diff --git a/gptme/cli.py b/gptme/cli.py
index 81dc1b40..76df2755 100644
--- a/gptme/cli.py
+++ b/gptme/cli.py
@@ -4,7 +4,9 @@
 import os
 import re
 import readline  # noqa: F401
+import signal
 import sys
+import time
 import urllib.parse
 from collections.abc import Generator
 from datetime import datetime
@@ -185,6 +187,9 @@ def main(
     prompts = [p.strip() for p in "\n\n".join(prompts).split(sep) if p]
     prompt_msgs = [Message("user", p) for p in prompts]
 
+    # register a handler for Ctrl-C
+    signal.signal(signal.SIGINT, handle_keyboard_interrupt)
+
     chat(
         prompt_msgs,
         initial_msgs,
@@ -198,6 +203,44 @@ def main(
     )
 
 
+# Set up a KeyboardInterrupt handler to handle Ctrl-C during the chat loop
+interruptible = False
+last_interrupt_time = 0.0
+
+
+def handle_keyboard_interrupt(signum, frame):
+    """
+    This handler allows interruption of the assistant or tool execution when in an interruptible state,
+    while still providing a safeguard against accidental exits during user input.
+    """
+    global last_interrupt_time
+    current_time = time.time()
+    timeout = 1
+
+    if interruptible:
+        raise KeyboardInterrupt
+
+    if current_time - last_interrupt_time <= timeout:
+        console.log("Second interrupt received, exiting...")
+        sys.exit(0)
+
+    last_interrupt_time = current_time
+    console.print()
+    console.log(
+        f"Interrupt received. Press Ctrl-C again within {timeout} seconds to exit."
+    )
+
+
+def set_interruptible():
+    global interruptible
+    interruptible = True
+
+
+def clear_interruptible():
+    global interruptible
+    interruptible = False
+
+
 def chat(
     prompt_msgs: list[Message],
     initial_msgs: list[Message],
@@ -277,7 +320,16 @@ def chat(
 
                 # Generate and execute response for this prompt
                 while True:
-                    response_msgs = list(step(log, no_confirm, stream=stream))
+                    set_interruptible()
+                    try:
+                        response_msgs = list(step(log, no_confirm, stream=stream))
+                    except KeyboardInterrupt:
+                        console.log("Interrupted. Stopping current execution.")
+                        log.append(Message("system", "Interrupted"))
+                        break
+                    finally:
+                        clear_interruptible()
+
                     for response_msg in response_msgs:
                         log.append(response_msg)
                         # run any user-commands, if msg is from user
@@ -309,6 +361,7 @@ def chat(
             break
 
         # ask for input if no prompt, generate reply, and run tools
+        clear_interruptible()  # Ensure we're not interruptible during user input
         for msg in step(log, no_confirm, stream=stream):  # pragma: no cover
             log.append(msg)
             # run any user-commands, if msg is from user
@@ -341,7 +394,8 @@ def step(
         msg = _include_paths(msg)
         yield msg
 
-    # print response
+    # generate response and run tools
+    set_interruptible()
     try:
         # performs reduction/context trimming, if necessary
         msgs = log.prepare_messages()
@@ -357,7 +411,10 @@ def step(
             yield msg_response.replace(quiet=True)
             yield from execute_msg(msg_response, ask=not no_confirm)
     except KeyboardInterrupt:
+        clear_interruptible()
         yield Message("system", "Interrupted")
+    finally:
+        clear_interruptible()
 
 
 def get_name(name: str) -> Path: