diff --git a/gptel-transient.el b/gptel-transient.el
index f6fba6e4..77f2378f 100644
--- a/gptel-transient.el
+++ b/gptel-transient.el
@@ -720,6 +720,7 @@ Also format its value in the Transient menu."
     (gptel--infix-variable-scope)
     (gptel--infix-provider)
     (gptel--infix-max-tokens)
+    (gptel--infix-rolling-window-prompt)
     (gptel--infix-num-messages-to-send
      :if (lambda () (and gptel-expert-commands
                     (or gptel-mode gptel-track-response))))
@@ -1303,6 +1304,27 @@ supports.  See `gptel-track-media' for more information."
   (transient-setup))
 
 ;; ** Infix for additional directive
+(transient-define-infix gptel--infix-rolling-window-prompt ()
+  "Control prompt truncation for model context window.
+When enabled, gptel will automatically truncate prompts to fit the model's
+context window using the specified fraction (or 90% by default)."
+  :description "Auto-truncate prompt"
+  :class 'gptel-lisp-variable
+  :variable 'gptel-rolling-window-prompt
+  :set-value #'gptel--set-with-scope
+  :display-nil "Disable"
+  :display-map '((t . "Enable (90%)"))
+  :key "-w"
+  :prompt "Prompt truncation: "
+  :reader (lambda (prompt &rest _)
+            (let* ((choices '(("disable" . nil)
+                              ("enable (90%)" . t)
+                              ("custom fraction" . number)))
+                   (choice (completing-read prompt choices nil t)))
+              (if (equal choice "custom fraction")
+                  (let ((val (read-number "Fraction of context window (0.1-1.0): " 0.9)))
+                    (if (and (>= val 0.1) (<= val 1.0)) val (error "Invalid fraction")))
+                (cdr (assoc choice choices))))))
 
 (transient-define-infix gptel--infix-add-directive ()
   "Additional directive intended for the next query only.
diff --git a/gptel.el b/gptel.el
index c3636287..3719f130 100644
--- a/gptel.el
+++ b/gptel.el
@@ -304,7 +304,7 @@ command line arguments."
   'gptel-prompt-transform-functions "0.9.9")
 
 (defcustom gptel-prompt-transform-functions
-  '(gptel--transform-apply-preset gptel--transform-add-context)
+  '(gptel--transform-apply-preset gptel--transform-add-context gptel--transform-truncate-prompt)
   "Handlers to augment or transform a query before sending it.
 
 This hook is called in a temporary buffer containing the text to
@@ -336,6 +336,22 @@ locally for a specific buffer, or chat topic, or only the context of a
 certain task."
   :type 'hook)
 
+(defcustom gptel-rolling-window-prompt nil
+  "Automatically truncate prompts to fit the model's context window.
+When non-nil, gptel will try to keep the prompt size below the
+model's advertised context window by removing the oldest parts of the
+conversation.
+
+- Set to `t` to enable (uses 90% of the context window as a safety margin).
+- Set to a number between 0.1 and 1.0 to specify the exact fraction of the
+  context window to use (e.g., 0.8 for 80%).
+- Set to nil to disable."
+  :group 'gptel
+  :type '(choice
+          (const :tag "Enable (use 90% of context window)" t)
+          (const :tag "Disable" nil)
+          (number :tag "Use fraction of context window")))
+
 (defcustom gptel-post-request-hook nil
   "Hook run after sending a gptel request.
 
@@ -1169,6 +1185,18 @@ in any way.")
   "Curl executable to use."
   (if (stringp gptel-use-curl) gptel-use-curl "curl"))
 
+(defun gptel--transform-truncate-prompt ()
+  "Truncate the prompt buffer to fit the current model's context window.
+This function is intended to be run from `gptel-prompt-transform-functions`.
+It respects the `gptel-rolling-window-prompt` user option."
+  (when (and gptel-rolling-window-prompt (get gptel-model :context-window))
+    (let* ((context-window-k (get gptel-model :context-window))
+           (safety-margin (if (numberp gptel-rolling-window-prompt) gptel-rolling-window-prompt 0.9))
+           (max-chars (round (* context-window-k 1000 3 safety-margin)))) ; Approx 4 chars/token
+      (when (> (buffer-size) max-chars)
+        (message "gptel: Truncating prompt to the last %d characters." max-chars)
+        (delete-region (point-min) (- (point-max) max-chars))))))
+
 (defun gptel--transform-add-context (callback fsm)
   (if (and gptel-use-context gptel-context--alist)
       (gptel-context--wrap callback (plist-get (gptel-fsm-info fsm) :data))