diff --git a/tests/WP_SQLite_Driver_Tests.php b/tests/WP_SQLite_Driver_Tests.php
index 51411385..8307b2cc 100644
--- a/tests/WP_SQLite_Driver_Tests.php
+++ b/tests/WP_SQLite_Driver_Tests.php
@@ -11238,4 +11238,28 @@ public function testVersionFunction(): void {
 		$result = $this->engine->query( 'SELECT VERSION()' );
 		$this->assertSame( '8.0.38', $result[0]->{'VERSION()'} );
 	}
+
+	/**
+	 * Test CREATE TABLE with DEFAULT (now()) - GitHub issue #300
+	 * Tests that DEFAULT with function calls in parentheses works correctly in AST driver.
+	 *
+	 * @see https://github.com/WordPress/sqlite-database-integration/issues/300
+	 */
+	public function testCreateTableWithDefaultNowFunction(): void {
+		// Test the exact SQL from the issue
+		$this->assertQuery(
+			'CREATE TABLE `test_now_default` (
+				`id` int NOT NULL,
+				`updated` timestamp NOT NULL DEFAULT (now()) ON UPDATE CURRENT_TIMESTAMP
+			) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_520_ci;'
+		);
+
+		// Insert a row to verify the default value works
+		$this->assertQuery( 'INSERT INTO test_now_default (id) VALUES (1)' );
+		$result = $this->assertQuery( 'SELECT * FROM test_now_default WHERE id = 1' );
+		$this->assertCount( 1, $result );
+
+		// Verify the updated timestamp was set (should match YYYY-MM-DD HH:MM:SS format)
+		$this->assertRegExp( '/\d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d/', $result[0]->updated );
+	}
 }
diff --git a/tests/WP_SQLite_Translator_Tests.php b/tests/WP_SQLite_Translator_Tests.php
index a892fe72..e73368d0 100644
--- a/tests/WP_SQLite_Translator_Tests.php
+++ b/tests/WP_SQLite_Translator_Tests.php
@@ -3510,4 +3510,41 @@ public static function mysqlVariablesToTest() {
 			array( '@@sEssIOn.sqL_moDe' ),
 		);
 	}
+
+	/**
+	 * Test CREATE TABLE with DEFAULT (now()) - GitHub issue #300
+	 * Tests that DEFAULT with function calls in parentheses works correctly.
+	 */
+	public function testCreateTableWithDefaultNowFunction() {
+		// Test the exact SQL from the issue
+		$this->assertQuery(
+			'CREATE TABLE `test_now_default` (
+				`id` int NOT NULL,
+				`updated` timestamp NOT NULL DEFAULT (now()) ON UPDATE CURRENT_TIMESTAMP
+			) ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_520_ci;'
+		);
+
+		// Verify the table was created successfully
+		$results = $this->assertQuery( 'DESCRIBE test_now_default;' );
+		$this->assertCount( 2, $results );
+
+		// Verify the updated column has the correct properties
+		$updated_field = $results[1];
+		$this->assertEquals( 'updated', $updated_field->Field );
+		$this->assertEquals( 'timestamp', $updated_field->Type );
+		$this->assertEquals( 'NO', $updated_field->Null );
+
+		// Insert a row to verify the default value works
+		$this->assertQuery( 'INSERT INTO test_now_default (id) VALUES (1)' );
+		$result = $this->assertQuery( 'SELECT * FROM test_now_default WHERE id = 1' );
+		$this->assertCount( 1, $result );
+
+		// Verify the updated timestamp was set (should match YYYY-MM-DD HH:MM:SS format)
+		$this->assertRegExp( '/\d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d/', $result[0]->updated );
+
+		// Test ON UPDATE trigger works
+		$this->assertQuery( 'UPDATE test_now_default SET id = 2 WHERE id = 1' );
+		$result = $this->assertQuery( 'SELECT * FROM test_now_default WHERE id = 2' );
+		$this->assertRegExp( '/\d\d\d\d-\d\d-\d\d \d\d:\d\d:\d\d/', $result[0]->updated );
+	}
 }
diff --git a/wp-includes/sqlite-ast/class-wp-sqlite-information-schema-builder.php b/wp-includes/sqlite-ast/class-wp-sqlite-information-schema-builder.php
index 252573fd..34396816 100644
--- a/wp-includes/sqlite-ast/class-wp-sqlite-information-schema-builder.php
+++ b/wp-includes/sqlite-ast/class-wp-sqlite-information-schema-builder.php
@@ -2088,6 +2088,25 @@ private function get_column_default( WP_Parser_Node $node ): ?string {
 			return $this->get_value( $signed_literal );
 		}
 
+		// DEFAULT (expression) - MySQL 8.0.13+ supports exprWithParentheses
+		$expr_with_parens = $default_attr->get_first_child_node( 'exprWithParentheses' );
+		if ( $expr_with_parens ) {
+			// For now, only support simple function calls like (now()), (CURRENT_TIMESTAMP)
+			// Check if it's (now()) or (NOW())
+			$now_tokens = $expr_with_parens->get_descendant_tokens( WP_MySQL_Lexer::NOW_SYMBOL );
+			if ( ! empty( $now_tokens ) ) {
+				return 'CURRENT_TIMESTAMP';
+			}
+
+			// Check if it's (CURRENT_TIMESTAMP) or (CURRENT_TIMESTAMP())
+			$current_ts_tokens = $expr_with_parens->get_descendant_tokens( WP_MySQL_Lexer::CURRENT_TIMESTAMP_SYMBOL );
+			if ( ! empty( $current_ts_tokens ) ) {
+				return 'CURRENT_TIMESTAMP';
+			}
+
+			// For any other complex expressions, throw an exception
+			throw new Exception( 'DEFAULT values with complex expressions are not yet supported. Only (now()) and (CURRENT_TIMESTAMP) are currently supported.' );
+		}
 		throw new Exception( 'DEFAULT values with expressions are not yet supported.' );
 	}
 
diff --git a/wp-includes/sqlite/class-wp-sqlite-translator.php b/wp-includes/sqlite/class-wp-sqlite-translator.php
index c0ac1b85..c7582210 100644
--- a/wp-includes/sqlite/class-wp-sqlite-translator.php
+++ b/wp-includes/sqlite/class-wp-sqlite-translator.php
@@ -1149,7 +1149,28 @@ private function parse_mysql_create_table_field() {
 				WP_SQLite_Token::FLAG_KEYWORD_FUNCTION,
 				array( 'DEFAULT' )
 			) ) {
-				$result->default = $this->rewriter->consume()->token;
+				// Consume the next token (could be a value, opening paren, etc.)
+				$default_token   = $this->rewriter->consume();
+				$result->default = $default_token->token;
+
+				// Check if the default value is wrapped in parentheses (for function calls like (now()))
+				if ( $default_token->matches( WP_SQLite_Token::TYPE_OPERATOR, null, array( '(' ) ) ) {
+					// Track parenthesis depth to consume the complete expression
+					$paren_depth   = 1;
+					$default_value = '(';
+
+					while ( $paren_depth > 0 && ( $next_token = $this->rewriter->consume() ) ) {
+						$default_value .= $next_token->token;
+
+						if ( $next_token->matches( WP_SQLite_Token::TYPE_OPERATOR, null, array( '(' ) ) ) {
+							++$paren_depth;
+						} elseif ( $next_token->matches( WP_SQLite_Token::TYPE_OPERATOR, null, array( ')' ) ) ) {
+							--$paren_depth;
+						}
+					}
+
+					$result->default = $default_value;
+				}
 				continue;
 			}