diff --git a/packages/core/src/utils/__tests__/query-transformer.test.ts b/packages/core/src/utils/__tests__/query-transformer.test.ts
index 6fcafe54b..6c02f3702 100644
--- a/packages/core/src/utils/__tests__/query-transformer.test.ts
+++ b/packages/core/src/utils/__tests__/query-transformer.test.ts
@@ -21,7 +21,7 @@ import { expect, test } from "vitest";
 import { transformQuery } from "../query-transformer.js";
 
 function lt2(str: string) {
-  return `(">${str}" OR ${str} OR "${str}<")`;
+  return `(">${str}" OR "${str}" OR "${str}<")`;
 }
 
 const TRANSFORM_QUERY_TESTS = [
@@ -65,14 +65,14 @@ const TRANSFORM_QUERY_TESTS = [
   ["foo + OR", `foo AND ${lt2("+")}`],
   ['"special -phrase*"', '"special -phrase*"'],
   ["foo* + bar*", `"foo*" AND ${lt2("+")} AND "bar*"`],
-  ["(foo + bar) -baz", `(foo AND ${lt2("+")} AND bar) AND "-baz"`],
+  ["(foo + bar) -baz", `"(foo" AND ${lt2("+")} AND "bar)" AND "-baz"`],
   ['"phrase with "quotes""', '"phrase with ""quotes"""'],
   [
     'foo + "bar -baz" OR "qux*"',
     `foo AND ${lt2("+")} AND "bar -baz" OR "qux*"`
   ],
   ["foo + bar + ", `foo AND ${lt2("+")} AND bar AND ${lt2("+")}`],
-  ["+foo bar", `+foo AND bar`],
+  ["+foo bar", `"+foo" AND bar`],
   ["foo*bar*", `"foo*bar*"`],
   ['"escaped "quotes""', '"escaped ""quotes"""'],
   ["-hello-world", `"-hello-world"`],
diff --git a/packages/core/src/utils/query-transformer.ts b/packages/core/src/utils/query-transformer.ts
index 1be3b0bb9..82a28ce30 100644
--- a/packages/core/src/utils/query-transformer.ts
+++ b/packages/core/src/utils/query-transformer.ts
@@ -33,19 +33,20 @@ type OperatorNode = {
   type: "AND" | "OR" | "NOT";
 };
 
+const INVALID_CHARS = /[:<>./\\()$&=#!\-+~§@^?,;'"[\]{}|]/;
 function escapeSQLString(str: string): string {
   if (str.startsWith('"') && str.endsWith('"')) {
     const innerStr = str.slice(1, -1).replace(/"/g, '""');
     return `"${innerStr}"`;
   }
 
-  const maybeColspec = /[:<>./\\()$&=#!\-\+\~§@^?,;'"\[\]{}|]/.test(str);
+  const isInvalidChar = INVALID_CHARS.test(str);
   const isWildcard =
     str.startsWith("*") ||
     str.endsWith("*") ||
     str.startsWith("%") ||
     str.endsWith("%");
-  if (maybeColspec || isWildcard) {
+  if (isInvalidChar || isWildcard) {
     return `"${str}"`;
   }
 
@@ -155,6 +156,21 @@ function generateSQL(ast: QueryNode): string {
             result.push(`(">${value}"`, "OR", value, "OR", `"${value}<")`);
             result.push("AND");
             continue;
+          } else if (
+            value.length === 3 &&
+            value[0] === '"' &&
+            value[2] === '"' &&
+            !["<", ">"].includes(value[1])
+          ) {
+            result.push(
+              `(">${value[1]}"`,
+              "OR",
+              value,
+              "OR",
+              `"${value[1]}<")`
+            );
+            result.push("AND");
+            continue;
           }
 
           result.push(value);