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SFTP (sshd_config) not respecting match user half the time

pl flag

I installed OpenSSH on a Windows 2019 server and added this to the sshd_config file:

Subsystem   sftp    sftp-server.exe -d C:\SFTP\Vendors

Match user sftp-vendor1
    ChrootDirectory C:\SFTP\Vendors\vendor1
    ForceCommand internal-sftp

I then created the user locally and gave them access to the path in ChrootDirectory.

When I connect to the server via SFTP, half of the time I get this (expected result):

enter image description here

But other times, I get this:

enter image description here

It does this using the cli as well. Any idea why it only seems to work sometimes?

mangohost

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