diff --git a/headscale/Dockerfile b/headscale/Dockerfile
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--- /dev/null
+++ b/headscale/Dockerfile
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+# Builder image
+FROM docker.io/golang:1.19.0-bullseye AS build
+ARG VERSION=v0.17.0-beta4
+ENV GOPATH /go
+
+RUN apt-get install -y git && \
+    git clone https://github.com/juanfont/headscale -b $VERSION /go/src/headscale
+
+WORKDIR /go/src/headscale
+
+RUN go mod download
+
+RUN CGO_ENABLED=0 GOOS=linux go install -tags ts2019 -ldflags="-s -w -X github.com/juanfont/headscale/cmd/headscale/cli.Version=$VERSION" -a ./cmd/headscale
+RUN strip /go/bin/headscale
+RUN test -e /go/bin/headscale
+
+# Production image
+# Note that we do not use "distroless" because we actually want to have a shell in the image
+# to run app.sh (in order to perform custom initialization)
+FROM docker.io/golang:1.19.0-bullseye
+
+COPY --from=build /go/bin/headscale /bin/headscale
+ENV TZ UTC
+
+ADD app.sh /
+
+RUN chmod +x /app.sh
+
+EXPOSE 8080/tcp
+# State path
+# Note that configuration should be mounted or added in /etc/headscale
+VOLUME /var/lib/headscale
+CMD ["/app.sh"]
diff --git a/headscale/app.sh b/headscale/app.sh
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--- /dev/null
+++ b/headscale/app.sh
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+#!/bin/sh
+
+touch /var/lib/headscale/db.sqlite
+mkdir /var/lib/headscale/.cache
+exec headscale -c /etc/headscale/config.yaml serve
diff --git a/uptime-kuma-tailscale/Dockerfile b/uptime-kuma-tailscale/Dockerfile
new file mode 100644
index 0000000..45da3c6
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+++ b/uptime-kuma-tailscale/Dockerfile
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+# Uptime Kuma image with an ephemeral Tailscale daemon included
+# Used on fly.io because it does not support sidecar containers
+# The tailscale ephemeral key should be provided via the env variable TAILSCALE_KEY
+# custom tailscale control plane can be specified with TAILSCALE_SERVER
+FROM louislam/uptime-kuma:1.18.5
+# Default tailscale login server
+ENV TAILSCALE_SERVER=https://controlplane.tailscale.com
+ENV TAILSCALE_HOSTNAME=uptime-kuma
+
+RUN apt update && apt install -y curl bash iptables
+
+RUN curl -fsSL https://pkgs.tailscale.com/stable/debian/bullseye.noarmor.gpg | tee /usr/share/keyrings/tailscale-archive-keyring.gpg
+RUN curl -fsSL https://pkgs.tailscale.com/stable/debian/bullseye.tailscale-keyring.list | tee /etc/apt/sources.list.d/tailscale.list
+
+RUN apt update && apt install -y tailscale
+
+COPY run.sh /
+
+RUN chmod +x /run.sh
+
+CMD [ "/run.sh" ]
diff --git a/uptime-kuma-tailscale/run.sh b/uptime-kuma-tailscale/run.sh
new file mode 100644
index 0000000..5de8d4b
--- /dev/null
+++ b/uptime-kuma-tailscale/run.sh
@@ -0,0 +1,6 @@
+#!/usr/bin/env bash
+
+/usr/sbin/tailscaled -state=mem: &
+sleep 1
+tailscale up --login-server=$TAILSCALE_SERVER --authkey=$TAILSCALE_KEY --hostname=$TAILSCALE_HOSTNAME
+node /app/server/server.js