diff --git a/charts/shipyard/templates/statefulset-airflow-worker.yaml b/charts/shipyard/templates/statefulset-airflow-worker.yaml
index 64a3997e..12c738d7 100644
--- a/charts/shipyard/templates/statefulset-airflow-worker.yaml
+++ b/charts/shipyard/templates/statefulset-airflow-worker.yaml
@@ -149,6 +149,8 @@ spec:
           imagePullPolicy: {{ .Values.images.pull_policy }}
 {{ tuple $envAll $envAll.Values.pod.resources.airflow.logrotate | include "helm-toolkit.snippets.kubernetes_resources" | indent 10 }}
           env:
+          - name: PERCENT_MAX_LOG_FS_USAGE
+            value: {{ .Values.logrotate.percent_max_log_fs_usage | quote }}
           - name: DAYS_BEFORE_LOG_DELETION
             value: {{ .Values.logrotate.days_before_deletion | quote }}
           - name: LOGROTATE_PATH
diff --git a/charts/shipyard/values.yaml b/charts/shipyard/values.yaml
index 38f4c564..06601ceb 100644
--- a/charts/shipyard/values.yaml
+++ b/charts/shipyard/values.yaml
@@ -146,6 +146,7 @@ volume_worker:
 
 logrotate:
   days_before_deletion: 30
+  percent_max_log_fs_usage: 80
 
 # typically overriden by environmental
 # values, but should include all endpoints
diff --git a/images/airflow/script/airflow_logrotate.sh b/images/airflow/script/airflow_logrotate.sh
index fee7f1f0..40924ee2 100755
--- a/images/airflow/script/airflow_logrotate.sh
+++ b/images/airflow/script/airflow_logrotate.sh
@@ -16,6 +16,10 @@
 
 set -ex
 
+get_usage() {
+    df /usr/local/airflow/logs/ --output='pcent' | grep -o '[0-9]*'
+}
+
 while true; do
 
     # Delete logs that are more than 30 days old in the directories
@@ -23,6 +27,14 @@ while true; do
     # Delete empty directories under the Airflow log path
     find ${LOGROTATE_PATH} \( -type f -name '*.log' -mtime +${DAYS_BEFORE_LOG_DELETION} -o -type d -empty \) -print -delete
 
+    # Delete oldest logs and empty directories when
+    # the Airflow log path filesystem reaches max usage
+    CURR_USAGE=$(get_usage)
+    while [ $CURR_USAGE -gt ${PERCENT_MAX_LOG_FS_USAGE} ]; do
+      find ${LOGROTATE_PATH} \( -type f -name '*.log' -o -type d -empty \) -printf '%T+ %p\n' | sort | head -n 1 | xargs -r -l1 sh -c 'rm -rf $1'
+      CURR_USAGE=$(get_usage)
+    done
+
     # Sleep for 1 hr between each wait loop
     sleep 3600