diff --git a/collects/tests/typed-scheme/succeed/pr10939.rkt b/collects/tests/typed-scheme/succeed/pr10939.rkt
new file mode 100644
index 00000000..75e5fcfd
--- /dev/null
+++ b/collects/tests/typed-scheme/succeed/pr10939.rkt
@@ -0,0 +1,8 @@
+#lang typed/scheme
+
+(define-type (T elem)
+  (U 'other a:empty))
+
+(define-predicate a:list? (T Any))
+
+(define-struct: a:empty ())
diff --git a/collects/tests/typed-scheme/succeed/pr11504.rkt b/collects/tests/typed-scheme/succeed/pr11504.rkt
new file mode 100644
index 00000000..e319bab3
--- /dev/null
+++ b/collects/tests/typed-scheme/succeed/pr11504.rkt
@@ -0,0 +1,7 @@
+#lang typed/racket
+
+(define-type Animal (U cat dog))
+(define-predicate animal? Animal)
+
+(struct: cat ([lives : Natural]))
+(struct: dog ([bark : Natural] [bite : Natural]))
diff --git a/collects/typed-scheme/private/type-contract.rkt b/collects/typed-scheme/private/type-contract.rkt
index d9f5331d..12b4fc26 100644
--- a/collects/typed-scheme/private/type-contract.rkt
+++ b/collects/typed-scheme/private/type-contract.rkt
@@ -40,7 +40,7 @@
                            #:typed-side #f
                            #:flat flat?
                            (lambda () (tc-error/stx prop "Type ~a could not be converted to a contract." typ)))])
-         (syntax/loc stx (define-values (n) cnt))))]
+         (quasisyntax/loc stx (define-values (n) (recursive-contract cnt #,(if flat? #'#:flat #'#:impersonator))))))]
     [_ (int-err "should never happen - not a define-values: ~a" (syntax->datum stx))]))
 
 (define (change-contract-fixups forms)