diff --git a/collects/drracket/private/eval-helpers.rkt b/collects/drracket/private/eval-helpers.rkt
index 64a69ec5a0..aae20c13b6 100644
--- a/collects/drracket/private/eval-helpers.rkt
+++ b/collects/drracket/private/eval-helpers.rkt
@@ -5,6 +5,7 @@
          compiler/cm
          setup/dirs
          planet/config
+         pkg/lib
          (prefix-in *** '#%foreign) ;; just to make sure it is here
          )
 
@@ -86,7 +87,10 @@
                         (list (CACHE-DIR) cd)
                         (list (CACHE-DIR)))])
       (manager-skip-file-handler
-       (λ (p) (file-stamp-in-paths p no-dirs))))))
+       (λ (p) (or (file-stamp-in-paths p no-dirs)
+                  (let ([pkg (path->pkg p)])
+                    (and pkg
+                         (file-stamp-in-paths p (list (pkg-directory pkg)))))))))))
 
 (define (transform-module filename stx raise-hopeless-syntax-error)
   (define-values (mod name lang body)
diff --git a/collects/tests/drracket/populate-compiled.rkt b/collects/tests/drracket/populate-compiled.rkt
new file mode 100644
index 0000000000..6718c46351
--- /dev/null
+++ b/collects/tests/drracket/populate-compiled.rkt
@@ -0,0 +1,94 @@
+#lang racket/base
+(require racket/file
+         racket/system
+         compiler/find-exe
+         pkg/lib)
+
+(unless (eq? 'user (default-pkg-scope))
+  (error "Run this test with `user' default package scope"))
+
+(define dir (make-temporary-file "~a" 'directory))
+(define pkg-dir (build-path dir "popcomp-pkg"))
+(define coll-dir (build-path pkg-dir "popcomp"))
+(define pkg2-dir (build-path dir "popcomp2-pkg"))
+(define coll2-dir (build-path pkg2-dir "popcomp2"))
+
+(make-directory* coll-dir)
+(make-directory* coll2-dir)
+
+(call-with-output-file*
+ (build-path coll-dir "main.rkt")
+ (lambda (o)
+   (fprintf o "#lang racket/base\n")
+   (write '(provide popcomp) o)
+   (write '(define popcomp (gensym 'popcomp)) o)))
+
+(call-with-output-file*
+ (build-path coll2-dir "main.rkt")
+ (lambda (o)
+   (fprintf o "#lang racket/base\n")
+   (write '(provide popcomp2) o)
+   (write '(define popcomp2 (gensym 'popcomp2)) o)))
+
+(call-with-output-file*
+ (build-path dir "y.rkt")
+ (lambda (o)
+   (fprintf o "#lang racket/base\n")
+   (write '(provide y) o)
+   (write '(define y (gensym 'y)) o)))
+
+(call-with-output-file*
+ (build-path dir "x.rkt")
+ (lambda (o)
+   (fprintf o "#lang racket/base\n")
+   (write '(require "y.rkt" popcomp popcomp2) o)))
+
+(define (system*/error . args)
+  (unless (apply system* args)
+    (error "failed")))
+
+(define addon-dir (build-path dir "addon"))
+(make-directory* addon-dir)
+(void (putenv "PLTADDONDIR" (path->string addon-dir)))
+
+(system*/error (find-exe) 
+               "-l" "raco" "pkg" "install" "--no-setup" "--link"
+               pkg-dir
+               pkg2-dir)
+(system*/error (find-exe) 
+               "-e" 
+               "(require (submod tests/drracket/populate-compiled go))"
+               (build-path dir "x.rkt"))
+
+(delete-directory/files dir)
+
+;; ----------------------------------------
+
+(module go racket/base
+  (require "private/drracket-test-util.rkt"
+           racket/gui/base
+           racket/class
+           racket/path
+           racket/file)
+
+  (define (check-compiled compiled? path)
+    (unless (equal? compiled? (file-exists? path))
+      (error 'check-compiled
+             "expected ~acompiled: ~a"
+             (if compiled? "" "not ")
+             path)))
+  
+  (fire-up-drracket-and-run-tests 
+   (λ ()
+      (let ([drs (wait-for-drracket-frame)])
+        (define x (vector-ref (current-command-line-arguments) 0))
+        (define dir (path-only x))
+        
+        (do-execute drs)
+
+        (define popcomp-main-zo
+          (build-path dir "popcomp-pkg" "popcomp" "compiled" "drracket" "errortrace" "main_rkt.zo"))
+
+        (check-compiled #t (build-path dir "compiled" "drracket" "errortrace" "y_rkt.zo"))
+        (check-compiled #f popcomp-main-zo)
+        (check-compiled #f (build-path dir "popcomp2-pkg" "popcomp2" "compiled" "drracket" "errortrace" "main_rkt.zo"))))))