diff --git a/.github/workflows/check_dependencies.yml b/.github/workflows/check_dependencies.yml
new file mode 100644
index 00000000..c5cb32f5
--- /dev/null
+++ b/.github/workflows/check_dependencies.yml
@@ -0,0 +1,20 @@
+name: Check Dependencies
+
+on:
+  pull_request:
+
+jobs:
+  check:
+    runs-on: ubuntu-latest
+    strategy:
+      matrix:
+        python-version: ['3.8', '3.9', '3.10', '3.11', '3.12']
+        architecture: ['linux/amd64', 'linux/arm64']
+    steps:
+      - uses: actions/checkout@v3
+
+      - name: Check Dependencies
+        run: |
+          ARCHITECTURE=${{ matrix.architecture }} \
+              PYTHON_VERSION=${{ matrix.python-version }} \
+              ./scripts/check_dependencies.sh
diff --git a/scripts/check_dependencies.sh b/scripts/check_dependencies.sh
new file mode 100755
index 00000000..eab419d8
--- /dev/null
+++ b/scripts/check_dependencies.sh
@@ -0,0 +1,55 @@
+#!/bin/bash -ex
+
+# This script checks to make sure that the vendored version of requests shipped
+# with pip meets the minimum required version of requests as defined by the
+# datadog package.
+
+if [[ -z $ARCHITECTURE ]]; then
+    DOCKER_DEFAULT_PLATFORM='linux/amd64'
+else
+    DOCKER_DEFAULT_PLATFORM=$ARCHITECTURE
+fi
+
+if [[ -z $PYTHON_VERSION ]]; then
+    PYTHON_VERSION=latest
+fi
+
+# create virtual environment
+rm -rf venv
+pip install virtualenv
+virtualenv venv
+source venv/bin/activate
+
+# determine highest available version of requests
+pip install .
+highest=$(pip freeze | grep requests | tr -d 'requests==')
+echo "Highest available version of requests: $highest"
+
+# determine minumum required version of requests
+pip uninstall -y requests
+pip install uv
+uv pip install --resolution=lowest .
+lowest=$(pip freeze | grep requests | tr -d 'requests==')
+echo "Minimum required version of requests: $lowest"
+
+# determine version of requests packaged with pip
+vendored=$(
+    DOCKER_DEFAULT_PLATFORM=$DOCKER_DEFAULT_PLATFORM \
+        docker run --entrypoint='' public.ecr.aws/lambda/python:$PYTHON_VERSION \
+        python -c "import pip._vendor.requests; print(pip._vendor.requests.__version__)"
+)
+echo "Version of vendored requests: $vendored"
+
+# compare versions
+compared=$(python -c "
+parse = lambda v: tuple(map(int, v.split('.')))
+print(parse('$lowest') <= parse('$vendored'))")
+
+if [[ $compared == "True" ]]; then
+    echo "The vendored version of requests meets the minimum requirement"
+    echo "  lowest required ($lowest) <= vendored version ($vendored) <= highest available ($highest)"
+else
+    echo "The vendored version of requests does not meet the minimum requirement"
+    echo "  vendered version ($vendored) < lowest required ($lowest) <= highest available ($highest)"
+    exit 1
+fi