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Probably because NTLM authentication relies on receiving 401 responses. It works like
Send un authenticated request
Receive 401 response with header that lists supported auth mechanisms
Send NTLM negotiate message
Receive 401 response with NTLM challenge message
Send NTLM authenticate message
Receive 200 response as user is now authenticated.
I don't know how the Retry operations change the behaviour but it could be that it adds a hook to 401 responses and continues to try and send the same message (retry) without any of the NTLM messages.
Hello,
The requests-ntlm is not working if the requets is under retry:
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