diff --git a/CHANGELOG.md b/CHANGELOG.md
index db325da7..44093dc5 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -49,6 +49,8 @@
   `tweak.allow-overflowing-double-width-glyphs`.
 * Regression: crash when a single-char, double-width glyph is in the
   last column, and `tweak.allow-overflowing-double-width-glyphs=yes`.
+* FD exhaustion when repeatedly entering/exiting URL mode with many
+  URLs.
 
 
 ### Security
diff --git a/url-mode.c b/url-mode.c
index 5f56a2f6..8ac5631e 100644
--- a/url-mode.c
+++ b/url-mode.c
@@ -14,6 +14,7 @@
 #include "grid.h"
 #include "render.h"
 #include "selection.h"
+#include "shm.h"
 #include "spawn.h"
 #include "terminal.h"
 #include "uri.h"
@@ -728,7 +729,9 @@ urls_reset(struct terminal *term)
 
     if (term->window != NULL) {
         tll_foreach(term->window->urls, it) {
+            const struct url *url = it->item.url;
             wayl_win_subsurface_destroy(&it->item.surf);
+            shm_purge(term->wl->shm, shm_cookie_url(url));
             tll_remove(term->window->urls, it);
         }
     }
diff --git a/wayland.c b/wayland.c
index 80fef88a..ecc4f31e 100644
--- a/wayland.c
+++ b/wayland.c
@@ -26,6 +26,7 @@
 #include "input.h"
 #include "render.h"
 #include "selection.h"
+#include "shm.h"
 #include "util.h"
 #include "xmalloc.h"
 
@@ -1410,6 +1411,9 @@ wayl_win_destroy(struct wl_window *win)
     if (win == NULL)
         return;
 
+    struct terminal *term = win->term;
+    struct wl_shm *shm = term->wl->shm;
+
     if (win->csd.move_timeout_fd != -1)
         close(win->csd.move_timeout_fd);
 
@@ -1457,6 +1461,7 @@ wayl_win_destroy(struct wl_window *win)
 
     tll_foreach(win->urls, it) {
         wayl_win_subsurface_destroy(&it->item.surf);
+        shm_purge(shm, shm_cookie_url(it->item.url));
         tll_remove(win->urls, it);
     }