diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index fa4244bc66..2b0d9743f2 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -34,7 +34,7 @@ jobs:
         with:
           python-version: ${{ env[matrix.python-version] }}
       - name: Install tox
-        run: pip install -U tox-factor
+        run: pip install tox==3.27.1 tox-factor
       - name: Cache tox environment
         # Preserves .tox directory between runs for faster installs
         uses: actions/cache@v1
@@ -107,7 +107,7 @@ jobs:
         with:
           python-version: 3.9
       - name: Install tox
-        run: pip install -U tox
+        run: pip install tox==3.27.1
       - name: Install libsnappy-dev
         if: ${{ matrix.tox-environment == 'lint' }}
         run: sudo apt-get install -y libsnappy-dev
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 4d003ea11c..a159bd1f03 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -32,7 +32,7 @@ some aspects of development, including testing against multiple Python versions.
 To install `tox`, run:
 
 ```console
-$ pip install tox
+$ pip install tox==3.27.1
 ```
 
 You can run `tox` with the following arguments:
@@ -103,7 +103,7 @@ Run tests:
 
 ```sh
 # make sure you have all supported versions of Python installed
-$ pip install tox  # only first time.
+$ pip install tox==3.27.1  # only first time.
 $ tox  # execute in the root of the repository
 ```
 
@@ -162,7 +162,7 @@ For a deeper discussion, see: https://github.com/open-telemetry/opentelemetry-sp
 ## Running Tests Locally
 
 1. Go to your Contrib repo directory. `git clone git@github.com:open-telemetry/opentelemetry-python-contrib.git && cd opentelemetry-python-contrib`.
-2. Make sure you have `tox` installed. `pip install tox`.
+2. Make sure you have `tox` installed. `pip install tox==3.27.1`.
 3. Run `tox` without any arguments to run tests for all the packages. Read more about [tox](https://tox.readthedocs.io/en/latest/).
 
 ### Testing against a different Core repo branch/commit
diff --git a/README.md b/README.md
index 79db46a1ae..4c2f07f66a 100644
--- a/README.md
+++ b/README.md
@@ -124,7 +124,7 @@ Emeritus Maintainers:
 1. Go to your Contrib repo directory. `cd ~/git/opentelemetry-python-contrib`.
 2. Create a virtual env in your Contrib repo directory. `python3 -m venv my_test_venv`.
 3. Activate your virtual env. `source my_test_venv/bin/activate`.
-4. Make sure you have `tox` installed. `pip install tox`.
+4. Make sure you have `tox` installed. `pip install tox==3.27.1`.
 5. Run tests for a package. (e.g. `tox -e test-instrumentation-flask`.)
 
 ### Thanks to all the people who already contributed!