diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 5f21e5f7047..7dd064acde8 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -131,6 +131,11 @@ jobs:
       DBT_TEST_USER_1: dbt_test_user_1
       DBT_TEST_USER_2: dbt_test_user_2
       DBT_TEST_USER_3: dbt_test_user_3
+      DD_CIVISIBILITY_AGENTLESS_ENABLED: true
+      DD_API_KEY: ${{ secrets.DATADOG_API_KEY }}
+      DD_SITE: datadoghq.com
+      DD_ENV: ci
+      DD_SERVICE: ${{ github.event.repository.name }}
 
     steps:
       - name: Check out the repository
@@ -161,7 +166,7 @@ jobs:
           tox --version
 
       - name: Run tests
-        run: tox
+        run: tox -- --ddtrace
 
       - name: Get current date
         if: always()
diff --git a/.github/workflows/test-repeater.yml b/.github/workflows/test-repeater.yml
index 27fbe4729ff..e414792140c 100644
--- a/.github/workflows/test-repeater.yml
+++ b/.github/workflows/test-repeater.yml
@@ -75,6 +75,11 @@ jobs:
       DBT_TEST_USER_1: dbt_test_user_1
       DBT_TEST_USER_2: dbt_test_user_2
       DBT_TEST_USER_3: dbt_test_user_3
+      DD_CIVISIBILITY_AGENTLESS_ENABLED: true
+      DD_API_KEY: ${{ secrets.DATADOG_API_KEY }}
+      DD_SITE: datadoghq.com
+      DD_ENV: ci
+      DD_SERVICE: ${{ github.event.repository.name }}
 
     steps:
       - name: "Checkout code"
@@ -116,7 +121,7 @@ jobs:
           for ((i=1; i<=${{ inputs.num_runs_per_batch }}; i++))
           do
             echo "Running pytest iteration $i..."
-            python -m pytest ${{ inputs.test_path }}
+            python -m pytest --ddtrace ${{ inputs.test_path }}
             exit_code=$?
 
             if [[ $exit_code -eq 0 ]]; then
diff --git a/dev-requirements.txt b/dev-requirements.txt
index e4b51c03081..a6dcd63dc35 100644
--- a/dev-requirements.txt
+++ b/dev-requirements.txt
@@ -1,5 +1,6 @@
 black==23.3.0
 bumpversion
+ddtrace
 docutils
 flake8
 flaky
diff --git a/tox.ini b/tox.ini
index 4a1a63634ca..b313673137b 100644
--- a/tox.ini
+++ b/tox.ini
@@ -23,6 +23,8 @@ passenv =
   DBT_*
   POSTGRES_TEST_*
   PYTEST_ADDOPTS
+  DD_SERVICE
+  DD_ENV
 commands =
   {envpython} -m pytest --cov=core {posargs} tests/functional -k "not tests/functional/graph_selection"
   {envpython} -m pytest --cov=core {posargs} tests/functional/graph_selection