diff --git a/boot.sh b/boot.sh
index af72a7b9..7e2f05fa 100644
--- a/boot.sh
+++ b/boot.sh
@@ -1,13 +1,33 @@
 #!/bin/sh
 source venv/bin/activate
 
-echo "Updating database"
-while python manage.py migrate ; status=$? ; [ $status -eq 1 ]; do
-        echo "Migration failed (error #${status})! Database may not be ready yet, retrying in 5 seconds..."
-        sleep 5
+echo "Migrating database"
+
+attempt=0
+max_attempts=20
+while python manage.py migrate; \
+      status=$?; \
+      attempt=$((attempt+1)); \
+      [ $status -eq 1 ] \
+   && [ $attempt -le $max_attempts ]; do
+    echo -e "\n!!! Migration failed (error ${status}, attempt ${attempt}/${max_attempts})."
+    echo "!!! Database may not be ready yet or system is misconfigured."
+    echo -e "!!! Retrying in 5 seconds...\n"
+    sleep 5
 done
+
+if [ $attempt -gt $max_attempts ]; then
+    echo -e "\n!!! Migration failed. Maximum attempts exceeded."
+    echo "!!! Please check logs above - misconfiguration is very likely."
+    echo "!!! Shutting down container."
+    exit 1 # exit with error to make the container stop
+fi
+
+echo "Generating static files"
+
 python manage.py collectstatic_js_reverse
 python manage.py collectstatic --noinput
+
 echo "Done"
 
 chmod -R 755 /opt/recipes/mediafiles