diff --git a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/base-env/base-env-numeric.rkt b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/base-env/base-env-numeric.rkt
index 71a72f78..6ee88126 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/base-env/base-env-numeric.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-lib/typed-racket/base-env/base-env-numeric.rkt
@@ -656,6 +656,13 @@
           (-> -Zero neg pos)
           (-> -Zero non-pos non-neg)))
 
+  ;; Used because (- min-fixnum) > max-fixnum
+  (define (half-negation-pattern pos neg non-neg non-pos)
+    (list (-> pos neg)
+          (-> non-neg non-pos)
+          (-> -Zero pos neg)
+          (-> -Zero non-neg non-pos)))
+
   (define abs-cases ; used both for abs and magnitude
     (list
      (map unop (list -Zero -One -PosByte -Byte -PosIndex -Index -PosFixnum -NonNegFixnum))
@@ -1181,7 +1188,7 @@
 
 [- (from-cases
     (binop -Zero)
-    (negation-pattern -PosFixnum -NegFixnum -NonNegFixnum -NonPosFixnum)
+    (half-negation-pattern -PosFixnum -NegFixnum -NonNegFixnum -NonPosFixnum)
     (negation-pattern -PosInt -NegInt -Nat -NonPosInt)
     (negation-pattern -PosRat -NegRat -NonNegRat -NonPosRat)
     (negation-pattern -PosFlonum -NegFlonum -NonNegFlonum -NonPosFlonum)
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
index 382b74fd..517e40da 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/unit-tests/typecheck-tests.rkt
@@ -242,7 +242,8 @@
         (tc-e (+ 3 4) -PosIndex)
         (tc-e (- 1) -NegFixnum)
         (tc-e (- 1073741823) -NegFixnum)
-        (tc-e (- -4) -PosFixnum)
+        (tc-e (- -4) -PosInt)
+        (tc-e (- (ann -5 Nonpositive-Fixnum)) -Nat)
         (tc-e/t 1152921504606846975 -PosInt)
         (tc-e/t -1152921504606846975 -NegInt)
         (tc-e (- 3253463567262345623) -NegInt)