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We have a similar issue as described in JENKINS-3350 Connect to update center via HTTP proxy that requires NTLM authentication
But our proxy does not require NTLM authentication, it just likes it best. I found this out via reading the log entries generated by the apache httpclient during an attempt to download a plugin. There you can read
Dec 15, 2015 12:43:02 PM FINE org.apache.commons.httpclient.auth.AuthChallengeProcessor selectAuthScheme Supported authentication schemes in the order of preference: [ntlm, digest, basic] Dec 15, 2015 12:43:02 PM INFO org.apache.commons.httpclient.auth.AuthChallengeProcessor selectAuthScheme ntlm authentication scheme selected Dec 15, 2015 12:43:02 PM FINE org.apache.commons.httpclient.auth.AuthChallengeProcessor processChallenge Using authentication scheme: ntlm Dec 15, 2015 12:43:02 PM FINE org.apache.commons.httpclient.auth.AuthChallengeProcessor processChallenge Authorization challenge processed
To highlight it
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Supported authentication schemes in the order of preference: ntlm, digest, basic
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ntlm authentication scheme selected - automatically by apache http client
So in our case we could get around all this hassle if there was an option on the proxy page to define the authentication scheme the http client shall use. If I find the time I will have a look if I can propose a pull request.
I have attached a small draft how it could look like 
Why the priority major? For me it is rather cumbersome to manually download all plugins in order to upload them into jenkins via the internal plugin upload page. Moreover the nice feature of the self-updating jenkins is broken for us.
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