diff --git a/deployments/simplex/backup.sh b/deployments/simplex/backup.sh
index c5e8271..cf43301 100644
--- a/deployments/simplex/backup.sh
+++ b/deployments/simplex/backup.sh
@@ -98,6 +98,7 @@ TARGETS=(
     # Current environment and docker-compose setup
     "$SIMPLEX_DIR/.env"
     "$SIMPLEX_DIR/docker-compose.yml"
+    "$SIMPLEX_DIR/caddy_conf/Caddyfile"
     "$SIMPLEX_DIR/print-addresses.sh"
     
     # Tor configs
diff --git a/deployments/simplex/deploy-simplex.sh b/deployments/simplex/deploy-simplex.sh
index 66e5b47..38c0685 100644
--- a/deployments/simplex/deploy-simplex.sh
+++ b/deployments/simplex/deploy-simplex.sh
@@ -221,7 +221,7 @@ done
 # 5. Lay out /opt/simplex
 # ----------------------------------------------------------------------------
 log "Writing compose stack to ${INSTALL_DIR}..."
-mkdir -p "$INSTALL_DIR"/tor_conf
+mkdir -p "$INSTALL_DIR"/tor_conf "$INSTALL_DIR"/caddy_conf
 cd "$INSTALL_DIR"
 
 cat > .env <<EOF
@@ -235,53 +235,56 @@ CERT_PATH=${CERT_PATH}
 EOF
 chmod 600 .env
 
+# Caddyfile. This used to be produced by a caddy-init container whose `command:`
+# was a YAML FOLDED scalar (`>`): the closing `}` and the heredoc's `EOF` were
+# both at the scalar's base indent, so YAML folded them into `} EOF`, leaving the
+# heredoc unterminated and the script a parse error. caddy-init exited 2 on every
+# run, `service_completed_successfully` never fired, and nothing downstream of
+# caddy ever started. Generating the file here removes the whole class of problem
+# -- and, unlike the old `if [ ! -f ]` guard, applies a changed DOMAIN/ACME_EMAIL/
+# KEY_TYPE on a re-run instead of freezing them at the first deploy.
+#
+# The heredoc is deliberately UNQUOTED so ${DOMAIN}/${ACME_EMAIL}/${KEY_TYPE}
+# expand here. Caddy's own {uri} has no `$` so it survives; any future Caddy
+# {$ENV} placeholder must be escaped as \${...}.
+CADDY_CHANGED=0
+cat > caddy_conf/Caddyfile.new <<EOF
+{
+  email ${ACME_EMAIL}
+}
+
+http://smp.${DOMAIN} {
+  redir https://smp.${DOMAIN}{uri} permanent
+}
+
+smp.${DOMAIN}:8443 {
+  tls { key_type ${KEY_TYPE} }
+  reverse_proxy smp-server:8000
+}
+
+http://xftp.${DOMAIN} {
+  redir https://xftp.${DOMAIN}{uri} permanent
+}
+
+xftp.${DOMAIN}:8443 {
+  tls { key_type ${KEY_TYPE} }
+  reverse_proxy xftp-server:8000
+}
+EOF
+# `cmp -s` exits 1 when the files differ, so it stays inside an `if` condition --
+# never `cmp -s A B && CADDY_CHANGED=1`, which trips set -e when they match.
+if [[ -f caddy_conf/Caddyfile ]] && ! cmp -s caddy_conf/Caddyfile caddy_conf/Caddyfile.new; then
+    CADDY_CHANGED=1
+fi
+mv -f caddy_conf/Caddyfile.new caddy_conf/Caddyfile
+chmod 0644 caddy_conf/Caddyfile
+
 cat > docker-compose.yml <<'YAML'
 name: simplex
 
 services:
-  caddy-init:
-    image: alpine:latest
-    command: >
-      sh -c '
-        if [ ! -f /etc/caddy/Caddyfile ]; then
-          cat > /etc/caddy/Caddyfile <<EOF
-      {
-        email ${ACME_EMAIL}
-      }
-
-      http://smp.${DOMAIN} {
-        redir https://smp.${DOMAIN}{uri} permanent
-      }
-
-      smp.${DOMAIN}:8443 {
-        tls { key_type ${KEY_TYPE} }
-        reverse_proxy smp-server:8000
-      }
-
-      http://xftp.${DOMAIN} {
-        redir https://xftp.${DOMAIN}{uri} permanent
-      }
-
-      xftp.${DOMAIN}:8443 {
-        tls { key_type ${KEY_TYPE} }
-        reverse_proxy xftp-server:8000
-      }
-      EOF
-        fi
-      '
-    environment:
-      DOMAIN: ${DOMAIN:?}
-      ACME_EMAIL: ${ACME_EMAIL:?}
-      KEY_TYPE: ${KEY_TYPE:-rsa4096}
-    volumes:
-      - ./caddy_conf:/etc/caddy
-    restart: "no"
-
   caddy:
     image: caddy:2-alpine
-    depends_on:
-      caddy-init:
-        condition: service_completed_successfully
     cap_add:
       - NET_ADMIN
     ports:
@@ -494,7 +497,18 @@ rc-update add simplex default
 log "Pulling images and starting the stack..."
 cd "$INSTALL_DIR"
 docker compose pull
+# A bind-mounted file's CONTENTS are not part of the compose config hash, so a
+# changed Caddyfile does not by itself cause a recreate and `up -d` would leave
+# it unloaded. Only restart when it actually changed AND compose did not already
+# replace the container -- restarting Caddy seconds after a first start would
+# interrupt the initial ACME issuance for nothing.
+_caddy_before="$(docker compose ps -q caddy 2>/dev/null || true)"
 docker compose up -d
+_caddy_after="$(docker compose ps -q caddy 2>/dev/null || true)"
+if (( CADDY_CHANGED )) && [[ -n "$_caddy_before" && "$_caddy_before" == "$_caddy_after" ]]; then
+    log "Caddyfile changed; restarting Caddy to load it..."
+    docker compose restart caddy || warn "Could not restart Caddy; run: cd $INSTALL_DIR && docker compose restart caddy"
+fi
 
 log "Waiting up to 90s for Tor to publish hidden services..."
 for _ in $(seq 1 90); do
diff --git a/deployments/simplex/restore.sh b/deployments/simplex/restore.sh
index b5759b8..f7ff471 100644
--- a/deployments/simplex/restore.sh
+++ b/deployments/simplex/restore.sh
@@ -238,6 +238,7 @@ SIMPLEX_FILES=(
     "docker-compose.yml" 
     "print-addresses.sh"
     "tor_conf/"
+    "caddy_conf/"
 )
 
 for item in "${SIMPLEX_FILES[@]}"; do