diff --git a/changelog.d/15887.misc b/changelog.d/15887.misc
new file mode 100644
index 000000000..7c1005078
--- /dev/null
+++ b/changelog.d/15887.misc
@@ -0,0 +1 @@
+Fix background schema updates failing over a large upgrade gap.
diff --git a/synapse/storage/schema/main/delta/78/05_mitigate_stream_ordering_update_race.py b/synapse/storage/schema/main/delta/78/05_mitigate_stream_ordering_update_race.py
new file mode 100644
index 000000000..1a22f6a40
--- /dev/null
+++ b/synapse/storage/schema/main/delta/78/05_mitigate_stream_ordering_update_race.py
@@ -0,0 +1,70 @@
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+#  Unless required by applicable law or agreed to in writing, software
+#  distributed under the License is distributed on an "AS IS" BASIS,
+#  WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+#  See the License for the specific language governing permissions and
+#  limitations under the License.
+
+
+from synapse.storage.database import LoggingTransaction
+from synapse.storage.engines import BaseDatabaseEngine, PostgresEngine
+
+
+def run_create(
+    cur: LoggingTransaction,
+    database_engine: BaseDatabaseEngine,
+) -> None:
+    """
+    An attempt to mitigate a painful race between foreground and background updates
+    touching the `stream_ordering` column of the events table. More info can be found
+    at https://github.com/matrix-org/synapse/issues/15677.
+    """
+
+    # technically the bg update we're concerned with below should only have been added in
+    # postgres but it doesn't hurt to be extra careful
+    if isinstance(database_engine, PostgresEngine):
+        select_sql = """
+            SELECT 1 FROM background_updates
+                WHERE update_name = 'replace_stream_ordering_column'
+        """
+        cur.execute(select_sql)
+        res = cur.fetchone()
+
+        # if the background update `replace_stream_ordering_column` is still pending, we need
+        # to drop the indexes added in 7403, and re-add them to the column `stream_ordering2`
+        # with the idea that they will be preserved when the column is renamed `stream_ordering`
+        # after the background update has finished
+        if res:
+            drop_cse_sql = """
+            ALTER TABLE current_state_events DROP CONSTRAINT event_stream_ordering_fkey
+            """
+            cur.execute(drop_cse_sql)
+
+            drop_lcm_sql = """
+            ALTER TABLE local_current_membership DROP CONSTRAINT event_stream_ordering_fkey
+            """
+            cur.execute(drop_lcm_sql)
+
+            drop_rm_sql = """
+            ALTER TABLE room_memberships DROP CONSTRAINT event_stream_ordering_fkey
+            """
+            cur.execute(drop_rm_sql)
+
+            add_cse_sql = """
+            ALTER TABLE current_state_events ADD CONSTRAINT event_stream_ordering_fkey
+            FOREIGN KEY (event_stream_ordering) REFERENCES events(stream_ordering2) NOT VALID;
+            """
+            cur.execute(add_cse_sql)
+
+            add_lcm_sql = """
+            ALTER TABLE local_current_membership ADD CONSTRAINT event_stream_ordering_fkey
+            FOREIGN KEY (event_stream_ordering) REFERENCES events(stream_ordering2) NOT VALID;
+            """
+            cur.execute(add_lcm_sql)
+
+            add_rm_sql = """
+            ALTER TABLE room_memberships ADD CONSTRAINT event_stream_ordering_fkey
+            FOREIGN KEY (event_stream_ordering) REFERENCES events(stream_ordering2) NOT VALID;
+            """
+            cur.execute(add_rm_sql)