diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/filter-ops.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/filter-ops.rkt
index c7de9b7e..c02e1bcd 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/filter-ops.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/types/filter-ops.rkt
@@ -110,14 +110,26 @@
            (loop (cdr props) others)]
           [p (loop (cdr props) (cons p others))]))))
 
+;; invert-filter: Filter/c -> Filter/c
+;; Logically inverts a filter.
+(define (invert-filter p)
+  (match p
+    [(Bot:) -top]
+    [(Top:) -bot]
+    [(TypeFilter: t p o) (-not-filter t o p)]
+    [(NotTypeFilter: t p o) (-filter t o p)]
+    [(AndFilter: fs) (apply -or (map invert-filter fs))]
+    [(OrFilter: fs) (apply -and (map invert-filter fs))]
+    [(ImpFilter: f1 f2) (-and f1 (invert-filter f2))]))
 
+;; -imp: Filter/c Filter/c -> Filter/c
+;; Smart constructor for make-ImpFilter
 (define (-imp p1 p2)
   (match* (p1 p2)
     [((Bot:) _) -top]
     [(_ (Top:)) -top]
     [((Top:) _) p2]
-    [((TypeFilter: t p o) (Bot:)) (-not-filter t o p)]
-    [((NotTypeFilter: t p o) (Bot:)) (-filter t o p)]
+    [(_ (Bot:)) (invert-filter p1)]
     [(_ _) (make-ImpFilter p1 p2)]))
 
 (define (-or . args)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/filter-tests.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/filter-tests.rkt
index 12910bcf..f1ce0776 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/filter-tests.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/filter-tests.rkt
@@ -111,6 +111,8 @@
       (check-equal? (-imp (-filter -Symbol #'x) -top) -top)
       (check-equal? (-imp (-filter -Symbol #'x) -bot) (-not-filter -Symbol #'x))
       (check-equal? (-imp (-not-filter -Symbol #'x) -bot) (-filter -Symbol #'x))
+      (check-equal? (-imp (-imp (-not-filter -Symbol #'x) (-not-filter -Symbol #'y)) -bot)
+                    (-and (-not-filter -Symbol #'x) (-filter -Symbol #'y)))
       (check-equal?
         (-imp (-not-filter -Symbol #'x)
               (-not-filter -Symbol #'y))