diff --git a/src/expr.rs b/src/expr.rs
index db8d5b921..8216191c2 100644
--- a/src/expr.rs
+++ b/src/expr.rs
@@ -1284,7 +1284,7 @@ pub(crate) mod parsing {
                 if precedence == Precedence::Compare {
                     if let Expr::Binary(lhs) = &lhs {
                         if Precedence::of_binop(&lhs.op) == Precedence::Compare {
-                            break;
+                            return Err(input.error("comparison operators cannot be chained"));
                         }
                     }
                 }
@@ -1346,7 +1346,7 @@ pub(crate) mod parsing {
                 if precedence == Precedence::Compare {
                     if let Expr::Binary(lhs) = &lhs {
                         if Precedence::of_binop(&lhs.op) == Precedence::Compare {
-                            break;
+                            return Err(input.error("comparison operators cannot be chained"));
                         }
                     }
                 }
diff --git a/tests/test_expr.rs b/tests/test_expr.rs
index d20cce8d6..399972c42 100644
--- a/tests/test_expr.rs
+++ b/tests/test_expr.rs
@@ -642,6 +642,15 @@ fn test_assign_range_precedence() {
     syn::parse_str::<Expr>("() .. () += ()").unwrap_err();
 }
 
+#[test]
+fn test_chained_comparison() {
+    // https://github.com/dtolnay/syn/issues/1738
+    let _ = syn::parse_str::<Expr>("a = a < a <");
+
+    let err = syn::parse_str::<Expr>("a < a < a").unwrap_err();
+    assert_eq!("comparison operators cannot be chained", err.to_string());
+}
+
 #[test]
 fn test_fixup() {
     struct FlattenParens;