diff --git a/src/picowatch.py b/src/picowatch.py
index cc2ee06..2f834ff 100644
--- a/src/picowatch.py
+++ b/src/picowatch.py
@@ -191,6 +191,7 @@ class Telnet:
 
 class Pyboard(object):
     i: int = 0
+    boot_status: bool = False
     serial: Union[Serial, Telnet]
 
     def __init__(self, device: str, baudrate: int = 115200, login: str = 'micro', password: str = 'python'):
@@ -231,6 +232,7 @@ class Pyboard(object):
         self.serial.write(b'\x02')
 
     def send_ctrl_c(self) -> bytes:
+        self.boot_status = False
         # Ctrl-C cancels any input, or interrupts the currently running code.
         for _ in range(0, 2):
             self.serial.write(b'\x03')
@@ -251,14 +253,14 @@ class Pyboard(object):
 
     def read_until(self, delimiter: bytes, stream_output: bool = False, show_status: bool = False) -> Optional[bytes]:
         data = b''
-        timeout = 0
+        timeout = 300
         max_len = len(delimiter)
-
-        while not timeout >= 1000:
+        
+        while timeout > 0:
             if data.endswith(delimiter):
                 return data
             elif self.serial.inWaiting() > 0:
-                timeout = 0
+                timeout = 300
                 data += self.serial.read(1)
 
                 if stream_output:
@@ -268,8 +270,8 @@ class Pyboard(object):
                 elif show_status:
                     self.transfer_status()
             else:
-                timeout += 1
-                time.sleep(0.0001)
+                timeout -= 1
+                time.sleep(0.01)
 
     def boot(self):
         data = b''
@@ -280,13 +282,21 @@ class Pyboard(object):
         if not self.read_until(self.send_ctrl_d()):
             raise Exception('REPL: could not soft reboot')
 
-        while not data.endswith(b'\r\nMicroPython v') and not data.endswith(b'.\r\n>>>'):
-            if self.serial.inWaiting():
-                data = data[-15:] + self.serial.read(1)
-                sys.stdout.buffer.write(data[-1:])
-                sys.stdout.buffer.flush()
+        output_status = True
+        self.boot_status = True
 
-        sys.stdout.buffer.write(b'\r' + b' ' * 20 + b'\r')
+        while self.boot_status and output_status:
+            if self.serial.inWaiting():
+                sys.stdout.buffer.write((data := data[-15:] + self.serial.read(1))[-1:])
+                sys.stdout.buffer.flush()
+                output_status = not data.endswith(b'\r\nMicroPython v') and not data.endswith(b'.\r\n>>>')
+        
+        if not output_status:
+            sys.stdout.buffer.write(b'\r<<< Program terminated\r\n')
+        elif not self.boot_status:
+            sys.stdout.buffer.write(b'\r<<< Program terminated with <KeyboardInterrupt> Exception\r\n')
+        
+        self.boot_status = False
 
     def __enter__(self):
         self.send_ctrl_c()
@@ -340,9 +350,9 @@ class Pyboard(object):
                 for call in traceback[1][:-2].split('\\r\\n'):
                     reason += f'{call}\n'
 
-                raise Exception('' + reason.strip())
+                raise Exception('\r' + reason.strip())
             else:
-                raise Exception(exception)
+                raise Exception('\r' + exception)
 
         return data.strip()