I have also tested in 5.8 and 6.6 both show the same condition, 6.6 shows 
errors for it however. I have also imported my certificates into wireshark. 

Just to confirm this is the firewall 192.168.1.1 port 3128 is squid going to 
iMac that is attempting TSL1.3 I have nosslv3 set also. The firewall is where I 
grabbed the pcap from 
Sent from my iPhone

> On Jul 5, 2024, at 11:52, Jonathan Lee <jonathanlee...@gmail.com> wrote:
> 
> If it’s encrypted at TLS1.3 it should still work with the approved 
> certificate authority as it is imported to my devices I own. I just enable 
> TLS1.3 right?
> 
>> On Jul 5, 2024, at 11:28, <jonathanlee...@gmail.com> 
>> <jonathanlee...@gmail.com> wrote:
>> 
>> The only one I got a certificate from was the non iMac
>> 
>> The iMac keeps sending change cipher requests and wants TLS1.3 over and over 
>> as soon as a TLS1.2 pops up it works
>> 
>> That one has the certificate however that system the Toshiba does not have 
>> any issues with this error. I highly suspect that I need to enable TLS1.3 
>> would you agree?
>> 
>> -----Original Message-----
>> From: Alex Rousskov <rouss...@measurement-factory.com>
>> Sent: Friday, July 5, 2024 11:02 AM
>> To: squid-users <squid-users@lists.squid-cache.org>
>> Cc: Jonathan Lee <jonathanlee...@gmail.com>
>> Subject: Re: [squid-users] Squid Cache Issues migration from 5.8 to 6.6
>> 
>> On 2024-07-05 12:02, Jonathan Lee wrote:
>> 
>>>> Alex: I recommend determining what that CA is in these cases (e.g., by 
>>>> capturing raw TLS packets and matching them with connection information 
>>>> from A000417 error messages in cache.log or %err_detail in access.log).
>> 
>> 
>>> I have Wireshark running do I just look for information with
>>> ssl.handshake.type == 1
>> 
>>> Or is there a wireshark particular filter you would like ran to help with 
>>> isolation?
>> 
>> 
>> Please use Wireshark to determine the name of CA that issued the certificate 
>> that Squid sent to the client in the failing test case. If you are not sure, 
>> feel free to share issuer and subject fields of all certificates that Squid 
>> sent to the client in that test case (there may be two of each if Squid sent 
>> two certificates). Or even share a pointer to the entire (compressed) raw 
>> test case packet capture in pcap format!
>> 
>> These certificates are a part of standard TLS handshake, and Wireshark 
>> usually displays their fields when one studies TLS handshake bytes using 
>> Wireshark UI.
>> 
>> I do not know what filter would work best, but there should be just a 
>> handful of TLS handshake packets to examine for the test case, so no filter 
>> should be necessary.
>> 
>> 
>> HTH,
>> 
>> Alex.
>> 
>> 
>> 
>>>> On Jul 5, 2024, at 08:23, Jonathan Lee <jonathanlee...@gmail.com> wrote:
>>>> 
>>>> Thanks for the email and support with this. I will get wireshark
>>>> running on the client and get the info required. Yes the information
>>>> prior is from the firewall side outside of the proxy testing from the
>>>> demilitarized zone area. I wanted to test this first to rule that out
>>>> as it’s coming in from that first and hits the proxy next Sent from
>>>> my iPhone
>>>> 
>>>>> On Jul 5, 2024, at 06:33, Alex Rousskov 
>>>>> <rouss...@measurement-factory.com> wrote:
>>>>> 
>>>>> On 2024-07-04 19:12, Jonathan Lee wrote:
>>>>>> You also stated .. " my current working theory suggests that we are 
>>>>>> looking at a (default) signUntrusted use case.”
>>>>>> I noticed for Squid documents that default is now set to off ..
>>>>> 
>>>>> The http_port option you are looking at now is not the directive I was 
>>>>> talking about earlier.
>>>>> 
>>>>>> http_port
>>>>>> tls-default-ca[=off]
>>>>>>  Whether to use the system Trusted CAs. Default is OFF.
>>>>>> Would enabling this resolve the problem in Squid 6.6 for error.
>>>>> 
>>>>> 
>>>>> No, the above poorly documented http_port option is for validating 
>>>>> _client_ certificates. It has been off since Squid v4 AFAICT. Your 
>>>>> clients are not sending client certificates to Squid.
>>>>> 
>>>>> According to the working theory, the problem we are solving is related to 
>>>>> server certificates. http_port tls-default-ca option does not affect 
>>>>> server certificate validation. Server certificate validation should use 
>>>>> default CAs by default.
>>>>> 
>>>>> Outside of SslBump, server certificate validation is controlled by 
>>>>> tls_outgoing_options default-ca option. That option defaults to "on". I 
>>>>> am not sure whether SslBump honors that directive/option though. There 
>>>>> are known related bugs in that area. However, we are jumping ahead of 
>>>>> ourselves. We should confirm the working theory first.
>>>>> 
>>>>>> The squid.conf.documented lists it incorrectly
>>>>> 
>>>>> Squid has many directives and a directive may have many options. One 
>>>>> should not use an directive option name instead of a directive name. One 
>>>>> should not use an option from one directive with another directive. Squid 
>>>>> naming is often inconsistent; be careful.
>>>>> 
>>>>> * http_port is a directive. tls-default-ca is an option for that 
>>>>> directive. It is used for client certificate validation. It defaults to 
>>>>> "off" (because client certificates are rarely signed by well-known 
>>>>> (a.k.a. "default") CAs preinstalled in many deployment environments).
>>>>> 
>>>>> * tls_outgoing_options is a directive. default-ca is an option for that 
>>>>> directive. It is used for server certificate validation outside of 
>>>>> SslBump contexts (at least!). It defaults to "on" (because server 
>>>>> certificates are usually signed by well-known (a.k.a. "default") CAs 
>>>>> preinstalled in many deployment environments).
>>>>> 
>>>>> AFAICT, the documentation in question is not wrong (but is insufficient).
>>>>> 
>>>>> Again, I do not recommend changing any Squid configuration 
>>>>> directives/options at this triage state.
>>>>> 
>>>>> Alex.
>>>>> 
>> 
>> <tlschange.PNG>
> 
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