diff --git a/core/trino-main/src/main/java/io/trino/sql/planner/RelationPlanner.java b/core/trino-main/src/main/java/io/trino/sql/planner/RelationPlanner.java
index c112292a9cc7..44713ddf4336 100644
--- a/core/trino-main/src/main/java/io/trino/sql/planner/RelationPlanner.java
+++ b/core/trino-main/src/main/java/io/trino/sql/planner/RelationPlanner.java
@@ -296,26 +296,23 @@ private RelationPlan addColumnMasks(Table table, RelationPlan plan)
         PlanBuilder planBuilder = newPlanBuilder(plan, analysis, lambdaDeclarationToSymbolMap)
                 .withScope(analysis.getAccessControlScope(table), plan.getFieldMappings()); // The fields in the access control scope has the same layout as those for the table scope
 
+        Map<Symbol, Expression> assignments = new LinkedHashMap<>();
+        for (Symbol symbol : planBuilder.getRoot().getOutputSymbols()) {
+            assignments.put(symbol, symbol.toSymbolReference());
+        }
         for (int i = 0; i < plan.getDescriptor().getAllFieldCount(); i++) {
             Field field = plan.getDescriptor().getFieldByIndex(i);
-
             for (Expression mask : columnMasks.getOrDefault(field.getName().orElseThrow(), ImmutableList.of())) {
                 planBuilder = subqueryPlanner.handleSubqueries(planBuilder, mask, analysis.getSubqueries(mask));
-
-                Map<Symbol, Expression> assignments = new LinkedHashMap<>();
-                for (Symbol symbol : planBuilder.getRoot().getOutputSymbols()) {
-                    assignments.put(symbol, symbol.toSymbolReference());
-                }
                 assignments.put(plan.getFieldMappings().get(i), coerceIfNecessary(analysis, mask, planBuilder.rewrite(mask)));
-
-                planBuilder = planBuilder
-                        .withNewRoot(new ProjectNode(
-                                idAllocator.getNextId(),
-                                planBuilder.getRoot(),
-                                Assignments.copyOf(assignments)));
             }
         }
 
+        planBuilder = planBuilder
+                .withNewRoot(new ProjectNode(
+                        idAllocator.getNextId(),
+                        planBuilder.getRoot(),
+                        Assignments.copyOf(assignments)));
         return new RelationPlan(planBuilder.getRoot(), plan.getScope(), plan.getFieldMappings(), outerContext);
     }
 
diff --git a/core/trino-main/src/test/java/io/trino/sql/query/TestColumnMask.java b/core/trino-main/src/test/java/io/trino/sql/query/TestColumnMask.java
index e42a7a647563..f6e8084a0627 100644
--- a/core/trino-main/src/test/java/io/trino/sql/query/TestColumnMask.java
+++ b/core/trino-main/src/test/java/io/trino/sql/query/TestColumnMask.java
@@ -180,7 +180,7 @@ public void testSimpleMask()
     }
 
     @Test
-    public void testMultipleMasksOnSameColumn()
+    public void testMultipleMasksOnDifferentColumns()
     {
         accessControl.reset();
         accessControl.columnMask(
@@ -191,31 +191,134 @@ public void testMultipleMasksOnSameColumn()
 
         accessControl.columnMask(
                 new QualifiedObjectName(CATALOG, "tiny", "orders"),
-                "custkey",
+                "orderstatus",
                 USER,
-                new ViewExpression(USER, Optional.empty(), Optional.empty(), "custkey * 2"));
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "'X'"));
 
-        assertThat(assertions.query("SELECT custkey FROM orders WHERE orderkey = 1")).matches("VALUES BIGINT '-740'");
+        assertThat(assertions.query("SELECT custkey, orderstatus FROM orders WHERE orderkey = 1"))
+                .matches("VALUES (BIGINT '-370', 'X')");
     }
 
     @Test
-    public void testMultipleMasksOnDifferentColumns()
+    public void testMultipleMasksUsingOtherMaskedColumns()
     {
+        String query = "SELECT comment, orderstatus, clerk FROM orders WHERE orderkey = 1";
+        String expected = "VALUES (CAST('nstructions sleep furiously among ' as varchar(79)), 'O', 'Clerk#000000951')";
+
+        accessControl.reset();
+        assertThat(assertions.query(query)).matches(expected);
+
+        // mask "clerk" and "orderstatus" using "comment" ("comment" appears after both in table definition)
+        // columns will not be masked since rules are not apply to row values
         accessControl.reset();
         accessControl.columnMask(
                 new QualifiedObjectName(CATALOG, "tiny", "orders"),
-                "custkey",
+                "comment",
                 USER,
-                new ViewExpression(USER, Optional.empty(), Optional.empty(), "-custkey"));
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "cast(regexp_replace(comment,'(password: [^ ]+)','password: ****') as varchar(79))"));
 
         accessControl.columnMask(
                 new QualifiedObjectName(CATALOG, "tiny", "orders"),
                 "orderstatus",
                 USER,
-                new ViewExpression(USER, Optional.empty(), Optional.empty(), "'X'"));
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(comment,'(country: [^ ]+)') IN ('country: 1'), '*', orderstatus)"));
 
-        assertThat(assertions.query("SELECT custkey, orderstatus FROM orders WHERE orderkey = 1"))
-                .matches("VALUES (BIGINT '-370', 'X')");
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "clerk",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(comment,'(country: [^ ]+)') IN ('country: 1'), '***', clerk)"));
+
+        assertThat(assertions.query(query)).matches(expected);
+
+        // mask "comment" using "clerk" ("clerk" column appears before "comment" in table definition)
+        // columns will not be masked since rules are not apply to row values
+        accessControl.reset();
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "clerk",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "cast(regexp_replace(clerk,'(password: [^ ]+)','password: ****') as varchar(15))"));
+
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "comment",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(clerk,'(country: [^ ]+)') IN ('country: 1'), '***', comment)"));
+
+        assertThat(assertions.query(query)).matches(expected);
+
+        // now add mask for "orderstatus" using "clerk"
+        // columns will not be masked since rules are not apply to row values
+        accessControl.reset();
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "clerk",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "cast(regexp_replace(clerk,'(password: [^ ]+)','password: ****') as varchar(15))"));
+
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "orderstatus",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(clerk,'(country: [^ ]+)') IN ('country: 1'), '*', orderstatus)"));
+
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "comment",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(clerk,'(country: [^ ]+)') IN ('country: 1'), '***', comment)"));
+
+        assertThat(assertions.query(query)).matches(expected);
+
+        query = "SELECT comment, orderstatus, clerk FROM orders WHERE orderkey = 39";
+
+        accessControl.reset();
+        assertThat(assertions.query(query))
+                .matches("VALUES (CAST('ole express, ironic requests: ir' as varchar(79)), 'O', 'Clerk#000000659')");
+
+        // mask "comment" and "orderstatus" using "clerk" ("clerk" appears before "comment" table definition)
+        accessControl.reset();
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "clerk",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "cast(regexp_replace(clerk,'(Clerk#)','***#') as varchar(15))"));
+
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "comment",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(clerk,'([1-9]+)') IN ('659'), '***', comment)"));
+
+        assertThat(assertions.query(query))
+                .matches("VALUES (CAST('***' as varchar(79)), 'O', CAST('***#000000659' as varchar(15)))");
+
+        assertThat(assertions.query("SELECT comment, orderstatus, clerk, length(clerk) FROM orders WHERE orderkey = 39"))
+                .matches("VALUES (CAST('***' as varchar(79)), 'O', CAST('***#000000659' as varchar(15)), bigint'13')");
+
+        // mask "comment" and "orderstatus" using "clerk" ("clerk" appears before "comment" table definition)
+        accessControl.reset();
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "clerk",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "cast(regexp_replace(clerk,'(Clerk#)','***#') as varchar(15))"));
+
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "orderstatus",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(clerk,'([1-9]+)') IN ('659'), '*', orderstatus)"));
+
+        accessControl.columnMask(
+                new QualifiedObjectName(CATALOG, "tiny", "orders"),
+                "comment",
+                USER,
+                new ViewExpression(USER, Optional.empty(), Optional.empty(), "if(regexp_extract(clerk,'([1-9]+)') IN ('659'), '***', comment)"));
+
+        assertThat(assertions.query(query))
+                .matches("VALUES (CAST('***' as varchar(79)), '*', CAST('***#000000659' as varchar(15)))");
     }
 
     @Test