diff --git a/src/shared/install.c b/src/shared/install.c
index 3522af67ec..8195436564 100644
--- a/src/shared/install.c
+++ b/src/shared/install.c
@@ -3283,7 +3283,7 @@ static int split_pattern_into_name_and_instances(const char *pattern, char **out
         return 0;
 }
 
-static int presets_find_config(RuntimeScope scope, const char *root_dir, char ***files) {
+static int presets_find_config(RuntimeScope scope, const char *root_dir, char ***ret) {
         static const char* const initrd_dirs[] = { CONF_PATHS("systemd/initrd-preset"), NULL };
         static const char* const system_dirs[] = { CONF_PATHS("systemd/system-preset"), NULL };
         static const char* const user_dirs[] = { CONF_PATHS("systemd/user-preset"), NULL };
@@ -3298,13 +3298,26 @@ 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
                 assert_not_reached();
 
-        return conf_files_list_strv(files, ".preset", root_dir, 0, dirs);
+        return conf_files_list_strv(ret, ".preset", root_dir, 0, dirs);
 }
 
 static int read_presets(RuntimeScope scope, const char *root_dir, UnitFilePresets *presets) {