diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-annotation.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-annotation.rkt
index adec08e9..88e0e121 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-annotation.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/private/type-annotation.rkt
@@ -11,6 +11,7 @@
          racket/match)
 
 (provide type-annotation
+         type-annotation^
          get-type
          get-types
          get-type/infer
@@ -44,6 +45,11 @@
      (attribute i.type)]
     [_ #f]))
 
+(define-syntax-class type-annotation^
+  [pattern i:id
+           #:attr type (type-annotation #'i)
+           #:when (attribute type)])
+
 ;(trace type-annotation)
 
 (define (type-ascription stx)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-let-unit.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-let-unit.rkt
index 90880105..f9c2b8e4 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-let-unit.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/typecheck/tc-let-unit.rkt
@@ -2,7 +2,7 @@
 
 (require "../utils/utils.rkt"
          (except-in (types utils abbrev union filter-ops) -> ->* one-of/c)
-         (only-in (types abbrev) (-> t:->))
+         (only-in (types abbrev) (-> t:->) [->* t:->*])
          (private type-annotation parse-type syntax-properties)
          (env lexical-env type-alias-env type-alias-helper mvar-env
               global-env type-env-structs scoped-tvar-env)
@@ -302,9 +302,10 @@
 ;; say that this binding is only called in tail position
 (define ((tc-expr-t/maybe-expected expected) e)
   (syntax-parse e #:literal-sets (kernel-literals)
-    [(~and (#%plain-lambda () _) _:tail-position^)
+    [(~and (#%plain-lambda (fmls:type-annotation^ ...) _) _:tail-position^)
      #:when expected
-     (tc-expr/check e (ret (t:-> (tc-results->values expected))))]
+     (define arg-tys (attribute fmls.type))
+     (tc-expr/check e (ret (t:->* arg-tys (tc-results->values expected))))]
     [_:tail-position^
      #:when expected
      (tc-expr/check e expected)]