diff --git a/Dockerfile b/Dockerfile
index ef877d69..4d7d6a58 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -19,5 +19,7 @@ FROM docker.io/debian:bullseye-slim
 COPY --from=build /go/bin/headscale /bin/headscale
 ENV TZ UTC
 
+RUN mkdir -p /var/run/headscale
+
 EXPOSE 8080/tcp
 CMD ["headscale"]
diff --git a/Dockerfile.debug b/Dockerfile.debug
index 3a751ecd..7cd609cf 100644
--- a/Dockerfile.debug
+++ b/Dockerfile.debug
@@ -18,6 +18,8 @@ FROM docker.io/golang:1.20.0-bullseye
 COPY --from=build /go/bin/headscale /bin/headscale
 ENV TZ UTC
 
+RUN mkdir -p /var/run/headscale
+
 # Need to reset the entrypoint or everything will run as a busybox script
 ENTRYPOINT []
 EXPOSE 8080/tcp