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==> GET http://xy/z HTTP/1.1
<== HTTP/1.0 401 Unauthorized / Proxy-Connection: close

When bypassing Squid (squid/3.0.STABLE6), I get the HTTP basic authentication prompt, as it should.

Is there a specific setting that controls this behaviour, or is this actually a bug?

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I think I found the solution. Squid isn't really HTTP 1.1 compliant and thus intereferes with advanced stuff like persistent connections.

You can see here under 8.1.2 that there is an open issue described as "assume http/1.1 servers will maintain persistent connections even after error responses from the server".

So: server sends 401 => squid closes the connection => BASIC auth doesn't work

Sad but true.

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