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https://issues.apache.org/jira/browse/HTTPCLIENT-1272?page=com.atlassian.jira.plugin.system.issuetabpanels:all-tabpanel
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Oleg Kalnichevski resolved HTTPCLIENT-1272.
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    Resolution: Won't Fix

Daz
Actually, when user credentials are not applicable for NTLM authentication (for 
instance, when represented by UsernamePasswordCrednentials instead of 
NTCredentials) the NTLM auth scheme should fail and HttpClient should pick the 
next available scheme (BASIC in your case). So, instead of giving HttpClient 
incomplete NTCredentials with bogus domain and workstation attributes, try 
giving it UsernamePasswordCrednentials and see what happens.

I am going to close this issue as WONTFIX. While it would be permissible to 
retry authentication with BASIC scheme in the context of a corporate proxy on a 
secure corporate network, it would be pretty irresponsible to automatically 
send user credentials in clear text to an arbitrary host after having a more 
secure scheme failed due to credentials being invalid. I hope you agree.

Oleg  
                
> HttpClient does not retry failed PROXY authentication when multiple 
> challenges are present
> ------------------------------------------------------------------------------------------
>
>                 Key: HTTPCLIENT-1272
>                 URL: https://issues.apache.org/jira/browse/HTTPCLIENT-1272
>             Project: HttpComponents HttpClient
>          Issue Type: Bug
>          Components: HttpClient
>    Affects Versions: 4.2.2
>            Reporter: Daz DeBoer
>
> Similar to HTTPCLIENT-1107, but for Proxy authentication. It appears that 
> subsequent authentication schemes are not attempted if an earlier scheme 
> fails.
> In our case, a proxy supports Negotiate, NTLM and BASIC authentication. When 
> NTML authentication fails due to the wrong credentials being supplied, BASIC 
> authentication is never attempted against the proxy.
> I am a Gradle core developer, and we use HttpClient internally for dependency 
> resolution. This issue was reported by one of our users.

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