diff --git a/src/main/services/database/postgresql.ts b/src/main/services/database/postgresql.ts
index 57bf6e9..cf5aa4a 100644
--- a/src/main/services/database/postgresql.ts
+++ b/src/main/services/database/postgresql.ts
@@ -15,9 +15,20 @@ export type { PostgreSqlConfig } from '../../types/database.types'
  * SQL keywords that should NOT be double-quoted during identifier preprocessing.
  * PostgreSQL lowercases unquoted identifiers, but SSMA-migrated databases
  * have uppercase column names that require double-quoting to preserve case.
+ *
+ * This list covers PostgreSQL reserved words across multiple categories:
+ * - DML (Data Manipulation Language)
+ * - DDL (Data Definition Language)
+ * - Window functions
+ * - CTEs (Common Table Expressions)
+ * - Advanced GROUP BY clauses
+ * - JSON operations
+ * - Type system
+ * - Table sampling
+ * - Transaction control
  */
 const SQL_KEYWORDS = new Set([
-  // DML
+  // ==================== DML (Data Manipulation Language) ====================
   'SELECT',
   'FROM',
   'WHERE',
@@ -33,7 +44,8 @@ const SQL_KEYWORDS = new Set([
   'UPDATE',
   'SET',
   'DELETE',
-  // Ordering & limiting
+
+  // ==================== Ordering & Limiting ====================
   'ORDER',
   'BY',
   'ASC',
@@ -44,7 +56,8 @@ const SQL_KEYWORDS = new Set([
   'NEXT',
   'ROWS',
   'ONLY',
-  // Joins
+
+  // ==================== Joins ====================
   'JOIN',
   'LEFT',
   'RIGHT',
@@ -53,16 +66,67 @@ const SQL_KEYWORDS = new Set([
   'CROSS',
   'FULL',
   'ON',
-  // Set operations
+  'NATURAL',
+  'LATERAL',
+
+  // ==================== Set Operations ====================
   'UNION',
   'ALL',
   'INTERSECT',
   'EXCEPT',
-  // Grouping
+
+  // ==================== Grouping & Aggregation ====================
   'GROUP',
   'HAVING',
   'DISTINCT',
-  // DDL
+  'GROUPING',
+  'SETS',
+  'ROLLUP',
+  'CUBE',
+  'FILTER',
+  'WITHIN',
+
+  // ==================== Window Functions ====================
+  'OVER',
+  'PARTITION',
+  'WINDOW',
+  'RANGE',
+  'UNBOUNDED',
+  'PRECEDING',
+  'FOLLOWING',
+  'CURRENT',
+  'ROW',
+  'GROUPS',
+  'EXCLUDE',
+  'TIES',
+  'RANK',
+  'DENSE_RANK',
+  'ROW_NUMBER',
+  'NTILE',
+  'LAG',
+  'LEAD',
+  'FIRST_VALUE',
+  'LAST_VALUE',
+  'NTH_VALUE',
+
+  // ==================== CTE (Common Table Expressions) ====================
+  'WITH',
+  'RECURSIVE',
+  'MATERIALIZED',
+  'SEARCH',
+  'CYCLE',
+  'PATH',
+  'ROOT',
+  'SIBLINGS',
+
+  // ==================== CASE Expressions ====================
+  'CASE',
+  'WHEN',
+  'THEN',
+  'ELSE',
+  'END',
+
+  // ==================== DDL (Data Definition Language) ====================
   'CREATE',
   'ALTER',
   'DROP',
@@ -73,7 +137,15 @@ const SQL_KEYWORDS = new Set([
   'MODIFY',
   'RENAME',
   'TO',
-  // PostgreSQL specific
+  'GENERATED',
+  'ALWAYS',
+  'IDENTITY',
+  'INCLUDE',
+  'TEMP',
+  'TEMPORARY',
+  'UNLOGGED',
+
+  // ==================== PostgreSQL Specific - UPSERT/MERGE ====================
   'CONFLICT',
   'DO',
   'NOTHING',
@@ -82,32 +154,76 @@ const SQL_KEYWORDS = new Set([
   'MERGE',
   'USING',
   'MATCHED',
-  'WHEN',
-  'THEN',
-  'ELSE',
-  'END',
   'TARGET',
   'SOURCE',
-  // Functions
+
+  // ==================== Aggregate Functions ====================
   'COUNT',
   'SUM',
   'AVG',
   'MIN',
   'MAX',
   'EXISTS',
-  'CURRENT_TIMESTAMP',
-  'NOW',
-  'GETDATE',
   'COALESCE',
   'NULLIF',
   'CAST',
   'AS',
-  // Transaction
+
+  // ==================== JSON Operations ====================
+  'JSON',
+  'JSONB',
+  'JSON_ARRAY',
+  'JSON_OBJECT',
+  'JSON_AGG',
+  'JSONB_AGG',
+  'JSONB_OBJECT_AGG',
+
+  // ==================== Types & Casting ====================
+  'DECIMAL',
+  'NUMERIC',
+  'BOOLEAN',
+  'CHARACTER',
+  'VARYING',
+  'PRECISION',
+  'REAL',
+  'DOUBLE',
+  'FLOAT',
+  'TEXT',
+  'INTEGER',
+  'SERIAL',
+  'BIGINT',
+  'SMALLINT',
+  'DATE',
+  'TIME',
+  'TIMESTAMP',
+  'TIMESTAMPTZ',
+  'TIMEZONE',
+  'INTERVAL',
+  'BIGSERIAL',
+  'SMALLSERIAL',
+
+  // ==================== Table Sampling ====================
+  'TABLESAMPLE',
+  'BERNOULLI',
+  'SYSTEM',
+  'REPEATABLE',
+  'SEED',
+
+  // ==================== Transaction Control ====================
   'BEGIN',
   'COMMIT',
   'ROLLBACK',
   'SAVEPOINT',
-  // Types & values
+  'WORK',
+  'ISOLATION',
+  'LEVEL',
+  'READ',
+  'WRITE',
+  'COMMITTED',
+  'REPEATABLE',
+  'SERIALIZABLE',
+
+  // ==================== Types & Values ====================
   'TRUE',
   'FALSE',
   'DEFAULT',
@@ -118,23 +234,65 @@ const SQL_KEYWORDS = new Set([
   'CONSTRAINT',
   'UNIQUE',
   'CHECK',
-  'CASE',
+  'NULLS',
+  'FIRST',
+  'LAST',
+
+  // ==================== Pattern Matching ====================
   'BETWEEN',
   'LIKE',
   'ILIKE',
+  'SIMILAR',
+  'ESCAPE',
   'ANY',
   'SOME',
-  // Common
-  'IF',
-  'WITH',
-  'RECURSIVE',
-  'OVER',
-  'PARTITION',
-  'WINDOW',
-  'ROW',
-  'FIRST',
+
+  // ==================== Functions & Procedures ====================
   'AFTER',
-  'BEFORE'
+  'BEFORE',
+  'EACH',
+  'STATEMENT',
+  'TRIGGER',
+  'FUNCTION',
+  'PROCEDURE',
+  'LANGUAGE',
+  'SQL',
+  'PLPGSQL',
+  'RETURNS',
+  'CALLED',
+  'STRICT',
+  'SECURITY',
+  'INVOKER',
+  'DEFINER',
+  'VOLATILE',
+  'STABLE',
+  'IMMUTABLE',
+  'PARALLEL',
+  'SAFE',
+  'RESTRICTED',
+  'UNSAFE',
+
+  // ==================== Utility Commands ====================
+  'CONCURRENTLY',
+  'REINDEX',
+  'VACUUM',
+  'ANALYZE',
+  'EXPLAIN',
+  'LOCAL',
+  'GLOBAL',
+  'ORDINALITY',
+  'FREEZE',
+  'VERBOSE',
+  'BUFFERS',
+  'FORMAT',
+  'XML',
+  'YAML',
+
+  // ==================== Additional Reserved Words ====================
+  'IF',
+  'CURRENT_TIMESTAMP',
+  'NOW',
+  'GETDATE'
 ])
 
 /**
@@ -286,7 +444,31 @@ export class PostgreSqlService implements IDatabaseService {
         user: this.config.user,
         password: this.config.password,
         database: this.config.database,
-        max: this.config.maxPoolSize ?? 10
+        max: this.config.maxPoolSize ?? 10,
+        /**
+         * Connection timeout in milliseconds.
+         * Time to wait when connecting to PostgreSQL before failing.
+         * Prevents hanging during network issues or server overload.
+         */
+        connectionTimeoutMillis: 10000,
+        /**
+         * PostgreSQL statement timeout in milliseconds.
+         * Limits execution time for individual SQL statements.
+         * Prevents long-running queries from blocking the connection pool.
+         */
+        statement_timeout: 30000,
+        /**
+         * Idle connection timeout in milliseconds.
+         * Closes connections that have been idle for this duration.
+         * Frees up pool resources and prevents stale connections.
+         */
+        idleTimeoutMillis: 30000,
+        /**
+         * Query timeout in milliseconds (pg driver level).
+         * Fallback protection to abort queries that exceed this duration.
+         * Should be longer than statement_timeout to allow PG to handle first.
+         */
+        query_timeout: 60000
       })
 
       // Test connection
diff --git a/tests/unit/postgresql.test.ts b/tests/unit/postgresql.test.ts
index fe18f7b..647a9e7 100644
--- a/tests/unit/postgresql.test.ts
+++ b/tests/unit/postgresql.test.ts
@@ -206,4 +206,225 @@ describe('prepareSql', () => {
     expect(result).toContain('as count')
     expect(result).toContain('"UserName"')
   })
+
+  // ==================== Window Functions ====================
+
+  it('should handle ROW_NUMBER() OVER (PARTITION BY ... ORDER BY ...)', () => {
+    const sql = `
+      SELECT UserName, ROW_NUMBER() OVER (PARTITION BY UserType ORDER BY CreatedAt DESC) as rn
+      FROM "dbo"."BIPUsers"
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"UserName"')
+    expect(result).toContain('"UserType"')
+    expect(result).toContain('"CreatedAt"')
+    expect(result).not.toContain('"ROW_NUMBER"')
+    expect(result).not.toContain('"OVER"')
+    expect(result).not.toContain('"PARTITION"')
+    expect(result).not.toContain('"ORDER"')
+  })
+
+  it('should handle RANK() and DENSE_RANK()', () => {
+    const sql = `
+      SELECT MaterialCode, RANK() OVER (ORDER BY Quantity DESC) as rnk, DENSE_RANK() OVER (ORDER BY Quantity DESC) as drnk
+      FROM "dbo"."Materials"
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"MaterialCode"')
+    expect(result).toContain('"Quantity"')
+    expect(result).not.toContain('"RANK"')
+    expect(result).not.toContain('"DENSE_RANK"')
+  })
+
+  it('should handle LAG() and LEAD()', () => {
+    const sql = `
+      SELECT OrderId, LAG(TotalAmount, 1) OVER (ORDER BY OrderDate) as prevAmount, LEAD(TotalAmount, 1) OVER (ORDER BY OrderDate) as nextAmount
+      FROM "dbo"."Orders"
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"OrderId"')
+    expect(result).toContain('"TotalAmount"')
+    expect(result).toContain('"OrderDate"')
+    expect(result).not.toContain('"LAG"')
+    expect(result).not.toContain('"LEAD"')
+  })
+
+  // ==================== CTEs (Common Table Expressions) ====================
+
+  it('should handle WITH clause', () => {
+    const sql = `
+      WITH UserSummary AS (
+        SELECT UserId, COUNT(OrderId) as OrderCount
+        FROM "dbo"."Orders"
+        GROUP BY UserId
+      )
+      SELECT UserName, OrderCount
+      FROM UserSummary
+      JOIN "dbo"."BIPUsers" ON UserSummary.UserId = "dbo"."BIPUsers".ID
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"UserId"')
+    expect(result).toContain('"OrderId"')
+    expect(result).toContain('"UserName"')
+    expect(result).not.toContain('"WITH"')
+    expect(result).not.toContain('"AS"')
+    expect(result).not.toContain('"FROM"')
+    expect(result).not.toContain('"JOIN"')
+    expect(result).not.toContain('"ON"')
+  })
+
+  it('should handle recursive CTE', () => {
+    const sql = `
+      WITH RECURSIVE CategoryTree AS (
+        SELECT CategoryId, ParentCategoryId, CategoryName, 0 as Level
+        FROM "dbo"."Categories"
+        WHERE ParentCategoryId IS NULL
+        UNION ALL
+        SELECT c.CategoryId, c.ParentCategoryId, c.CategoryName, ct.Level + 1
+        FROM "dbo"."Categories" c
+        INNER JOIN CategoryTree ct ON c.ParentCategoryId = ct.CategoryId
+      )
+      SELECT * FROM CategoryTree
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"CategoryId"')
+    expect(result).toContain('"ParentCategoryId"')
+    expect(result).toContain('"CategoryName"')
+    expect(result).not.toContain('"WITH"')
+    expect(result).not.toContain('"RECURSIVE"')
+    expect(result).not.toContain('"UNION"')
+    expect(result).not.toContain('"ALL"')
+    expect(result).not.toContain('"INNER"')
+    expect(result).not.toContain('"JOIN"')
+  })
+
+  // ==================== Advanced Grouping ====================
+
+  it('should handle ROLLUP', () => {
+    const sql = `
+      SELECT DepartmentId, JobTitle, COUNT(*) as EmployeeCount
+      FROM "dbo"."Employees"
+      GROUP BY ROLLUP (DepartmentId, JobTitle)
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"DepartmentId"')
+    expect(result).toContain('"JobTitle"')
+    expect(result).not.toContain('"GROUP"')
+    expect(result).not.toContain('"BY"')
+    expect(result).not.toContain('"ROLLUP"')
+  })
+
+  it('should handle CUBE', () => {
+    const sql = `
+      SELECT Year, Quarter, Region, SUM(SalesAmount) as TotalSales
+      FROM "dbo"."Sales"
+      GROUP BY CUBE (Year, Quarter, Region)
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"Year"')
+    expect(result).toContain('"Quarter"')
+    expect(result).toContain('"Region"')
+    expect(result).toContain('"SalesAmount"')
+    expect(result).not.toContain('"CUBE"')
+    expect(result).not.toContain('"GROUP"')
+    expect(result).not.toContain('"BY"')
+  })
+
+  it('should handle GROUPING SETS', () => {
+    const sql = `
+      SELECT DepartmentId, JobTitle, COUNT(*) as EmployeeCount
+      FROM "dbo"."Employees"
+      GROUP BY GROUPING SETS ((DepartmentId, JobTitle), (DepartmentId), ())
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"DepartmentId"')
+    expect(result).toContain('"JobTitle"')
+    expect(result).not.toContain('"GROUPING"')
+    expect(result).not.toContain('"SETS"')
+    expect(result).not.toContain('"GROUP"')
+    expect(result).not.toContain('"BY"')
+  })
+
+  // ==================== CASE Expressions ====================
+
+  it('should handle simple CASE', () => {
+    const sql = `
+      SELECT UserName, CASE UserType
+        WHEN 'admin' THEN 'Administrator'
+        WHEN 'user' THEN 'Regular User'
+        ELSE 'Guest'
+      END as UserRole
+      FROM "dbo"."BIPUsers"
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"UserName"')
+    expect(result).toContain('"UserType"')
+    expect(result).not.toContain('"CASE"')
+    expect(result).not.toContain('"WHEN"')
+    expect(result).not.toContain('"THEN"')
+    expect(result).not.toContain('"ELSE"')
+    expect(result).not.toContain('"END"')
+  })
+
+  it('should handle searched CASE', () => {
+    const sql = `
+      SELECT OrderId, TotalAmount,
+        CASE
+          WHEN TotalAmount > 10000 THEN 'Large'
+          WHEN TotalAmount > 1000 THEN 'Medium'
+          ELSE 'Small'
+        END as OrderSize
+      FROM "dbo"."Orders"
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"OrderId"')
+    expect(result).toContain('"TotalAmount"')
+    expect(result).not.toContain('"CASE"')
+    expect(result).not.toContain('"WHEN"')
+    expect(result).not.toContain('"THEN"')
+    expect(result).not.toContain('"ELSE"')
+    expect(result).not.toContain('"END"')
+  })
+
+  // ==================== Set Operations ====================
+
+  it('should handle UNION, UNION ALL, INTERSECT, EXCEPT', () => {
+    const sql = `
+      SELECT UserId FROM "dbo"."ActiveUsers"
+      UNION
+      SELECT UserId FROM "dbo"."PremiumUsers"
+      UNION ALL
+      SELECT UserId FROM "dbo"."TrialUsers"
+      INTERSECT
+      SELECT UserId FROM "dbo"."VerifiedUsers"
+      EXCEPT
+      SELECT UserId FROM "dbo"."BannedUsers"
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"UserId"')
+    expect(result).not.toContain('"UNION"')
+    expect(result).not.toContain('"ALL"')
+    expect(result).not.toContain('"INTERSECT"')
+    expect(result).not.toContain('"EXCEPT"')
+    expect(result).not.toContain('"SELECT"')
+    expect(result).not.toContain('"FROM"')
+  })
+
+  // ==================== JSON Operators ====================
+
+  it('should handle -> and ->> operators', () => {
+    const sql = `
+      SELECT UserId, ProfileData->'address'->>'city' as City, ProfileData->'contact'->>'phone' as Phone
+      FROM "dbo"."Users"
+      WHERE ProfileData->'preferences'->>'newsletter' = 'true'
+    `
+    const result = prepareSql(sql)
+    expect(result).toContain('"UserId"')
+    expect(result).toContain('"ProfileData"')
+    expect(result).toContain('->')
+    expect(result).toContain('->>')
+    expect(result).not.toContain('"SELECT"')
+    expect(result).not.toContain('"FROM"')
+    expect(result).not.toContain('"WHERE"')
+  })
 })