diff --git a/core/translate/optimizer.rs b/core/translate/optimizer.rs
index a65468c89..ec657c58c 100644
--- a/core/translate/optimizer.rs
+++ b/core/translate/optimizer.rs
@@ -743,9 +743,17 @@ impl Optimizable for ast::Expr {
                     rhs.check_index_scan(table_index, referenced_tables, available_indexes)?;
                 if rhs_index.is_some() {
                     // swap lhs and rhs
+                    let swapped_operator = match *op {
+                        ast::Operator::Equals => ast::Operator::Equals,
+                        ast::Operator::Greater => ast::Operator::Less,
+                        ast::Operator::GreaterEquals => ast::Operator::LessEquals,
+                        ast::Operator::Less => ast::Operator::Greater,
+                        ast::Operator::LessEquals => ast::Operator::GreaterEquals,
+                        _ => unreachable!(),
+                    };
                     let lhs_new = rhs.take_ownership();
                     let rhs_new = lhs.take_ownership();
-                    *self = Self::Binary(Box::new(lhs_new), *op, Box::new(rhs_new));
+                    *self = Self::Binary(Box::new(lhs_new), swapped_operator, Box::new(rhs_new));
                     return Ok(rhs_index);
                 }
                 Ok(None)
diff --git a/testing/where.test b/testing/where.test
index 8a568d0fc..feb4e812a 100755
--- a/testing/where.test
+++ b/testing/where.test
@@ -338,3 +338,8 @@ do_execsql_test between-price-range-with-names {
     AND (name = 'sweatshirt' OR name = 'sneakers');
 } {5|sweatshirt|74.0
 8|sneakers|82.0}
+
+do_execsql_test where-between-true-and-2 {
+    select id from users where id between true and 2;
+} {1
+2}