diff --git a/src/backend/utils/sort/tuplesort.c b/src/backend/utils/sort/tuplesort.c
index 60223929e5..6c828d99d5 100644
--- a/src/backend/utils/sort/tuplesort.c
+++ b/src/backend/utils/sort/tuplesort.c
@@ -884,6 +884,7 @@ tuplesort_begin_cluster(TupleDesc tupDesc,
 {
 	Tuplesortstate *state = tuplesort_begin_common(workMem, coordinate,
 												   randomAccess);
+	AttrNumber	leading;
 	ScanKey		indexScanKey;
 	MemoryContext oldcontext;
 	int			i;
@@ -916,6 +917,7 @@ tuplesort_begin_cluster(TupleDesc tupDesc,
 	state->abbrevNext = 10;
 
 	state->indexInfo = BuildIndexInfo(indexRel);
+	leading = state->indexInfo->ii_IndexAttrNumbers[0];
 
 	state->tupDesc = tupDesc;	/* assume we need not copy tupDesc */
 
@@ -954,7 +956,7 @@ tuplesort_begin_cluster(TupleDesc tupDesc,
 			(scanKey->sk_flags & SK_BT_NULLS_FIRST) != 0;
 		sortKey->ssup_attno = scanKey->sk_attno;
 		/* Convey if abbreviation optimization is applicable in principle */
-		sortKey->abbreviate = (i == 0);
+		sortKey->abbreviate = (i == 0 && leading != 0);
 
 		AssertState(sortKey->ssup_attno != 0);
 
diff --git a/src/test/regress/expected/cluster.out b/src/test/regress/expected/cluster.out
index 2bb62212ea..344bab5dc0 100644
--- a/src/test/regress/expected/cluster.out
+++ b/src/test/regress/expected/cluster.out
@@ -466,10 +466,131 @@ where row(hundred, thousand, tenthous) <= row(lhundred, lthousand, ltenthous);
 
 reset enable_indexscan;
 reset maintenance_work_mem;
+-- test CLUSTER on expression index
+CREATE TABLE clstr_expression(id serial primary key, a int, b text COLLATE "C");
+INSERT INTO clstr_expression(a, b) SELECT g.i % 42, 'prefix'||g.i FROM generate_series(1, 133) g(i);
+CREATE INDEX clstr_expression_minus_a ON clstr_expression ((-a), b);
+CREATE INDEX clstr_expression_upper_b ON clstr_expression ((upper(b)));
+-- verify indexes work before cluster
+BEGIN;
+SET LOCAL enable_seqscan = false;
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+                          QUERY PLAN                           
+---------------------------------------------------------------
+ Index Scan using clstr_expression_upper_b on clstr_expression
+   Index Cond: (upper(b) = 'PREFIX3'::text)
+(2 rows)
+
+SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+ id | a |    b    
+----+---+---------
+  3 | 3 | prefix3
+(1 row)
+
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+                          QUERY PLAN                           
+---------------------------------------------------------------
+ Index Scan using clstr_expression_minus_a on clstr_expression
+   Index Cond: ((- a) = '-3'::integer)
+(2 rows)
+
+SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+ id  | a |     b     
+-----+---+-----------
+ 129 | 3 | prefix129
+   3 | 3 | prefix3
+  45 | 3 | prefix45
+  87 | 3 | prefix87
+(4 rows)
+
+COMMIT;
+-- and after clustering on clstr_expression_minus_a
+CLUSTER clstr_expression USING clstr_expression_minus_a;
+WITH rows AS
+  (SELECT ctid, lag(a) OVER (ORDER BY ctid) AS la, a FROM clstr_expression)
+SELECT * FROM rows WHERE la < a;
+ ctid | la | a 
+------+----+---
+(0 rows)
+
+BEGIN;
+SET LOCAL enable_seqscan = false;
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+                          QUERY PLAN                           
+---------------------------------------------------------------
+ Index Scan using clstr_expression_upper_b on clstr_expression
+   Index Cond: (upper(b) = 'PREFIX3'::text)
+(2 rows)
+
+SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+ id | a |    b    
+----+---+---------
+  3 | 3 | prefix3
+(1 row)
+
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+                          QUERY PLAN                           
+---------------------------------------------------------------
+ Index Scan using clstr_expression_minus_a on clstr_expression
+   Index Cond: ((- a) = '-3'::integer)
+(2 rows)
+
+SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+ id  | a |     b     
+-----+---+-----------
+ 129 | 3 | prefix129
+   3 | 3 | prefix3
+  45 | 3 | prefix45
+  87 | 3 | prefix87
+(4 rows)
+
+COMMIT;
+-- and after clustering on clstr_expression_upper_b
+CLUSTER clstr_expression USING clstr_expression_upper_b;
+WITH rows AS
+  (SELECT ctid, lag(b) OVER (ORDER BY ctid) AS lb, b FROM clstr_expression)
+SELECT * FROM rows WHERE upper(lb) > upper(b);
+ ctid | lb | b 
+------+----+---
+(0 rows)
+
+BEGIN;
+SET LOCAL enable_seqscan = false;
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+                          QUERY PLAN                           
+---------------------------------------------------------------
+ Index Scan using clstr_expression_upper_b on clstr_expression
+   Index Cond: (upper(b) = 'PREFIX3'::text)
+(2 rows)
+
+SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+ id | a |    b    
+----+---+---------
+  3 | 3 | prefix3
+(1 row)
+
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+                          QUERY PLAN                           
+---------------------------------------------------------------
+ Index Scan using clstr_expression_minus_a on clstr_expression
+   Index Cond: ((- a) = '-3'::integer)
+(2 rows)
+
+SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+ id  | a |     b     
+-----+---+-----------
+ 129 | 3 | prefix129
+   3 | 3 | prefix3
+  45 | 3 | prefix45
+  87 | 3 | prefix87
+(4 rows)
+
+COMMIT;
 -- clean up
 DROP TABLE clustertest;
 DROP TABLE clstr_1;
 DROP TABLE clstr_2;
 DROP TABLE clstr_3;
 DROP TABLE clstr_4;
+DROP TABLE clstr_expression;
 DROP USER regress_clstr_user;
diff --git a/src/test/regress/sql/cluster.sql b/src/test/regress/sql/cluster.sql
index 522bfeead4..29ca9835ed 100644
--- a/src/test/regress/sql/cluster.sql
+++ b/src/test/regress/sql/cluster.sql
@@ -222,10 +222,53 @@ where row(hundred, thousand, tenthous) <= row(lhundred, lthousand, ltenthous);
 reset enable_indexscan;
 reset maintenance_work_mem;
 
+-- test CLUSTER on expression index
+CREATE TABLE clstr_expression(id serial primary key, a int, b text COLLATE "C");
+INSERT INTO clstr_expression(a, b) SELECT g.i % 42, 'prefix'||g.i FROM generate_series(1, 133) g(i);
+CREATE INDEX clstr_expression_minus_a ON clstr_expression ((-a), b);
+CREATE INDEX clstr_expression_upper_b ON clstr_expression ((upper(b)));
+
+-- verify indexes work before cluster
+BEGIN;
+SET LOCAL enable_seqscan = false;
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+COMMIT;
+
+-- and after clustering on clstr_expression_minus_a
+CLUSTER clstr_expression USING clstr_expression_minus_a;
+WITH rows AS
+  (SELECT ctid, lag(a) OVER (ORDER BY ctid) AS la, a FROM clstr_expression)
+SELECT * FROM rows WHERE la < a;
+BEGIN;
+SET LOCAL enable_seqscan = false;
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+COMMIT;
+
+-- and after clustering on clstr_expression_upper_b
+CLUSTER clstr_expression USING clstr_expression_upper_b;
+WITH rows AS
+  (SELECT ctid, lag(b) OVER (ORDER BY ctid) AS lb, b FROM clstr_expression)
+SELECT * FROM rows WHERE upper(lb) > upper(b);
+BEGIN;
+SET LOCAL enable_seqscan = false;
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+SELECT * FROM clstr_expression WHERE upper(b) = 'PREFIX3';
+EXPLAIN (COSTS OFF) SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+SELECT * FROM clstr_expression WHERE -a = -3 ORDER BY -a, b;
+COMMIT;
+
 -- clean up
 DROP TABLE clustertest;
 DROP TABLE clstr_1;
 DROP TABLE clstr_2;
 DROP TABLE clstr_3;
 DROP TABLE clstr_4;
+DROP TABLE clstr_expression;
+
 DROP USER regress_clstr_user;