diff --git a/synapse/logging/context.py b/synapse/logging/context.py
index b456c31f7071..60af53ae093c 100644
--- a/synapse/logging/context.py
+++ b/synapse/logging/context.py
@@ -611,10 +611,20 @@ def make_deferred_yieldable(deferred):
         # immediately. We may as well optimise out the logcontext faffery.
         return deferred
 
-    # ok, we can't be sure that a yield won't block, so let's reset the
+    if LoggingContext.current_context() is LoggingContext.sentinel:
+        # We're already in the sentinel context, so there's nothing to do. If we
+        # did attempt to "restore" the log context then we could easily clobber
+        # another log context that had been saved during the generation of this
+        # deferred.
+        # This makes it safe to call `make_deferred_yieldable` on deferreds that
+        # already have set the log contexts.
+        return deferred
+
+    # Ok, we can't be sure that a yield won't block, so let's reset the
     # logcontext, and add a callback to the deferred to restore it.
-    prev_context = LoggingContext.set_current_context(LoggingContext.sentinel)
-    deferred.addBoth(_set_context_cb, prev_context)
+    if LoggingContext.current_context() is not LoggingContext.sentinel:
+        prev_context = LoggingContext.set_current_context(LoggingContext.sentinel)
+        deferred.addBoth(_set_context_cb, prev_context)
     return deferred
 
 
diff --git a/tests/util/test_logcontext.py b/tests/util/test_logcontext.py
index 8b8455c8b7b0..bdb4fb7eb05b 100644
--- a/tests/util/test_logcontext.py
+++ b/tests/util/test_logcontext.py
@@ -174,6 +174,29 @@ def test_make_deferred_yieldable_on_non_deferred(self):
             self.assertEqual(r, "bum")
             self._check_test_key("one")
 
+    @defer.inlineCallbacks
+    def test_make_deferred_yieldable_reentrant(self):
+        """Test that `make_deferred_yieldable` does the right thing on deferreds
+        that already follow log context rules, i.e. wrapping a deferred with
+        `make_deferred_yieldable` multiple times.
+        """
+
+        sentinel_context = LoggingContext.current_context()
+
+        with LoggingContext() as context_one:
+            context_one.request = "one"
+
+            d1 = make_deferred_yieldable(_chained_deferred_function())
+            d2 = make_deferred_yieldable(d1)
+
+            # make sure that the context was reset by make_deferred_yieldable
+            self.assertIs(LoggingContext.current_context(), sentinel_context)
+
+            yield d2
+
+            # now it should be restored
+            self._check_test_key("one")
+
     def test_nested_logging_context(self):
         with LoggingContext(request="foo"):
             nested_context = nested_logging_context(suffix="bar")