diff --git a/lisp/gateway-tui-main.lisp b/lisp/gateway-tui-main.lisp
index 2ab33a4..876e730 100644
--- a/lisp/gateway-tui-main.lisp
+++ b/lisp/gateway-tui-main.lisp
@@ -197,15 +197,28 @@
                  (sleep 0.5)))))
 
 (defun connect-daemon (&optional (host "127.0.0.1") (port 9105))
-  (handler-case
-      (let ((s (usocket:socket-connect host port :timeout 10)))
-        (setf (st :stream) (usocket:socket-stream s) (st :connected) t)
-        (bt:make-thread (lambda () (reader-loop (st :stream))) :name "tui-reader")
-        (add-msg :system "* Connected *")
-        t)
-    (error (c)
-      (add-msg :system (format nil "* Connection failed: ~a *" c))
-      nil)))
+  (add-msg :system "* Connecting to daemon... *")
+  (loop for attempt from 1 to 3
+        for backoff = 0 then 3
+        do (sleep backoff)
+           (handler-case
+               (let ((s (usocket:socket-connect host port :timeout 5)))
+                 (setf (st :stream) (usocket:socket-stream s)
+                       (st :connected) t)
+                 (bt:make-thread (lambda () (reader-loop (st :stream)))
+                                :name "tui-reader")
+                 (add-msg :system (format nil "* Connected v~a *" "0.2.0"))
+                 (return-from connect-daemon t))
+             (usocket:connection-refused-error (c)
+               (when (= attempt 3)
+                 (add-msg :system (format nil "* No daemon on port ~a after ~a attempts *"
+                                         port attempt))))
+             (error (c)
+               (add-msg :system (format nil "* Connection attempt ~a failed: ~a *"
+                                        attempt c))
+               (when (= attempt 3)
+                 (add-msg :system "* TIP: run 'passepartout daemon' first *")))))
+  nil)
 
 (defun disconnect-daemon ()
   (when (st :stream)
diff --git a/org/gateway-tui-main.org b/org/gateway-tui-main.org
index 8e722be..6065e48 100644
--- a/org/gateway-tui-main.org
+++ b/org/gateway-tui-main.org
@@ -231,15 +231,28 @@ Event handlers + daemon I/O + main loop.
 ** Connection
 #+begin_src lisp
 (defun connect-daemon (&optional (host "127.0.0.1") (port 9105))
-  (handler-case
-      (let ((s (usocket:socket-connect host port :timeout 10)))
-        (setf (st :stream) (usocket:socket-stream s) (st :connected) t)
-        (bt:make-thread (lambda () (reader-loop (st :stream))) :name "tui-reader")
-        (add-msg :system "* Connected *")
-        t)
-    (error (c)
-      (add-msg :system (format nil "* Connection failed: ~a *" c))
-      nil)))
+  (add-msg :system "* Connecting to daemon... *")
+  (loop for attempt from 1 to 3
+        for backoff = 0 then 3
+        do (sleep backoff)
+           (handler-case
+               (let ((s (usocket:socket-connect host port :timeout 5)))
+                 (setf (st :stream) (usocket:socket-stream s)
+                       (st :connected) t)
+                 (bt:make-thread (lambda () (reader-loop (st :stream)))
+                                :name "tui-reader")
+                 (add-msg :system (format nil "* Connected v~a *" "0.2.0"))
+                 (return-from connect-daemon t))
+             (usocket:connection-refused-error (c)
+               (when (= attempt 3)
+                 (add-msg :system (format nil "* No daemon on port ~a after ~a attempts *"
+                                         port attempt))))
+             (error (c)
+               (add-msg :system (format nil "* Connection attempt ~a failed: ~a *"
+                                        attempt c))
+               (when (= attempt 3)
+                 (add-msg :system "* TIP: run 'passepartout daemon' first *")))))
+  nil)
 
 (defun disconnect-daemon ()
   (when (st :stream)