diff --git a/bin/docker-compose b/bin/docker-compose
index 4111c803827..ef450980ddf 100755
--- a/bin/docker-compose
+++ b/bin/docker-compose
@@ -49,6 +49,50 @@ SHELLHUB_POSTGRES_EXTERNAL=$(env_var SHELLHUB_POSTGRES_EXTERNAL false)
 SHELLHUB_BILLING=$(env_var SHELLHUB_BILLING "")
 EXTRA_COMPOSE_FILE=${EXTRA_COMPOSE_FILE:-$(env_var EXTRA_COMPOSE_FILE "")}
 
+sbin_path="$PATH:/usr/sbin:/sbin"
+
+daemon_is_rootless() {
+    docker info --format '{{.SecurityOptions}}' 2>/dev/null | grep -q 'name=rootless'
+}
+
+daemon_socket() {
+    docker_host=${DOCKER_HOST:-$(docker context inspect --format '{{.Endpoints.docker.Host}}' 2>/dev/null || true)}
+    case "$docker_host" in
+        unix://*) echo "${docker_host#unix://}" ;;
+    esac
+}
+
+rootlesskit_capabilities() {
+    rootlesskit=$(command -v rootlesskit 2>/dev/null || true)
+    PATH="$sbin_path" getcap "$rootlesskit" 2>/dev/null
+}
+
+lowest_published_port() {
+    http_port=$(env_var SHELLHUB_HTTP_PORT 80)
+    ssh_port=$(env_var SHELLHUB_SSH_PORT 22)
+    ssh_port=${ssh_port##*:}
+    [ "$ssh_port" -lt "$http_port" ] && echo "$ssh_port" || echo "$http_port"
+}
+
+if [ "$SHELLHUB_ENV" = "development" ] && daemon_is_rootless; then
+    socket=$(daemon_socket)
+    [ -z "$socket" ] || export SHELLHUB_DEV_DOCKER_SOCKET="$socket"
+
+    port=$(lowest_published_port)
+    unprivileged_start=$(PATH="$sbin_path" sysctl -n net.ipv4.ip_unprivileged_port_start 2>/dev/null || echo 1024)
+    if [ "$port" -lt "$unprivileged_start" ]; then
+        capabilities=$(rootlesskit_capabilities) && getcap_status=0 || getcap_status=$?
+        if [ "$getcap_status" -eq 127 ]; then
+            echo "⚠️ WARNING: getcap not found, cannot tell whether rootless Docker may publish port $port." >&2
+        elif ! echo "$capabilities" | grep -q 'cap_net_bind_service'; then
+            echo "🚫 ERROR: rootless Docker cannot publish port $port. Either grant rootlesskit the capability:" >&2
+            echo "    sudo setcap cap_net_bind_service=ep \"\$(command -v rootlesskit)\" && systemctl --user restart docker" >&2
+            echo "  or set SHELLHUB_HTTP_PORT and SHELLHUB_SSH_PORT to $unprivileged_start or above in .env.override." >&2
+            exit 1
+        fi
+    fi
+fi
+
 # COMPOSE_ENV_FILES — last file wins. Order chosen so that:
 #   - CE defaults are the base
 #   - enterprise defaults augment when edition is enterprise or cloud
diff --git a/docker-compose.dev.yml b/docker-compose.dev.yml
index 2adb73805ea..bc5a22bb01c 100644
--- a/docker-compose.dev.yml
+++ b/docker-compose.dev.yml
@@ -13,13 +13,14 @@ services:
       - ./pkg:/go/src/github.com/shellhub-io/shellhub/pkg
       - ./openapi:/go/src/github.com/shellhub-io/shellhub/openapi
       - ./tests:/go/src/github.com/shellhub-io/shellhub/tests
-      - /var/run/docker.sock:/var/run/docker.sock
+      - ${SHELLHUB_DEV_DOCKER_SOCKET:-/var/run/docker.sock}:/var/run/docker.sock
       - ./.golangci.yaml:/.golangci.yaml
       - ./.mockery.yaml:/go/src/github.com/shellhub-io/shellhub/.mockery.yaml
       - ./go.sum:/go/src/github.com/shellhub-io/shellhub/go.sum
       - ./install.sh:/go/src/github.com/shellhub-io/shellhub/install.sh
     environment:
       - TESTCONTAINERS_DOCKER_NETWORK=${SHELLHUB_NETWORK}
+      - TESTCONTAINERS_DOCKER_SOCKET_OVERRIDE=${SHELLHUB_DEV_DOCKER_SOCKET:-/var/run/docker.sock}
       - SHELLHUB_EDITION=${SHELLHUB_EDITION}
       - SHELLHUB_ENV=${SHELLHUB_ENV}
   ui:
diff --git a/tests/compose/helpers.bash b/tests/compose/helpers.bash
index b060a6f0e0c..6b5f7f52aed 100644
--- a/tests/compose/helpers.bash
+++ b/tests/compose/helpers.bash
@@ -8,11 +8,8 @@
 
 REPO_ROOT="$(cd "$(dirname "${BASH_SOURCE[0]}")/../.." && pwd -P)"
 
-unset EXTRA_COMPOSE_FILE
+unset EXTRA_COMPOSE_FILE DOCKER_HOST SHELLHUB_DEV_DOCKER_SOCKET
 
-# Run the wrapper with the given override variables written to a tmpfile,
-# while replacing `docker` in PATH with a stub that just echoes the env
-# the wrapper exported.
 # Usage: capture_with VAR1=value VAR2=value ...
 capture_with() {
     local stub_dir="$BATS_TEST_TMPDIR/stub"
@@ -20,11 +17,33 @@ capture_with() {
         mkdir -p "$stub_dir"
         cat > "$stub_dir/docker" <<'EOF'
 #!/bin/sh
-echo "COMPOSE_FILE=$COMPOSE_FILE"
-echo "COMPOSE_ENV_FILES=$COMPOSE_ENV_FILES"
-echo "COMPOSE_PROFILES=$COMPOSE_PROFILES"
+case "$1" in
+    context)
+        echo "${STUB_DOCKER_ENDPOINT:-unix:///var/run/docker.sock}"
+        ;;
+    info)
+        [ -z "${STUB_DOCKER_INFO_FAILS:-}" ] || exit 1
+        echo "[${STUB_DOCKER_SECURITY:-name=seccomp,profile=builtin name=cgroupns}]"
+        ;;
+    *)
+        echo "COMPOSE_FILE=$COMPOSE_FILE"
+        echo "COMPOSE_ENV_FILES=$COMPOSE_ENV_FILES"
+        echo "COMPOSE_PROFILES=$COMPOSE_PROFILES"
+        echo "SHELLHUB_DEV_DOCKER_SOCKET=$SHELLHUB_DEV_DOCKER_SOCKET"
+        ;;
+esac
 EOF
-        chmod +x "$stub_dir/docker"
+        cat > "$stub_dir/getcap" <<'EOF'
+#!/bin/sh
+[ -z "${STUB_NO_GETCAP:-}" ] || exit 127
+[ -z "${STUB_GETCAP:-}" ] || echo "$1 $STUB_GETCAP"
+EOF
+        cat > "$stub_dir/sysctl" <<'EOF'
+#!/bin/sh
+echo "${STUB_SYSCTL_UNPRIVILEGED_PORT_START:-1024}"
+EOF
+        : > "$stub_dir/rootlesskit"
+        chmod +x "$stub_dir"/*
     fi
 
     local tmp
diff --git a/tests/compose/wrapper.bats b/tests/compose/wrapper.bats
index 2a16b7f0c51..902c7032037 100644
--- a/tests/compose/wrapper.bats
+++ b/tests/compose/wrapper.bats
@@ -97,3 +97,103 @@ load helpers
     out=$(capture_with SHELLHUB_POSTGRES_EXTERNAL=false)
     [[ "$out" == *"docker-compose.postgres.yml"* ]]
 }
+
+@test "docker socket: a rootful daemon leaves the variable unset" {
+    export STUB_DOCKER_ENDPOINT=unix:///home/dev/.docker/run/docker.sock
+    out=$(capture_with SHELLHUB_ENV=development)
+    grep -qx 'SHELLHUB_DEV_DOCKER_SOCKET=' <<< "$out"
+}
+
+@test "docker socket: a rootless daemon resolves to the context's socket" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_DOCKER_ENDPOINT=unix:///run/user/1000/docker.sock
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=8080 SHELLHUB_SSH_PORT=2222)
+    [[ "$out" == *"SHELLHUB_DEV_DOCKER_SOCKET=/run/user/1000/docker.sock"* ]]
+}
+
+@test "docker socket: DOCKER_HOST with a unix socket wins over the context" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_DOCKER_ENDPOINT=unix:///run/user/1000/docker.sock
+    out=$(DOCKER_HOST=unix:///tmp/other.sock capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=8080 SHELLHUB_SSH_PORT=2222)
+    [[ "$out" == *"SHELLHUB_DEV_DOCKER_SOCKET=/tmp/other.sock"* ]]
+}
+
+@test "docker socket: DOCKER_HOST with tcp leaves the variable unset" {
+    export STUB_DOCKER_SECURITY="name=rootless"
+    out=$(DOCKER_HOST=tcp://10.0.0.1:2375 capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=8080 SHELLHUB_SSH_PORT=2222)
+    grep -qx 'SHELLHUB_DEV_DOCKER_SOCKET=' <<< "$out"
+}
+
+@test "docker socket: not resolved outside development" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_DOCKER_ENDPOINT=unix:///run/user/1000/docker.sock
+    out=$(capture_with)
+    grep -qx 'SHELLHUB_DEV_DOCKER_SOCKET=' <<< "$out"
+}
+
+@test "rootless guard: a privileged port without the capability aborts and names setcap" {
+    export STUB_DOCKER_SECURITY="name=rootless name=seccomp,profile=builtin"
+    run capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=80
+    [ "$status" -ne 0 ]
+    [[ "$output" == *"setcap cap_net_bind_service=ep"* ]]
+}
+
+@test "rootless guard: the ssh port counts too" {
+    export STUB_DOCKER_SECURITY="name=rootless"
+    run capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=8080 SHELLHUB_SSH_PORT=22
+    [ "$status" -ne 0 ]
+    [[ "$output" == *"port 22"* ]]
+}
+
+@test "rootless guard: the ssh port keeps its bind address out of the comparison" {
+    export STUB_DOCKER_SECURITY="name=rootless"
+    run capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=8080 SHELLHUB_SSH_PORT=127.0.0.1:22
+    [ "$status" -ne 0 ]
+    [[ "$output" == *"port 22"* ]]
+}
+
+@test "rootless guard: a missing getcap warns and lets the stack start" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_NO_GETCAP=1
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=80)
+    [[ "$out" == *"getcap not found"* ]]
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}
+
+@test "rootless guard: the capability on rootlesskit lets a privileged port through" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_GETCAP="cap_net_bind_service=ep"
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=80)
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}
+
+@test "rootless guard: a sysctl that frees the port lets it through" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_SYSCTL_UNPRIVILEGED_PORT_START=0
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=80 SHELLHUB_SSH_PORT=22)
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}
+
+@test "rootless guard: a sysctl above 1024 makes a higher port privileged too" {
+    export STUB_DOCKER_SECURITY="name=rootless" STUB_SYSCTL_UNPRIVILEGED_PORT_START=2048
+    run capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=1500 SHELLHUB_SSH_PORT=2222
+    [ "$status" -ne 0 ]
+    [[ "$output" == *"port 1500"* ]]
+}
+
+@test "rootless guard: unprivileged ports pass" {
+    export STUB_DOCKER_SECURITY="name=rootless"
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=8080 SHELLHUB_SSH_PORT=2222)
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}
+
+@test "rootless guard: a rootful daemon ignores privileged ports" {
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=80)
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}
+
+@test "rootless guard: only in development" {
+    export STUB_DOCKER_SECURITY="name=rootless"
+    out=$(capture_with SHELLHUB_HTTP_PORT=80)
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}
+
+@test "rootless guard: a failing docker info skips the guard" {
+    export STUB_DOCKER_INFO_FAILS=1
+    out=$(capture_with SHELLHUB_ENV=development SHELLHUB_HTTP_PORT=80)
+    [[ "$out" == *"COMPOSE_FILE="* ]]
+}