diff --git a/lib/message.cc b/lib/message.cc
index 5ccca95a..1b1a071a 100644
--- a/lib/message.cc
+++ b/lib/message.cc
@@ -941,6 +941,7 @@ _notmuch_message_add_filename (notmuch_message_t *message,
 {
     const char *relative, *directory;
     notmuch_status_t status;
+    notmuch_private_status_t private_status;
     void *local = talloc_new (message);
     char *direntry;
 
@@ -964,10 +965,17 @@ _notmuch_message_add_filename (notmuch_message_t *message,
 
     /* New file-direntry allows navigating to this message with
      * notmuch_directory_get_child_files() . */
-    status = COERCE_STATUS (_notmuch_message_add_term (message, "file-direntry", direntry),
-			    "adding file-direntry term");
-    if (status)
-	return status;
+    private_status = _notmuch_message_add_term (message, "file-direntry", direntry);
+    switch (private_status) {
+    case NOTMUCH_PRIVATE_STATUS_SUCCESS:
+	break;
+    case NOTMUCH_PRIVATE_STATUS_TERM_TOO_LONG:
+	_notmuch_database_log (message->notmuch, "filename too long for file-direntry term: %s\n",
+			       filename);
+	return NOTMUCH_STATUS_PATH_ERROR;
+    default:
+	return COERCE_STATUS (private_status, "adding file-direntry term");
+    }
 
     status = _notmuch_message_add_folder_terms (message, directory);
     if (status)
diff --git a/lib/notmuch.h b/lib/notmuch.h
index 0b0540b1..ce375c04 100644
--- a/lib/notmuch.h
+++ b/lib/notmuch.h
@@ -293,6 +293,8 @@ typedef struct _notmuch_indexopts notmuch_indexopts_t;
  *
  * NOTMUCH_STATUS_OUT_OF_MEMORY: Out of memory.
  *
+ * NOTMUCH_STATUS_PATH_ERROR: filename is too long
+ *
  * NOTMUCH_STATUS_FILE_ERROR: An error occurred trying to create the
  *	database file (such as permission denied, or file not found,
  *	etc.), or the database already exists.
diff --git a/notmuch-new.c b/notmuch-new.c
index 346e6469..4a53e3eb 100644
--- a/notmuch-new.c
+++ b/notmuch-new.c
@@ -413,6 +413,10 @@ add_file (notmuch_database_t *notmuch, const char *filename,
     case NOTMUCH_STATUS_FILE_NOT_EMAIL:
 	fprintf (stderr, "Note: Ignoring non-mail file: %s\n", filename);
 	break;
+    case NOTMUCH_STATUS_PATH_ERROR:
+	fprintf (stderr, "Note: Ignoring non-indexable path: %s\n", filename);
+	(void) print_status_database ("add_file", notmuch, status);
+	break;
     case NOTMUCH_STATUS_FILE_ERROR:
 	/* Someone renamed/removed the file between scandir and now. */
 	state->vanished_files++;
diff --git a/test/T050-new.sh b/test/T050-new.sh
index c4a51a05..09c2bfc6 100755
--- a/test/T050-new.sh
+++ b/test/T050-new.sh
@@ -384,7 +384,6 @@ EOF
 test_expect_equal_file EXPECTED OUTPUT
 
 test_begin_subtest "Long file names have reasonable diagnostics"
-test_subtest_known_broken
 printf -v name 'f%.0s' {1..234}
 generate_message "[filename]=$name"
 notmuch new 2>&1 | notmuch_dir_sanitize >OUTPUT