Why "My Documents" Acts Weird in cmd.exe

On modern Windows, My Documents is not a normal folder. It is a legacy junction kept for old software. A junction is an NTFS reparse point that silently redirects one path to another, and Windows intentionally blocks listing it.

Initial behavior

C:\Users\handrew>dir /b Documents

No output because the folder was empty.

C:\Users\handrew>dir /b "My Documents"
File Not Found

This looks like the folder does not exist, but it actually does.

If a script insists on enumerating "My Documents", it will always think the folder is missing even though file reads and writes still work through the junction.

Creating files

C:\Users\handrew>type nul> "This is Documents">Documents\this_is_documents.txt

C:\Users\handrew>type nul> "This is My Documents">"My Documents"\this_is_my_documents.txt

Both commands succeed.

C:\Users\handrew>dir /b "My Documents"
File Not Found

Still cannot list it.

C:\Users\handrew>dir /b Documents
this_is_documents.txt
this_is_my_documents.txt

The file written through My Documents shows up in Documents.

Dir /al flag shows the junction

C:\Users\handrew>dir /al . | find "ocument"
<JUNCTION>     Local Settings [C:\Users\handrew\AppData\Local]

My Documents is a real NTFS junction, the kind Microsoft documents here: Hard Links and Junctions.

Trying to list from inside

C:\Users\handrew>cd "My Documents"

C:\Users\handrew\My Documents>dir
File Not Found

Listing is blocked on purpose.

Permissions explain everything

C:\Users\handrew>icacls "My Documents"
My Documents Everyone:(DENY)(RD)
             NT AUTHORITY\SYSTEM:(I)(OI)(CI)(F)
             BUILTIN\Administrators:(I)(OI)(CI)(F)
             WINDOWS11H2\handrew:(I)(OI)(CI)(F)

RD means Read Data or List Directory.

Windows allows path resolution and file creation, but blocks enumeration. This prevents infinite recursion and forces modern software to use the real Documents folder.

Explorer hides all of this. cmd.exe shows the cracks.

Bottom line: treat "Documents" as the real path, and expect legacy names like "My Documents" to resolve but not list. This was tested on Microsoft Windows 11 24H2 (OS Build 26100.7623).

Other junctions

C:\Users\handrew>dir /al

 Directory of C:\Users\handrew

11/09/2025  01:32 PM    <JUNCTION>     Application Data [C:\Users\handrew\AppData\Roaming]
11/09/2025  01:32 PM    <JUNCTION>     Cookies [C:\Users\handrew\AppData\Local\Microsoft\Windows\INetCookies]
11/09/2025  01:32 PM    <JUNCTION>     Local Settings [C:\Users\handrew\AppData\Local]
11/09/2025  01:32 PM    <JUNCTION>     My Documents [C:\Users\handrew\Documents]
11/09/2025  01:32 PM    <JUNCTION>     NetHood [C:\Users\handrew\AppData\Roaming\Microsoft\Windows\Network Shortcuts]
02/08/2026  01:54 PM    <DIR>          OneDrive
11/09/2025  01:32 PM    <JUNCTION>     PrintHood [C:\Users\handrew\AppData\Roaming\Microsoft\Windows\Printer Shortcuts]
11/09/2025  01:32 PM    <JUNCTION>     Recent [C:\Users\handrew\AppData\Roaming\Microsoft\Windows\Recent]
11/09/2025  01:32 PM    <JUNCTION>     SendTo [C:\Users\handrew\AppData\Roaming\Microsoft\Windows\SendTo]
11/09/2025  01:32 PM    <JUNCTION>     Start Menu [C:\Users\handrew\AppData\Roaming\Microsoft\Windows\Start Menu]
11/09/2025  01:32 PM    <JUNCTION>     Templates [C:\Users\handrew\AppData\Roaming\Microsoft\Windows\Templates]

C:\Users\handrew>dir /al c:\ProgramData

 Directory of c:\ProgramData

11/09/2025  11:30 AM    <JUNCTION>     Application Data [C:\ProgramData]
11/09/2025  11:30 AM    <JUNCTION>     Desktop [C:\Users\Public\Desktop]
11/09/2025  11:30 AM    <JUNCTION>     Documents [C:\Users\Public\Documents]
11/09/2025  11:30 AM    <JUNCTION>     Start Menu [C:\ProgramData\Microsoft\Windows\Start Menu]
11/09/2025  11:30 AM    <JUNCTION>     Templates [C:\ProgramData\Microsoft\Windows\Templates]

C:\Users\handrew>dir /al c:\users\public\documents

 Directory of c:\users\public\documents

11/09/2025  11:30 AM    <JUNCTION>     My Music [C:\Users\Public\Music]
11/09/2025  11:30 AM    <JUNCTION>     My Pictures [C:\Users\Public\Pictures]
11/09/2025  11:30 AM    <JUNCTION>     My Videos [C:\Users\Public\Videos]