diff --git a/cheroot/makefile.py b/cheroot/makefile.py
index f5780a1ede..0376655548 100644
--- a/cheroot/makefile.py
+++ b/cheroot/makefile.py
@@ -26,13 +26,17 @@ def write(self, b):
     def _flush_unlocked(self):
         self._checkClosed('flush of closed file')
         while self._write_buf:
+            n = None
             try:
                 # ssl sockets only except 'bytes', not bytearrays
                 # so perhaps we should conditionally wrap this for perf?
-                n = self.raw.write(bytes(self._write_buf))
+                n = self.raw.write(
+                    bytes(self._write_buf[:SOCK_WRITE_BLOCKSIZE]),
+                )
             except io.BlockingIOError as e:
                 n = e.characters_written
-            del self._write_buf[:n]
+            if n:
+                del self._write_buf[:n]
 
 
 class StreamReader(io.BufferedReader):
diff --git a/cheroot/test/test_makefile.py b/cheroot/test/test_makefile.py
index d65d4ea268..6a65dd574e 100644
--- a/cheroot/test/test_makefile.py
+++ b/cheroot/test/test_makefile.py
@@ -51,3 +51,46 @@ def test_bytes_written():
     wfile = makefile.MakeFile(sock, 'w')
     wfile.write(b'bar')
     assert wfile.bytes_written == 3
+
+
+class _RawWriteBlockOnce:
+    """Mock raw.write() that returns None on the first call, then writes normally."""
+
+    def __init__(self):
+        """Initialize _RawWriteBlockOnce."""
+        self.call_count = 0
+        self.written = bytearray()
+
+    def __call__(self, chunk):
+        """Return None on first call to simulate a blocked socket write."""
+        self.call_count += 1
+        if self.call_count == 1:
+            return (
+                None  # simulates socket returning None on first blocked write
+            )
+        self.written.extend(chunk)
+        return len(chunk)
+
+
+def test_flush_when_raw_write_returns_none():
+    """_flush_unlocked() must not treat None from raw.write() as a byte count.
+
+    io.RawIOBase.write() returns None when a non-blocking socket cannot accept
+    data. del self._write_buf[:None] is equivalent to del self._write_buf[:]
+    which silently clears the entire buffer, truncating the response without
+    raising an exception.
+    """
+    data = b'x' * (makefile.SOCK_WRITE_BLOCKSIZE * 2)  # stress the write loop
+
+    sock = MockSocket()
+    wfile = makefile.MakeFile(sock, 'w')
+    wfile._write_buf.extend(data)
+
+    mock = _RawWriteBlockOnce()
+    wfile.raw.write = mock
+    wfile._flush_unlocked()
+
+    assert bytes(mock.written) == data, (
+        f'Expected {len(data)} bytes but only {len(mock.written)} reached raw.write(): '
+        'buffer was silently discarded when raw.write() returned None'
+    )
diff --git a/docs/changelog-fragments.d/822.bugfix.rst b/docs/changelog-fragments.d/822.bugfix.rst
new file mode 100644
index 0000000000..97493eeb59
--- /dev/null
+++ b/docs/changelog-fragments.d/822.bugfix.rst
@@ -0,0 +1,3 @@
+Fixed a bug that could cause premature clearing of the write buffer when a socket write is blocked.
+
+-- by :user:`cbbm142`
diff --git a/docs/spelling_wordlist.txt b/docs/spelling_wordlist.txt
index 06b204518e..981a6b3f97 100644
--- a/docs/spelling_wordlist.txt
+++ b/docs/spelling_wordlist.txt
@@ -5,6 +5,7 @@ backports
 bugfixes
 builtin
 b'xb
+buf
 compat
 config
 conftest
@@ -22,6 +23,7 @@ hardcoded
 hostname
 inclusivity
 intersphinx
+io
 iterable
 linter
 linters
@@ -48,6 +50,7 @@ preconfigure
 py
 pytest
 pythonic
+RawIOBase
 readonly
 rebase
 Refactor