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https://issues.apache.org/jira/browse/HTTPCLIENT-1272?page=com.atlassian.jira.plugin.system.issuetabpanels:comment-tabpanel&focusedCommentId=13528320#comment-13528320
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Oleg Kalnichevski commented on HTTPCLIENT-1272:
-----------------------------------------------

Hi Daz
I am not entirely sure HttpClient's behaviour is that wrong. Out of 3 
challenges provided by the server it picks up 'Negotiate' first. Failing to 
generate a response using 'Negotiate' it moves onto the next preferred scheme 
NTLM. (So, evidently, HTTPCLIENT-1107 fix works as intended). It succeeds in 
generating a response to the challenge using NTLM, which is then rejected by 
the server due to invalid credentials. I am not quite sure HttpClient should 
re-attempt authentication using a weaker scheme at this point.
---
08:32:14.340 [DEBUG] 
[org.apache.http.client.protocol.RequestProxyAuthentication] Generating 
response to an authentication challenge using Negotiate scheme
08:32:14.340 [DEBUG] [org.apache.http.impl.auth.SPNegoScheme] init MYPROXY:8080
08:32:14.372 [WARN] 
[org.apache.http.client.protocol.RequestProxyAuthentication] NEGOTIATE 
authentication error: Invalid name provided (Mechanism level: Could not load 
configuration file C:\WINDOWS\krb5.ini (The system cannot find the file 
specified))
08:32:14.372 [DEBUG] 
[org.apache.http.client.protocol.RequestProxyAuthentication] Generating 
response to an authentication challenge using ntlm scheme
---

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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