diff --git a/app_llvm_test b/app_llvm_test
new file mode 100644
index 00000000..a21c6c33
Binary files /dev/null and b/app_llvm_test differ
diff --git a/src/ast.rs b/src/ast.rs
index 518af381..220652e1 100644
--- a/src/ast.rs
+++ b/src/ast.rs
@@ -333,6 +333,7 @@ pub enum BinaryOperator {
     Multiply,
     Divide,
     Modulo,
+    Shl,      // << shift-left (Phase 1)
     Equal,
     NotEqual,
     Less,
@@ -361,6 +362,7 @@ impl fmt::Display for BinaryOperator {
             BinaryOperator::Multiply => "*",
             BinaryOperator::Divide => "/",
             BinaryOperator::Modulo => "%",
+            BinaryOperator::Shl => "<<",
             BinaryOperator::Equal => "==",
             BinaryOperator::NotEqual => "!=",
             BinaryOperator::Less => "<",
diff --git a/src/interpreter/expressions/operators.rs b/src/interpreter/expressions/operators.rs
index 7f0ceed4..d49c250a 100644
--- a/src/interpreter/expressions/operators.rs
+++ b/src/interpreter/expressions/operators.rs
@@ -323,6 +323,19 @@ impl NyashInterpreter {
                 }
             }
             
+            BinaryOperator::Shl => {
+                // Integer-only left shift
+                if let (Some(li), Some(ri)) = (
+                    crate::runtime::semantics::coerce_to_i64(left_val.as_ref()),
+                    crate::runtime::semantics::coerce_to_i64(right_val.as_ref()),
+                ) {
+                    return Ok(Box::new(IntegerBox::new(li.wrapping_shl(ri as u32))));
+                }
+                Err(RuntimeError::TypeError { 
+                    message: format!("Shift-left '<<' requires integers (got {} and {})", left_val.type_name(), right_val.type_name()) 
+                })
+            }
+            
             BinaryOperator::Less => {
                 let result = CompareBox::less(left_val.as_ref(), right_val.as_ref());
                 Ok(Box::new(result))
diff --git a/src/interpreter/operators.rs b/src/interpreter/operators.rs
index fbf3f205..fbb78b77 100644
--- a/src/interpreter/operators.rs
+++ b/src/interpreter/operators.rs
@@ -256,6 +256,17 @@ impl NyashInterpreter {
                     Ok(Box::new(BoolBox::new(self.is_truthy(right_val))))
                 }
             },
+            
+            BinaryOperator::Shl => {
+                if let (Some(li), Some(ri)) = (
+                    left_val.as_any().downcast_ref::<IntegerBox>(),
+                    right_val.as_any().downcast_ref::<IntegerBox>(),
+                ) {
+                    Ok(Box::new(IntegerBox::new(li.value.wrapping_shl(ri.value as u32))))
+                } else {
+                    Err(RuntimeError::InvalidOperation { message: format!("Shift-left '<<' requires integers (got {} and {})", left_val.type_name(), right_val.type_name()) })
+                }
+            },
         }
     }
 
diff --git a/src/mir/builder/ops.rs b/src/mir/builder/ops.rs
index 88004a31..1235df25 100644
--- a/src/mir/builder/ops.rs
+++ b/src/mir/builder/ops.rs
@@ -114,6 +114,7 @@ impl super::MirBuilder {
             BinaryOperator::Multiply => Ok(BinaryOpType::Arithmetic(BinaryOp::Mul)),
             BinaryOperator::Divide => Ok(BinaryOpType::Arithmetic(BinaryOp::Div)),
             BinaryOperator::Modulo => Ok(BinaryOpType::Arithmetic(BinaryOp::Mod)),
+            BinaryOperator::Shl => Ok(BinaryOpType::Arithmetic(BinaryOp::Shl)),
             BinaryOperator::Equal => Ok(BinaryOpType::Comparison(CompareOp::Eq)),
             BinaryOperator::NotEqual => Ok(BinaryOpType::Comparison(CompareOp::Ne)),
             BinaryOperator::Less => Ok(BinaryOpType::Comparison(CompareOp::Lt)),
diff --git a/src/parser/expressions.rs b/src/parser/expressions.rs
index d288728d..5c6bf4a8 100644
--- a/src/parser/expressions.rs
+++ b/src/parser/expressions.rs
@@ -231,13 +231,13 @@ impl NyashParser {
     
     /// 項をパース: + - >>
     fn parse_term(&mut self) -> Result<ASTNode, ParseError> {
-        let mut expr = self.parse_factor()?;
+        let mut expr = self.parse_shift()?;
         
         while self.match_token(&TokenType::PLUS) || self.match_token(&TokenType::MINUS) || self.match_token(&TokenType::ARROW) {
             if self.match_token(&TokenType::ARROW) {
                 // >> Arrow演算子
                 self.advance();
-                let right = self.parse_factor()?;
+                let right = self.parse_shift()?;
                 expr = ASTNode::Arrow {
                     sender: Box::new(expr),
                     receiver: Box::new(right),
@@ -250,7 +250,7 @@ impl NyashParser {
                     _ => unreachable!(),
                 };
                 self.advance();
-                let right = self.parse_factor()?;
+                let right = self.parse_shift()?;
                 if std::env::var("NYASH_GRAMMAR_DIFF").ok().as_deref() == Some("1") {
                     let name = match operator { BinaryOperator::Add=>"add", BinaryOperator::Subtract=>"sub", _=>"term" };
                     let ok = crate::grammar::engine::get().syntax_is_allowed_binop(name);
@@ -268,6 +268,22 @@ impl NyashParser {
         Ok(expr)
     }
     
+    /// シフトをパース: << のみ（Phase 1）
+    fn parse_shift(&mut self) -> Result<ASTNode, ParseError> {
+        let mut expr = self.parse_factor()?;
+        while self.match_token(&TokenType::SHIFT_LEFT) {
+            self.advance(); // consume '<<'
+            let rhs = self.parse_factor()?;
+            expr = ASTNode::BinaryOp {
+                operator: BinaryOperator::Shl,
+                left: Box::new(expr),
+                right: Box::new(rhs),
+                span: Span::unknown(),
+            };
+        }
+        Ok(expr)
+    }
+    
     /// 因子をパース: * /
     fn parse_factor(&mut self) -> Result<ASTNode, ParseError> {
         let mut expr = self.parse_unary()?;
diff --git a/src/tokenizer.rs b/src/tokenizer.rs
index 51c311ef..21f78584 100644
--- a/src/tokenizer.rs
+++ b/src/tokenizer.rs
@@ -59,6 +59,7 @@ pub enum TokenType {
     
     // 演算子 (長いものから先に定義)
     ARROW,           // >> (legacy arrow)
+    SHIFT_LEFT,      // << (bitwise shift-left)
     FAT_ARROW,       // => (peek arms)
     EQUALS,          // ==
     NotEquals,       // !=
@@ -269,6 +270,12 @@ impl NyashTokenizer {
                 self.advance();
                 Ok(Token::new(TokenType::NotEquals, start_line, start_column))
             }
+            // Shift-left must be detected before <= and <
+            Some('<') if self.peek_char() == Some('<') => {
+                self.advance();
+                self.advance();
+                Ok(Token::new(TokenType::SHIFT_LEFT, start_line, start_column))
+            }
             Some('<') if self.peek_char() == Some('=') => {
                 self.advance();
                 self.advance();