run_poetry_command("pyenv exec pip install --upgrade pip")
                 run_poetry_command("pyenv exec pip install -r"\
                                    "#{NativeHelpers.python_requirements_path}")
               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 d6227207c5c..15f38ffbc5e 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
@@ -313,6 +313,7 @@ def install_required_python
           return if run_command("pyenv versions").include?("#{python_version}\n")
 
           run_command("pyenv install -s #{python_version}")
+          run_command("pyenv exec pip install --upgrade pip")
           run_command("pyenv exec pip install -r"\
                       "#{NativeHelpers.python_requirements_path}")
         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 a7d2913d90b..89a875a388e 100644
--- a/python/lib/dependabot/python/update_checker/pipenv_version_resolver.rb
+++ b/python/lib/dependabot/python/update_checker/pipenv_version_resolver.rb
@@ -323,6 +323,7 @@ def install_required_python
 
           requirements_path = NativeHelpers.python_requirements_path
           run_command("pyenv install -s #{python_version}")
+          run_command("pyenv exec pip install --upgrade pip")
           run_command("pyenv exec pip install -r "\
                       "#{requirements_path}")
         end
diff --git a/python/lib/dependabot/python/update_checker/poetry_version_resolver.rb b/python/lib/dependabot/python/update_checker/poetry_version_resolver.rb
index 3170be35ea4..46d5c97d7f9 100644
--- a/python/lib/dependabot/python/update_checker/poetry_version_resolver.rb
+++ b/python/lib/dependabot/python/update_checker/poetry_version_resolver.rb
@@ -79,6 +79,7 @@ def fetch_latest_resolvable_version_string(requirement:)
 
                 if python_version && !pre_installed_python?(python_version)
                   run_poetry_command("pyenv install -s #{python_version}")
+                  run_poetry_command("pyenv exec pip install --upgrade pip")
                   run_poetry_command(
                     "pyenv exec pip install -r "\
                     "#{NativeHelpers.python_requirements_path}"
diff --git a/python/spec/dependabot/python/file_updater/poetry_file_updater_spec.rb b/python/spec/dependabot/python/file_updater/poetry_file_updater_spec.rb
index 2a5e54a58db..a9fca8374d9 100644
--- a/python/spec/dependabot/python/file_updater/poetry_file_updater_spec.rb
+++ b/python/spec/dependabot/python/file_updater/poetry_file_updater_spec.rb
@@ -116,7 +116,7 @@
       end
     end
 
-    context "with a supported python version" do
+    context "with a supported python version", :slow do
       let(:python_version) { "3.6.9" }
       let(:pyproject_fixture_name) { "python_36.toml" }
       let(:lockfile_fixture_name) { "python_36.lock" }