diff --git a/coverage.sh b/coverage.sh
index deb233a..a05b75a 100755
--- a/coverage.sh
+++ b/coverage.sh
@@ -127,7 +127,7 @@ if [ ! -e shared/hooks/eatmydata/customize.sh ] || [ hooks/eatmydata/customize.s
 	fi
 fi
 starttime=
-total=182
+total=183
 skipped=0
 runtests=0
 i=1
@@ -712,7 +712,48 @@ else
 	runtests=$((runtests+1))
 fi
 
-print_header "mode=unshare,variant=apt: root without cap_sys_admin"
+# Same as above but this time we run mmdebstrap in root mode from inside
+# an unshare chroot.
+print_header "mode=root,variant=apt: root mode inside unshare chroot"
+cat << END > shared/test.sh
+#!/bin/sh
+set -eu
+export LC_ALL=C.UTF-8
+if [ ! -e /mmdebstrap-testenv ]; then
+	echo "this test modifies the system and should only be run inside a container" >&2
+	exit 1
+fi
+[ "\$(whoami)" = "root" ]
+adduser --gecos user --disabled-password user
+sysctl -w kernel.unprivileged_userns_clone=1
+cat << 'SCRIPT' > script.sh
+#!/bin/sh
+set -eu
+rootfs="\$1"
+mkdir -p "\$rootfs/mnt"
+[ -e /usr/bin/mmdebstrap ] && cp -aT /usr/bin/mmdebstrap "\$rootfs/usr/bin/mmdebstrap"
+[ -e ./mmdebstrap ] && cp -aT ./mmdebstrap "\$rootfs/mnt/mmdebstrap"
+chroot "\$rootfs" env --chdir=/mnt \
+	$CMD --mode=root --variant=apt \
+	$DEFAULT_DIST /tmp/debian-chroot.tar $mirror
+SCRIPT
+chmod +x script.sh
+runuser -u user -- $CMD --mode=unshare --variant=apt --include=perl,mount \
+	--customize-hook=./script.sh \
+	--customize-hook="download /tmp/debian-chroot.tar /tmp/debian-chroot.tar" \
+	$DEFAULT_DIST /dev/null $mirror
+tar -tf /tmp/debian-chroot.tar | sort | diff -u tar1.txt -
+rm /tmp/debian-chroot.tar script.sh
+END
+if [ "$HAVE_QEMU" = "yes" ]; then
+	./run_qemu.sh
+	runtests=$((runtests+1))
+else
+	echo "HAVE_QEMU != yes -- Skipping test..." >&2
+	skipped=$((skipped+1))
+fi
+
+print_header "mode=root,variant=apt: root without cap_sys_admin"
 cat << END > shared/test.sh
 #!/bin/sh
 set -eu
diff --git a/mmdebstrap b/mmdebstrap
index 4c062c5..72611f4 100755
--- a/mmdebstrap
+++ b/mmdebstrap
@@ -1181,15 +1181,35 @@ sub run_chroot {
             warning("skipping bind-mounting /sys because"
                   . " /sys on the outside is not a directory");
         } elsif ($options->{mode} eq 'root') {
-            push @cleanup_tasks, sub {
-                0 == system('umount', "$options->{root}/sys")
-                  or warn "umount /sys failed: $?";
-            };
-            0 == system(
-                'mount', '-t',                     'sysfs',
-                '-o',    'ro,nosuid,nodev,noexec', 'sys',
-                "$options->{root}/sys"
-            ) or error "mount /sys failed: $?";
+            # we don't know whether we run in root mode inside an unshared
+            # user namespace or as real root so we first try the real mount and
+            # then fall back to mounting in a way that works in unshared mode
+            if (
+                0 == system(
+                    'mount',                  '-t',
+                    'sysfs',                  '-o',
+                    'ro,nosuid,nodev,noexec', 'sys',
+                    "$options->{root}/sys"
+                )
+            ) {
+                push @cleanup_tasks, sub {
+                    0 == system('umount', "$options->{root}/sys")
+                      or warn "umount /sys failed: $?";
+                };
+            } elsif (
+                0 == system('mount', '-o', 'rbind', '/sys',
+                    "$options->{root}/sys")) {
+                push @cleanup_tasks, sub {
+                    # since we cannot write to /etc/mtab we need --no-mtab
+                    # unmounting /sys only seems to be successful with --lazy
+                    0 == system(
+                        'umount', '--no-mtab',
+                        '--lazy', "$options->{root}/sys"
+                    ) or warn "umount /sys failed: $?";
+                };
+            } else {
+                error "mount /sys failed: $?";
+            }
         } elsif ($options->{mode} eq 'unshare') {
             # naturally we have to clean up after ourselves in sudo mode where
             # we do a real mount. But we also need to unmount in unshare mode
@@ -1236,24 +1256,42 @@ sub run_chroot {
             warning("skipping bind-mounting /proc because"
                   . " /proc on the outside is not a directory");
         } elsif ($options->{mode} eq 'root') {
-            push @cleanup_tasks, sub {
-                # some maintainer scripts mount additional stuff into /proc
-                # which we need to unmount beforehand
-                if (
-                    is_mountpoint(
-                        $options->{root} . "/proc/sys/fs/binfmt_misc"
-                    )
-                ) {
-                    0 == system('umount',
-                        "$options->{root}/proc/sys/fs/binfmt_misc")
-                      or error "umount /proc/sys/fs/binfmt_misc failed: $?";
-                }
-                0 == system('umount', "$options->{root}/proc")
-                  or error "umount /proc failed: $?";
-            };
-            0 == system('mount', '-t', 'proc', '-o', 'ro', 'proc',
-                "$options->{root}/proc")
-              or error "mount /proc failed: $?";
+            # we don't know whether we run in root mode inside an unshared
+            # user namespace or as real root so we first try the real mount and
+            # then fall back to mounting in a way that works in unshared
+            if (
+                0 == system(
+                    'mount', '-t', 'proc', '-o', 'ro', 'proc',
+                    "$options->{root}/proc"
+                )
+            ) {
+                push @cleanup_tasks, sub {
+                    # some maintainer scripts mount additional stuff into /proc
+                    # which we need to unmount beforehand
+                    if (
+                        is_mountpoint(
+                            $options->{root} . "/proc/sys/fs/binfmt_misc"
+                        )
+                    ) {
+                        0 == system('umount',
+                            "$options->{root}/proc/sys/fs/binfmt_misc")
+                          or error
+                          "umount /proc/sys/fs/binfmt_misc failed: $?";
+                    }
+                    0 == system('umount', "$options->{root}/proc")
+                      or error "umount /proc failed: $?";
+                };
+            } elsif (
+                0 == system('mount', '-t', 'proc', 'proc',
+                    "$options->{root}/proc")) {
+                push @cleanup_tasks, sub {
+                    # since we cannot write to /etc/mtab we need --no-mtab
+                    0 == system('umount', '--no-mtab', "$options->{root}/proc")
+                      or error "umount /proc failed: $?";
+                };
+            } else {
+                error "mount /proc failed: $?";
+            }
         } elsif ($options->{mode} eq 'unshare') {
             # naturally we have to clean up after ourselves in sudo mode where
             # we do a real mount. But we also need to unmount in unshare mode