diff --git a/Dockerfile b/Dockerfile
index f3a1837238e..e84d4d956bb 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,15 +1,15 @@
 # use a builder image for building cloudflare
 ARG TARGET_GOOS
 ARG TARGET_GOARCH
-FROM golang:1.26.8 AS builder
+FROM golang:1.27.1 AS builder
 ENV GO111MODULE=on \
-  CGO_ENABLED=0 \
-  GOPROXY=https://athens.cfdata.org|https://proxy.golang.org|direct \
-  TARGET_GOOS=${TARGET_GOOS} \
-  TARGET_GOARCH=${TARGET_GOARCH} \
-  # the CONTAINER_BUILD envvar is used set github.com/cloudflare/cloudflared/metrics.Runtime=virtual
-  # which changes how cloudflared binds the metrics server
-  CONTAINER_BUILD=1
+    CGO_ENABLED=0 \
+    GOPROXY=https://athens.cfdata.org|https://proxy.golang.org|direct \
+    TARGET_GOOS=${TARGET_GOOS} \
+    TARGET_GOARCH=${TARGET_GOARCH} \
+    # the CONTAINER_BUILD envvar is used set github.com/cloudflare/cloudflared/metrics.Runtime=virtual
+    # which changes how cloudflared binds the metrics server
+    CONTAINER_BUILD=1
 
 
 WORKDIR /go/src/github.com/cloudflare/cloudflared/
@@ -23,13 +23,22 @@ COPY . .
 # compile cloudflared
 RUN make cloudflared
 
-# use a distroless base image with glibc
-FROM gcr.io/distroless/base-debian13:nonroot@sha256:0896741ba5bafd3ac87ea025a5f578952f2d238ddc3614cb368acc983a687aa2
+FROM alpine:3.24
 
 LABEL org.opencontainers.image.source="https://github.com/cloudflare/cloudflared"
 
+RUN apk add --no-cache ca-certificates && \
+    addgroup -g 65532 nonroot && \
+    adduser -D -H -u 65532 -G nonroot nonroot
+
 # copy our compiled binary
-COPY --from=builder --chown=nonroot /go/src/github.com/cloudflare/cloudflared/cloudflared /usr/local/bin/
+COPY --from=builder --chown=65532:65532 /go/src/github.com/cloudflare/cloudflared/cloudflared /usr/local/bin/
+
+# Healthcheck
+ENV TUNNEL_METRICS=0.0.0.0:2000
+
+HEALTHCHECK --interval=30s --timeout=5s --start-period=10s --retries=3 \
+    CMD ["cloudflared", "tunnel", "--metrics", "127.0.0.1:2000", "ready"]
 
 # run as nonroot user
 # We need to use numeric user id's because Kubernetes doesn't support strings:
diff --git a/Dockerfile.amd64 b/Dockerfile.amd64
index 812e7b6778e..3d01cebd62e 100644
--- a/Dockerfile.amd64
+++ b/Dockerfile.amd64
@@ -1,11 +1,11 @@
 # use a builder image for building cloudflare
-FROM golang:1.26.8 AS builder
+FROM golang:1.27.1 AS builder
 ENV GO111MODULE=on \
-  CGO_ENABLED=0 \
-  GOPROXY=https://athens.cfdata.org|https://proxy.golang.org|direct \
-  # the CONTAINER_BUILD envvar is used set github.com/cloudflare/cloudflared/metrics.Runtime=virtual
-  # which changes how cloudflared binds the metrics server
-  CONTAINER_BUILD=1 
+    CGO_ENABLED=0 \
+    GOPROXY=https://athens.cfdata.org|https://proxy.golang.org|direct \
+    # the CONTAINER_BUILD envvar is used set github.com/cloudflare/cloudflared/metrics.Runtime=virtual
+    # which changes how cloudflared binds the metrics server
+    CONTAINER_BUILD=1 
 
 WORKDIR /go/src/github.com/cloudflare/cloudflared/
 
@@ -18,13 +18,22 @@ COPY . .
 # compile cloudflared
 RUN GOOS=linux GOARCH=amd64 make cloudflared
 
-# use a distroless base image with glibc
-FROM gcr.io/distroless/base-debian13:nonroot-amd64@sha256:65795e700eda57743efe12537e031042bd7832a19cc23f772acf2057dc7566f1
+FROM alpine:3.24
 
 LABEL org.opencontainers.image.source="https://github.com/cloudflare/cloudflared"
 
+RUN apk add --no-cache ca-certificates && \
+    addgroup -g 65532 nonroot && \
+    adduser -D -H -u 65532 -G nonroot nonroot
+
 # copy our compiled binary
-COPY --from=builder --chown=nonroot /go/src/github.com/cloudflare/cloudflared/cloudflared /usr/local/bin/
+COPY --from=builder --chown=65532:65532 /go/src/github.com/cloudflare/cloudflared/cloudflared /usr/local/bin/
+
+# Healthcheck
+ENV TUNNEL_METRICS=0.0.0.0:2000
+
+HEALTHCHECK --interval=30s --timeout=5s --start-period=10s --retries=3 \
+    CMD ["cloudflared", "tunnel", "--metrics", "127.0.0.1:2000", "ready"]
 
 # run as nonroot user
 # We need to use numeric user id's because Kubernetes doesn't support strings:
diff --git a/Dockerfile.arm64 b/Dockerfile.arm64
index 9db8a45bcb6..c0fa57cb957 100644
--- a/Dockerfile.arm64
+++ b/Dockerfile.arm64
@@ -1,11 +1,11 @@
 # use a builder image for building cloudflare
-FROM golang:1.26.8 AS builder
+FROM golang:1.27.1 AS builder
 ENV GO111MODULE=on \
-  CGO_ENABLED=0 \
-  GOPROXY=https://athens.cfdata.org|https://proxy.golang.org|direct \
-  # the CONTAINER_BUILD envvar is used set github.com/cloudflare/cloudflared/metrics.Runtime=virtual
-  # which changes how cloudflared binds the metrics server
-  CONTAINER_BUILD=1
+    CGO_ENABLED=0 \
+    GOPROXY=https://athens.cfdata.org|https://proxy.golang.org|direct \
+    # the CONTAINER_BUILD envvar is used set github.com/cloudflare/cloudflared/metrics.Runtime=virtual
+    # which changes how cloudflared binds the metrics server
+    CONTAINER_BUILD=1
 
 WORKDIR /go/src/github.com/cloudflare/cloudflared/
 
@@ -18,13 +18,22 @@ COPY . .
 # compile cloudflared
 RUN GOOS=linux GOARCH=arm64 make cloudflared
 
-# use a distroless base image with glibc
-FROM gcr.io/distroless/base-debian13:nonroot-arm64@sha256:7a4876f88e7fe3190972c274b679b3473f61e8d990a4dce3627961b3e22a0eaf
+FROM alpine:3.24
 
 LABEL org.opencontainers.image.source="https://github.com/cloudflare/cloudflared"
 
+RUN apk add --no-cache ca-certificates && \
+    addgroup -g 65532 nonroot && \
+    adduser -D -H -u 65532 -G nonroot nonroot
+
 # copy our compiled binary
-COPY --from=builder --chown=nonroot /go/src/github.com/cloudflare/cloudflared/cloudflared /usr/local/bin/
+COPY --from=builder --chown=65532:65532 /go/src/github.com/cloudflare/cloudflared/cloudflared /usr/local/bin/
+
+# Healthcheck
+ENV TUNNEL_METRICS=0.0.0.0:2000
+
+HEALTHCHECK --interval=30s --timeout=5s --start-period=10s --retries=3 \
+    CMD ["cloudflared", "tunnel", "--metrics", "127.0.0.1:2000", "ready"]
 
 # run as nonroot user
 # We need to use numeric user id's because Kubernetes doesn't support strings:
diff --git a/go.mod b/go.mod
index 8c737df1cfb..1eeac7ae5ac 100644
--- a/go.mod
+++ b/go.mod
@@ -1,6 +1,6 @@
 module github.com/cloudflare/cloudflared
 
-go 1.26
+go 1.26.0
 
 require (
 	github.com/cloudflare/backoff v0.0.0-20240920015135-e46b80a3a7d0
@@ -36,7 +36,7 @@ require (
 	go.opentelemetry.io/proto/otlp v1.11.0
 	go.uber.org/automaxprocs v1.6.0
 	go.uber.org/mock v0.5.2
-	golang.org/x/crypto v0.55.0
+	golang.org/x/crypto v0.56.0
 	golang.org/x/net v0.58.0
 	golang.org/x/sync v0.22.0
 	golang.org/x/sys v0.47.0
diff --git a/go.sum b/go.sum
index 32ae4c92aa7..8101c74ec18 100644
--- a/go.sum
+++ b/go.sum
@@ -237,8 +237,8 @@ golang.org/x/arch v0.4.0 h1:A8WCeEWhLwPBKNbFi5Wv5UTCBx5zzubnXDlMOFAzFMc=
 golang.org/x/arch v0.4.0/go.mod h1:5om86z9Hs0C8fWVUuoMHwpExlXzs5Tkyp9hOrfG7pp8=
 golang.org/x/crypto v0.0.0-20190308221718-c2843e01d9a2/go.mod h1:djNgcEr1/C05ACkg1iLfiJU5Ep61QUkGW8qpdssI0+w=
 golang.org/x/crypto v0.0.0-20191011191535-87dc89f01550/go.mod h1:yigFU9vqHzYiE8UmvKecakEJjdnWj3jj499lnFckfCI=
-golang.org/x/crypto v0.55.0 h1:+KWHjbgOaAQ66dh/YlkZKHlz9ZUlq61AFirAR9ntP8M=
-golang.org/x/crypto v0.55.0/go.mod h1:uq0V9dE/fzQuJtbnL+2EhWOE63vo164FY8xqEnV9xis=
+golang.org/x/crypto v0.56.0 h1:GUh5Ii4J5jtcseSMiRqr1jXCNHoxjeV9Fmekc2oLy6Y=
+golang.org/x/crypto v0.56.0/go.mod h1:OMW5y6CY9l38uPLmxU6l6pwcXp1obtLo3e6gT7gQR2I=
 golang.org/x/lint v0.0.0-20200302205851-738671d3881b/go.mod h1:3xt1FjdF8hUf6vQPIChWIBhFzV8gjjsPE/fR3IyQdNY=
 golang.org/x/mod v0.1.1-0.20191105210325-c90efee705ee/go.mod h1:QqPTAvyqsEbceGzBzNggFXnrqF1CaUcvgkdR5Ot7KZg=
 golang.org/x/net v0.0.0-20190404232315-eb5bcb51f2a3/go.mod h1:t9HGtf8HONx5eT2rtn7q6eTqICYqUVnKs3thJo3Qplg=