diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-apply.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-apply.rkt
index a7efd782..a2a58cc9 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-apply.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-apply.rkt
@@ -185,11 +185,11 @@
                    (eq? (cdr drest) dotted-var)
                    (= (length domain) (length arg-tys))
                    (match full-tail-ty
-                     [(Listof: tail-arg-ty)
+                     [(List: tail-arg-tys #:tail (Listof: tail-arg-ty))
                       (infer/vararg
                         fixed-vars (list dotted-var)
-                        (cons tail-arg-ty arg-tys)
-                        (cons (car drest) domain)
+                        (cons tail-arg-ty (append tail-arg-tys arg-tys))
+                        (cons (car drest) (append (map (λ _ (car drest)) tail-arg-tys) domain))
                         rest
                         range)]
                      [(List: tail-arg-tys)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/match-expanders.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/match-expanders.rkt
index 6e1b859e..386048b4 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/match-expanders.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/match-expanders.rkt
@@ -28,16 +28,22 @@
   (lambda (stx)
     (syntax-parse stx
       [(_ elem-pats)
-       #'(app untuple (? values elem-pats))])))
+       #'(app untuple (? values elem-pats) (Value: '()))]
+      [(_ elem-pats #:tail tail-pat)
+       #'(app untuple (? values elem-pats) tail-pat)])))
 
+;; Type/c -> (or/c (values/c #f #f) (values/c (listof Type/c) Type/c)))
+;; Returns the prefix of types that are consed on to the last type (a non finite-pair type).
+;; The last type may contain pairs if it is a list type.
 (define (untuple t)
   (let loop ((t t) (seen (set)))
-    (and (not (set-member? seen (Type-seq t)))
-         (match (resolve t)
-           [(Value: '()) null]
-           [(Pair: a b) (cond [(loop b (set-add seen (Type-seq t))) => (lambda (l) (cons a l))]
-                              [else #f])]
-           [_ #f]))))
+    (if (not (set-member? seen (Type-seq t)))
+        (match (resolve t)
+          [(Pair: a b)
+           (define-values (elems tail) (loop b (set-add seen (Type-seq t))))
+           (values (cons a elems) tail)]
+          [_ (values null t)])
+        (values null t))))
 
 (define-match-expander MListof:
   (lambda (stx)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
index 389a8589..f1733ad5 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
@@ -2851,7 +2851,13 @@
          (let: ([f : (All (b ...) (Any ... b -> Any)) (lambda x 'x)])
            (lambda xs (apply f xs)))
          #:ret (ret (->* (list) Univ Univ))
-         #:expected (ret (->* (list)  Univ Univ))]
+         #:expected (ret (->* (list) Univ Univ))]
+
+       [tc-e
+         (let: ([f : (All (b ...) (Any ... b -> Any)) (lambda x 'x)])
+           (lambda xs (apply f (ann (cons 'y xs) (cons Symbol (Listof Any))))))
+         #:ret (ret (->* (list) Univ Univ))
+         #:expected (ret (->* (list) Univ Univ))]
 
        [tc-e
          (let ()
@@ -2878,8 +2884,6 @@
          -Symbol
          #:expected (ret -Symbol)]
 
-
-
         )
   (test-suite
    "tc-literal tests"