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Re: Rewriting HTTP to HTTPS for generic package proxy

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On 2024-07-10 16:57, Fiehe, Christoph wrote:

I am just trying to find something that helps to narrow down the
problem. What I want to achieve is, that a client can use HTTP in the
LAN, so that Squid can cache distribution packages without making use
of SSL intercepting when repos are only accessible via HTTPS.

OK.


In that case the secure connection must start at the proxy and end on
the target server with or without any upstream proxies in betweem.

It depends on whether you trust the parent proxy:

If you trust the parent proxy, then you can use two secure connections:

1.1. child - parent (TLS; no CONNECT)
1.2. parent - origin (TLS; no CONNECT)

If you do not trust the parent proxy, then, yes, you will need a tunnel:

2.1. child - parent (CONNECT)
2.2. child - origin (TLS inside the CONNECT tunnel)

N.B. CONNECT request in 2.1 may be plain text (common) or encrypted (rare); I am ignoring the difference between those two subcases for now.


We have the following setup:

client -> downstream proxy -> upstream proxy -> https://download.docker.com

Now let us assume the client wants to retrieve the following resource http://download.docker.com/linux/ubuntu/dists/jammy/InRelease from the upstream proxy.

The client initiates a HTTP GET request and sends it to the downstream proxy. Now, the URL gets rewritten.

OK.


It indicates to use a HTTPS connection instead in order to talk to the target server, in our case the result is https://download.docker.com/linux/ubuntu/dists/jammy/InRelease.

Yes, but HTTPS scheme does not imply that the child Squid has to use CONNECT. There are two possible scenarios detailed above. I do not know which of them applies to your use case.


Now comes the critical point: From my understanding – it may be wrongof course - the downstream server now has to send a CONNECT request to the upstream server

Yes, provided the child (downstream) proxy does not trust that parent (upstream) proxy. That is scenario 2. Scenario 1 is different.


to advise him to establish a secure connection to the target server.

No, the CONNECT tunnel itself is just a pair of TCP connections. The parent proxy "secures" nothing but basic TCP connectivity. It is the child proxy that negotiates TLS (over/inside that tunnel) with the origin server.


After creation, the downstream proxy can retrieve the resource and
send it back to the client via plain HTTP.

Yes.



I suppose, that the GnuTLS occurs because of a missing SSL handshake
between downstream proxy and download.docker.com.

At this time, I can only say that a TLS negotiation error occurs (while child Squid is using the encryption library it probably should not be using for this). It is not yet clear to me whether child Squid is negotiating with the wrong hop or something goes wrong during negotiation with the right hop.

As the next steps, I recommend switching to OpenSSL and, if that alone does not help, sharing new errors and determining whether you want to use scenario 1 (no CONNECT), scenario 2 (CONNECT), or either (whichever works): Do you trust the parent Squid?


HTH,

Alex.


-----Ursprüngliche Nachricht-----
Von: Alex Rousskov <rousskov@xxxxxxxxxxxxxxxxxxxxxxx>
Gesendet: Mittwoch, 10. Juli 2024 22:15
An: squid-users@xxxxxxxxxxxxxxxxxxxxx
Cc: Fiehe, Christoph <c.fiehe@xxxxxxxxxxx>
Betreff: AW:  Rewriting HTTP to HTTPS for generic package proxy

On 2024-07-10 15:31, Fiehe, Christoph wrote:
The problem is that the proxy just forwards the client GET request to the upstream proxy

Why does sending a GET request to the upstream proxy represent a problem
in your use case? I cannot find anything in your prior messages on this
thread that would preclude sending a GET request to the upstream proxy.


but in that case a CONNECT is required.

Why?

Please do not interpret my response as implying that this "must send
CONNECT" requirement is wrong (or correct). At this point, I am just
trying to understand what problem(s) you are trying to solve beyond the
one you have originally described.


Thank you,

Alex.

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