diff --git a/src/field.cpp b/src/field.cpp
index ee62b7fa..344347b4 100644
--- a/src/field.cpp
+++ b/src/field.cpp
@@ -489,16 +489,16 @@ Option<bool> filter::parse_filter_query(const std::string& filter_query,
         return tokenize_op;
     }
 
-    if (tokens.size() > 100) {
-        return Option<bool>(400, "Filter expression is not valid.");
-    }
-
     std::queue<std::string> postfix;
     Option<bool> toPostfix_op = toPostfix(tokens, postfix);
     if (!toPostfix_op.ok()) {
         return toPostfix_op;
     }
 
+    if (postfix.size() > 100) {
+        return Option<bool>(400, "`filter_by` has too many operations.");
+    }
+
     Option<bool> toParseTree_op = toParseTree(postfix,
                                               root,
                                               search_schema,
diff --git a/test/collection_filtering_test.cpp b/test/collection_filtering_test.cpp
index 1628c2dc..0e736e23 100644
--- a/test/collection_filtering_test.cpp
+++ b/test/collection_filtering_test.cpp
@@ -2627,5 +2627,27 @@ TEST_F(CollectionFilteringTest, ComplexFilterQuery) {
         ASSERT_STREQ(id.c_str(), result_id.c_str());
     }
 
+    std::string extreme_filter = "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5))) ||"
+                                 "(years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5)))";
+
+    auto search_op = coll->search("Jeremy", {"name"}, extreme_filter,
+                                  {}, sort_fields_desc, {0}, 10, 1, FREQUENCY, {false});
+    ASSERT_TRUE(search_op.ok());
+    ASSERT_EQ(1, search_op.get()["hits"].size());
+
+    extreme_filter += "|| (years:>2000 && ((age:<30 && rating:>5) || (age:>50 && rating:<5)))";
+    search_op = coll->search("Jeremy", {"name"}, extreme_filter,
+                             {}, sort_fields_desc, {0}, 10, 1, FREQUENCY, {false});
+    ASSERT_FALSE(search_op.ok());
+    ASSERT_EQ("`filter_by` has too many operations.", search_op.error());
+
     collectionManager.drop_collection("ComplexFilterQueryCollection");
 }
\ No newline at end of file