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 c8c039b3..4483ade4 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
@@ -1197,6 +1197,7 @@
     (-> -PosFixnum -One -NonNegFixnum)
     (-> -PosInt -One -Nat)
     (-> -NonNegFixnum -NonNegFixnum -Fixnum)
+    (-> -NegFixnum -NonPosFixnum -Fixnum)
     (->* (list -PosInt -NonPosInt) -NonPosInt -PosInt)
     (->* (list -Nat -NonPosInt) -NonPosInt -Nat)
     (->* (list -NegInt -Nat) -Nat -NegInt)
@@ -2098,4 +2099,4 @@
 [unsafe-make-flrectangular (make-flrectangular-type)]
 [unsafe-flreal-part (flreal-part-type)]
 [unsafe-flimag-part (flimag-part-type)]
-[unsafe-flrandom (flrandom-type)]
\ No newline at end of file
+[unsafe-flrandom (flrandom-type)]
diff --git a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/optimizer/missed-optimizations/fixnum.rkt b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/optimizer/missed-optimizations/fixnum.rkt
index cab65619..3b0815c4 100644
--- a/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/optimizer/missed-optimizations/fixnum.rkt
+++ b/pkgs/typed-racket-pkgs/typed-racket-test/tests/typed-racket/optimizer/missed-optimizations/fixnum.rkt
@@ -1,16 +1,35 @@
 #;#;
 #<<END
-TR info: fixnum.rkt 37:0 (fx* (values (ann x Index)) (values (ann y Index))) -- non-optimized fixnum op
-TR info: fixnum.rkt 40:0 (fx+ (+ 300 301) (+ 301 302)) -- non-optimized fixnum op
-TR info: fixnum.rkt 41:0 (fxquotient -4 -5) -- non-optimized fixnum op
-TR missed opt: fixnum.rkt 35:0 (+ (ann z Fixnum) 234) -- out of fixnum range
-TR missed opt: fixnum.rkt 36:0 (* (ann x Index) (ann y Index)) -- out of fixnum range
-TR missed opt: fixnum.rkt 39:0 (+ (+ 300 301) (+ 301 302)) -- out of fixnum range
-TR opt: fixnum.rkt 32:10 (* x y) -- fixnum bounded expr
-TR opt: fixnum.rkt 39:15 (+ 301 302) -- fixnum bounded expr
-TR opt: fixnum.rkt 39:3 (+ 300 301) -- fixnum bounded expr
-TR opt: fixnum.rkt 40:17 (+ 301 302) -- fixnum bounded expr
-TR opt: fixnum.rkt 40:5 (+ 300 301) -- fixnum bounded expr
+TR info: fixnum.rkt 105:28 (- 1 (expt 2 (- (system-type (quote word)) 2))) -- possible exact real arith
+TR info: fixnum.rkt 73:0 (fx* (values (ann x Index)) (values (ann y Index))) -- non-optimized fixnum op
+TR info: fixnum.rkt 76:0 (fx+ (+ 300 301) (+ 301 302)) -- non-optimized fixnum op
+TR info: fixnum.rkt 77:0 (fxquotient -4 -5) -- non-optimized fixnum op
+TR missed opt: fixnum.rkt 101:3 (+ max-fixnum max-fixnum) -- out of fixnum range
+TR missed opt: fixnum.rkt 102:3 (+ min-fixnum min-fixnum) -- out of fixnum range
+TR missed opt: fixnum.rkt 106:3 (quotient min-fixnum -1) -- out of fixnum range
+TR missed opt: fixnum.rkt 71:0 (+ (ann z Fixnum) 234) -- out of fixnum range
+TR missed opt: fixnum.rkt 72:0 (* (ann x Index) (ann y Index)) -- out of fixnum range
+TR missed opt: fixnum.rkt 75:0 (+ (+ 300 301) (+ 301 302)) -- out of fixnum range
+TR missed opt: fixnum.rkt 88:0 (sub1 min-fixnum) -- out of fixnum range
+TR missed opt: fixnum.rkt 94:0 (add1 max-fixnum) -- out of fixnum range
+TR missed opt: fixnum.rkt 98:3 (- max-fixnum min-fixnum) -- out of fixnum range
+TR missed opt: fixnum.rkt 99:3 (- min-fixnum max-fixnum) -- out of fixnum range
+TR opt: fixnum.rkt 103:0 (= (+ max-fixnum min-fixnum) -1) -- binary fixnum comp
+TR opt: fixnum.rkt 103:3 (+ max-fixnum min-fixnum) -- fixnum bounded expr
+TR opt: fixnum.rkt 105:3 (quotient max-fixnum -1) -- nonzero fixnum bounded expr
+TR opt: fixnum.rkt 68:10 (* x y) -- fixnum bounded expr
+TR opt: fixnum.rkt 75:15 (+ 301 302) -- fixnum bounded expr
+TR opt: fixnum.rkt 75:3 (+ 300 301) -- fixnum bounded expr
+TR opt: fixnum.rkt 76:17 (+ 301 302) -- fixnum bounded expr
+TR opt: fixnum.rkt 76:5 (+ 300 301) -- fixnum bounded expr
+TR opt: fixnum.rkt 89:0 (add1 min-fixnum) -- fixnum add1
+TR opt: fixnum.rkt 91:0 (- max-fixnum) -- unary fixnum
+TR opt: fixnum.rkt 92:0 (abs max-fixnum) -- fixnum fxabs
+TR opt: fixnum.rkt 93:0 (sub1 max-fixnum) -- fixnum sub1
+TR opt: fixnum.rkt 96:0 (= (- max-fixnum max-fixnum) 0) -- binary fixnum comp
+TR opt: fixnum.rkt 96:3 (- max-fixnum max-fixnum) -- fixnum bounded expr
+TR opt: fixnum.rkt 97:0 (= (- min-fixnum min-fixnum) 0) -- binary fixnum comp
+TR opt: fixnum.rkt 97:3 (- min-fixnum min-fixnum) -- fixnum bounded expr
 END
 #<<END
 468
@@ -20,6 +39,23 @@ END
 1204
 1204
 0
+4611686018427387904
+4611686018427387904
+-4611686018427387905
+-4611686018427387903
+-4611686018427387903
+4611686018427387903
+4611686018427387902
+4611686018427387904
+#t
+#t
+#t
+#t
+#t
+#t
+#t
+#t
+#t
 
 END
 #lang typed/racket
@@ -39,3 +75,32 @@ END
 (+ (+ 300 301) (+ 301 302))
 (fx+ (+ 300 301) (+ 301 302)) ; not reported, by design
 (fxquotient -4 -5) ; not reported, by design
+
+(: min-fixnum Negative-Fixnum)
+(define min-fixnum
+  (cast (- (expt 2 (- (system-type 'word) 2))) Negative-Fixnum))
+(: max-fixnum Positive-Fixnum)
+(define max-fixnum
+  (cast (- (expt 2 (- (system-type 'word) 2)) 1) Positive-Fixnum))
+
+(- min-fixnum)
+(abs min-fixnum)
+(sub1 min-fixnum)
+(add1 min-fixnum)
+
+(- max-fixnum)
+(abs max-fixnum)
+(sub1 max-fixnum)
+(add1 max-fixnum)
+
+(= (- max-fixnum max-fixnum) 0)
+(= (- min-fixnum min-fixnum) 0)
+(= (- max-fixnum min-fixnum) (- (expt 2 (sub1 (system-type 'word))) 1))
+(= (- min-fixnum max-fixnum) (- 1 (expt 2 (sub1 (system-type 'word)))))
+
+(= (+ max-fixnum max-fixnum) (- (expt 2 (sub1 (system-type 'word))) 2))
+(= (+ min-fixnum min-fixnum) (- (expt 2 (sub1 (system-type 'word)))))
+(= (+ max-fixnum min-fixnum) -1)
+
+(= (quotient max-fixnum -1) (- 1 (expt 2 (- (system-type 'word) 2))))
+(= (quotient min-fixnum -1) (expt 2 (- (system-type 'word) 2)))