diff --git a/collects/tests/typed-scheme/fail/pr11686.rkt b/collects/tests/typed-scheme/fail/pr11686.rkt
new file mode 100644
index 0000000000..dda25a69b4
--- /dev/null
+++ b/collects/tests/typed-scheme/fail/pr11686.rkt
@@ -0,0 +1,29 @@
+#;
+(exn-pred exn:fail:contract?)
+
+#lang racket/load
+
+(module T typed/racket
+  
+  (struct: [X] doll ([contents : X]))
+  
+  (define-type RussianDoll
+    (Rec RD (U 'center (doll RD))))
+  
+  (: f (RussianDoll -> RussianDoll))
+  (define (f rd) rd)
+
+  (: md (All (x) (x -> (doll x))))
+  (define md doll)
+  
+  (provide (all-defined-out)))
+
+(module U racket
+ (require 'T)
+ (f (md 3)))
+
+(require 'U)
+
+
+
+
diff --git a/collects/tests/typed-scheme/succeed/pr11686.rkt b/collects/tests/typed-scheme/succeed/pr11686.rkt
new file mode 100644
index 0000000000..5930ad133e
--- /dev/null
+++ b/collects/tests/typed-scheme/succeed/pr11686.rkt
@@ -0,0 +1,15 @@
+#lang racket/load
+
+(module T typed/racket
+  
+  (struct: [X] doll ([contents : X]))
+  
+  (define-type RussianDoll
+    (Rec RD (U 'center (doll RD))))
+  
+  (: f (RussianDoll -> RussianDoll))
+  (define (f rd) rd)
+  
+  (provide (all-defined-out)))
+
+(require 'T)
diff --git a/collects/typed-scheme/private/type-contract.rkt b/collects/typed-scheme/private/type-contract.rkt
index 20bda229ca..98d53fdf30 100644
--- a/collects/typed-scheme/private/type-contract.rkt
+++ b/collects/typed-scheme/private/type-contract.rkt
@@ -237,26 +237,42 @@
            [poly? 
             (with-syntax* ([(rec blame val) (generate-temporaries '(rec blame val))]
                            [maker maker-id]
-                           [cnt-name nm]
-                           [(fld-cnts ...)
-                            (for/list ([fty flds]
+                           [cnt-name nm])
+              ;If it should be a flat contract, we make flat contracts for the type of each field,
+              ;extract the predicates, and apply the predicates to the corresponding field value
+              (if flat?
+                #`(letrec ([rec
+                            (make-flat-contract
+                             #:name 'cnt-name
+                             #:first-order
+                              (lambda (val)
+                               (and
+                                (#,pred? val)
+                                #,@(for/list ([fty flds] [f-acc acc-ids])
+                                    #`((flat-contract-predicate
+                                       #,(t->c fty #:seen (cons (cons ty #'(recursive-contract rec)) structs-seen)))
+                                       (#,f-acc val))))))])
+                    rec)
+                ;Should make this case a chaperone/impersonator contract
+                (with-syntax ([(fld-cnts ...)
+                              (for/list ([fty flds]
                                        [f-acc acc-ids]
                                        [m? mut?])
-                #`(((contract-projection
-                     #,(t->c fty #:seen (cons (cons ty #'(recursive-contract rec)) structs-seen)))
-                    blame)
-                   (#,f-acc val)))])
-                #`(letrec ([rec 
-                            (make-contract 
-                             #:name 'cnt-name
-                             #:first-order #,pred?
-                             #:projection 
-                             (lambda (blame)
-                               (lambda (val)
-                                 (unless (#,pred? val)
-                                   (raise-blame-error blame val "expected ~a value, got ~v" 'cnt-name val))
-                                 (maker fld-cnts ...))))])
-                    rec))]
+                               #`(((contract-projection
+                                    #,(t->c fty #:seen (cons (cons ty #'(recursive-contract rec)) structs-seen)))
+                                   blame)
+                                  (#,f-acc val)))])
+                  #`(letrec ([rec
+                              (make-contract
+                               #:name 'cnt-name
+                               #:first-order #,pred?
+                               #:projection
+                               (lambda (blame)
+                                 (lambda (val)
+                                   (unless (#,pred? val)
+                                     (raise-blame-error blame val "expected ~a value, got ~v" 'cnt-name val))
+                                   (maker fld-cnts ...))))])
+                      rec))))]
            [else #`(flat-named-contract '#,(syntax-e pred?) #,(cert pred?))])]
         [(Syntax: (Base: 'Symbol _ _ _)) #'identifier?]
         [(Syntax: t) #`(syntax/c #,(t->c t))]