diff --git a/source3/libsmb/clifile.c b/source3/libsmb/clifile.c
index faabaeba59a..2907a6f5866 100644
--- a/source3/libsmb/clifile.c
+++ b/source3/libsmb/clifile.c
@@ -1705,6 +1705,7 @@ struct tevent_req *cli_rmdir_send(TALLOC_CTX *mem_ctx,
 	struct tevent_req *req = NULL, *subreq = NULL;
 	struct cli_rmdir_state *state = NULL;
 	uint8_t additional_flags = 0;
+	uint16_t additional_flags2 = 0;
 	uint8_t *bytes = NULL;
 
 	req = tevent_req_create(mem_ctx, &state, struct cli_rmdir_state);
@@ -1724,8 +1725,13 @@ struct tevent_req *cli_rmdir_send(TALLOC_CTX *mem_ctx,
 		return tevent_req_post(req, ev);
 	}
 
-	subreq = cli_smb_send(state, ev, cli, SMBrmdir, additional_flags, 0,
-			      0, NULL, talloc_get_size(bytes), bytes);
+	if (clistr_is_previous_version_path(dname)) {
+		additional_flags2 = FLAGS2_REPARSE_PATH;
+	}
+
+	subreq = cli_smb_send(state, ev, cli, SMBrmdir, additional_flags,
+			additional_flags2,
+			0, NULL, talloc_get_size(bytes), bytes);
 	if (tevent_req_nomem(subreq, req)) {
 		return tevent_req_post(req, ev);
 	}