diff --git a/Dockerfile b/Dockerfile
index 88a79c2..b365c88 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -36,6 +36,7 @@ COPY agent/*.sh /agent/
 COPY --from=builder /src/serial/main /run/serial.bin
 
 RUN ["chmod", "+x", "/run/run.sh"]
+RUN ["chmod", "+x", "/run/check.sh"]
 RUN ["chmod", "+x", "/run/server.sh"]
 RUN ["chmod", "+x", "/run/serial.bin"]
 
@@ -68,6 +69,6 @@ LABEL org.opencontainers.image.version=${VERSION_ARG}
 LABEL org.opencontainers.image.url=https://hub.docker.com/r/kroese/virtual-dsm/
 LABEL org.opencontainers.image.source=https://github.com/kroese/virtual-dsm/
 
-HEALTHCHECK --interval=30s --timeout=2s CMD curl -ILfSs http://20.20.20.21:5000/ || exit 1
+HEALTHCHECK --interval=30s --retries=1 CMD /run/check.sh
 
 ENTRYPOINT ["/run/run.sh"]
diff --git a/run/check.sh b/run/check.sh
new file mode 100644
index 0000000..88c39b3
--- /dev/null
+++ b/run/check.sh
@@ -0,0 +1,22 @@
+#!/usr/bin/env bash
+set -eu
+
+# Docker Healthcheck
+
+PORT=5000
+FILE="/var/dsm.ip"
+
+if [ ! -f "${FILE}" ]; then
+  echo "IP not assigned"
+  exit 1
+fi
+
+IP=$(cat "${FILE}")
+
+if ! curl -m 3 -ILfSs "http://${IP}:${PORT}/"; then
+  echo "Failed to reach ${IP}"
+  exit 1
+fi
+
+echo "Healthcheck OK for ${IP}"
+exit 0
diff --git a/run/network.sh b/run/network.sh
index 988af56..cb4e561 100644
--- a/run/network.sh
+++ b/run/network.sh
@@ -46,6 +46,9 @@ configureDHCP() {
     echo "ERROR: Cannot retrieve IP from DHCP using MAC ${VM_NET_MAC}" && exit 16
   fi
 
+  # Store IP for Docker healthcheck
+  echo "${DHCP_IP}" > "/var/dsm.ip"
+
   ip a flush "${VM_NET_TAP}"
 
   TAP_PATH="/dev/tap$(</sys/class/net/${VM_NET_TAP}/ifindex)"
@@ -83,6 +86,9 @@ configureNAT () {
   VM_NET_IP='20.20.20.21'
   VM_NET_TAP="_VmNatTap"
 
+  # Store IP for Docker healthcheck
+  echo "${VM_NET_IP}" > "/var/dsm.ip"
+
   #Create bridge with static IP for the VM guest
   brctl addbr dockerbridge
   ip addr add ${VM_NET_IP%.*}.1/24 broadcast ${VM_NET_IP%.*}.255 dev dockerbridge