diff --git a/.github/scripts/apply-code-quality-ruleset.sh b/.github/scripts/apply-code-quality-ruleset.sh
index 1e1dd419..932f64e6 100755
--- a/.github/scripts/apply-code-quality-ruleset.sh
+++ b/.github/scripts/apply-code-quality-ruleset.sh
@@ -11,8 +11,13 @@
 #   - agent-shield / AgentShield          agent-shield.yml, caller job: agent-shield, reusable job: AgentShield
 #   - dependency-audit / Detect ecosystems  dependency-audit.yml, caller job: dependency-audit, reusable job: Detect ecosystems
 #
+# Bypass actors configured (required on every ruleset targeting main — see #399):
+#   - OrganizationAdmin (bypass_mode: always)                             emergency admin override
+#   - dependabot-automerge-petry (actor_id: 3167543, bypass_mode: always) enables Dependabot auto-merge
+#
 # Standard reference:
 #   https://github.com/petry-projects/.github/blob/main/standards/github-settings.md#code-quality--required-checks-ruleset-all-repositories
+#   https://github.com/petry-projects/.github/blob/main/standards/github-settings.md#bypass-actors--required-on-every-ruleset-targeting-main
 #
 # Usage:
 #   GH_TOKEN=<admin-token> bash .github/scripts/apply-code-quality-ruleset.sh
@@ -37,7 +42,30 @@ export GH_TOKEN
 EXISTING_ID=$(gh api "repos/$REPO/rulesets" \
   --jq ".[] | select(.name == \"$RULESET_NAME\") | .id" 2>/dev/null || true)
 
-PAYLOAD=$(jq -n '{
+# Required bypass actors per org standard (see #399)
+REQUIRED_BYPASS_ORG_ADMIN='{"actor_type":"OrganizationAdmin","bypass_mode":"always"}'
+REQUIRED_BYPASS_DEPENDABOT='{"actor_id":3167543,"actor_type":"Integration","bypass_mode":"always"}'
+REQUIRED_BYPASS_ACTORS=$(jq -n \
+  --argjson org_admin "$REQUIRED_BYPASS_ORG_ADMIN" \
+  --argjson dependabot "$REQUIRED_BYPASS_DEPENDABOT" \
+  '[$org_admin, $dependabot]')
+
+# When updating an existing ruleset, fetch its current bypass actors and merge them
+# with the required actors so that other legitimate bypass actors are not silently removed.
+if [ -n "$EXISTING_ID" ]; then
+  EXISTING_BYPASS=$(gh api "repos/$REPO/rulesets/$EXISTING_ID" \
+    --jq '.bypass_actors // []' 2>/dev/null || echo "[]")
+  BYPASS_ACTORS=$(echo "$EXISTING_BYPASS" | \
+    jq --argjson req "$REQUIRED_BYPASS_ACTORS" \
+      'map(select(
+         .actor_type != "OrganizationAdmin" and
+         (.actor_type != "Integration" or .actor_id != 3167543)
+       )) + $req')
+else
+  BYPASS_ACTORS=$REQUIRED_BYPASS_ACTORS
+fi
+
+PAYLOAD=$(jq -n --argjson bypass_actors "$BYPASS_ACTORS" '{
   name: "code-quality",
   target: "branch",
   enforcement: "active",
@@ -61,7 +89,7 @@ PAYLOAD=$(jq -n '{
       }
     }
   ],
-  bypass_actors: []
+  bypass_actors: $bypass_actors
 }')
 
 if [ -n "$EXISTING_ID" ]; then
diff --git a/.github/scripts/tests/apply-code-quality-ruleset.bats b/.github/scripts/tests/apply-code-quality-ruleset.bats
index b6836b93..1a2b9ff8 100644
--- a/.github/scripts/tests/apply-code-quality-ruleset.bats
+++ b/.github/scripts/tests/apply-code-quality-ruleset.bats
@@ -44,3 +44,52 @@ assert_required_check() {
 @test "script requires the dependency-audit / Detect ecosystems status check" {
   assert_required_check "dependency-audit / Detect ecosystems"
 }
+
+@test "payload includes the OrganizationAdmin bypass actor with bypass_mode always" {
+  export GH_TOKEN="mock-token"
+  gh() {
+    if [ "$1" = "api" ]; then
+      if [ "$2" = "repos/petry-projects/markets/rulesets" ]; then
+        echo ""
+        return 0
+      elif [ "$2" = "-X" ] && [ "$3" = "POST" ]; then
+        cat > "$BATS_TEST_TMPDIR/payload.json"
+        echo '{"id": 12345}'
+        return 0
+      fi
+    fi
+    command gh "$@"
+  }
+  export -f gh
+
+  run bash "$SCRIPT"
+  [ "$status" -eq 0 ]
+
+  jq -e '.bypass_actors == [{"actor_type":"OrganizationAdmin","bypass_mode":"always"},{"actor_id":3167543,"actor_type":"Integration","bypass_mode":"always"}]' "$BATS_TEST_TMPDIR/payload.json"
+}
+
+@test "update preserves existing bypass actors while ensuring OrganizationAdmin is present" {
+  export GH_TOKEN="mock-token"
+  gh() {
+    if [ "$1" = "api" ]; then
+      if [ "$2" = "repos/petry-projects/markets/rulesets" ]; then
+        echo "999"
+        return 0
+      elif [ "$2" = "repos/petry-projects/markets/rulesets/999" ] && [ "$3" = "--jq" ]; then
+        echo '[{"actor_type":"RepositoryRole","bypass_mode":"pull_request"}]'
+        return 0
+      elif [ "$2" = "-X" ] && [ "$3" = "PUT" ]; then
+        cat > "$BATS_TEST_TMPDIR/payload.json"
+        echo '{}'
+        return 0
+      fi
+    fi
+    command gh "$@"
+  }
+  export -f gh
+
+  run bash "$SCRIPT"
+  [ "$status" -eq 0 ]
+
+  jq -e '.bypass_actors == [{"actor_type":"RepositoryRole","bypass_mode":"pull_request"},{"actor_type":"OrganizationAdmin","bypass_mode":"always"},{"actor_id":3167543,"actor_type":"Integration","bypass_mode":"always"}]' "$BATS_TEST_TMPDIR/payload.json"
+}