diff --git a/src/shared/install.c b/src/shared/install.c
index 4ed6a0962a..8195436564 100644
--- a/src/shared/install.c
+++ b/src/shared/install.c
@@ -3298,7 +3298,20 @@ static int presets_find_config(RuntimeScope scope, const char *root_dir, char **
                 if (r < 0 && r != -ENOENT)
                         return r;
 
-                dirs = r >= 0 ? initrd_dirs : system_dirs;
+                /* Make sure that we fall back to the system preset directories if we're operating on a root
+                 * directory without initrd preset directories. This makes sure that we don't regress when
+                 * using a newer systemctl to operate on a root directory with an older version of systemd
+                 * installed that doesn't yet known about initrd preset directories. */
+                if (r >= 0)
+                        STRV_FOREACH(d, initrd_dirs) {
+                                r = chase_and_access(*d, root_dir, CHASE_PREFIX_ROOT, F_OK, /* ret_path= */ NULL);
+                                if (r >= 0)
+                                        return conf_files_list_strv(ret, ".preset", root_dir, 0, initrd_dirs);
+                                if (r != -ENOENT)
+                                        return r;
+                        }
+
+                dirs = system_dirs;
         } else if (IN_SET(scope, RUNTIME_SCOPE_GLOBAL, RUNTIME_SCOPE_USER))
                 dirs = user_dirs;
         else