diff --git a/core/translate/optimizer.rs b/core/translate/optimizer.rs
index f71cb9728..7c29b8834 100644
--- a/core/translate/optimizer.rs
+++ b/core/translate/optimizer.rs
@@ -797,6 +797,47 @@ enum BinaryExprSide {
     Rhs,
 }
 
+/// Recursively unwrap parentheses from an expression
+/// e.g. (((t.x > 5))) -> t.x > 5
+fn unwrap_parens<T>(expr: T) -> Result<T>
+where
+    T: UnwrapParens,
+{
+    expr.unwrap_parens()
+}
+
+trait UnwrapParens {
+    fn unwrap_parens(self) -> Result<Self>
+    where
+        Self: Sized;
+}
+
+impl UnwrapParens for &ast::Expr {
+    fn unwrap_parens(self) -> Result<Self> {
+        match self {
+            ast::Expr::Column { .. } => Ok(self),
+            ast::Expr::Parenthesized(exprs) => match exprs.len() {
+                1 => unwrap_parens(exprs.first().unwrap()),
+                _ => crate::bail_parse_error!("expected single expression in parentheses"),
+            },
+            _ => Ok(self),
+        }
+    }
+}
+
+impl UnwrapParens for ast::Expr {
+    fn unwrap_parens(self) -> Result<Self> {
+        match self {
+            ast::Expr::Column { .. } => Ok(self),
+            ast::Expr::Parenthesized(mut exprs) => match exprs.len() {
+                1 => unwrap_parens(exprs.pop().unwrap()),
+                _ => crate::bail_parse_error!("expected single expression in parentheses"),
+            },
+            _ => Ok(self),
+        }
+    }
+}
+
 /// Get the position of a column in an index
 /// For example, if there is an index on table T(x,y) then y's position in the index is 1.
 fn get_column_position_in_index(
@@ -804,20 +845,20 @@ fn get_column_position_in_index(
     table_index: usize,
     table_reference: &TableReference,
     index: &Arc<Index>,
-) -> Option<usize> {
-    let ast::Expr::Column { table, column, .. } = expr else {
-        return None;
+) -> Result<Option<usize>> {
+    let ast::Expr::Column { table, column, .. } = unwrap_parens(expr)? else {
+        return Ok(None);
     };
     if *table != table_index {
-        return None;
+        return Ok(None);
     }
     let Some(column) = table_reference.table.get_column_at(*column) else {
-        return None;
+        return Ok(None);
     };
-    index
+    Ok(index
         .columns
         .iter()
-        .position(|col| Some(&col.name) == column.name.as_ref())
+        .position(|col| Some(&col.name) == column.name.as_ref()))
 }
 
 /// Find all [IndexConstraint]s for a given WHERE clause
@@ -839,7 +880,7 @@ fn find_index_constraints(
                 continue;
             }
             // Skip terms that are not binary comparisons
-            let ast::Expr::Binary(lhs, operator, rhs) = &term.expr else {
+            let ast::Expr::Binary(lhs, operator, rhs) = unwrap_parens(&term.expr)? else {
                 continue;
             };
             // Only consider index scans for binary ops that are comparisons
@@ -868,7 +909,7 @@ fn find_index_constraints(
 
             // Check if lhs is a column that is in the i'th position of the index
             if Some(position_in_index)
-                == get_column_position_in_index(lhs, table_index, table_reference, index)
+                == get_column_position_in_index(lhs, table_index, table_reference, index)?
             {
                 out_constraints.push(IndexConstraint {
                     operator: *operator,
@@ -879,7 +920,7 @@ fn find_index_constraints(
             }
             // Check if rhs is a column that is in the i'th position of the index
             if Some(position_in_index)
-                == get_column_position_in_index(rhs, table_index, table_reference, index)
+                == get_column_position_in_index(rhs, table_index, table_reference, index)?
             {
                 out_constraints.push(IndexConstraint {
                     operator: opposite_cmp_op(*operator), // swap the operator since e.g. if condition is 5 >= x, we want to use x <= 5
@@ -931,7 +972,8 @@ pub fn build_seek_def_from_index_constraints(
         // Extract the other expression from the binary WhereTerm (i.e. the one being compared to the index column)
         let (idx, side) = constraint.position_in_where_clause;
         let where_term = &mut where_clause[idx];
-        let ast::Expr::Binary(lhs, _, rhs) = where_term.expr.take_ownership() else {
+        let ast::Expr::Binary(lhs, _, rhs) = unwrap_parens(where_term.expr.take_ownership())?
+        else {
             crate::bail_parse_error!("expected binary expression");
         };
         let cmp_expr = if side == BinaryExprSide::Lhs {