diff --git a/src/EFCore.SqlServer/Query/Internal/SearchConditionConverter.cs b/src/EFCore.SqlServer/Query/Internal/SearchConditionConverter.cs
index 5e827602edc..0420834209a 100644
--- a/src/EFCore.SqlServer/Query/Internal/SearchConditionConverter.cs
+++ b/src/EFCore.SqlServer/Query/Internal/SearchConditionConverter.cs
@@ -206,9 +206,11 @@ protected virtual Expression VisitSqlBinary(SqlBinaryExpression binary, bool inS
 
         if (binary.OperatorType is ExpressionType.NotEqual or ExpressionType.Equal)
         {
+            var leftType = newLeft.TypeMapping?.Converter?.ProviderClrType ?? newLeft.Type;
+            var rightType = newRight.TypeMapping?.Converter?.ProviderClrType ?? newRight.Type;
             if (!inSearchConditionContext
-                && (newLeft.Type == typeof(bool) || newLeft.Type.IsEnum || newLeft.Type.IsInteger())
-                && (newRight.Type == typeof(bool) || newRight.Type.IsEnum || newRight.Type.IsInteger()))
+                && (leftType == typeof(bool) || leftType.IsEnum || leftType.IsInteger())
+                && (rightType == typeof(bool) || rightType.IsEnum || rightType.IsInteger()))
             {
                 // "lhs != rhs" is the same as "CAST(lhs ^ rhs AS BIT)", except that
                 // the first is a boolean, the second is a BIT
@@ -265,7 +267,9 @@ protected virtual Expression VisitSqlUnary(SqlUnaryExpression sqlUnaryExpression
             case ExpressionType.Not when sqlUnaryExpression.Type == typeof(bool):
             {
                 // when possible, avoid converting to/from predicate form
-                if (!inSearchConditionContext && sqlUnaryExpression.Operand is not (ExistsExpression or InExpression or LikeExpression))
+                if (!inSearchConditionContext &&
+                    sqlUnaryExpression.TypeMapping?.Converter is null &&
+                    sqlUnaryExpression.Operand is not (ExistsExpression or InExpression or LikeExpression))
                 {
                     var negatedOperand = (SqlExpression)Visit(sqlUnaryExpression.Operand);