diff --git a/pkgs/racket-test/tests/racket/contract/random-generate.rkt b/pkgs/racket-test/tests/racket/contract/random-generate.rkt
index 3ab888a1f3..8d8042dab6 100644
--- a/pkgs/racket-test/tests/racket/contract/random-generate.rkt
+++ b/pkgs/racket-test/tests/racket/contract/random-generate.rkt
@@ -59,8 +59,10 @@
 (check-not-exn (λ () (test-contract-generation (<=/c 0.0))))
 (check-not-exn (λ () (test-contract-generation (>/c 0))))
 (check-not-exn (λ () (test-contract-generation (>/c 0.0))))
+(check-not-exn (λ () (test-contract-generation (>/c -inf.0))))
 (check-not-exn (λ () (test-contract-generation (</c 0))))
 (check-not-exn (λ () (test-contract-generation (</c 0.0))))
+(check-not-exn (λ () (test-contract-generation (</c +inf.0))))
 (check-not-exn (λ () (test-contract-generation (=/c 0))))
 (check-not-exn (λ () (test-contract-generation (=/c 0.0))))
 (check-not-exn (λ () (test-contract-generation (or/c boolean? boolean?))))
diff --git a/racket/collects/racket/contract/private/misc.rkt b/racket/collects/racket/contract/private/misc.rkt
index 93c596d086..937ff86613 100644
--- a/racket/collects/racket/contract/private/misc.rkt
+++ b/racket/collects/racket/contract/private/misc.rkt
@@ -257,13 +257,39 @@
    #:generate
    (λ (ctc)
      (define x (</>-ctc-x ctc))
-     (λ (fuel)
-       (λ ()
-         (rand-choice
-          [1/10 (-/+ +inf.0)]
-          [1/10 (-/+ x 0.01)]
-          [4/10 (-/+ x (random))]
-          [else (-/+ x (random 4294967087))]))))
+     (cond
+       [(and (= x +inf.0) (equal? name '</c))
+        (λ (fuel)
+          (λ ()
+            (rand-choice
+             [1/10 -inf.0]
+             [2/10 (random)]
+             [2/10 (- (random))]
+             [2/10 (random 4294967087)]
+             [2/10 (- (random 4294967087))]
+             [else 0])))]
+       [(and (= x -inf.0) (equal? name '</c))
+        (λ (fuel) #f)]
+       [(and (= x +inf.0) (equal? name '>/c))
+        (λ (fuel) #f)]
+       [(and (= x -inf.0) (equal? name '>/c))
+        (λ (fuel)
+          (λ ()
+            (rand-choice
+             [1/10 +inf.0]
+             [2/10 (random)]
+             [2/10 (- (random))]
+             [2/10 (random 4294967087)]
+             [2/10 (- (random 4294967087))]
+             [else 0])))]
+       [else
+        (λ (fuel)
+          (λ ()
+            (rand-choice
+             [1/10 (-/+ +inf.0)]
+             [1/10 (-/+ x 0.01)]
+             [4/10 (-/+ x (random))]
+             [else (-/+ x (random 4294967087))])))]))
    #:stronger </>-ctc-stronger
    #:equivalent </>-ctc-equivalent))