diff --git a/org/channel-tui-main.org b/org/channel-tui-main.org
index 3371c85..cf4c8f8 100644
--- a/org/channel-tui-main.org
+++ b/org/channel-tui-main.org
@@ -756,35 +756,31 @@ supplied (e.g. \"/\"), pre-fill the select filter with it."
 
 ** Connection
 #+BEGIN_SRC lisp :tangle /home/user/.local/share/passepartout/lisp/channel-tui-main.lisp
-(defun connect-daemon (&optional (host "127.0.0.1") (port 9105))
-  (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)))
+(defun connect-daemon (&optional (host "127.0.0.1") (start-port 9105) (end-port 9115))
+  "Connect to daemon, trying ports START-PORT to END-PORT."
+  (add-msg :system (format nil "* Connecting to daemon... *"))
+  (loop for port from start-port to end-port
+        do (handler-case
+               (let ((s (usocket:socket-connect host port :timeout 2)))
                  (setf (st :stream) (usocket:socket-stream s)
                        (st :connected) t)
+                 (add-msg :system (format nil "* Connected to daemon on port ~d *" port))
                   (bt:make-thread (lambda () (reader-loop (st :stream)))
                                  :name "tui-reader")
                   (return-from connect-daemon t))
-             (usocket:connection-refused-error (c)
-                (declare (ignore c))
-                (when (= attempt 3)
-                 (add-msg :system (format nil "* No daemon on port ~a after ~a attempts *"
-                                         port attempt))))
+             (usocket:connection-refused-error ()
+               (when (= port end-port)
+                 (add-msg :system (format nil "* No daemon on ports ~d-~d *" start-port end-port))))
              (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 *")))))
+               (when (= port end-port)
+                 (add-msg :system (format nil "* No daemon on ports ~d-~d (error: ~a) *" start-port end-port c))))))
   nil)
 
 (defun disconnect-daemon ()
   (when (st :stream)
     (ignore-errors (close (st :stream)))
     (setf (st :stream) nil (st :connected) nil)
-    (add-msg :system "* Disconnected *")))
+    (add-msg :system (format nil "* Disconnected [now=~a] *" (now))))
 #+END_SRC
 
 ** Main Loop
diff --git a/org/core-pipeline.org b/org/core-pipeline.org
index ad154b1..cf4708a 100644
--- a/org/core-pipeline.org
+++ b/org/core-pipeline.org
@@ -367,7 +367,10 @@ Boot sequence:
   
   (when (fboundp 'events-start-heartbeat)
     (events-start-heartbeat))
-  (start-daemon)
+  (handler-case (start-daemon)
+    (error (c)
+      (log-message "DAEMON: Failed to start — ~a" c)
+      (format *error-output* "~&DAEMON: Failed to start — ~a~%" c)))
 
   #+sbcl
   (sb-sys:enable-interrupt sb-unix:sigint
diff --git a/org/core-transport.org b/org/core-transport.org
index 2c44f6e..2709699 100644
--- a/org/core-transport.org
+++ b/org/core-transport.org
@@ -147,6 +147,7 @@ The daemon sends a handshake message on connection, then enters a read loop, inj
 
 #+begin_src lisp
 (defvar *daemon-socket* nil)
+(defvar *daemon-port* nil "The port the daemon is actually listening on (may differ from default if 9105 was in use).")
 
 (defun client-handle-connection (socket)
   "Handles a single TUI/CLI client connection in a dedicated thread."
@@ -174,18 +175,30 @@ The daemon sends a handshake message on connection, then enters a read loop, inj
       (error (c) (log-message "CLIENT ERROR: ~a" c)))
     (ignore-errors (usocket:socket-close socket))))
 
-(defun start-daemon (&key (port 9105))
-  "Starts the network listener for TUI/CLI clients."
-  (setf *daemon-socket* (usocket:socket-listen "127.0.0.1" port :reuse-address t))
-  (log-message "DAEMON: Listening on localhost:~a" port)
-  (bt:make-thread
-   (lambda ()
-     (loop
-       (let ((client-socket (usocket:socket-accept *daemon-socket*)))
-         (when client-socket
-           (bt:make-thread (lambda () (client-handle-connection client-socket))
-                          :name "passepartout-client-handler")))))
-   :name "passepartout-server-listener"))
+(defun start-daemon (&key (port 9105) (max-retries 10))
+  "Starts the network listener for TUI/CLI clients.
+If PORT is taken, tries subsequent ports up to PORT+MAX-RETRIES."
+  (loop for attempt from 0 below max-retries
+        for p = (+ port attempt)
+        do (handler-case
+               (progn
+                 (setf *daemon-socket* (usocket:socket-listen "127.0.0.1" p :reuse-address t))
+                 (log-message "DAEMON: Listening on localhost:~a" p)
+                 (setf *daemon-port* p)
+                 (bt:make-thread
+                  (lambda ()
+                    (loop
+                      (let ((client-socket (usocket:socket-accept *daemon-socket*)))
+                        (when client-socket
+                          (bt:make-thread (lambda () (client-handle-connection client-socket))
+                                         :name "passepartout-client-handler")))))
+                  :name "passepartout-server-listener")
+                 (return p))
+             (usocket:address-in-use-error ()
+               (when (= attempt (1- max-retries))
+                 (log-message "DAEMON: All ports ~d-~d in use — giving up" port (+ port max-retries -1))
+                 (error "No available port for daemon"))
+               (log-message "DAEMON: Port ~d in use, trying ~d..." p (1+ p))))))
 #+end_src
 
 ** Handshake Logic