diff --git a/backend/app/services/esp32_lib_manager.py b/backend/app/services/esp32_lib_manager.py
index b04c26e5..9effd6a7 100644
--- a/backend/app/services/esp32_lib_manager.py
+++ b/backend/app/services/esp32_lib_manager.py
@@ -152,9 +152,16 @@ class _UartBuffer:
         """Add one byte. Returns decoded string when a flush occurs, else None."""
         with self._lock:
             self._buf.append(byte_val)
-            # Flush on newline, carriage return, period, or max size
-            # This ensures progress dots '...' don't buffer endlessly.
-            if byte_val in (ord('\n'), ord('\r'), ord('.')) or len(self._buf) >= self.flush_size:
+            # Flush on newline, carriage return, period, EOT, or max size.
+            # The dots keep a progress line from buffering endlessly; EOT
+            # (Ctrl-D, 0x04) is there because MicroPython's raw REPL answers
+            # every statement with `OK` <EOT> traceback <EOT> `>` and not one
+            # newline in it. Held here, that answer never reaches the uploader
+            # waiting on it, and a MicroPython project times out mid-upload
+            # with the board sitting idle at the prompt. It only surfaced once
+            # the uploader started waiting for the board instead of pasting
+            # blind (see frontend simulation/micropythonSession.ts).
+            if byte_val in (ord('\n'), ord('\r'), ord('.'), 0x04) or len(self._buf) >= self.flush_size:
                 text = self._buf.decode('utf-8', errors='replace')
                 self._buf.clear()
                 return text
diff --git a/test/backend/unit/test_uart_buffer_flush.py b/test/backend/unit/test_uart_buffer_flush.py
new file mode 100644
index 00000000..b93da25b
--- /dev/null
+++ b/test/backend/unit/test_uart_buffer_flush.py
@@ -0,0 +1,46 @@
+"""
+When the UART buffer lets go of what it has (issue #260 verification).
+
+MicroPython's raw REPL answers every statement with `OK` <EOT> traceback <EOT>
+`>` and not a single newline. The buffer used to flush only on newline,
+carriage return, a period or 256 bytes, so that answer sat in it — and the
+project uploader, which waits for the board's end-of-execution marker before
+sending the next step, timed out with the board idle at the prompt.
+"""
+import unittest
+
+from app.services.esp32_lib_manager import _UartBuffer
+
+
+def feed_all(buf: _UartBuffer, text: bytes) -> str:
+    """Everything the buffer released while consuming `text`."""
+    return ''.join(out for b in text if (out := buf.feed(b)) is not None)
+
+
+class TestUartBufferFlush(unittest.TestCase):
+    def test_raw_repl_answer_is_released(self):
+        out = feed_all(_UartBuffer(0), b'OK\x04\x04>')
+        self.assertEqual(out.count('\x04'), 2)
+
+    def test_answer_carrying_a_traceback_is_released(self):
+        out = feed_all(_UartBuffer(0), b'OK\x04OSError: 28\x04>')
+        self.assertEqual(out.count('\x04'), 2)
+        self.assertIn('OSError: 28', out)
+
+    def test_the_trailing_prompt_still_waits(self):
+        """`>` is not a boundary; it rides out with the next flush. The
+        uploader keys on the EOT pair, so this is fine."""
+        buf = _UartBuffer(0)
+        out = feed_all(buf, b'OK\x04\x04>')
+        self.assertFalse(out.endswith('>'))
+        self.assertEqual(buf.flush(), '>')
+
+    def test_ordinary_lines_still_flush_on_newline(self):
+        self.assertEqual(feed_all(_UartBuffer(0), b'hello\n'), 'hello\n')
+
+    def test_progress_dots_still_flush(self):
+        self.assertEqual(feed_all(_UartBuffer(0), b'...'), '...')
+
+    def test_size_limit_still_applies(self):
+        buf = _UartBuffer(0, flush_size=8)
+        self.assertEqual(feed_all(buf, b'abcdefgh'), 'abcdefgh')