diff --git a/www/caddy/Makefile b/www/caddy/Makefile
index 78ebc97e544d..cc999d13b787 100644
--- a/www/caddy/Makefile
+++ b/www/caddy/Makefile
@@ -1,37 +1,40 @@
 PORTNAME=	caddy
 DISTVERSIONPREFIX=	v
 DISTVERSION=	2.7.5
 CATEGORIES=	www
 DIST_SUBDIR=	caddy
 
 MAINTAINER=	adamw@FreeBSD.org
 COMMENT=	Fast, cross-platform HTTP/2 web server with automatic HTTPS
 WWW=		https://caddyserver.com
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 USES=		cpe go:modules
 CPE_VENDOR=	caddyserver
 
+USERS=		www
+GROUPS=		www
+
 USE_RC_SUBR=	caddy
 SUB_FILES=	Caddyfile.sample caddy pkg-message
 
 CONFLICTS_INSTALL=	caddy-custom
 
 PLIST_FILES=	bin/${PORTNAME} \
 		"@sample ${ETCDIR_REL}/Caddyfile.sample"
 
 GO_BUILDFLAGS+=	-ldflags='-X github.com/caddyserver/caddy/v2.CustomVersion=${DISTVERSIONFULL}'
 
 GO_TARGET=	./cmd/caddy
 # If go.mod is sufficient:
 GO_MODULE=	github.com/caddyserver/caddy/v2
 # If modules must be specified manually:
 #.include "${.CURDIR}/modules.mk"
 
 post-install:
 	${MKDIR} ${STAGEDIR}${ETCDIR}
 	${INSTALL_DATA} ${WRKDIR}/Caddyfile.sample ${STAGEDIR}${ETCDIR}
 
 .include <bsd.port.mk>
diff --git a/www/caddy/files/caddy.in b/www/caddy/files/caddy.in
index 8e46cd93aae9..37babe7889d3 100644
--- a/www/caddy/files/caddy.in
+++ b/www/caddy/files/caddy.in
@@ -1,135 +1,164 @@
 #!/bin/sh
 
 # PROVIDE: caddy
 # REQUIRE: LOGIN DAEMON NETWORKING
 # KEYWORD: shutdown
 
-# To enable caddy, add 'caddy_enable="YES"' to /etc/rc.conf or
-# /etc/rc.conf.local
+# To enable caddy:
+#
+# - Edit %%ETCDIR%%/Caddyfile
+#   See https://caddyserver.com/docs/
+# - Run 'service enable caddy'
+#
+# Note while Caddy currently defaults to running as root:wheel, it is strongly
+# recommended to run the server as an unprivileged user, such as www:www.
+#
+# - Use security/portacl-rc to enable privileged port binding:
+#
+#   # pkg install security/portacl-rc
+#   # sysrc portacl_users+=www
+#   # sysrc portacl_user_www_tcp="http https"
+#   # sysrc portacl_user_www_udp="https"
+#   # service portacl enable
+#   # service portacl start
+#
+# - Configure caddy to run as www:www
+#
+#   # sysrc caddy_user=www caddy_group=www
+#
+# - Note if Caddy has been started as root previously, files in
+#   /var/log/caddy, /var/db/caddy, and /var/run/caddy may require their ownership
+#   changing manually.
 
 # Optional settings:
 # caddy_command (string):     Full path to the caddy binary
 # caddy_config (string):      Full path to caddy config file
 #                             (%%ETCDIR%%/Caddyfile)
 # caddy_adapter (string):     Config adapter type (caddyfile)
+# caddy_admin (string):       Default administration endpoint
+#                             (unix//var/run/caddy/caddy.sock)
 # caddy_directory (string):   Root for caddy storage (ACME certs, etc.)
 #                             (/var/db/caddy)
 # caddy_extra_flags (string): Extra flags passed to caddy start
 # caddy_logdir (string):      Where caddy logs are stored
 #                             (/var/log/caddy)
 # caddy_logfile (string):     Location of process log (${caddy_logdir}/caddy.log)
 #                             This is for startup/shutdown/error messages.
 #                             To create an access log, see:
 #                             https://caddyserver.com/docs/caddyfile/directives/log
 # caddy_user (user):          User to run caddy (root)
 # caddy_group (group):        Group to run caddy (wheel)
 #
 # This script will honor XDG_CONFIG_HOME/XDG_DATA_HOME. Caddy will create a
 # .../caddy subdir in each of those. By default, they are subdirs of /var/db/caddy.
 # See https://caddyserver.com/docs/conventions#data-directory
 
 . /etc/rc.subr
 
 name=caddy
 rcvar=caddy_enable
 desc="Powerful, enterprise-ready, open source web server with automatic HTTPS written in Go"
 
 load_rc_config $name
 
 # Defaults
 : ${caddy_enable:=NO}
 : ${caddy_adapter:=caddyfile}
 : ${caddy_config:="%%ETCDIR%%/Caddyfile"}
+: ${caddy_admin:="unix//var/run/${name}/${name}.sock"}
 : ${caddy_command:="%%PREFIX%%/bin/${name}"}
 : ${caddy_directory:=/var/db/caddy}
 : ${caddy_extra_flags:=""}
 : ${caddy_logdir:="/var/log/${name}"}
 : ${caddy_logfile:="${caddy_logdir}/${name}.log"}
 : ${caddy_user:="root"}
 : ${caddy_group:="wheel"}
 
 # Config and base directories
 : ${XDG_CONFIG_HOME:="${caddy_directory}/config"}
 : ${XDG_DATA_HOME:="${caddy_directory}/data"}
 export XDG_CONFIG_HOME XDG_DATA_HOME
 
+# Default admin interface
+export CADDY_ADMIN="${caddy_admin}"
+
 command="${caddy_command}"
 pidfile="/var/run/${name}/${name}.pid"
 
 required_files="${caddy_config} ${caddy_command}"
 
 start_precmd="caddy_precmd"
 start_cmd="caddy_start"
 stop_precmd="caddy_prestop"
 
 # JSON is the native format, so there is no "adapter" for it
 if [ "${caddy_adapter}" = "json" ]; then
     caddy_flags="--config ${caddy_config}"
 else
     caddy_flags="--config ${caddy_config} --adapter ${caddy_adapter}"
 fi
 
 # Extra Commands
 extra_commands="configtest reload reloadssl"
 configtest_cmd="caddy_execute validate ${caddy_flags}"
 reload_cmd="caddy_execute reload ${caddy_flags}"
 reloadssl_cmd="caddy_execute reload --force ${caddy_flags}"
 
 caddy_execute()
 {
     /usr/bin/su -m "${caddy_user}" -c "${caddy_command} $*"
 }
 
 caddy_precmd()
 {
     # Create required directories and set permissions
     /usr/bin/install -d -m 755 -o "${caddy_user}" -g "${caddy_group}" ${caddy_directory}
     /usr/bin/install -d -m 700 -o "${caddy_user}" -g "${caddy_group}" ${caddy_directory}/config
     /usr/bin/install -d -m 700 -o "${caddy_user}" -g "${caddy_group}" ${caddy_directory}/data
     /usr/bin/install -d -m 755 -o "${caddy_user}" -g "${caddy_group}" ${caddy_logdir}
     /usr/bin/install -d -m 700 -o "${caddy_user}" -g "${caddy_group}" /var/run/caddy
     if [ -e ${caddy_logfile} ]; then
         /bin/chmod 644 ${caddy_logfile}
         /usr/sbin/chown root:wheel ${caddy_logfile}
     else
         /usr/bin/install -m 644 -o root -g wheel /dev/null ${caddy_logfile}
     fi
 }
 
 caddy_start()
 {
     echo -n "Starting caddy... "
     /usr/bin/su -m ${caddy_user} -c "${caddy_command} start ${caddy_flags} \
         ${caddy_extra_flags} --pidfile ${pidfile}" >> ${caddy_logfile} 2>&1
     if [ $? -eq 0 ] && ps -ax -o pid | grep -q "$(cat ${pidfile})"; then
         echo "done"
         echo "Log: ${caddy_logfile}"
     else
         echo "Error: Caddy failed to start"
         echo "Check the caddy log: ${caddy_logfile}"
     fi
 }
 
 caddy_prestop()
 {
     local result
 
     echo -n "Stopping caddy... "
 
-    result="$(caddy_execute stop 2>&1)"
+    result="$(caddy_execute stop ${caddy_flags} 2>&1)"
     if [ ${?} -eq 0 ]; then
         echo "done"
         exit 0
     else
         if echo "${result}" | grep -q "connection refused"; then
             echo "admin interface unavailable; using pidfile"
             return 0
         else
             echo "Error: Unable to stop caddy"
             echo "Check the caddy log: ${caddy_logfile}"
             return 1
         fi
     fi
 }
 
 run_rc_command "$1"
diff --git a/www/caddy/files/pkg-message.in b/www/caddy/files/pkg-message.in
index 661e81dde602..321e6b87bc36 100644
--- a/www/caddy/files/pkg-message.in
+++ b/www/caddy/files/pkg-message.in
@@ -1,41 +1,111 @@
 [
 {
   type: install
   message: <<INSTALL
 To enable caddy:
 
 - Edit %%ETCDIR%%/Caddyfile
   See https://caddyserver.com/docs/
-- Add caddy_enable="YES" to /etc/rc.conf
+- Run 'service enable caddy'
+
+Note while Caddy currently defaults to running as root:wheel, it is strongly
+recommended to run the server as an unprivileged user, such as www:www --
+
+- Use security/portacl-rc to enable privileged port binding:
+
+  # pkg install security/portacl-rc
+  # sysrc portacl_users+=www
+  # sysrc portacl_user_www_tcp="http https"
+  # sysrc portacl_user_www_udp="https"
+  # service portacl enable
+  # service portacl start
+
+- Configure caddy to run as www:www
+
+  # sysrc caddy_user=www caddy_group=www
+
+- Note if Caddy has been started as root previously, files in
+  /var/log/caddy, /var/db/caddy, and /var/run/caddy may require their ownership
+  changing manually.
 
 %%PREFIX%%/etc/rc.d/caddy has the following defaults:
 
 - Server log: /var/log/caddy/caddy.log
   (runtime messages, NOT an access.log)
 - Automatic SSL certificate storage: /var/db/caddy/data/caddy/
-- Runs as root:wheel (you can run as another user, like www,
-  but caddy will be unable to bind to low-numbered ports,
-  including 80 and 443)
+- Administration endpoint: //unix/var/run/caddy/caddy.sock
+- Runs as root:wheel (this will change to www:www in the future)
 
 INSTALL
 }
 {
   type: upgrade
-  maximum_version: 2.3.0
+  maximum_version: "2.3.0"
   message: <<UPGRADE
 The default locations for caddy runtime files have changed!
 
 - Caddy's runtime log is now /var/log/caddy/caddy.log
   (was /var/log/caddy.log)
 
 - Automatic SSL certs are now stored in /var/db/caddy/data/caddy
   (was /root/.local/share/caddy)
 
 - Configuration autosaves are now stored in /var/db/caddy/config/caddy
   (was /root/.config/caddy)
 
 You can change these defaults. See %%PREFIX%%/etc/rc.d/caddy
 
+UPGRADE
+}
+{
+  type: upgrade
+  maximum_version: "2.7.4_2"
+  message: <<UPGRADE
+The default Caddy administration endpoint location has been changed from
+localhost:2019 to a protected Unix domain socket located in
+/var/run/caddy/caddy.sock
+
+This can be overridden with the `caddy_admin` rc variable, or by specifiying
+an alternative in the Caddyfile `admin` section, documented here:
+
+  https://caddyserver.com/docs/caddyfile/options#admin
+
+The previous default, particularly paired with the server running as root,
+may have serious security implications for shared machines with untrusted
+users.
+
+UPGRADE
+}
+{
+  type: upgrade
+  message: <<UPGRADE
+It is STRONGLY RECOMMENDED to run Caddy as an unprivileged user, such as
+www:www, rather than the current default of root:wheel.
+
+If you have relied upon earlier defaults:
+
+- Use security/portacl-rc to enable privileged port binding:
+
+  # pkg install security/portacl-rc
+  # sysrc portacl_users+=www
+  # sysrc portacl_user_www_tcp="http https"
+  # sysrc portacl_user_www_udp="https"
+  # service portacl enable
+  # service portacl start
+
+- Stop the server, and update ownership on Caddy runtime files:
+
+  # service caddy stop
+  # chown -r www:www /var/db/caddy /var/log/caddy /var/run/caddy
+
+Other changes may be necessary depending on your exact Caddy
+configuration.
+
+- Change the default runtime user, and restart the server:
+
+  # sysrc caddy_user=www caddy_group=www
+  # service caddy start
+
 UPGRADE
 }
 ]