diff --git a/pkgs/racket-test-core/tests/racket/path.rktl b/pkgs/racket-test-core/tests/racket/path.rktl
index 99a577d5f5..4166afd5f2 100644
--- a/pkgs/racket-test-core/tests/racket/path.rktl
+++ b/pkgs/racket-test-core/tests/racket/path.rktl
@@ -944,6 +944,8 @@
     (test (bytes->path #"../") simplify-path (bytes->path #"../") #f)
     (test (bytes->path #"../") simplify-path (bytes->path #"..//") #f)
     (test (bytes->path #"../") simplify-path (bytes->path #"..//./") #f)
+    (test (bytes->path #"/x") simplify-path (bytes->path #"/../../x") #f)
+    (test (bytes->path #"/") simplify-path (bytes->path #"/x/../..") #f)
     (test (bytes->path #"x/") path->directory-path (bytes->path #"x"))
     (test (bytes->path #"x/") path->directory-path (bytes->path #"x/"))
     (test (bytes->path #"x/./") path->directory-path (bytes->path #"x/."))
diff --git a/racket/src/cs/schemified/io.scm b/racket/src/cs/schemified/io.scm
index f986bdf569..6dca0c65ee 100644
--- a/racket/src/cs/schemified/io.scm
+++ b/racket/src/cs/schemified/io.scm
@@ -25003,11 +25003,20 @@
                                                        accum_0)
                                                       (if (eq? 'up (car l_1))
                                                         (if (pair? accum_0)
-                                                          (let ((app_0
-                                                                 (cdr l_1)))
+                                                          (if (if (null?
+                                                                   (cdr
+                                                                    accum_0))
+                                                                (1/absolute-path?
+                                                                 (car accum_0))
+                                                                #f)
                                                             (loop_0
-                                                             app_0
-                                                             (cdr accum_0)))
+                                                             (cdr l_1)
+                                                             accum_0)
+                                                            (let ((app_0
+                                                                   (cdr l_1)))
+                                                              (loop_0
+                                                               app_0
+                                                               (cdr accum_0))))
                                                           (cons
                                                            'up
                                                            (loop_0
diff --git a/racket/src/io/path/simplify-nofs.rkt b/racket/src/io/path/simplify-nofs.rkt
index 61c4060b5e..504073bd08 100644
--- a/racket/src/io/path/simplify-nofs.rkt
+++ b/racket/src/io/path/simplify-nofs.rkt
@@ -8,7 +8,8 @@
          "directory-path.rkt"
          "complete.rkt"
          "parameter.rkt"
-         "windows.rkt")
+         "windows.rkt"
+         "relativity.rkt")
 
 (provide simplify-path-syntactically)
 
@@ -52,7 +53,13 @@
                   [(eq? 'up (car l))
                    (cond
                      [(pair? accum)
-                      (loop (cdr l) (cdr accum))]
+                      (cond
+                        [(and (null? (cdr accum))
+                              (absolute-path? (car accum)))
+                         ;; for 'up at root, just keep the root
+                         (loop (cdr l) accum)]
+                        [else
+                         (loop (cdr l) (cdr accum))])]
                      [else
                       (cons 'up (loop (cdr l) null))])]
                   [else (loop (cdr l) (cons (car l) accum))])))