diff --git a/sysutils/debootstrap/Makefile b/sysutils/debootstrap/Makefile
index 97d754cb3b90..a9febc33c241 100644
--- a/sysutils/debootstrap/Makefile
+++ b/sysutils/debootstrap/Makefile
@@ -1,51 +1,52 @@
 PORTNAME=	debootstrap
 PORTVERSION=	1.0.128
+PORTREVISION=	1
 CATEGORIES=	sysutils
 MASTER_SITES=	DEBIAN
 DISTNAME=	${PORTNAME}_${PORTVERSION}
 
 MAINTAINER=	nc@FreeBSD.org
 COMMENT=	Install Debian or Ubuntu base system into a directory
 WWW=		https://wiki.debian.org/Debootstrap
 
 LICENSE=	MIT
 LICENSE_FILE=	${WRKSRC}/debian/copyright
 
 RUN_DEPENDS=	wget:ftp/wget \
 		bash:shells/bash \
 		${LOCALBASE}/bin/grep:textproc/gnugrep \
 		gpgv2:security/gnupg \
 		${LOCALBASE}/share/keyrings/ubuntu-archive-keyring.gpg:security/ubuntu-keyring
 
 WRKSRC=		${WRKDIR}/${PORTNAME}
 NO_BUILD=	yes
 NO_ARCH=	yes
 USES=		gmake perl5
 USE_PERL5=	run
 
 post-patch:
 	@${REINPLACE_CMD} -e 's,%%PREFIX%%,${PREFIX},g' \
 		${WRKSRC}/Makefile \
 		${WRKSRC}/debootstrap
 	@${REINPLACE_CMD} -e 's,%%DATADIR%%,${DATADIR},g' \
 		${WRKSRC}/Makefile \
 		${WRKSRC}/debootstrap
 	@${REINPLACE_CMD} -e 's,%%LOCALBASE%%,${LOCALBASE},g' \
 		${WRKSRC}/Makefile \
 		${WRKSRC}/debootstrap
 	@${REINPLACE_CMD} -e 's,gpgv,gpgv2,g' \
 		${WRKSRC}/Makefile \
 		${WRKSRC}/debootstrap \
 		${WRKSRC}/functions
 	@${FIND} ${WRKSRC}/scripts -type f | \
 		${XARGS} ${REINPLACE_CMD} -e 's,/usr/share/keyrings,${LOCALBASE}/share/keyrings,g'
 
 	# Workaround for bin/255525
 	@${REINPLACE_CMD} -e 's,grep,${LOCALBASE}/bin/grep,g' \
 		${WRKSRC}/functions
 
 post-install:
 	${INSTALL_MAN} ${WRKSRC}/debootstrap.8 \
 		${STAGEDIR}${MAN8PREFIX}/man/man8/debootstrap.8
 
 .include <bsd.port.mk>
diff --git a/sysutils/debootstrap/files/patch-Makefile b/sysutils/debootstrap/files/patch-Makefile
index 6b4e6b5164d7..db211f5a422d 100644
--- a/sysutils/debootstrap/files/patch-Makefile
+++ b/sysutils/debootstrap/files/patch-Makefile
@@ -1,21 +1,21 @@
---- Makefile.orig	2019-07-06 11:22:30 UTC
+--- Makefile.orig	2021-04-06 19:52:02 UTC
 +++ Makefile
-@@ -5,14 +5,12 @@ all:
+@@ -5,14 +5,13 @@ all:
  
  clean:
  
 -DSDIR=$(DESTDIR)/usr/share/debootstrap
-+DSDIR=$(DESTDIR)%%DATADIR%%
++DSDIR=$(DESTDIR)/usr/local/share/debootstrap
  install:
  	mkdir -p $(DSDIR)/scripts
 -	mkdir -p $(DESTDIR)/usr/sbin
-+	mkdir -p $(DESTDIR)%%PREFIX%%/sbin
++	mkdir -p $(DESTDIR)/usr/local/sbin
  
  	cp -a scripts/* $(DSDIR)/scripts/
 -	install -o root -g root -m 0644 functions $(DSDIR)/
 +	cp -a functions $(DSDIR)/
  
 -	sed 's/@VERSION@/$(VERSION)/g' debootstrap >$(DESTDIR)/usr/sbin/debootstrap
 -	chown root:root $(DESTDIR)/usr/sbin/debootstrap
--	chmod 0755 $(DESTDIR)/usr/sbin/debootstrap
-+	sed 's/@VERSION@/$(VERSION)/g' debootstrap >$(DESTDIR)%%PREFIX%%/sbin/debootstrap
+ 	chmod 0755 $(DESTDIR)/usr/sbin/debootstrap
++	sed 's/@VERSION@/$(VERSION)/g' debootstrap >$(DESTDIR)/usr/local/sbin/debootstrap
diff --git a/sysutils/debootstrap/files/patch-debootstrap b/sysutils/debootstrap/files/patch-debootstrap
index b8b633661c06..82733b633193 100644
--- a/sysutils/debootstrap/files/patch-debootstrap
+++ b/sysutils/debootstrap/files/patch-debootstrap
@@ -1,47 +1,58 @@
---- debootstrap.orig	2020-03-13 02:03:08 UTC
+--- debootstrap.orig	2022-10-14 11:16:30 UTC
 +++ debootstrap
 @@ -1,4 +1,4 @@
 -#!/bin/sh
-+#!%%LOCALBASE%%/bin/bash
++#!/usr/local/bin/bash
  set -e
  
  VERSION='@VERSION@'
 @@ -14,7 +14,7 @@ if [ -z "$DEBOOTSTRAP_DIR" ]; then
  	if [ -x /debootstrap/debootstrap ]; then
  		DEBOOTSTRAP_DIR=/debootstrap
  	else
 -		DEBOOTSTRAP_DIR=/usr/share/debootstrap
-+		DEBOOTSTRAP_DIR=%%DATADIR%%
++		DEBOOTSTRAP_DIR=/usr/local/share/debootstrap
  	fi
  fi
  
-@@ -516,13 +516,7 @@ fi
+@@ -379,8 +379,8 @@ if [ $# != 0 ] ; then
+ 		shift
+ 		;;
+ 	    --keyring|--keyring=?*)
+-		if ! gpgv --version >/dev/null 2>&1; then
+-			error 1 NEEDGPGV "gpgv not installed, but required for Release verification"
++		if ! gpgv2 --version >/dev/null 2>&1; then
++			error 1 NEEDGPGV "gpgv2 not installed, but required for Release verification"
+ 		fi
+ 		if [ "$1" = "--keyring" ] && [ -n "$2" ]; then
+ 			KEYRING="$2"
+@@ -536,13 +536,7 @@ fi
  
  ###########################################################################
  
 -if in_path dpkg && \
 -     dpkg --print-architecture >/dev/null 2>&1; then
 -	HOST_ARCH=$(/usr/bin/dpkg --print-architecture)
 -elif in_path udpkg && \
 -     udpkg --print-architecture >/dev/null 2>&1; then
 -	HOST_ARCH=$(/usr/bin/udpkg --print-architecture)
 -elif [ -e "$DEBOOTSTRAP_DIR/arch" ]; then
 +if [ -e "$DEBOOTSTRAP_DIR/arch" ]; then
  	HOST_ARCH=$(cat "$DEBOOTSTRAP_DIR/arch")
  fi
  HOST_OS="$HOST_ARCH"
-@@ -542,6 +536,14 @@ if [ -z "$HOST_OS" ]; then
+@@ -562,6 +556,14 @@ if [ -z "$HOST_OS" ]; then
  			HOST_OS=freebsd
  		;;
  	esac
 +fi
 +
 +if [ "$HOST_OS" = "freebsd" -a -z "$HOST_ARCH" ]; then
 +	HOST_ARCH=`/sbin/sysctl -n hw.machine_arch`
 +	if [ "$HOST_ARCH" = "aarch64" ]; then
 +		HOST_ARCH=arm64
 +	fi
 +	EXTRACTOR_OVERRIDE=ar
  fi
  
  if [ -z "$ARCH" ]; then
diff --git a/sysutils/debootstrap/files/patch-scripts-gutsy b/sysutils/debootstrap/files/patch-scripts-gutsy
index 354c3c57e883..18b91b19d176 100644
--- a/sysutils/debootstrap/files/patch-scripts-gutsy
+++ b/sysutils/debootstrap/files/patch-scripts-gutsy
@@ -1,51 +1,51 @@
---- scripts/gutsy.orig	2020-03-13 02:04:21 UTC
+--- scripts/gutsy.orig	2023-02-08 17:55:01 UTC
 +++ scripts/gutsy
-@@ -242,10 +242,21 @@ echo \"Warning: Fake initctl called, doing nothing\"" 
+@@ -296,10 +296,21 @@ echo \"Warning: Fake initctl called, doing nothing\"" 
  		predep=$(without "$(without "$(resolve_deps $predep)" "$required")" "$done_predeps")
  		# XXX: progress is tricky due to how dpkg_progress works
  		# -- cjwatson 2009-07-29
 +		# This step sometimes fails due to some missing functionality in Linuxulator.  Just ignore it.
 +		set +e
  		p; smallyes '' |
  		in_target dpkg --force-overwrite --force-confold --skip-same-version --install $(debfor $predep)
 +		rc=$?
  		base=$(without "$base" "$predep")
  		done_predeps="$done_predeps $predep"
 +
 +		if [ $rc != 0 ]; then
 +			warning FREEBSD_00 "Applying FreeBSD-specific workaround..."
 +			# ... for "Failed to mount /etc/machine-id: Bad address" with Focal.
 +			in_target truncate -s0 /var/lib/dpkg/info/systemd.postinst
 +			in_target dpkg --configure systemd
 +		fi
 +		set -e
  	done
  
  	if [ -n "$base" ]; then
-@@ -256,10 +267,13 @@ echo \"Warning: Fake initctl called, doing nothing\"" 
+@@ -310,10 +321,13 @@ echo \"Warning: Fake initctl called, doing nothing\"" 
  
  		info CONFBASE "Configuring the base system..."
  
 +		# This step sometimes fails due to some missing functionality in Linuxulator.  Just ignore it.
 +		set +e
  		smallyes '' |
  			(repeatn 5 in_target_failmsg CONF_BASE_FAIL_FIVE "Failure while configuring base packages.  This will be re-attempted up to five times." "" \
  			dpkg --status-fd 8 --force-confold --skip-same-version --configure -a 8>&1 1>&7 || echo EXITCODE $?) |
  			dpkg_progress $baseprog $bases CONFBASE "Configuring base system" CONFIGURING
 +		set -e
  	fi
  
  	if [ -x "$TARGET/sbin/initctl.REAL" ]; then
-@@ -267,6 +281,12 @@ echo \"Warning: Fake initctl called, doing nothing\"" 
+@@ -321,6 +335,12 @@ echo \"Warning: Fake initctl called, doing nothing\"" 
  	fi
  	mv "$TARGET/sbin/start-stop-daemon.REAL" "$TARGET/sbin/start-stop-daemon"
  	rm -f "$TARGET/usr/sbin/policy-rc.d"
 +
 +	echo \
 +"# Workaround for Linuxulator missing mremap(2) support; without it,
 +# apt(8) fails like this:
 +# E: Dynamic MMap ran out of room. Please increase the size of APT::Cache-Start.
 +APT::Cache-Start 251658240;" >> "$TARGET/etc/apt/apt.conf.d/00freebsd"
  
  	progress $bases $bases CONFBASE "Configuring base system"
  	info BASESUCCESS "Base system installed successfully."
diff --git a/sysutils/debootstrap/files/patch-scripts_debian-common b/sysutils/debootstrap/files/patch-scripts_debian-common
index 8027154f25e4..0eb7c31d2064 100644
--- a/sysutils/debootstrap/files/patch-scripts_debian-common
+++ b/sysutils/debootstrap/files/patch-scripts_debian-common
@@ -1,37 +1,37 @@
---- scripts/debian-common.orig	2020-03-13 02:04:21 UTC
+--- scripts/debian-common.orig	2023-02-08 17:55:01 UTC
 +++ scripts/debian-common
-@@ -200,10 +200,21 @@ echo \"Warning: Fake start-stop-daemon called, doing n
+@@ -215,10 +215,21 @@ echo \"Warning: Fake start-stop-daemon called, doing n
  		predep=$(without "$(without "$(resolve_deps $predep)" "$required")" "$done_predeps")
  		# XXX: progress is tricky due to how dpkg_progress works
  		# -- cjwatson 2009-07-29
 +		# This step sometimes fails due to some missing functionality in Linuxulator.  Just ignore it.
 +		set +e
  		p; smallyes '' |
  		in_target dpkg --force-overwrite --force-confold --skip-same-version --install $(debfor $predep)
 +		rc=$?
  		base=$(without "$base" "$predep")
  		done_predeps="$done_predeps $predep"
 +
 +		if [ $rc != 0 ]; then
 +			warning FREEBSD_00 "Applying FreeBSD-specific workaround..."
 +			# ... for "Failed to mount /etc/machine-id: Bad address" with Focal.
 +			in_target truncate -s0 /var/lib/dpkg/info/systemd.postinst
 +			in_target dpkg --configure systemd
 +		fi
 +		set -e
  	done
  
  	if [ -n "$base" ]; then
-@@ -222,6 +233,12 @@ echo \"Warning: Fake start-stop-daemon called, doing n
+@@ -237,6 +248,12 @@ echo \"Warning: Fake start-stop-daemon called, doing n
  
  	mv "$TARGET/sbin/start-stop-daemon.REAL" "$TARGET/sbin/start-stop-daemon"
  	rm -f "$TARGET/usr/sbin/policy-rc.d"
 +
 +	echo \
 +"# Workaround for Linuxulator missing mremap(2) support; without it,
 +# apt(8) fails like this:
 +# E: Dynamic MMap ran out of room. Please increase the size of APT::Cache-Start.
 +APT::Cache-Start 251658240;" >> "$TARGET/etc/apt/apt.conf.d/00freebsd"
  
  	progress $bases $bases CONFBASE "Configuring base system"
  	info BASESUCCESS "Base system installed successfully."