diff --git a/plugins/woocommerce/changelog/e2e-release-fix-upload-test b/plugins/woocommerce/changelog/e2e-release-fix-upload-test
new file mode 100644
index 00000000000..571ed84a0f9
--- /dev/null
+++ b/plugins/woocommerce/changelog/e2e-release-fix-upload-test
@@ -0,0 +1,4 @@
+Significance: patch
+Type: dev
+
+Fix recent failures in "Smoke test release" workflow.
diff --git a/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh b/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh
index 623f4caa128..32662b68a5c 100755
--- a/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh
+++ b/plugins/woocommerce/tests/e2e-pw/bin/test-env-setup.sh
@@ -8,7 +8,9 @@ echo -e 'Normalize permissions for wp-content directory \n'
 docker-compose -f $(wp-env install-path)/docker-compose.yml run --rm -u www-data -e HOME=/tmp tests-wordpress sh -c "chmod -c ugo+w /var/www/html/wp-config.php \
 && chmod -c ugo+w /var/www/html/wp-content \
 && chmod -c ugo+w /var/www/html/wp-content/themes \
-&& chmod -c ugo+w /var/www/html/wp-content/plugins"
+&& chmod -c ugo+w /var/www/html/wp-content/plugins \
+&& mkdir -p /var/www/html/wp-content/upgrade \
+&& chmod -c ugo+w /var/www/html/wp-content/upgrade"
 
 docker-compose -f $(wp-env install-path)/docker-compose.yml run --rm -u www-data -e HOME=/tmp tests-cli sh -c "ls \
 && wp theme install twentynineteen --activate \