diff --git a/xwayland/selection/outgoing.c b/xwayland/selection/outgoing.c
index 943e4d1a..190fb741 100644
--- a/xwayland/selection/outgoing.c
+++ b/xwayland/selection/outgoing.c
@@ -71,9 +71,11 @@ static void xwm_selection_transfer_destroy_outgoing(
 	struct wlr_xwm_selection *selection = transfer->selection;
 	bool was_first = transfer == xwm_selection_transfer_get_first(selection);
 	wl_list_remove(&transfer->outgoing_link);
+	wlr_log(WLR_DEBUG, "Destroying transfer %p", transfer);
 
 	// Start next queued transfer if we just removed the active one.
 	if (was_first && !wl_list_empty(&selection->outgoing)) {
+		wlr_log(WLR_DEBUG, "Destroyed transfer was active, starting next");
 		xwm_selection_transfer_start_outgoing(
 			xwm_selection_transfer_get_first(selection));
 	}
@@ -230,6 +232,8 @@ static void xwm_selection_transfer_start_outgoing(
 	struct wlr_xwm *xwm = transfer->selection->xwm;
 	struct wl_event_loop *loop =
 		wl_display_get_event_loop(xwm->xwayland->wl_display);
+	wlr_log(WLR_DEBUG, "Starting transfer %p", transfer);
+	assert(transfer == xwm_selection_transfer_get_first(transfer->selection));
 	transfer->source = wl_event_loop_add_fd(loop, transfer->source_fd,
 		WL_EVENT_READABLE, xwm_data_source_read, transfer);
 }
@@ -312,14 +316,34 @@ static void xwm_selection_send_data(struct wlr_xwm_selection *selection,
 	transfer->source_fd = p[0];
 
 	wlr_log(WLR_DEBUG, "Sending Wayland selection %u to Xwayland window with "
-		"MIME type %s, target %u", req->target, mime_type, req->target);
+		"MIME type %s, target %u, transfer %p", req->target, mime_type,
+		req->target, transfer);
 	xwm_selection_source_send(selection, mime_type, p[1]);
 
+	// It seems that if we ever try to reply to a selection request after
+	// another has been sent by the same requestor, the requestor never reads
+	// from it. It appears to only ever read from the latest, so purge stale
+	// transfers to prevent clipboard hangs.
+	struct wlr_xwm_selection_transfer *outgoing, *tmp;
+	wl_list_for_each_safe(outgoing, tmp, &selection->outgoing, outgoing_link) {
+		if (transfer->request.requestor == outgoing->request.requestor) {
+			wlr_log(WLR_DEBUG, "Destroying stale transfer %p", outgoing);
+			xwm_selection_send_notify(selection->xwm, &outgoing->request, false);
+			xwm_selection_transfer_destroy_outgoing(outgoing);
+		}
+	}
+
 	wl_list_insert(&selection->outgoing, &transfer->outgoing_link);
 
 	// We can only handle one transfer at a time
 	if (wl_list_length(&selection->outgoing) == 1) {
+		wlr_log(WLR_DEBUG, "No transfer active, starting %p now", transfer);
 		xwm_selection_transfer_start_outgoing(transfer);
+	} else {
+		struct wlr_xwm_selection_transfer *outgoing;
+		wl_list_for_each(outgoing, &selection->outgoing, outgoing_link) {
+			wlr_log(WLR_DEBUG, "Transfer %p still queued", outgoing);
+		}
 	}
 }