diff --git a/edb/server/pgcon/pgcon.pyx b/edb/server/pgcon/pgcon.pyx
index 202c3b0e1db..c1f162f69c6 100644
--- a/edb/server/pgcon/pgcon.pyx
+++ b/edb/server/pgcon/pgcon.pyx
@@ -130,13 +130,31 @@ def _set_tcp_keepalive(transport):
     # against AWS RDS. We are keeping the TCP keepalive for generic
     # Postgres connections as the kernel overhead is considered low, and
     # in certain cases it does save us some reconnection time.
+    #
+    # In case of high-availability Postgres, TCP keepalive is necessary to
+    # disconnect from a failing master node, if no other failover information
+    # is available.
     sock = transport.get_extra_info('socket')
     sock.setsockopt(socket.SOL_SOCKET, socket.SO_KEEPALIVE, 1)
+
+    # TCP_KEEPIDLE: the time (in seconds) the connection needs to remain idle
+    # before TCP starts sending keepalive probes. This is socket.TCP_KEEPIDLE
+    # on Linux, and socket.TCP_KEEPALIVE on macOS from Python 3.10.
     if hasattr(socket, 'TCP_KEEPIDLE'):
         sock.setsockopt(socket.IPPROTO_TCP,
                         socket.TCP_KEEPIDLE, TCP_KEEPIDLE)
+    if hasattr(socket, 'TCP_KEEPALIVE'):
+        sock.setsockopt(socket.IPPROTO_TCP,
+                        socket.TCP_KEEPALIVE, TCP_KEEPIDLE)
+
+    # TCP_KEEPINTVL: The time (in seconds) between individual keepalive probes.
+    if hasattr(socket, 'TCP_KEEPINTVL'):
         sock.setsockopt(socket.IPPROTO_TCP,
                         socket.TCP_KEEPINTVL, TCP_KEEPINTVL)
+
+    # TCP_KEEPCNT: The maximum number of keepalive probes TCP should send
+    # before dropping the connection.
+    if hasattr(socket, 'TCP_KEEPCNT'):
         sock.setsockopt(socket.IPPROTO_TCP,
                         socket.TCP_KEEPCNT, TCP_KEEPCNT)
 
diff --git a/edb/server/server.py b/edb/server/server.py
index 47d0bcb6fe8..a60dc224c72 100644
--- a/edb/server/server.py
+++ b/edb/server/server.py
@@ -904,7 +904,7 @@ async def _reconnect_sys_pgcon(self):
                 try:
                     conn = await self._pg_connect(defines.EDGEDB_SYSTEM_DB)
                     break
-                except ConnectionError:
+                except (ConnectionError, TimeoutError):
                     # Keep retrying as far as:
                     #   1. The EdgeDB server is still serving,
                     #   2. We still cannot connect to the Postgres cluster, or