diff --git a/commands/run.sh b/commands/run.sh
index a0aae523..4edd9cbe 100755
--- a/commands/run.sh
+++ b/commands/run.sh
@@ -1,6 +1,8 @@
 #!/bin/bash
 set -ueo pipefail
 
+. "$DIR/../lib/log.bash"
+
 # Run takes a service name, pulls down any pre-built image for that name
 # and then runs docker-compose run a generated project name
 
@@ -423,35 +425,30 @@ elif [[ ${#command[@]} -gt 0 ]] ; then
 fi
 
 ensure_stopped() {
-  echo '+++ :warning: Signal received, stopping container'
-  docker stop "${container_name}" || true
+  log 143
+  echo '+++ :warning: Signal received, stopping container gracefully'
+  # docker stop "${container_name}" || true
+  compose_cleanup ${run_service}
   echo '~~~ Last log lines that may be missing above (if container was not already removed)'
   docker logs "${container_name}" || true
-  exitcode='TRAP'
+  exit 143
 }
 
-trap ensure_stopped SIGINT SIGTERM SIGQUIT
+trap 'ensure_stopped "$?"' SIGINT SIGTERM SIGQUIT
 
 if [[ "${BUILDKITE_PLUGIN_DOCKER_COMPOSE_COLLAPSE_RUN_LOG_GROUP:-false}" = "true" ]]; then
   group_type="---"
 else
   group_type="+++"
 fi
-# Disable -e to prevent cancelling step if the command fails for whatever reason
-set +e
-( # subshell is necessary to trap signals (compose v2 fails to stop otherwise)
+
+exitcode=0
+(
   echo "${group_type} :docker: Running ${display_command[*]:-} in service $run_service" >&2
   run_docker_compose "${run_params[@]}"
-)
-exitcode=$?
-
-# Restore -e as an option.
-set -e
+) || exitcode=$?
 
-if [[ $exitcode = "TRAP" ]]; then
-  # command failed due to cancellation signal, make sure there is an error but no further output
-  exitcode=-1
-elif [[ $exitcode -ne 0 ]] ; then
+if [[ $exitcode -ne 0 ]] ; then
   echo "^^^ +++"
   echo "+++ :warning: Failed to run command, exited with $exitcode, run params:"
   echo "${run_params[@]}"
@@ -465,4 +462,4 @@ if [[ -n "${BUILDKITE_AGENT_ACCESS_TOKEN:-}" ]] ; then
   fi
 fi
 
-return "$exitcode"
+return "$exitcode"
\ No newline at end of file
diff --git a/hooks/pre-exit b/hooks/pre-exit
index f3bd61d4..8f1b4d82 100755
--- a/hooks/pre-exit
+++ b/hooks/pre-exit
@@ -15,5 +15,5 @@ if [[ -n "$(plugin_read_list RUN)" ]] && [[ "$(plugin_read_config CLEANUP "true"
   . "$DIR/../lib/run.bash"
 
   echo "~~~ :docker: Cleaning up after docker-compose" >&2
-  compose_cleanup
+  compose_cleanup ""
 fi
diff --git a/lib/log.bash b/lib/log.bash
new file mode 100644
index 00000000..d66e4980
--- /dev/null
+++ b/lib/log.bash
@@ -0,0 +1,40 @@
+#!/bin/bash
+
+log() {
+  msg="SIG $1 received, process exiting"
+  echo "${msg}"
+  buildkite-agent meta-data set "dd_tags.job-signal-${BUILDKITE_STEP_KEY}" "$1"
+  buildkite-agent meta-data set "dd_tags.step-error-code-${BUILDKITE_STEP_KEY}" "$1"
+  buildkite-agent meta-data set "dd_tags.job-error-code-${BUILDKITE_JOB_ID}" "$1"
+
+  echo "$(pidof buildkite-agent) is the pid of the buildkite agent" || true
+
+  send_job_signaled_to_dd "${msg}" "${1}"
+}
+
+send_job_signaled_to_dd() {
+  send_event_to_dd '{ "title": "Job '"${BUILDKITE_STEP_KEY}"' received signal", "text": "'"${1}"'", "alert_type": "error", "tags": [ "ci:job_signal", "exit_status:'"${2}"'", "job_name:'"${BUILDKITE_STEP_KEY}"'", "build_id:'"${BUILDKITE_BUILD_ID}"'", "branch:'"${BUILDKITE_BRANCH}"'", "hs_source:docker_compose_plugin", "env:ci" ] }'
+}
+
+send_event_to_dd() {
+  if command -v curl >/dev/null 2>&1; then
+    echo "Using curl to send event to Datadog"
+    curl -X POST "https://api.datadoghq.com/api/v1/events" \
+      -H "Accept: application/json" \
+      -H "Content-Type: application/json" \
+      -H "DD-API-KEY: ${DD_API_KEY}" \
+      -d "$1"
+  elif command -v wget >/dev/null 2>&1; then
+    echo "Using wget to send event to Datadog"
+    wget \
+      --header="Accept: application/json" \
+      --header="Content-Type: application/json" \
+      --header="DD-API-KEY: ${DD_API_KEY}" \
+      --post-data="$1" \
+      --output-document - \
+      https://api.datadoghq.com/api/v1/events
+  else
+    echo "No suitable network tool found to send event to Datadog"
+    exit 1
+  fi
+}
diff --git a/lib/run.bash b/lib/run.bash
index f531292a..522ef069 100644
--- a/lib/run.bash
+++ b/lib/run.bash
@@ -1,14 +1,15 @@
 #!/bin/bash
 
-compose_cleanup() {
-  if [[ "$(plugin_read_config GRACEFUL_SHUTDOWN 'false')" == "false" ]]; then
-    # Send all containers a SIGKILL
-    run_docker_compose kill || true
-  else
-    # Send all containers a friendly SIGTERM, followed by a SIGKILL after exceeding the stop_grace_period
-    run_docker_compose stop || true
+kill_or_wait_for_stop() {
+
+  if [[ "$(plugin_read_config GRACEFUL_SHUTDOWN 'false')" == "true" ]]; then
+    # This will block until the container exits
+    run_docker_compose wait "$1"
+    container_exit_code=$?
+    echo "exit code was $container_exit_code"
   fi
 
+  # This will kill the container if it hasn't exited yet
   # `compose down` doesn't support force removing images
   if [[ "$(plugin_read_config LEAVE_VOLUMES 'false')" == "false" ]]; then
     run_docker_compose rm --force -v || true
@@ -24,6 +25,18 @@ compose_cleanup() {
   fi
 }
 
+compose_cleanup() {
+  kill_or_wait_for_stop "$1" &
+  sleep 1
+  
+  # No need to call kill directly for GRACEFUL_SHUTDOWN == false since rm --force will send the same kill signal
+  if [[ "$(plugin_read_config GRACEFUL_SHUTDOWN 'false')" == "true" ]]; then
+    echo "graceful shutdown was true, stopping ${1}"
+    # Send all containers a friendly SIGTERM, followed by a SIGKILL after exceeding the stop_grace_period
+    run_docker_compose stop "$1" || true
+  fi
+}
+
 # Checks for failed containers and writes logs for them the the provided dir
 check_linked_containers_and_save_logs() {
   local service="$1"
diff --git a/tests/cleanup.bats b/tests/cleanup.bats
old mode 100644
new mode 100755
index adb69f18..1bec6d49
--- a/tests/cleanup.bats
+++ b/tests/cleanup.bats
@@ -17,13 +17,13 @@ load '../lib/run'
   export BUILDKITE_PLUGIN_DOCKER_COMPOSE_CLEANUP=true
 
   stub docker-compose \
-    "-f docker-compose.yml -p buildkite1111 kill : echo killing containers" \
-    "-f docker-compose.yml -p buildkite1111 rm --force -v : echo removing stopped containers" \
+    "-f docker-compose.yml -p buildkite1111 rm --force -v : echo killing and removing stopped containers" \
     "-f docker-compose.yml -p buildkite1111 down --remove-orphans --volumes : echo removing everything"
 
   run "$PWD"/hooks/pre-exit
 
   assert_success
   assert_output --partial "Cleaning up after docker-compose"
+
   unstub docker-compose
 }
diff --git a/tests/docker-compose-cleanup.bats b/tests/docker-compose-cleanup.bats
index a8843434..7cd3ada6 100644
--- a/tests/docker-compose-cleanup.bats
+++ b/tests/docker-compose-cleanup.bats
@@ -15,19 +15,19 @@ setup () {
   run compose_cleanup
 
   assert_success
-  assert_equal "${lines[0]}" "kill"
-  assert_equal "${lines[1]}" "rm --force -v"
-  assert_equal "${lines[2]}" "down --remove-orphans --volumes"
+  assert_equal "${lines[0]}" "rm --force -v"
+  assert_equal "${lines[1]}" "down --remove-orphans --volumes"
 }
 
 @test "Possible to gracefully shutdown containers in docker-compose cleanup" {
-  export BUILDKITE_PLUGIN_DOCKER_COMPOSE_GRACEFUL_SHUTDOWN=1
+  export BUILDKITE_PLUGIN_DOCKER_COMPOSE_GRACEFUL_SHUTDOWN="true"
   run compose_cleanup
 
   assert_success
-  assert_equal "${lines[0]}" "stop"
-  assert_equal "${lines[1]}" "rm --force -v"
-  assert_equal "${lines[2]}" "down --remove-orphans --volumes"
+  assert_output --partial "wait"
+  assert_equal "${lines[1]}" "exit code was 0"
+  assert_equal "${lines[2]}" "rm --force -v"
+  assert_equal "${lines[3]}" "down --remove-orphans --volumes"
 }
 
 @test "Possible to skip volume destruction in docker-compose cleanup" {
@@ -35,7 +35,6 @@ setup () {
   run compose_cleanup
 
   assert_success
-  assert_equal "${lines[0]}" "kill"
-  assert_equal "${lines[1]}" "rm --force"
-  assert_equal "${lines[2]}" "down --remove-orphans"
+  assert_equal "${lines[0]}" "rm --force"
+  assert_equal "${lines[1]}" "down --remove-orphans"
 }