diff --git a/cheroot/server.py b/cheroot/server.py
index 284cf17c72..418a86b7a4 100644
--- a/cheroot/server.py
+++ b/cheroot/server.py
@@ -1306,7 +1306,12 @@ def communicate(self):  # noqa: C901  # FIXME
         """
         request_seen = False
         try:
-            req = self.RequestHandlerClass(self.server, self)
+            req = self.RequestHandlerClass(
+                self.server,
+                self,
+                proxy_mode=self.server.proxy_mode,
+                strict_mode=self.server.strict_mode,
+            )
             req.parse_request()
             if self.server.stats['Enabled']:
                 self.requests_seen += 1
diff --git a/cheroot/test/test_server.py b/cheroot/test/test_server.py
index ae6e390a44..b434d88495 100644
--- a/cheroot/test/test_server.py
+++ b/cheroot/test/test_server.py
@@ -20,7 +20,7 @@
 from pypytools.gc.custom import DefaultGc
 
 from .._compat import IS_LINUX, IS_MACOS, IS_WINDOWS, SYS_PLATFORM, bton, ntob
-from ..server import IS_UID_GID_RESOLVABLE, Gateway, HTTPServer
+from ..server import IS_UID_GID_RESOLVABLE, Gateway, HTTPConnection, HTTPServer
 from ..testing import (
     ANY_INTERFACE_IPV4,
     ANY_INTERFACE_IPV6,
@@ -127,6 +127,58 @@ def test_stop_interrupts_serve():
     assert not serve_thread.is_alive()
 
 
+def test_communicate_uses_server_proxy_and_strict_mode():
+    """Check that parsed requests inherit proxy/strict mode from the server."""
+    httpserver = HTTPServer(
+        bind_addr=(ANY_INTERFACE_IPV4, EPHEMERAL_PORT),
+        gateway=Gateway,
+    )
+    request_init_args = []
+
+    class CapturingHTTPRequest:
+        """Capture request constructor args used during communication."""
+
+        def __init__(
+            self,
+            server,
+            conn,
+            proxy_mode=False,
+            strict_mode=True,
+        ):
+            request_init_args.append(
+                {
+                    'server': server,
+                    'conn': conn,
+                    'proxy_mode': proxy_mode,
+                    'strict_mode': strict_mode,
+                },
+            )
+            self.ready = False
+
+        def parse_request(self):
+            return None
+
+    conn = HTTPConnection(
+        httpserver,
+        types.SimpleNamespace(),
+        makefile=lambda _sock, _mode, _bufsize: types.SimpleNamespace(),
+    )
+    conn.RequestHandlerClass = CapturingHTTPRequest
+    httpserver.proxy_mode = True
+    httpserver.strict_mode = False
+
+    assert conn.communicate() is False
+
+    assert request_init_args == [
+        {
+            'server': httpserver,
+            'conn': conn,
+            'proxy_mode': True,
+            'strict_mode': False,
+        },
+    ]
+
+
 @pytest.mark.parametrize(
     'exc_cls',
     (
diff --git a/docs/changelog-fragments.d/831.bugfix.rst b/docs/changelog-fragments.d/831.bugfix.rst
new file mode 100644
index 0000000000..b44465d026
--- /dev/null
+++ b/docs/changelog-fragments.d/831.bugfix.rst
@@ -0,0 +1 @@
+Preserved server proxy and strict mode settings when parsing requests on accepted connections.