diff --git a/src/tmpfiles/tmpfiles.c b/src/tmpfiles/tmpfiles.c
index 82f6b8da2f..464384b22b 100644
--- a/src/tmpfiles/tmpfiles.c
+++ b/src/tmpfiles/tmpfiles.c
@@ -322,16 +322,7 @@ static int specifier_directory(
         if (r < 0)
                 return r;
 
-        if (arg_root) {
-                _cleanup_free_ char *j = NULL;
-
-                j = path_join(arg_root, p);
-                if (!j)
-                        return -ENOMEM;
-
-                *ret = TAKE_PTR(j);
-        } else
-                *ret = TAKE_PTR(p);
+        *ret = TAKE_PTR(p);
 
         return 0;
 }
@@ -817,9 +808,14 @@ static int dir_cleanup(
 
                         log_action("Would remove", "Removing", "%s directory \"%s\"", sub_path);
                         if (!arg_dry_run &&
-                            unlinkat(dirfd(d), de->d_name, AT_REMOVEDIR) < 0 &&
-                            !IN_SET(errno, ENOENT, ENOTEMPTY))
-                                r = log_warning_errno(errno, "Failed to remove directory \"%s\", ignoring: %m", sub_path);
+                            unlinkat(dirfd(d), de->d_name, AT_REMOVEDIR) < 0) {
+                                if (errno == ENOTEMPTY)
+                                        continue;
+                                if (errno != ENOENT)
+                                        r = log_warning_errno(errno, "Failed to remove directory \"%s\", ignoring: %m", sub_path);
+                        }
+
+                        deleted = true;
 
                 } else {
                         _cleanup_close_ int fd = -EBADF; /* This file descriptor is defined here so that the
@@ -2247,11 +2243,14 @@ static int copy_files(Context *c, Item *i) {
                 return log_error_errno(errno, "Failed to openat(%s): %m", i->path);
         }
 
+        if (r < 0 && !IN_SET(r, -EEXIST, -EROFS))
+                return log_error_errno(r, "Failed to copy files to %s: %m", i->path);
+
         if (fstat(fd, &st) < 0)
                 return log_error_errno(errno, "Failed to fstat(%s): %m", i->path);
 
-        if (stat(i->argument, &a) < 0)
-                return log_error_errno(errno, "Failed to stat(%s): %m", i->argument);
+        if (lstat(i->argument, &a) < 0)
+                return log_error_errno(errno, "Failed to lstat(%s): %m", i->argument);
 
         if (((st.st_mode ^ a.st_mode) & S_IFMT) != 0) {
                 log_debug("Can't copy to %s, file exists already and is of different type", i->path);
@@ -2689,16 +2688,30 @@ static int create_symlink(Context *c, Item *i) {
         assert(i);
 
         if (i->ignore_if_target_missing) {
-                r = chase(i->argument, arg_root, CHASE_SAFE|CHASE_PREFIX_ROOT|CHASE_NOFOLLOW, /* ret_path= */ NULL, /* ret_fd= */ NULL);
+                _cleanup_free_ char *target = NULL;
+                ChaseFlags chase_flags = CHASE_SAFE|CHASE_NOFOLLOW;
+
+                if (!path_is_absolute(i->argument)) {
+                        _cleanup_free_ char *dn = NULL;
+
+                        r = path_extract_directory(i->path, &dn);
+                        if (r < 0)
+                                return log_error_errno(r, "Failed to extract directory from path '%s': %m", i->path);
+
+                        target = path_join(dn, i->argument);
+                        if (!target)
+                                return log_oom();
+                } else
+                        chase_flags |= CHASE_PREFIX_ROOT;
+
+                r = chase(target ?: i->argument, arg_root, chase_flags, /* ret_path= */ NULL, /* ret_fd= */ NULL);
                 if (r == -ENOENT) {
                         /* Silently skip over lines where the source file is missing. */
-                        log_debug_errno(r, "Symlink source path '%s/%s' does not exist, skipping line.",
-                                        strempty(arg_root), skip_leading_slash(i->argument));
+                        log_debug_errno(r, "Symlink source path '%s' does not exist, skipping line.", i->argument);
                         return 0;
                 }
                 if (r < 0)
-                        return log_error_errno(r, "Failed to check if symlink source path '%s/%s' exists: %m",
-                                               strempty(arg_root), skip_leading_slash(i->argument));
+                        return log_error_errno(r, "Failed to check if symlink source path '%s' exists: %m", i->argument);
         }
 
         r = path_extract_filename(i->path, &bn);
@@ -4707,6 +4720,8 @@ static int read_config_file(
                         if (candidate_item && candidate_item->age_set) {
                                 i->age = candidate_item->age;
                                 i->age_set = true;
+                                i->age_by_file = candidate_item->age_by_file;
+                                i->age_by_dir = candidate_item->age_by_dir;
                         }
                 }
 
diff --git a/test/units/TEST-22-TMPFILES.03.sh b/test/units/TEST-22-TMPFILES.03.sh
index d75294207a..390932ec97 100755
--- a/test/units/TEST-22-TMPFILES.03.sh
+++ b/test/units/TEST-22-TMPFILES.03.sh
@@ -5,6 +5,9 @@
 set -eux
 set -o pipefail
 
+# shellcheck source=test/units/util.sh
+. "$(dirname "$0")"/util.sh
+
 rm -fr /tmp/{f,F,w}
 mkdir  /tmp/{f,F,w}
 touch /tmp/file-owned-by-root
@@ -190,6 +193,31 @@ F     /tmp/F/daemon/unsafe-symlink/exploit    0644 daemon daemon - -
 EOF
 test ! -e /tmp/F/daemon/unsafe-symlink/exploit
 
+#
+# 'C'
+#
+rm -rf /tmp/C-copy-failure-src /tmp/C-copy-failure-dst
+mkdir /tmp/C-copy-failure-src /tmp/C-copy-failure-dst
+printf payload >/tmp/C-copy-failure-src/file
+chmod 555 /tmp/C-copy-failure-dst
+
+(! runas nobody systemd-tmpfiles --create - <<EOF
+C     /tmp/C-copy-failure-dst    - - - - /tmp/C-copy-failure-src
+EOF
+)
+test ! -e /tmp/C-copy-failure-dst/file
+chmod 755 /tmp/C-copy-failure-dst
+rm -rf /tmp/C-copy-failure-src /tmp/C-copy-failure-dst
+
+rm -f /tmp/C-copy-link-src /tmp/C-copy-link-dst
+ln -s missing-target /tmp/C-copy-link-src
+systemd-tmpfiles --create - <<EOF
+C     /tmp/C-copy-link-dst    - - - - /tmp/C-copy-link-src
+EOF
+test -L /tmp/C-copy-link-dst
+test "$(readlink /tmp/C-copy-link-dst)" = "missing-target"
+rm -f /tmp/C-copy-link-src /tmp/C-copy-link-dst
+
 #
 # 'w'
 #
diff --git a/test/units/TEST-22-TMPFILES.12.sh b/test/units/TEST-22-TMPFILES.12.sh
index 44bb949825..b2288bcf01 100755
--- a/test/units/TEST-22-TMPFILES.12.sh
+++ b/test/units/TEST-22-TMPFILES.12.sh
@@ -204,3 +204,34 @@ test ! -d /tmp/ageby/d3
 
 # Cleanup the test directory (fail if not empty).
 rmdir /tmp/ageby
+
+# Removing an old child directory should restore the parent directory mtime.
+rm -rf /tmp/ageby-mtime
+mkdir -p /tmp/ageby-mtime/old-child
+touch --date "2020-01-01 00:00:00" /tmp/ageby-mtime/old-child /tmp/ageby-mtime
+before="$(stat -c %Y /tmp/ageby-mtime)"
+
+systemd-tmpfiles --clean - <<-EOF
+d /tmp/ageby-mtime - - - M:1s
+EOF
+
+after="$(stat -c %Y /tmp/ageby-mtime)"
+test "$before" = "$after"
+test ! -e /tmp/ageby-mtime/old-child
+rmdir /tmp/ageby-mtime
+
+# X entries inherit the parent cleanup age and its age-by fields.
+rm -rf /tmp/ageby-x-inherit
+mkdir -p /tmp/ageby-x-inherit/parent/child /tmp/ageby-x-inherit/parent/other
+printf old >/tmp/ageby-x-inherit/parent/child/file
+printf old >/tmp/ageby-x-inherit/parent/other/file
+touch --date "3 days ago" /tmp/ageby-x-inherit/parent/child/file /tmp/ageby-x-inherit/parent/other/file
+
+systemd-tmpfiles --clean - <<-EOF
+d /tmp/ageby-x-inherit/parent - - - m:1d
+X /tmp/ageby-x-inherit/parent/child - - - -
+EOF
+
+test ! -e /tmp/ageby-x-inherit/parent/child/file
+test ! -e /tmp/ageby-x-inherit/parent/other/file
+rm -rf /tmp/ageby-x-inherit
diff --git a/test/units/TEST-22-TMPFILES.15.sh b/test/units/TEST-22-TMPFILES.15.sh
index 14c26b8295..78be11357d 100755
--- a/test/units/TEST-22-TMPFILES.15.sh
+++ b/test/units/TEST-22-TMPFILES.15.sh
@@ -42,3 +42,48 @@ systemd-tmpfiles --create --root="$root" - <<EOF
 L     %h    - - - -
 EOF
 test "$(readlink "$dst")" = "$src"
+
+# Check that directory specifiers are not prefixed with --root twice.
+root='/tmp/L/3'
+rm -rf "$root"
+mkdir -p "$root"
+
+output="$(systemd-tmpfiles --create --dry-run --root="$root" - 2>&1 <<EOF
+d     %t/test    - - - -
+EOF
+)"
+[[ "$output" == *"Would create directory $root/run/test"* ]]
+[[ "$output" != *"$root$root"* ]]
+
+# Check that L? resolves relative targets from the symlink's parent directory.
+root='/tmp/L/4'
+rm -rf "$root"
+mkdir -p "$root"
+touch "$root/target"
+
+systemd-tmpfiles --create - <<EOF
+L?    $root/link    - - - - target
+EOF
+test "$(readlink "$root/link")" = "target"
+
+rm -f "$root/link" "$root/target"
+systemd-tmpfiles --create - <<EOF
+L?    $root/link    - - - - target
+EOF
+test ! -e "$root/link"
+
+# Check the same relative target lookup with --root=.
+rm -rf "$root"
+mkdir -p "$root/dir"
+touch "$root/dir/target"
+
+systemd-tmpfiles --create --root="$root" - <<EOF
+L?    /dir/link    - - - - target
+EOF
+test "$(readlink "$root/dir/link")" = "target"
+
+rm -f "$root/dir/link" "$root/dir/target"
+systemd-tmpfiles --create --root="$root" - <<EOF
+L?    /dir/link    - - - - target
+EOF
+test ! -e "$root/dir/link"