diff --git a/.jules/sentinel.md b/.jules/sentinel.md
index 3a5ef27423..f03130bdf6 100644
--- a/.jules/sentinel.md
+++ b/.jules/sentinel.md
@@ -7,3 +7,8 @@
 **Vulnerability:** The daemon configuration file (`~/.agor/config.yaml`) and its parent directory (`~/.agor`) were created with default file permissions (e.g., `0o755`/`0o644`), which made them readable by other users on the system. This file stores extremely sensitive information such as API keys and master JWT secrets.
 **Learning:** Default Node.js filesystem operations (`fs.writeFile` and `fs.mkdir`) do not enforce strict permissions unless explicitly specified with a `mode` parameter. When handling sensitive files, relying on the system `umask` is insufficient.
 **Prevention:** Always specify `mode: 0o600` for sensitive files and `mode: 0o700` for their parent directories. Additionally, use `fs.chmod` to retroactively secure existing files and directories that might have been created with permissive defaults.
+
+## 2026-07-23 - [SQL Injection Risk via sql.raw in jsonExtract]
+**Vulnerability:** The `jsonExtract` function in `packages/core/src/db/database-wrapper.ts` used `sql.raw` to insert JSON path keys into PostgreSQL `->` and `->>` operators without parameterization.
+**Learning:** Using `sql.raw` directly injects strings into the SQL query, bypassing parameterization and creating a potential SQL injection vulnerability if any JSON path keys are derived from user input.
+**Prevention:** In Drizzle ORM, never use `sql.raw()` to interpolate dynamic variables. To prevent SQL injection when working with PostgreSQL JSON operators (`->`, `->>`), always explicitly cast dynamic parameters to text (e.g., `sql\`->> (${key}::text)\``) to properly resolve the overloaded operator type. Use `sql.join` to safely combine these parameterized template literals when chaining multi-level paths.
diff --git a/packages/core/src/db/database-wrapper.ts b/packages/core/src/db/database-wrapper.ts
index d52d553e64..0f780ff0d3 100644
--- a/packages/core/src/db/database-wrapper.ts
+++ b/packages/core/src/db/database-wrapper.ts
@@ -105,15 +105,14 @@ export function jsonExtract(db: Database, column: SQL.Aliased | SQL | any, path:
   } else {
     // PostgreSQL: column->'path'->'to'->>'field'
     // Use -> for all but the last part (keeps as JSON), ->> for the last part (extracts as text)
-    // IMPORTANT: Use sql.raw() for JSON keys to avoid parameterization
     if (parts.length === 1) {
       // Single level: column->>'key'
-      return sql`${column}${sql.raw(`->>'${parts[0]}'`)}`;
+      return sql`${column} ->> (${parts[0]}::text)`;
     } else {
       // Multiple levels: column->'key1'->'key2'->>'key3'
-      const objectParts = parts.slice(0, -1).map((p) => sql.raw(`->'${p}'`));
+      const objectParts = parts.slice(0, -1).map((p) => sql`-> (${p}::text)`);
       const lastPart = parts[parts.length - 1];
-      return sql`${column}${sql.join(objectParts, sql``)}${sql.raw(`->>'${lastPart}'`)}`;
+      return sql`${column} ${sql.join(objectParts, sql` `)} ->> (${lastPart}::text)`;
     }
   }
 }
diff --git a/test-drizzle.ts b/test-drizzle.ts
new file mode 100644
index 0000000000..011347e604
--- /dev/null
+++ b/test-drizzle.ts
@@ -0,0 +1,9 @@
+import { sql } from 'drizzle-orm';
+
+const key = 'test';
+console.log(
+  sql`->> (${key}::text)`.toQuery({
+    escapeString: (str) => str,
+    escapeParam: (num, val) => `$${num}`,
+  })
+);
diff --git a/test2.ts b/test2.ts
new file mode 100644
index 0000000000..589aeb8b77
--- /dev/null
+++ b/test2.ts
@@ -0,0 +1,6 @@
+import { sql } from 'drizzle-orm';
+
+const key = 'test';
+console.log(
+  sql`->'${key}'`.toQuery({ escapeString: (str) => str, escapeParam: (num, val) => `$${num}` })
+);
diff --git a/test3.ts b/test3.ts
new file mode 100644
index 0000000000..fe09e80a17
--- /dev/null
+++ b/test3.ts
@@ -0,0 +1,9 @@
+import { sql } from 'drizzle-orm';
+
+const key = 'test';
+console.log(
+  sql`-> (${key}::text)`.toQuery({
+    escapeString: (str) => str,
+    escapeParam: (num, val) => `$${num}`,
+  })
+);
diff --git a/test4.ts b/test4.ts
new file mode 100644
index 0000000000..bc8c5959c5
--- /dev/null
+++ b/test4.ts
@@ -0,0 +1,12 @@
+import { sql } from 'drizzle-orm';
+
+const parts = ['genealogy', 'parent_session_id'];
+const column = sql`sessions.data`;
+const objectParts = parts.slice(0, -1).map((p) => sql`-> (${p}::text)`);
+const lastPart = parts[parts.length - 1];
+console.log(
+  sql`${column} ${sql.join(objectParts, sql` `)} ->> (${lastPart}::text)`.toQuery({
+    escapeString: (str) => str,
+    escapeParam: (num, val) => `$${num}`,
+  })
+);