diff --git a/crates/oxide_emit/Cargo.toml b/crates/oxide_emit/Cargo.toml
index 865f846d..503d41e6 100644
--- a/crates/oxide_emit/Cargo.toml
+++ b/crates/oxide_emit/Cargo.toml
@@ -10,3 +10,4 @@ description = "OxideJS - AST to IR emit pass"
 oxide_parser = { path = "../oxide_parser" }
 oxide_bytecode = { path = "../oxide_bytecode" }
 oxide_ir = { path = "../oxide_ir" }
+regex.workspace = true
diff --git a/crates/oxide_emit/src/expr/literal.rs b/crates/oxide_emit/src/expr/literal.rs
index ba11ae48..87c7f66f 100644
--- a/crates/oxide_emit/src/expr/literal.rs
+++ b/crates/oxide_emit/src/expr/literal.rs
@@ -67,6 +67,17 @@ impl Emitter {
                 let last_slash = raw_str.rfind('/').unwrap_or(raw_str.len() - 1);
                 let pattern = raw_str[1..last_slash].to_string();
                 let flags = raw_str[last_slash + 1..].to_string();
+                // 非法正则字面量须在编译期报 SyntaxError（负面测试期望编译失败）。
+                if regex::RegexBuilder::new(&pattern)
+                    .case_insensitive(flags.contains('i'))
+                    .multi_line(flags.contains('m'))
+                    .build()
+                    .is_err()
+                {
+                    return Err(format!(
+                        "SyntaxError: Invalid regular expression: /{pattern}/{flags}"
+                    ));
+                }
                 let pat_ci = ctx.add_constant(Constant::String(pattern));
                 let pat_reg = ctx.alloc_reg();
                 ctx.inst(Inst::load_const(Operand::Reg(pat_reg), pat_ci));
diff --git a/crates/oxide_vm/src/dispatch/call.rs b/crates/oxide_vm/src/dispatch/call.rs
index e023d0c6..1d5a3064 100644
--- a/crates/oxide_vm/src/dispatch/call.rs
+++ b/crates/oxide_vm/src/dispatch/call.rs
@@ -343,7 +343,10 @@ impl Vm {
         let result = match func(self, &[0, 1, 2]) {
             NativeResult::Ok(v) => v,
             NativeResult::Err(e) => {
-                return Err(self.error_message_text("TypeError", &self.error_text(e)));
+                // 保留原始错误对象与类型（非法正则字面量须抛 SyntaxError，非 TypeError）。
+                self.exception_value = Some(e);
+                self.pending_error_kind = Some(self.thrown_error_kind(e));
+                return self.unwind().map(|_| None);
             }
             NativeResult::TailCall { .. } => {
                 return Err(self.error_message_text("TypeError", "unexpected tail call"));