diff --git a/cheroot/makefile.py b/cheroot/makefile.py
index f5780a1ede..59c00e9769 100644
--- a/cheroot/makefile.py
+++ b/cheroot/makefile.py
@@ -2,12 +2,16 @@
 
 # prefer slower Python-based io module
 import _pyio as io
+import select
 import socket
 
 
 # Write only 16K at a time to sockets
 SOCK_WRITE_BLOCKSIZE = 16384
 
+# Seconds to wait for a blocked socket to become writable
+SOCK_WRITE_TIMEOUT = 10
+
 
 class BufferedWriter(io.BufferedWriter):
     """Faux file object attached to a socket object."""
@@ -26,12 +30,28 @@ 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
+            if n is None:
+                _, writable, _ = select.select(
+                    [],
+                    [self.raw],
+                    [],
+                    SOCK_WRITE_TIMEOUT,
+                )
+                if not writable:
+                    raise io.BlockingIOError(
+                        0,
+                        'raw stream blocked; no bytes written',
+                    )
+                continue
             del self._write_buf[:n]
 
 
diff --git a/cheroot/makefile.pyi b/cheroot/makefile.pyi
index 3f5ea2756b..8e8d57d73f 100644
--- a/cheroot/makefile.pyi
+++ b/cheroot/makefile.pyi
@@ -1,6 +1,7 @@
 import io
 
 SOCK_WRITE_BLOCKSIZE: int
+SOCK_WRITE_TIMEOUT: int
 
 class BufferedWriter(io.BufferedWriter):
     def write(self, b): ...
diff --git a/cheroot/test/test_makefile.py b/cheroot/test/test_makefile.py
index d65d4ea268..f0582dba15 100644
--- a/cheroot/test/test_makefile.py
+++ b/cheroot/test/test_makefile.py
@@ -51,3 +51,100 @@ def test_bytes_written():
     wfile = makefile.MakeFile(sock, 'w')
     wfile.write(b'bar')
     assert wfile.bytes_written == 3
+
+
+class _RawWriteBlockOnce:
+    """Mock raw.write() returning None once, then writing 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 write."""
+        self.call_count += 1
+        if self.call_count == 1:
+            return None
+        self.written.extend(chunk)
+        return len(chunk)
+
+    def fileno(self):
+        """Return a fake fd for select()."""
+        return -1
+
+
+class _RawWriteBlockAlways:
+    """Mock raw.write() that always returns None."""
+
+    def __init__(self):
+        """Initialize _RawWriteBlockAlways."""
+        self.call_count = 0
+
+    def __call__(self, chunk):
+        """Return None to simulate a permanently blocked socket."""
+        self.call_count += 1
+
+    def fileno(self):
+        """Return a fake fd for select()."""
+        return -1
+
+
+def test_flush_recovers_from_temporary_block(monkeypatch):
+    """_flush_unlocked() retries after select when raw.write() returns None.
+
+    A temporarily blocked socket should recover once select() reports
+    the socket is writable again, delivering all buffered data.
+    """
+    data = b'x' * (makefile.SOCK_WRITE_BLOCKSIZE * 2)
+
+    sock = MockSocket()
+    wfile = makefile.MakeFile(sock, 'w')
+    wfile._write_buf.extend(data)
+
+    mock = _RawWriteBlockOnce()
+    wfile.raw.write = mock
+
+    # select() reports writable immediately
+    monkeypatch.setattr(
+        'cheroot.makefile.select.select',
+        lambda _rlist, wlist, _xlist, _timeout: ([], wlist, []),
+    )
+    wfile._flush_unlocked()
+
+    assert bytes(mock.written) == data, (
+        'all buffered data should be written after select retry'
+    )
+
+
+def test_flush_raises_on_sustained_block(monkeypatch):
+    """_flush_unlocked() raises BlockingIOError after select timeout.
+
+    If the socket stays blocked past SOCK_WRITE_TIMEOUT, the write
+    buffer must be preserved and BlockingIOError raised.
+    """
+    import io
+
+    import pytest
+
+    data = b'x' * makefile.SOCK_WRITE_BLOCKSIZE
+
+    sock = MockSocket()
+    wfile = makefile.MakeFile(sock, 'w')
+    wfile._write_buf.extend(data)
+
+    mock = _RawWriteBlockAlways()
+    wfile.raw.write = mock
+
+    # select() reports not writable (timeout)
+    monkeypatch.setattr(
+        'cheroot.makefile.select.select',
+        lambda _rlist, _wlist, _xlist, _timeout: ([], [], []),
+    )
+
+    with pytest.raises(io.BlockingIOError):
+        wfile._flush_unlocked()
+
+    assert len(wfile._write_buf) == len(data), (
+        'write buffer must be preserved when socket stays blocked'
+    )
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