diff --git a/docs/chapters/configuration.rst b/docs/chapters/configuration.rst
index 99503016..64b39472 100644
--- a/docs/chapters/configuration.rst
+++ b/docs/chapters/configuration.rst
@@ -104,6 +104,23 @@ This is the default `bastille.conf` file.
   bastille_template_vnet="default/vnet"                                 ## default: "default/vnet"
   bastille_template_vlan="default/vlan"                                 ## default: "default/vlan"
 
+  ## Monitoring
+  bastille_monitor_cron_path="/usr/local/etc/cron.d/bastille-monitor"                           ## default: "/usr/local/etc/cron.d/bastille-monitor"
+  bastille_monitor_cron="*/5 * * * * root /usr/local/bin/bastille monitor ALL >/dev/null 2>&1"  ## default: "*/5 * * * * root /usr/local/bin/bastille monitor ALL >/dev/null 2>&1"
+  bastille_monitor_logfile="${bastille_logsdir}/monitor.log"                                    ## default: "${bastille_logsdir}/monitor.log"
+  bastille_monitor_healthchecks=""                                                              ## default: ""
+
+
+Notes
+-----
+
+The options here are fairly self-explanitory, but there are some things to note.
+
+* Bastille will mount the dataset it creates at ``bastille_prefix`` which
+  defaults to ``/usr/local/bastille``. So if you want to navigate to your jails,
+  you will use the ``bastille_prefix`` as the location because this is where the
+  will be mounted.
+
 Custom Configuration
 --------------------
 
diff --git a/docs/chapters/subcommands/index.rst b/docs/chapters/subcommands/index.rst
index ca46d87c..9139bb7e 100644
--- a/docs/chapters/subcommands/index.rst
+++ b/docs/chapters/subcommands/index.rst
@@ -23,6 +23,7 @@ Bastille sub-commands
    limits
    list
    migrate
+   monitor
    mount
    network
    pkg
diff --git a/docs/chapters/subcommands/monitor.rst b/docs/chapters/subcommands/monitor.rst
new file mode 100644
index 00000000..cd1a57a2
--- /dev/null
+++ b/docs/chapters/subcommands/monitor.rst
@@ -0,0 +1,81 @@
+monitor
+=======
+
+NEW in Bastille version 1.1.20250814
+
+The ``monitor`` sub-command adds, removes, lists and enables/disables monitoring for container services.
+
+
+Managing Bastille Monitor
+-------------------------
+
+To enable Bastille monitoring, run ``bastille monitor enable``.
+
+To disable Bastille monitoring, run ``bastille monitor disable``.
+
+We can always check if Bastille monitoring is active with ``bastille monitor status``.
+
+
+Managing Services
+-----------------
+
+Bastille Monitor will attempt to monitor any services defined for any given container. If the service is
+stopped, Bastille will attempt to restart it. Everything is logged in ``${bastille_monitor_logfile}``.
+
+To have Bastille monitor a service, run ``bastille monitor TARGET add SERVICE``. The ``SERVICE`` arg can also be a
+comma-separated list of services such as ``bastille monitor TARGET add SERVICE1,SERVICE2``.
+
+To remove a service from monitoring, we can run ``bastille monitor TARGET delete SERVICE``. These can also be a
+comma-separated list.
+
+To show all services that Bastille is monitoring, run ``bastille monitor TARGET list``.
+
+To list all jails that have a selected service defined for monitoring, run ``bastille monitor TARGET list SERVICE``.
+This option only accepts a single ``SERVICE``, and cannot be a comma-separated list.
+
+If you run ``bastille monitor TARGET``, without any args or actions, Bastille will run through the process of
+checking the status of each defined service, and attempt to start any that are stopped.
+
+Services can also be manually added or removed by editing the ``monitor`` file inside the jail directory, but
+is not recommended unless you are an advanced user.
+
+
+Configuration
+-------------
+
+The monitor sub-command is configurable via the ``bastille.conf`` file. See below
+for configuration defaults:
+
+.. code-block:: shell
+
+  bastille_monitor_cron_path="/usr/local/etc/cron.d/bastille-monitor"
+  bastille_monitor_cron="*/5 * * * * root /usr/local/bin/bastille monitor ALL >/dev/null 2&>1"
+  bastille_monitor_logfile="${bastille_logsdir}/monitor.log"
+  bastille_monitor_healthchecks=""
+
+
+Alerting modules
+----------------
+
+The first alerting module to be supported is Health Checks
+(https://healthchecks.io), which is both a free SaaS service (up to 20 checks)
+and provides a self-hosted option (see ``sysutils/py-healthchecks``).
+
+Simply configure the ``${bastille_monitor_healthchecks}`` variable with your Ping
+URL and you're done!
+
+
+Help
+----
+
+.. code-block:: shell
+
+    ishmael ~ # bastille monitor help
+    Usage: bastille monitor [option(s)] enable|disable|status
+                                        TARGET add|delete|list service1,service2
+                                        TARGET list [service]
+                                        TARGET
+
+      Options:
+
+      -x | --debug      Enable debug mode.
diff --git a/docs/chapters/usage.rst b/docs/chapters/usage.rst
index 2221de3e..774e0ed1 100644
--- a/docs/chapters/usage.rst
+++ b/docs/chapters/usage.rst
@@ -30,6 +30,7 @@ Usage
     limits      Apply resources limits to jail(s). See rctl(8) and cpuset(1).
     list        List jails, releases, templates and more...
     migrate     Migrate jail(s) to a remote system.
+    monitor     Monitor and attempt to restart jail service(s).
     mount       Mount file(s)/directorie(s) inside jail(s).
     network     Add or remove interface(s) from jail(s).
     pkg         Manage packages inside jail(s). See pkg(8).
@@ -53,4 +54,4 @@ Usage
 
   Use "bastille -v|--version" for version information.
   Use "bastille command -h|--help" for more information about a command.
-  Use "bastille -c|--config FILE command" to specify a non-default config file.
\ No newline at end of file
+  Use "bastille -c|--config FILE command" to specify a non-default config file.
diff --git a/usr/local/bin/bastille b/usr/local/bin/bastille
index 4bea13cb..05a7edc9 100755
--- a/usr/local/bin/bastille
+++ b/usr/local/bin/bastille
@@ -95,6 +95,7 @@ Available Commands:
   limits      Apply resources limits to jail(s). See rctl(8) and cpuset(1).
   list        List jails, releases, templates and more...
   migrate     Migrate jail(s) to a remote system.
+  monitor     Monitor and attempt to restart jail service(s).
   mount       Mount file(s)/directorie(s) inside jail(s).
   network     Add or remove interface(s) from jail(s).
   pkg         Manage packages inside jail(s). See pkg(8).
@@ -204,6 +205,7 @@ case "${CMD}" in
     limits| \
     list| \
     migrate| \
+    monitor| \
     mount| \
     network| \
     pkg| \
diff --git a/usr/local/etc/bastille/bastille.conf.sample b/usr/local/etc/bastille/bastille.conf.sample
index 9a571b38..561b4d77 100644
--- a/usr/local/etc/bastille/bastille.conf.sample
+++ b/usr/local/etc/bastille/bastille.conf.sample
@@ -88,3 +88,9 @@ bastille_template_clone="default/clone"                               ## default
 bastille_template_thin="default/thin"                                 ## default: "default/thin"
 bastille_template_vnet="default/vnet"                                 ## default: "default/vnet"
 bastille_template_vlan="default/vlan"                                 ## default: "default/vlan"
+
+## Monitoring
+bastille_monitor_cron_path="/usr/local/etc/cron.d/bastille-monitor"   ## default: "/usr/local/etc/cron.d/bastille-monitor"
+bastille_monitor_cron="*/5 * * * * root /usr/local/bin/bastille monitor ALL >/dev/null 2>&1"  # default: "*/5 * * * * root /usr/local/bin/bastille monitor ALL >/dev/null 2>&1"
+bastille_monitor_logfile="${bastille_logsdir}/monitor.log"            ## default: "${bastille_logsdir}/monitor.log"
+bastille_monitor_healthchecks=""                                      ## default: ""
diff --git a/usr/local/share/bastille/monitor.sh b/usr/local/share/bastille/monitor.sh
new file mode 100644
index 00000000..e46611e5
--- /dev/null
+++ b/usr/local/share/bastille/monitor.sh
@@ -0,0 +1,196 @@
+#!/bin/sh
+#
+# SPDX-License-Identifier: BSD-3-Clause
+#
+# Copyright (c) 2018-2025, Christer Edwards <christer.edwards@gmail.com>
+# All rights reserved.
+# Ressource limits added by Lars Engels github.com/bsdlme
+#
+# Redistribution and use in source and binary forms, with or without
+# modification, are permitted provided that the following conditions are met:
+#
+# * Redistributions of source code must retain the above copyright notice, this
+#   list of conditions and the following disclaimer.
+#
+# * Redistributions in binary form must reproduce the above copyright notice,
+#   this list of conditions and the following disclaimer in the documentation
+#   and/or other materials provided with the distribution.
+#
+# * Neither the name of the copyright holder nor the names of its
+#   contributors may be used to endorse or promote products derived from
+#   this software without specific prior written permission.
+#
+# THIS SOFTWARE IS PROVIDED BY THE COPYRIGHT HOLDERS AND CONTRIBUTORS "AS IS"
+# AND ANY EXPRESS OR IMPLIED WARRANTIES, INCLUDING, BUT NOT LIMITED TO, THE
+# IMPLIED WARRANTIES OF MERCHANTABILITY AND FITNESS FOR A PARTICULAR PURPOSE ARE
+# DISCLAIMED. IN NO EVENT SHALL THE COPYRIGHT HOLDER OR CONTRIBUTORS BE LIABLE
+# FOR ANY DIRECT, INDIRECT, INCIDENTAL, SPECIAL, EXEMPLARY, OR CONSEQUENTIAL
+# DAMAGES (INCLUDING, BUT NOT LIMITED TO, PROCUREMENT OF SUBSTITUTE GOODS OR
+# SERVICES; LOSS OF USE, DATA, OR PROFITS; OR BUSINESS INTERRUPTION) HOWEVER
+# CAUSED AND ON ANY THEORY OF LIABILITY, WHETHER IN CONTRACT, STRICT LIABILITY,
+# OR TORT (INCLUDING NEGLIGENCE OR OTHERWISE) ARISING IN ANY WAY OUT OF THE USE
+# OF THIS SOFTWARE, EVEN IF ADVISED OF THE POSSIBILITY OF SUCH DAMAGE.
+
+. /usr/local/share/bastille/common.sh
+
+usage() {
+    error_notify "Usage: bastille monitor [option(s)] enable|disable|status"
+    error_notify "                                    TARGET add|delete service1,service2"
+    error_notify "                                    TARGET list [service]"
+    error_notify "                                    TARGET"
+    cat << EOF
+
+    Options:
+
+    -x | --debug            Enable debug mode.
+
+EOF
+    exit 1
+}
+
+# Handle options.
+while [ "$#" -gt 0 ]; do
+    case "${1}" in
+        -h|--help|help)
+            usage
+            ;;
+        -x|--debug)
+            enable_debug
+            shift
+            ;;
+        -*)
+            error_exit "[ERROR]: Unknown Option: \"${1}\""
+            ;;
+        *)
+            break
+            ;;
+    esac
+done
+
+# Handle global actions.
+case "${1}" in
+    enable)
+        [ "$#" -eq 1 ] || usage
+        if [ ! -f "${bastille_monitor_cron_path}" ]; then
+            mkdir -p /usr/local/etc/cron.d
+            echo "${bastille_monitor_cron}" >> "${bastille_monitor_cron_path}"
+            echo "$(date '+%Y-%m-%d %H:%M:%S'): Added cron entry at ${bastille_monitor_cron_path}" >> "${bastille_monitor_logfile}"
+            info "\nBastille Monitor: Enabled\n"
+	        exit 0
+	    else
+            error_exit "\nBastille Monitor is already enabled."
+	    fi
+        ;;
+    disable)
+        [ "$#" -eq 1 ] || usage
+        if [ -f "${bastille_monitor_cron_path}" ]; then
+            rm -f "${bastille_monitor_cron_path}"
+            echo "$(date '+%Y-%m-%d %H:%M:%S'): Removed cron entry at ${bastille_monitor_cron_path}" >> "${bastille_monitor_logfile}"
+            info "\nBastille Monitor: Disabled\n"
+	        exit 0
+	    else
+            error_exit "\nBastille Monitor is not enabled."
+        fi
+        ;;
+    status)
+        [ "$#" -eq 1 ] || usage
+        if [ -f "${bastille_monitor_cron_path}" ]; then
+            info "\nBastille Monitor Status: Active\n"
+	        exit 0
+        else
+            info "\nBastille Monitor Status: Inactive\n"
+	        exit 1
+        fi
+        ;;
+esac
+
+if [ "$#" -eq 0 ]; then
+    usage
+fi
+
+TARGET="${1}"
+ACTION="${2}"
+SERVICE="${3}"
+SERVICE_FAILED=0
+
+bastille_root_check
+set_target "${TARGET}"
+
+for _jail in ${JAILS}; do
+
+    bastille_jail_monitor="${bastille_jailsdir}/${_jail}/monitor"
+
+    # Skip if jail is not running or no monitor file
+    if ! check_target_is_running "${_jail}" || [ ! -f "${bastille_jail_monitor}" ]; then
+        continue
+    fi
+
+    ## iterate service(s) and check service status; restart on failure
+    if [ -z "${ACTION}" ] && [ -f "${bastille_jail_monitor}" ]; then
+        for _service in $(xargs < "${bastille_jail_monitor}"); do
+            ## check service status
+            if ! jexec -l -U root "${_jail}" service "${_service}" status >/dev/null 2>/dev/null; then
+                echo "$(date '+%Y-%m-%d %H:%M:%S'): ${_service} service not running in ${_jail}. Restarting..." | tee -a "${bastille_monitor_logfile}"
+
+                ## attempt to restart the service if needed; update logs if unable
+                if ! jexec -l -U root "${_jail}" service "${_service}" restart; then
+                    echo "$(date '+%Y-%m-%d %H:%M:%S'): Failed to restart ${_service} service in ${_jail}." | tee -a "${bastille_monitor_logfile}"
+                    SERVICE_FAILED=1
+                fi
+            fi
+        done
+    elif [ -n "${ACTION}" ]; then
+        case ${ACTION} in
+            add)
+	            [ -z "${SERVICE}" ] && usage
+                for _service in $(echo "${SERVICE}" | tr , ' '); do
+                    if ! grep -Eqs "^${_service}\$" "${bastille_jail_monitor}"; then
+                        echo "${_service}" >> "${bastille_jail_monitor}"
+                        echo "$(date '+%Y-%m-%d %H:%M:%S'): Added monitor for ${_service} on ${_jail}" >> "${bastille_monitor_logfile}"
+                    fi
+                done
+                ;;
+            del*)
+	            [ -z "${SERVICE}" ] && usage
+                for _service in $(echo "${SERVICE}" | tr , ' '); do
+                    [ ! -f "${bastille_jail_monitor}" ] && break # skip if no monitor file
+                    if grep -Eqs "^${_service}\$" "${bastille_jail_monitor}"; then
+                        sed -i '' "/^${_service}\$/d" "${bastille_jail_monitor}"
+	                    echo "$(date '+%Y-%m-%d %H:%M:%S'): Removed monitor for ${_service} on ${_jail}" >> "${bastille_monitor_logfile}"
+		            fi
+                    # delete monitor file if empty
+                    [ ! -s "${bastille_jail_monitor}" ] && rm "${bastille_jail_monitor}"
+                done
+                ;;
+            list)
+                if [ -n "${SERVICE}" ]; then
+                    if echo "${SERVICE}" | grep ','; then
+                        usage # Only one service per query
+                    fi
+                    [ ! -f "${bastille_jail_monitor}" ] && continue # skip if there is no monitor file
+                    if grep -Eqs "^${SERVICE}\$" "${bastille_jail_monitor}"; then
+                        echo "${_jail}"
+			            continue
+                    fi
+                else
+                    if [ -f "${bastille_jail_monitor}" ]; then
+                        info "\n[${_jail}]:"
+                        xargs < "${bastille_jail_monitor}"
+                    fi
+                fi
+                ;;
+            *)
+                usage
+                ;;
+        esac
+    fi
+done
+
+# Final ping to healthcheck URL
+if [ "$SERVICE_FAILED" -eq 0 ]; then
+    if [ -n "${bastille_monitor_healthchecks}" ]; then
+        curl -fsS --retry 3 "${bastille_monitor_healthchecks}" > /dev/null 2>&1
+    else
+        curl -fsS --retry 3 "${bastille_monitor_healthchecks}/fail" > /dev/null 2>&1
+    fi
+fi
diff --git a/usr/local/share/man/man1/bastille-monitor.1 b/usr/local/share/man/man1/bastille-monitor.1
new file mode 100644
index 00000000..47e6af0e
--- /dev/null
+++ b/usr/local/share/man/man1/bastille-monitor.1
@@ -0,0 +1,133 @@
+.Dd 2025/12/12
+.Dt bastille-monitor 1
+.Os
+.Sh NAME
+.Nm bastille monitor
+.Nd Monitor and attempt to restart jail service(s). 
+.Sh SYNOPSIS
+.Nm
+.Op Fl x
+.Nm
+.Op Fl x
+.Ar enable|disable|status
+.Nm
+.Op Fl x
+.Ar TARGET
+.Sy add|delete
+.Ar SERVICE1,SERVICE2
+.Nm
+.Op Fl x
+.Sy list
+.Op SERVICE
+.Sh DESCRIPTION
+The
+.Nm
+sub-command will monitor jail services using the cron
+mechanism. It will attempt to restart them if/when
+they stop. See also
+.Xr bastille.conf 5 .
+.Bl -tag -width Ds
+.It Sy bastille monitor Oo Fl x Oc Ar TARGET
+.Bl -tag -width Ds
+.It Fl x , Fl -debug
+Enable debug mode.
+.El
+.Pp
+Calling
+.Nm
+with only a
+.Ar TARGET
+is how we initiante the checking/restarting
+of services. Any service(s) defined for
+.Ar TARGET
+will be restarted if they are stopped.
+.It Sy bastille monitor Oo Fl x Oc Sy enable|disable|status 
+.Bl -tag -width Ds
+.It Sy enable
+This will enable monitoring, adding a cron entry to be
+executed every 5 minutes, or the duration set
+in 'bastille_monitor_cron'. See
+.Xr bastille.conf 5 .
+.It Sy disable
+Disable the monitoring function. This will remove the
+cron entry.
+.It Sy status
+Check if the monitor is currently active or inactive.
+.It Fl x , Fl -debug
+Enable debug mode.
+.El
+.It Sy bastille monitor Oo Fl x Oc Ar TARGET Sy add|delete Ar SERVICE1,SERVICE2
+.Bl -tag -width Ds
+.It Sy add
+Add the
+.Ar SERVICE
+to the list of services to be monitored.
+.It Sy delete
+Remove the
+.Ar SERVICE
+from the monitoring list.
+.It Fl x , Fl -debug
+Enable debug mode.
+.El
+.It Sy bastille monitor Oo Fl x Oc Ar TARGET Sy list Op SERVICE
+.Bl -tag -width Ds
+.It Sy list
+List monitored service(s) for
+.Ar TARGET .
+If
+.Ar SERVICE
+is specified, list jail(s) that are monitoring that service.
+Note that it will only list the jails given in
+.Ar TARGET .
+.It Fl x , Fl -debug
+Enable debug mode.
+.Sh EXAMPLES
+.Bl -tag -width Ds
+.It Enable the monitoring service:
+.Sy bastille monitor enable
+.It Add nginx to the monitor list for myjail:
+.Sy bastille monitor myjail add nginx
+.It Add nginx and caddy to the monitor list for myjail:
+.Sy bastille monitor myjail add nginx,caddy
+.It Check which jails are monitoring caddy:
+.Sy bastille monitor ALL list caddy
+.Sh SEE ALSO
+.Xr bastille.conf 5 ,
+.Xr bastille-bootstrap 1 ,
+.Xr bastille-clone 1 ,
+.Xr bastille-cmd 1 ,
+.Xr bastille-config 1 ,
+.Xr bastille-console 1 ,
+.Xr bastille-convert 1 ,
+.Xr bastille-cp 1 ,
+.Xr bastille-create 1 ,
+.Xr bastille-destroy 1 ,
+.Xr bastille-edit 1 ,
+.Xr bastille-etcupdate 1 ,
+.Xr bastille-export 1 ,
+.Xr bastille-htop 1 ,
+.Xr bastille-import 1 ,
+.Xr bastille-jcp 1 ,
+.Xr bastille-limits 1 ,
+.Xr bastille-list 1 ,
+.Xr bastille-migrate 1 ,
+.Xr bastille-mount 1 ,
+.Xr bastille-network 1 ,
+.Xr bastille-pkg 1 ,
+.Xr bastille-rcp 1 ,
+.Xr bastille-rdr 1 ,
+.Xr bastille-rename 1 ,
+.Xr bastille-restart 1 ,
+.Xr bastille-service 1 ,
+.Xr bastille-setup 1 ,
+.Xr bastille-start 1 ,
+.Xr bastille-stop 1 ,
+.Xr bastille-sysrc 1 ,
+.Xr bastille-tags 1 ,
+.Xr bastille-template 1 ,
+.Xr bastille-top 1 ,
+.Xr bastille-umount 1 ,
+.Xr bastille-update 1 ,
+.Xr bastille-upgrade 1 ,
+.Xr bastille-verify 1 ,
+.Xr bastille-zfs 1
\ No newline at end of file
diff --git a/usr/local/share/man/man1/bastille.1 b/usr/local/share/man/man1/bastille.1
index 2fbd8972..a52b4c4c 100644
--- a/usr/local/share/man/man1/bastille.1
+++ b/usr/local/share/man/man1/bastille.1
@@ -69,6 +69,8 @@ and
 List jails, releases, templates and more...
 .It Sy migrate
 Migrate jail(s) to a remote system.
+.It Sy monitor
+Monitor and attempt to restart jail service(s).
 .It Sy mount
 Mount files(s)/directorie(s) inside jail(s).
 .It Sy network
diff --git a/usr/local/share/man/man5/bastille.conf.5 b/usr/local/share/man/man5/bastille.conf.5
index b16a932e..bc0fd2c0 100644
--- a/usr/local/share/man/man5/bastille.conf.5
+++ b/usr/local/share/man/man5/bastille.conf.5
@@ -128,6 +128,16 @@ The default template that is appled to thin jails.
 The default template that is appled to vnet jails.
 .It bastille_template_vlan
 The default template that is appled to vnet+vlan jails.
+.Ss MONITORING
+.It bastille_monitor_cron_path
+Cron file for automatic monitoring entry.
+.It bastille_monitor_cron
+Actual cron entry. The default is to check every 5 minutes.
+.It bastille_monitor_logfile
+Log storage.
+.It bastille_monitor_healthchecks
+This is the FQDN for optional alert services.
+Currently only supports 'healthchecks.io'.
 .Sh SEE ALSO
 .Xr bastille-bootstrap 1 ,
 .Xr bastille-clone 1 ,