diff --git a/src/backend/access/transam/xlog.c b/src/backend/access/transam/xlog.c
index fcbde10529..e431fbba31 100644
--- a/src/backend/access/transam/xlog.c
+++ b/src/backend/access/transam/xlog.c
@@ -7936,10 +7936,11 @@ xlog_redo(XLogReaderState *record)
 		memcpy(&xlrec, XLogRecGetData(record), sizeof(xl_end_of_recovery));
 
 		/*
-		 * For Hot Standby, we could treat this like a Shutdown Checkpoint,
-		 * but this case is rarer and harder to test, so the benefit doesn't
-		 * outweigh the potential extra cost of maintenance.
+		 * In standby mode, we could treat this like an end-of-recovery
+		 * checkpoint.
 		 */
+		if (StandbyMode)
+			RequestCheckpoint(CHECKPOINT_IMMEDIATE | CHECKPOINT_WAIT);
 
 		/*
 		 * We should've already switched to the new TLI before replaying this
diff --git a/src/bin/pg_rewind/t/010_standby_source_following_new_primary.pl b/src/bin/pg_rewind/t/010_standby_source_following_new_primary.pl
new file mode 100644
index 0000000000..3e5c8caab7
--- /dev/null
+++ b/src/bin/pg_rewind/t/010_standby_source_following_new_primary.pl
@@ -0,0 +1,145 @@
+
+# Copyright (c) 2021-2023, PostgreSQL Global Development Group
+
+#
+# Test using a standby server that follows new primary as the source.
+#
+# This sets up three nodes: A, B and C. First, A is the primary,
+# B follows A, and C follows B:
+#
+# A (primary) <--- B (standby) <--- C (standby)
+#
+#
+# Then we promote B, and insert some divergent rows in A and B:
+#
+# A (primary)      B (primary) <--- C (standby)
+#
+#
+# Finally, we run pg_rewind on A, to point it at C:
+#
+#                  B (primary) <--- C (standby) <--- A (standby)
+#
+# We was not able to rewind until checkpointing in this scenario due to
+# the bug that cascade standby (i.e. C) does not follow the new
+# primary's (i.e. B's) minRecoveryPoint and minRecoveryPointTLI.
+#
+# Since we're dealing with three nodes, we cannot use most of the
+# RewindTest functions as is.
+
+use strict;
+use warnings;
+use PostgreSQL::Test::Utils;
+use Test::More;
+
+use FindBin;
+use lib $FindBin::RealBin;
+use File::Copy;
+use PostgreSQL::Test::Cluster;
+use RewindTest;
+
+my $tmp_folder = PostgreSQL::Test::Utils::tempdir;
+
+my $node_a;
+my $node_b;
+my $node_c;
+
+# Set up node A, as primary
+#
+# A (primary)
+
+setup_cluster('a');
+start_primary();
+$node_a = $node_primary;
+
+# Create a test table and insert a row in primary.
+$node_a->safe_psql('postgres', "CREATE TABLE tbl1 (d text)");
+$node_a->safe_psql('postgres', "INSERT INTO tbl1 VALUES ('before promotion')");
+primary_psql("CHECKPOINT");
+
+# Set up node B and C, as cascaded standbys
+#
+# A (primary) <--- B (standby) <--- C (standby)
+$node_a->backup('my_backup');
+$node_b = PostgreSQL::Test::Cluster->new('node_b');
+$node_b->init_from_backup($node_a, 'my_backup', has_streaming => 1);
+$node_b->set_standby_mode();
+$node_b->start;
+
+$node_b->backup('my_backup');
+$node_c = PostgreSQL::Test::Cluster->new('node_c');
+$node_c->init_from_backup($node_b, 'my_backup', has_streaming => 1);
+$node_c->set_standby_mode();
+$node_c->start;
+
+# Promote B
+#
+# A (primary)      B (primary) <--- C (standby)
+
+$node_b->promote;
+
+# make sure end-of-recovery record is replicated to C before we continue
+$node_b->wait_for_catchup('node_c');
+
+# Insert a row in A. This causes A and B/C to have "diverged", so that it's
+# no longer possible to just apply the standy's logs over primary directory
+# - you need to rewind.
+$node_a->safe_psql('postgres',
+	"INSERT INTO tbl1 VALUES ('rewind this')");
+
+#
+# All set up. We're ready to run pg_rewind.
+#
+my $node_a_pgdata = $node_a->data_dir;
+
+# Stop the old primary node and be ready to perform the rewind.
+$node_a->stop('fast');
+
+# Keep a temporary postgresql.conf or it would be overwritten during the rewind.
+copy(
+	"$node_a_pgdata/postgresql.conf",
+	"$tmp_folder/node_a-postgresql.conf.tmp");
+
+{
+	# Temporarily unset PGAPPNAME so that the server doesn't
+	# inherit it.  Otherwise this could affect libpqwalreceiver
+	# connections in confusing ways.
+	local %ENV = %ENV;
+	delete $ENV{PGAPPNAME};
+
+	# Do rewind using a remote connection as source.
+	command_ok(
+		[
+			'pg_rewind', "--debug",
+			"--source-server", $node_c->connstr('postgres'),
+			"--target-pgdata=$node_a_pgdata", "--no-sync",
+		],
+		'pg_rewind remote');
+}
+
+# Now move back postgresql.conf with old settings
+move(
+	"$tmp_folder/node_a-postgresql.conf.tmp",
+	"$node_a_pgdata/postgresql.conf");
+
+# Restart the node.
+$node_a->start;
+
+# set RewindTest::node_primary to point to the rewound node, so that we can
+# use check_query()
+$node_primary = $node_a;
+
+# Verify that A has been successfully rewound.
+
+check_query(
+	'SELECT * FROM tbl1',
+	qq(before promotion
+),
+	'table content after rewind');
+
+# clean up
+$node_a->teardown_node;
+$node_b->teardown_node;
+$node_c->teardown_node;
+
+done_testing();
+