diff --git a/collects/tests/typed-scheme/optimizer/missed-optimizations/multi-file1.rkt b/collects/tests/typed-scheme/optimizer/missed-optimizations/multi-file1.rkt
new file mode 100644
index 0000000000..6e5d13bc8c
--- /dev/null
+++ b/collects/tests/typed-scheme/optimizer/missed-optimizations/multi-file1.rkt
@@ -0,0 +1,12 @@
+#;
+(
+TR missed opt: multi-file1.rkt 12:2 (* x 3) -- all args float-arg-expr, result not Float -- caused by: 12:7 3
+)
+
+#lang typed/racket
+
+(provide f)
+
+(: f : Float -> Real)
+(define (f x)
+  (* x 3))
diff --git a/collects/tests/typed-scheme/optimizer/missed-optimizations/multi-file2.rkt b/collects/tests/typed-scheme/optimizer/missed-optimizations/multi-file2.rkt
new file mode 100644
index 0000000000..16f7749889
--- /dev/null
+++ b/collects/tests/typed-scheme/optimizer/missed-optimizations/multi-file2.rkt
@@ -0,0 +1,13 @@
+#;
+(
+TR missed opt: multi-file1.rkt 12:2 (* x 3) -- all args float-arg-expr, result not Float -- caused by: 12:7 3
+TR opt: multi-file2.rkt 13:3 (* 3.4 (+ 3 5)) -- binary float
+TR opt: multi-file2.rkt 13:10 (+ 3 5) -- fixnum bounded expr
+81.6
+)
+
+#lang typed/racket
+
+(require "multi-file1.rkt")
+
+(f (* 3.4 (+ 3 5)))