diff --git a/.buildkite/vagrant-run.sh b/.buildkite/vagrant-run.sh
index a54aeb97d..e7a1458de 100755
--- a/.buildkite/vagrant-run.sh
+++ b/.buildkite/vagrant-run.sh
@@ -29,9 +29,27 @@ export GOOGLE_JSON_KEY_LOCATION="${KEY_PATH}"
 export DOCKER_USERNAME=sourcegraph
 export DOCKER_PASSWORD="$(gcloud secrets versions access latest --secret=DOCKER_PASSWORD_BUILDKITE_AGENT --quiet --project=sourcegraph-ci)"
 
+ssh_answers() {
+	vagrant ssh "$box" --no-tty --command true -- -o ConnectTimeout=15
+}
+
 echo --- ":vagrant: starting box $box"
 vagrant up "$box" --provider=google || exit_code=$?
 
+# vagrant up gives up when the VM stops answering SSH, which is not a test failure.
+# Retry the SSH connection to the same VM, then sync the repo and run the test on it
+if [ "$exit_code" != 0 ] && ! ssh_answers; then
+	for attempt in {1..10}; do
+		echo "$box does not answer SSH, retry $attempt of 10 in 15 seconds"
+		sleep 15
+		if ssh_answers; then
+			exit_code=0
+			vagrant provision "$box" || exit_code=$?
+			break
+		fi
+	done
+fi
+
 if [ "$exit_code" != 0 ]; then
 	vagrant scp "${box}:/deploy-sourcegraph-docker/*.log" ../
 	exit $exit_code