diff --git a/.dockerignore b/.dockerignore
index 43aeac7f6f4..bfe41dc2537 100644
--- a/.dockerignore
+++ b/.dockerignore
@@ -1,8 +1,21 @@
-/.bundle
+/.core-bash_history
+/.env
+/.envrc
 /.git
-/tmp/
-/helpers
-/spec
-gitignored
-/bundler/helpers/helpers/
-/python/helpers/helpers/
+/.vscode-server-insiders/
+/.vscode-server/
+/.vscode/
+/dependabot-*.gem
+/dry-run
+/pkg
+/vendor
+/tmp
+**/.bundle
+**/coverage
+**/Gemfile.lock
+**/node_modules
+!**/spec/fixtures/*
+git.store
+.byebug_history
+.DS_Store
+*.pyc
diff --git a/Dockerfile.ci b/Dockerfile.ci
index 5d8ef5b177e..92a3f2a4625 100644
--- a/Dockerfile.ci
+++ b/Dockerfile.ci
@@ -1,14 +1,27 @@
 FROM dependabot/dependabot-core
 
-# We pre-install these versions of python as they're known to be used in the
-# test suite. These used to be installed in-line, and pre-installing them helps
-# with the performance of the python test suite.
-RUN pyenv install -s 3.6.13 \
-  && pyenv install -s 3.7.1 \
-  && pyenv install -s 3.7.10 \
-  && git config --global user.name dependabot-ci \
+RUN git config --global user.name dependabot-ci \
   && git config --global user.email no-reply@github.com
 
 ARG CODE_DIR=/home/dependabot/dependabot-core
 WORKDIR ${CODE_DIR}
-COPY --chown=dependabot:dependabot . ${CODE_DIR}
+
+COPY --chown=dependabot:dependabot .rubocop.yml ${CODE_DIR}/.rubocop.yml
+COPY --chown=dependabot:dependabot omnibus ${CODE_DIR}/omnibus
+COPY --chown=dependabot:dependabot dep ${CODE_DIR}/dep
+COPY --chown=dependabot:dependabot git_submodules ${CODE_DIR}/git_submodules
+COPY --chown=dependabot:dependabot terraform ${CODE_DIR}/terraform
+COPY --chown=dependabot:dependabot github_actions ${CODE_DIR}/github_actions
+COPY --chown=dependabot:dependabot hex ${CODE_DIR}/hex
+COPY --chown=dependabot:dependabot elm ${CODE_DIR}/elm
+COPY --chown=dependabot:dependabot docker ${CODE_DIR}/docker
+COPY --chown=dependabot:dependabot nuget ${CODE_DIR}/nuget
+COPY --chown=dependabot:dependabot maven ${CODE_DIR}/maven
+COPY --chown=dependabot:dependabot gradle ${CODE_DIR}/gradle
+COPY --chown=dependabot:dependabot cargo ${CODE_DIR}/cargo
+COPY --chown=dependabot:dependabot composer ${CODE_DIR}/composer
+COPY --chown=dependabot:dependabot go_modules ${CODE_DIR}/go_modules
+COPY --chown=dependabot:dependabot python ${CODE_DIR}/python
+COPY --chown=dependabot:dependabot npm_and_yarn ${CODE_DIR}/npm_and_yarn
+COPY --chown=dependabot:dependabot bundler ${CODE_DIR}/bundler
+COPY --chown=dependabot:dependabot common ${CODE_DIR}/common
diff --git a/bundler/helpers/v1/.bundle/config b/bundler/helpers/v1/.bundle/config
deleted file mode 100644
index 04f57bd2ed9..00000000000
--- a/bundler/helpers/v1/.bundle/config
+++ /dev/null
@@ -1,2 +0,0 @@
----
-BUNDLE_PATH: ".bundle"
diff --git a/bundler/helpers/v1/.gitignore b/bundler/helpers/v1/.gitignore
index 9e978b139fa..c88c5c24353 100644
--- a/bundler/helpers/v1/.gitignore
+++ b/bundler/helpers/v1/.gitignore
@@ -1,5 +1,4 @@
-/.bundle/*
-!/.bundle/config
+/.bundle
 /.env
 /tmp
 /dependabot-*.gem
diff --git a/bundler/helpers/v1/build b/bundler/helpers/v1/build
index 3e31705c677..cbe7d6eaa5a 100755
--- a/bundler/helpers/v1/build
+++ b/bundler/helpers/v1/build
@@ -10,7 +10,6 @@ fi
 
 helpers_dir="$(dirname "${BASH_SOURCE[0]}")"
 cp -r \
-  "$helpers_dir/.bundle" \
   "$helpers_dir/lib" \
   "$helpers_dir/monkey_patches" \
   "$helpers_dir/run.rb" \
@@ -21,5 +20,6 @@ cd "$install_dir"
 
 # NOTE: Sets `BUNDLED WITH` to match the installed v1 version in Gemfile.lock
 # forcing native helpers to run with the same version
+BUNDLER_VERSION=2 bundle config set --local path ".bundle"
 BUNDLER_VERSION=1 bundle config set --local without "test"
 BUNDLER_VERSION=1 bundle install
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 2bbd1999f03..f0d2aa2ca9f 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
@@ -513,7 +513,10 @@
           let(:requirements_file) do
             Dependabot::DependencyFile.new(
               name: "runtime.txt",
-              content: "python-3.7.1"
+              content: fixture(
+                "requirements",
+                "version_not_specified_runtime.txt"
+              )
             )
           end
 
diff --git a/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb b/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb
index 9662d8ed306..d093b86a424 100644
--- a/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb
+++ b/python/spec/dependabot/python/update_checker/pipenv_version_resolver_spec.rb
@@ -5,8 +5,7 @@
 require "dependabot/dependency_file"
 require "dependabot/python/update_checker/pipenv_version_resolver"
 
-namespace = Dependabot::Python::UpdateChecker
-RSpec.describe namespace::PipenvVersionResolver do
+RSpec.describe Dependabot::Python::UpdateChecker::PipenvVersionResolver do
   let(:resolver) do
     described_class.new(
       dependency: dependency,
diff --git a/python/spec/fixtures/pip_compile_files/met_marker.in b/python/spec/fixtures/pip_compile_files/met_marker.in
index 9757b7ecf4e..30ef8567544 100644
--- a/python/spec/fixtures/pip_compile_files/met_marker.in
+++ b/python/spec/fixtures/pip_compile_files/met_marker.in
@@ -1,4 +1,4 @@
-flaky; python_version < '3.7'
+flaky; python_version < '2.8'
 pytest
 pytest-xdist
 mock
diff --git a/python/spec/fixtures/pyproject_files/exact_version.toml b/python/spec/fixtures/pyproject_files/exact_version.toml
index 2b6222cca04..3c47d0bd068 100644
--- a/python/spec/fixtures/pyproject_files/exact_version.toml
+++ b/python/spec/fixtures/pyproject_files/exact_version.toml
@@ -8,5 +8,5 @@ authors = ["Dependabot <support@dependabot.com>"]
 description = "Various small python projects."
 
 [tool.poetry.dependencies]
-python = "^3.7"
+python = "*"
 requests = "2.18.0"
diff --git a/python/spec/fixtures/pyproject_locks/exact_version.lock b/python/spec/fixtures/pyproject_locks/exact_version.lock
index 3c47fbeb584..563bb5509a3 100644
--- a/python/spec/fixtures/pyproject_locks/exact_version.lock
+++ b/python/spec/fixtures/pyproject_locks/exact_version.lock
@@ -52,7 +52,7 @@ version = "1.21.1"
 [metadata]
 content-hash = "a8d5762e953227a34625a209e9cc67a1c6fb2d7a971845829cf2f9cf61a5bd7c"
 platform = "*"
-python-versions = "^3.7"
+python-versions = "*"
 
 [metadata.hashes]
 certifi = ["13e698f54293db9f89122b0581843a782ad0934a4fe0172d2a980ba77fc61bb7", "9fa520c1bacfb634fa7af20a76bcbd3d5fb390481724c597da32c719a7dca4b0"]
diff --git a/python/spec/fixtures/requirements/pip_compile_met_marker.txt b/python/spec/fixtures/requirements/pip_compile_met_marker.txt
index 971444dc29e..3203b4acbf4 100644
--- a/python/spec/fixtures/requirements/pip_compile_met_marker.txt
+++ b/python/spec/fixtures/requirements/pip_compile_met_marker.txt
@@ -8,7 +8,7 @@ apipkg==1.5               # via execnet
 atomicwrites==1.3.0       # via pytest
 attrs==17.3.0
 execnet==1.6.0            # via pytest-xdist
-flaky==3.5.0 ; python_version < "3.7"
+flaky==3.5.0 ; python_version < "2.8"
 mock==3.0.3
 more-itertools==7.0.0     # via pytest
 pluggy==0.9.0             # via pytest