diff --git a/cider.el b/cider.el
index 1b21fd707..41ec02744 100644
--- a/cider.el
+++ b/cider.el
@@ -892,10 +892,15 @@ buffer."
     (cider--check-required-nrepl-version)
     (cider--check-clojure-version-supported)
     (cider--check-middleware-compatibility)
-    (cider--debug-init-connection)
     (cider--subscribe-repl-to-server-out)
     (when cider-auto-mode
       (cider-enable-on-existing-clojure-buffers))
+    ;; Middleware on cider-nrepl side is loaded dynamically on first
+    ;; usage. Loading middleware concurrently can lead to confusing issues
+    ;; (likely a clojure bug). Debug middleware is heavy, so enable it at the
+    ;; end and hope for the best. Ideally, the sequence of middleware loading
+    ;; should be done in a deferred chain.
+    (cider--debug-init-connection)
     (run-hooks 'cider-connected-hook)))
 
 (defun cider--disconnected-handler ()