diff --git a/tests/templates/kuttl/smoke/30-install-superset.yaml.j2 b/tests/templates/kuttl/smoke/30-install-superset.yaml.j2
index a280c3b0..1de4b50c 100644
--- a/tests/templates/kuttl/smoke/30-install-superset.yaml.j2
+++ b/tests/templates/kuttl/smoke/30-install-superset.yaml.j2
@@ -39,9 +39,20 @@ spec:
     config:
       logging:
         enableVectorAgent: {{ lookup('env', 'VECTOR_AGGREGATOR') | length > 0 }}
+    configOverrides:
+      superset_config.py:
+        EXPERIMENTAL_FILE_HEADER: |
+          COMMON_HEADER_VAR = "role-value"
+          ROLE_HEADER_VAR = "role-value"
+        EXPERIMENTAL_FILE_FOOTER: |
+          ROLE_FOOTER_VAR = "role-value"
     roleGroups:
       default:
         replicas: 1
+        configOverrides:
+          superset_config.py:
+            EXPERIMENTAL_FILE_HEADER: |
+              COMMON_HEADER_VAR = "group-value"
         envOverrides:
           COMMON_VAR: group-value # overrides role value
           GROUP_VAR: group-value # only defined here at group level
diff --git a/tests/templates/kuttl/smoke/31-assert.yaml b/tests/templates/kuttl/smoke/31-assert.yaml
index b9b151ac..aa98ee25 100644
--- a/tests/templates/kuttl/smoke/31-assert.yaml
+++ b/tests/templates/kuttl/smoke/31-assert.yaml
@@ -7,6 +7,30 @@ commands:
   # Test envOverrides
   #
   - script: |
-      kubectl -n $NAMESPACE get sts superset-node-default -o yaml | yq -e '.spec.template.spec.containers[] | select (.name == "superset") | .env[] | select (.name == "COMMON_VAR" and .value == "group-value")'
-      kubectl -n $NAMESPACE get sts superset-node-default -o yaml | yq -e '.spec.template.spec.containers[] | select (.name == "superset") | .env[] | select (.name == "GROUP_VAR" and .value == "group-value")'
-      kubectl -n $NAMESPACE get sts superset-node-default -o yaml | yq -e '.spec.template.spec.containers[] | select (.name == "superset") | .env[] | select (.name == "ROLE_VAR" and .value == "role-value")'
+      #!/usr/bin/env bash
+      set -euo pipefail
+
+      # Config Test Data
+      SUPERSET_CONFIG=$(
+          kubectl -n "$NAMESPACE" get cm superset-node-default -o yaml \
+          | yq -e '.data["superset_config.py"]'
+      )
+
+      # Config Test Assertions
+      echo "$SUPERSET_CONFIG" | grep 'COMMON_HEADER_VAR = "group-value"'
+      echo "$SUPERSET_CONFIG" | grep 'ROLE_FOOTER_VAR = "role-value"'
+      echo "$SUPERSET_CONFIG" | grep -v 'ROLE_HEADER_VAR = "role-value"'
+
+      # STS Spec Test Data
+      SUPERSET_NODE_DEFAULT_STS=$(kubectl -n "$NAMESPACE" get sts superset-node-default -o yaml)
+      YQ_FILTER='
+        .spec.template.spec.containers[]
+        | select(.name == "superset")
+        | .env[]
+        | select(.name == strenv(KEY) and .value == strenv(VALUE))
+      '
+
+      # STS Spec Test Assertions
+      echo "$SUPERSET_NODE_DEFAULT_STS" | KEY="COMMON_VAR" VALUE="group-value" yq -e "$YQ_FILTER"
+      echo "$SUPERSET_NODE_DEFAULT_STS" | KEY="GROUP_VAR" VALUE="group-value" yq -e "$YQ_FILTER"
+      echo "$SUPERSET_NODE_DEFAULT_STS" | KEY="ROLE_VAR" VALUE="role-value" yq -e "$YQ_FILTER"