diff --git a/racket/collects/racket/contract/private/misc.rkt b/racket/collects/racket/contract/private/misc.rkt
index f753204f3d..cf1885bfa2 100644
--- a/racket/collects/racket/contract/private/misc.rkt
+++ b/racket/collects/racket/contract/private/misc.rkt
@@ -592,18 +592,36 @@
   (cond
     [(zero? (hash-count env-hash))
      (rand-choice
-      [1/3 (any/c-simple-value)]
+      [1/3 (any/c-structured-value)]
       [1/3 (any/c-procedure env-hash fuel)]
       [else (any/c-from-predicate-generator env-hash fuel)])]
     [else
      (rand-choice
       [1/4 (oneof (hash-ref env-hash (oneof (hash-keys env-hash))))]
-      [1/4 (any/c-simple-value)]
+      [1/4 (any/c-structured-value)]
       [1/4 (any/c-procedure env-hash fuel)]
       [else (any/c-from-predicate-generator env-hash fuel)])]))
 
+(define (any/c-structured-value)
+  (let loop ([depth 3])
+    (cond
+      [(zero? depth) (any/c-simple-value)]
+      [else
+       (rand-choice
+        [1/10 (cons (loop (- depth 1)) (loop (- depth 1)))]
+        [1/10 (make-vector (random 10) (λ (_) (loop (- depth 1))))]
+        [1/10 (make-hash (for/list ([i (in-range (random 10))])
+                           (cons (loop (- depth 1))
+                                 (loop (- depth 1)))))]
+        [1/10 (make-immutable-hash (for/list ([i (in-range (random 10))])
+                                     (cons (loop (- depth 1))
+                                           (loop (- depth 1)))))]
+        [1/10 (box (loop (- depth 1)))]
+        [else (any/c-simple-value)])])))
+
 (define (any/c-simple-value)
   (oneof '(0 #f "" () #() -1 1 #t elephant)))
+
 (define (any/c-from-predicate-generator env fuel)
   ((hash-ref predicate-generator-table
              (oneof (hash-keys predicate-generator-table)))