diff --git a/sysutils/bastille/Makefile b/sysutils/bastille/Makefile
index e6ce288a2393..716ac1b2e134 100644
--- a/sysutils/bastille/Makefile
+++ b/sysutils/bastille/Makefile
@@ -1,37 +1,37 @@
 PORTNAME=	bastille
-DISTVERSION=	1.4.3.260429
+DISTVERSION=	1.4.4
 CATEGORIES=	sysutils
 MAINTAINER=	jdhurtado@orbiware.com
 # co-maintainer: snarfingcode666@gmail.com
 COMMENT=	Jail automation framework
 WWW=		https://bastillebsd.org
 
 LICENSE=	BSD3CLAUSE
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 USE_GITHUB=	yes
 GH_ACCOUNT=	BastilleBSD
 
 NO_ARCH=	yes
 NO_BUILD=	yes
 
 post-patch:
 	@${REINPLACE_CMD} \
 		-e 's|/usr/local/etc/bastille|${ETCDIR}|g' \
 		-e 's|/usr/local|${PREFIX}|g' \
 		${WRKSRC}/usr/local/etc/rc.d/bastille
 
 do-install:
 	${MKDIR} ${STAGEDIR}${ETCDIR}
 	${MKDIR} ${STAGEDIR}${DATADIR}
 	${INSTALL_SCRIPT} ${WRKSRC}/usr/local/bin/bastille ${STAGEDIR}${PREFIX}/bin
 	${INSTALL_DATA} ${WRKSRC}/usr/local/etc/bastille/bastille.conf.sample \
 		${STAGEDIR}${ETCDIR}/${PORTNAME}.conf.sample
 	${INSTALL_SCRIPT} ${WRKSRC}/usr/local/etc/rc.d/bastille \
 		${STAGEDIR}${PREFIX}/etc/rc.d
 	(cd ${WRKSRC}/usr/local/share/bastille && \
 		${COPYTREE_SHARE} . ${STAGEDIR}${DATADIR})
 	(cd ${WRKSRC}/usr/local/share/man && \
 		${COPYTREE_SHARE} . ${STAGEDIR}${PREFIX}/share/man)
 
 .include <bsd.port.mk>
diff --git a/sysutils/bastille/distinfo b/sysutils/bastille/distinfo
index c556e342fe45..bb1980397403 100644
--- a/sysutils/bastille/distinfo
+++ b/sysutils/bastille/distinfo
@@ -1,3 +1,3 @@
-TIMESTAMP = 1777575111
-SHA256 (BastilleBSD-bastille-1.4.3.260429_GH0.tar.gz) = b26215119df89b9a3fe2cf5d30faae99f569855e8504b63051c6b2a430e6c0ca
-SIZE (BastilleBSD-bastille-1.4.3.260429_GH0.tar.gz) = 724152
+TIMESTAMP = 1783864729
+SHA256 (BastilleBSD-bastille-1.4.4_GH0.tar.gz) = f83faf705c4d8b1f49fed074e2348aeb77f65e8b54446a680e22866988963536
+SIZE (BastilleBSD-bastille-1.4.4_GH0.tar.gz) = 716043
diff --git a/sysutils/bastille/pkg-message b/sysutils/bastille/pkg-message
new file mode 100644
index 000000000000..af5cee07238e
--- /dev/null
+++ b/sysutils/bastille/pkg-message
@@ -0,0 +1,19 @@
+[
+{ type: upgrade
+  maximum_version: "1.4.3.260429"
+  message: <<EOM
+
+The version naming scheme has changed to only include semantic versioning. eg: 1.x.x
+
+Bastille version 1.4.4 introduces a minor change to how it handles the rdr command.
+It requires an additional line inside `/etc/pf.conf` if you are using `bastille rdr`.
+Place the following line at the beginning of the `/etc/pf.conf` filtering section.
+
+anchor "bastille/*"
+
+See https://bastille.readthedocs.io/en/latest/chapters/networking.html#etc-pf-conf for
+details.
+
+EOM
+}
+]