diff --git a/pkgs/racket-test/tests/syntax/modcollapse.rkt b/pkgs/racket-test/tests/syntax/modcollapse.rkt
index 4dd5e95da5..2b315b61c1 100644
--- a/pkgs/racket-test/tests/syntax/modcollapse.rkt
+++ b/pkgs/racket-test/tests/syntax/modcollapse.rkt
@@ -122,3 +122,24 @@
 (check (collapse-module-path-index submod-submod-foo
                                    here)
        `(submod ,(build-path here-dir "foo.rkt") test))
+
+
+(define dirrel (module-path-index-join
+                "x/banana.rkt"
+                self))
+(check (collapse-module-path-index dirrel)
+       "x/banana.rkt")
+(check (collapse-module-path-index dirrel
+                                   here)
+       (build-path here-dir "x/banana.rkt"))
+
+(define rel-dirrel (module-path-index-join
+                    "apple.rkt"
+                    (module-path-index-join
+                     "x/banana.rkt"
+                     self)))
+(check (collapse-module-path-index rel-dirrel)
+       "x/apple.rkt")
+(check (collapse-module-path-index rel-dirrel
+                                   here)
+       (build-path here-dir "x" "apple.rkt"))
diff --git a/racket/collects/syntax/private/modcollapse-noctc.rkt b/racket/collects/syntax/private/modcollapse-noctc.rkt
index 0c1f87f75b..8124605758 100644
--- a/racket/collects/syntax/private/modcollapse-noctc.rkt
+++ b/racket/collects/syntax/private/modcollapse-noctc.rkt
@@ -420,7 +420,7 @@ Use syntax/modcollapse instead.
                 ;; Unix-style relative path string
                 (cond
                  [(string? prev)
-                  (define l (drop-right (explode-relpath-string s) 1))
+                  (define l (drop-right (explode-relpath-string prev) 1))
                   (if (null? l)
                       s
                       (string-join (append
@@ -428,7 +428,7 @@ Use syntax/modcollapse instead.
                                       (case e
                                         [(same) "."]
                                         [(up) ".."]
-                                        [else e]))
+                                        [else (path-element->string e)]))
                                     (list s))
                                    "/"))]
                  [(path? prev)
diff --git a/racket/collects/syntax/private/modhelp.rkt b/racket/collects/syntax/private/modhelp.rkt
index 8c4a188a96..5255f274f3 100644
--- a/racket/collects/syntax/private/modhelp.rkt
+++ b/racket/collects/syntax/private/modhelp.rkt
@@ -6,7 +6,7 @@
 (define (explode-relpath-string p)
   (map (lambda (p)
          (cond [(assoc p '((#"." . same) (#".." . up))) => cdr]
-               [else (bytes->path p)]))
+               [else (bytes->path-element p)]))
        (regexp-split #rx#"/+" (string->bytes/utf-8 p))))
 
 (define (module-path-v-string? v)