diff --git a/cheroot/makefile.py b/cheroot/makefile.py
index f5780a1ede..61faca3ed5 100644
--- a/cheroot/makefile.py
+++ b/cheroot/makefile.py
@@ -3,6 +3,9 @@
 # prefer slower Python-based io module
 import _pyio as io
 import socket
+import time
+
+from OpenSSL import SSL
 
 
 # Write only 16K at a time to sockets
@@ -31,7 +34,24 @@ def _flush_unlocked(self):
                 # so perhaps we should conditionally wrap this for perf?
                 n = self.raw.write(bytes(self._write_buf))
             except io.BlockingIOError as e:
+                # some data may have been written
+                # we need to remove that from the buffer before retryings
                 n = e.characters_written
+            except (
+                SSL.WantReadError,
+                SSL.WantWriteError,
+                SSL.WantX509LookupError,
+            ):
+                # these errors require retries with the same data
+                # regardless of whether data has already been written
+                continue
+            except OSError:
+                # This catches errors like EBADF (Bad File Descriptor)
+                # or EPIPE (Broken pipe), which indicate the underlying
+                # socket is already closed or invalid.
+                # Since this happens in __del__, we silently stop flushing.
+                self._write_buf.clear()
+                return  # Exit the function
             del self._write_buf[:n]
 
 
@@ -45,9 +65,22 @@ def __init__(self, sock, mode='r', bufsize=io.DEFAULT_BUFFER_SIZE):
 
     def read(self, *args, **kwargs):
         """Capture bytes read."""
-        val = super().read(*args, **kwargs)
-        self.bytes_read += len(val)
-        return val
+        MAX_ATTEMPTS = 10
+        last_error = None
+        for _ in range(MAX_ATTEMPTS):
+            try:
+                val = super().read(*args, **kwargs)
+            except (SSL.WantReadError, SSL.WantWriteError) as ssl_want_error:
+                last_error = ssl_want_error
+                time.sleep(0.1)
+            else:
+                self.bytes_read += len(val)
+                return val
+
+        # If we get here, all attempts failed
+        raise TimeoutError(
+            'Max retries exceeded while waiting for data.',
+        ) from last_error
 
     def has_data(self):
         """Return true if there is buffered data to read."""
diff --git a/cheroot/test/test_ssl.py b/cheroot/test/test_ssl.py
index 8fd597e33a..6efe181390 100644
--- a/cheroot/test/test_ssl.py
+++ b/cheroot/test/test_ssl.py
@@ -1,5 +1,6 @@
 """Tests for TLS support."""
 
+import errno
 import functools
 import http.client
 import json
@@ -17,6 +18,8 @@
 import requests
 import trustme
 
+from cheroot.makefile import BufferedWriter
+
 from .._compat import (
     IS_ABOVE_OPENSSL10,
     IS_ABOVE_OPENSSL31,
@@ -625,6 +628,186 @@ def test_ssl_env(  # noqa: C901  # FIXME
     )
 
 
+@pytest.fixture
+def mock_raw_open_socket(mocker):
+    """Return a mocked raw socket prepared for writing (closed=False)."""
+    # This fixture sets the state on the injected object
+    mock_raw = mocker.Mock(name='mock_raw_socket')
+    mock_raw.closed = False
+    return mock_raw
+
+
+@pytest.fixture
+def ssl_writer(mock_raw_open_socket):
+    """Return a BufferedWriter instance with a mocked raw socket."""
+    return BufferedWriter(mock_raw_open_socket)
+
+
+def test_want_write_error_retry(ssl_writer, mock_raw_open_socket):
+    """Test that WantWriteError causes retry with same data."""
+    test_data = b'hello world'
+
+    # set up mock socket so that when its write() method is called,
+    # we get WantWriteError first, then success on the second call
+    # indicated by returning the number of bytes written
+    mock_raw_open_socket.write.side_effect = [
+        OpenSSL.SSL.WantWriteError(),
+        len(test_data),
+    ]
+
+    bytes_written = ssl_writer.write(test_data)
+    assert bytes_written == len(test_data)
+
+    # Assert against the injected mock object
+    assert mock_raw_open_socket.write.call_count == 2
+
+
+def test_want_read_error_retry(ssl_writer, mock_raw_open_socket):
+    """Test that WantReadError causes retry with same data."""
+    test_data = b'test data'
+
+    # set up mock socket so that when its write() method is called,
+    # we get WantReadError first, then success on the second call
+    # indicated by returning the number of bytes written
+    mock_raw_open_socket.write.side_effect = [
+        OpenSSL.SSL.WantReadError(),
+        len(test_data),
+    ]
+
+    bytes_written = ssl_writer.write(test_data)
+    assert bytes_written == len(test_data)
+
+
+@pytest.fixture(
+    params=('builtin', 'pyopenssl'),
+)
+def adapter_type(request):
+    """Fixture that yields the name of the SSL adapter."""
+    return request.param
+
+
+@pytest.fixture
+def create_side_effects_factory(adapter_type):
+    """
+    Fixture that returns a factory function to create the side effect list.
+
+    The factory function returns a list of two items:
+    1. An error to be raised on the first call
+    2. The length of data written on the second call
+
+    It returns a function that takes one argument,
+    allowing the data length to be injected from the test function.
+    """
+    if adapter_type == 'pyopenssl':
+        failure_error = OpenSSL.SSL.WantWriteError()
+    else:  # adapter_type == 'builtin'
+        failure_error = BlockingIOError(
+            errno.EWOULDBLOCK,
+            'Resource temporarily unavailable',
+        )
+        failure_error.characters_written = 0
+
+    def generate_side_effects(data_length):  # noqa: WPS430
+        """Return the list: [failure_error, data_length]."""
+        return [
+            failure_error,
+            data_length,  # This uses the length provided by the test
+        ]
+
+    # Return the inner function
+    return generate_side_effects
+
+
+@pytest.fixture
+def ssl_writer_integration(
+    mocker,
+    mock_raw_open_socket,
+    adapter_type,
+    tls_certificate_chain_pem_path,
+    tls_certificate_private_key_pem_path,
+):
+    """
+    Set up mock SSL writer for integration test.
+
+    Mocks the lowest-level write/send method to simulate a
+    WantWriteError for the PYOPENSSL adapter, and a
+    BlockingIOError for the BUILTIN adapter.
+    """
+    # Set up SSL adapter
+    tls_adapter_cls = get_ssl_adapter_class(name=adapter_type)
+    tls_adapter = tls_adapter_cls(
+        tls_certificate_chain_pem_path,
+        tls_certificate_private_key_pem_path,
+    )
+
+    if adapter_type == 'pyopenssl':
+        # --- PYOPENSSL SETUP
+        # Ensure context is initialized, as required by an OpenSSL Connection
+        tls_adapter.context = tls_adapter.get_context()
+        # need to mock a dummy fd on the mocked raw socket
+        mock_raw_open_socket.fileno.return_value = 1
+
+        # Create an OpenSSL.SSL.Connection object using the mocked raw socket
+        ssl_conn = OpenSSL.SSL.Connection(
+            tls_adapter.context,
+            mock_raw_open_socket,
+        )
+        ssl_conn.set_connect_state()
+        ssl_conn.closed = False
+
+        # we need to mock a write method on the mocked raw socket
+        raw_io_object = ssl_conn
+        raw_io_object.write = mocker.Mock(name='ssl_conn_write_mock')
+    else:
+        # adapter_type == 'builtin'
+        # --- BUILTIN ADAPTER SETUP (Requires different mocking) ---
+        # we need to mock the adapter's own write and writable methods
+        raw_io_object = tls_adapter
+        raw_io_object.writable = mocker.Mock(return_value=True)
+        raw_io_object.write = mocker.Mock(
+            name='builtin_adapter_write',
+        )
+        raw_io_object.closed = False
+
+    # return mock assertion target
+    return raw_io_object
+
+
+def test_want_write_error_integration(
+    ssl_writer_integration,
+    create_side_effects_factory,
+):
+    """Integration test for SSL writer handling of WantWriteError.
+
+    This test gets called twice, once for each adapter type.
+    The fixture ssl_writer_integration sets up the mock write method.
+    The fixture create_side_effects_factory creates the side effect list
+    with the data length injected from this test function.
+    """
+    raw_io_object = ssl_writer_integration
+    test_data = b'integration test data'
+    successful_write_length = len(test_data)
+
+    # Call side effects factory function to create
+    # a two step list for the mock write method.
+    # First call raises error, second call returns length.
+    # We have to inject the length because the factory
+    # is created in a fixture that doesn't know the test data.
+    side_effects = create_side_effects_factory(successful_write_length)
+    raw_io_object.write.side_effect = side_effects
+
+    writer = BufferedWriter(raw_io_object)
+
+    # write data and then flush
+    # with the way the mock_write is set up this should fail once,
+    # and then succeed on the retry.
+    bytes_written = writer.write(test_data)
+    writer.flush()
+
+    assert bytes_written == successful_write_length
+    assert raw_io_object.write.call_count == 2
+
+
 @pytest.mark.parametrize(
     'ip_addr',
     (
diff --git a/docs/changelog-fragments.d/764.bugfix.rst b/docs/changelog-fragments.d/764.bugfix.rst
new file mode 100644
index 0000000000..053da889ea
--- /dev/null
+++ b/docs/changelog-fragments.d/764.bugfix.rst
@@ -0,0 +1,7 @@
+Added handling for WantWriteError and WantReadError in BufferedWriter
+and StreamReader to enable retries. This addresses long standing issues
+discussed in #245. The reliability of the fix relies on using pyOpenSSL
+v25.2.0 or greater, as earlier versions have known bugs that affect
+the retry logic.
+
+-- by :user:`julianz-`
diff --git a/docs/spelling_wordlist.txt b/docs/spelling_wordlist.txt
index f9020b9ce6..35e085a903 100644
--- a/docs/spelling_wordlist.txt
+++ b/docs/spelling_wordlist.txt
@@ -43,6 +43,7 @@ positionally
 pre
 preconfigure
 py
+pyOpenSSL
 pytest
 pythonic
 readonly