diff --git a/src/shared/dropin.c b/src/shared/dropin.c
index 96cd08aab2..6844c2b647 100644
--- a/src/shared/dropin.c
+++ b/src/shared/dropin.c
@@ -236,6 +236,10 @@ int unit_file_find_dropin_paths(
 
         assert(ret);
 
+        SET_FOREACH(name, names, i)
+                STRV_FOREACH(p, lookup_path)
+                        (void) unit_file_find_dirs(original_root, unit_path_cache, *p, name, dir_suffix, &dirs);
+
         /* All the names in the unit are of the same type so just grab one. */
         name = (char*) set_first(names);
         if (name) {
@@ -247,7 +251,7 @@ int unit_file_find_dropin_paths(
                                                "Failed to to derive unit type from unit name: %s",
                                                name);
 
-                /* Special top level drop in for "<unit type>.<suffix>". Add this first as it's the most generic
+                /* Special top level drop in for "<unit type>.<suffix>". Add this last as it's the most generic
                  * and should be able to be overridden by more specific drop-ins. */
                 STRV_FOREACH(p, lookup_path)
                         (void) unit_file_find_dirs(original_root,
@@ -258,10 +262,6 @@ int unit_file_find_dropin_paths(
                                                    &dirs);
         }
 
-        SET_FOREACH(name, names, i)
-                STRV_FOREACH(p, lookup_path)
-                        (void) unit_file_find_dirs(original_root, unit_path_cache, *p, name, dir_suffix, &dirs);
-
         if (strv_isempty(dirs)) {
                 *ret = NULL;
                 return 0;
diff --git a/test/TEST-15-DROPIN/test-dropin.sh b/test/TEST-15-DROPIN/test-dropin.sh
index fd500c1a0b..f80c9df107 100755
--- a/test/TEST-15-DROPIN/test-dropin.sh
+++ b/test/TEST-15-DROPIN/test-dropin.sh
@@ -117,6 +117,30 @@ EOF
     clear_services a b c
 }
 
+test_hierarchical_dropins () {
+    echo "Testing hierarchical dropins..."
+    echo "*** test service.d/ top level drop-in"
+    create_services a-b-c
+    check_ko a-b-c ExecCondition "/bin/echo service.d"
+    check_ko a-b-c ExecCondition "/bin/echo a-.service.d"
+    check_ko a-b-c ExecCondition "/bin/echo a-b-.service.d"
+    check_ko a-b-c ExecCondition "/bin/echo a-b-c.service.d"
+
+    for dropin in service.d a-.service.d a-b-.service.d a-b-c.service.d; do
+        mkdir -p /usr/lib/systemd/system/$dropin
+        echo "
+[Service]
+ExecCondition=/bin/echo $dropin
+        " > /usr/lib/systemd/system/$dropin/override.conf
+        check_ok a-b-c ExecCondition "/bin/echo $dropin"
+    done
+    for dropin in service.d a-.service.d a-b-.service.d a-b-c.service.d; do
+        rm -rf /usr/lib/systemd/system/$dropin
+    done
+
+    clear_services a-b-c
+}
+
 test_template_dropins () {
     echo "Testing template dropins..."
 
@@ -433,6 +457,7 @@ test_invalid_dropins () {
 }
 
 test_basic_dropins
+test_hierarchical_dropins
 test_template_dropins
 test_alias_dropins
 test_masked_dropins