diff --git a/changes/bug40499 b/changes/bug40499
new file mode 100644
index 0000000000..149e9bd200
--- /dev/null
+++ b/changes/bug40499
@@ -0,0 +1,7 @@
+  o Major bugfixes (client):
+    - Stop caching TCP connect failures to relays/bridges when we
+      initiated the connection as a client. Now we only cache connect
+      failures as a relay or bridge when we initiated them because
+      of an EXTEND request. Declining to re-attempt the client-based
+      connections could cause problems when we lose connectivity and
+      try to reconnect. Fixes bug 40499; bugfix on 0.3.3.4-alpha.
diff --git a/src/core/or/connection_or.c b/src/core/or/connection_or.c
index db9f93e6f6..0018b1dfd8 100644
--- a/src/core/or/connection_or.c
+++ b/src/core/or/connection_or.c
@@ -1316,6 +1316,13 @@ note_or_connect_failed(const or_connection_t *or_conn)
 
   tor_assert(or_conn);
 
+  if (or_conn->potentially_used_for_bootstrapping) {
+    /* Don't cache connection failures for connections we initiated ourself.
+     * If these direct connections fail, we're supposed to recognize that
+     * the destination is down and stop trying. See ticket 40499. */
+    return;
+  }
+
   ocf = or_connect_failure_find(or_conn);
   if (ocf == NULL) {
     ocf = or_connect_failure_new(or_conn);