I assume that everyone is aware that a single certificate expiry has caused 
issues all over the place since Thu Sep 30.  See 
https://www.theregister.com/2021/09/30/lets_encrypt_xero_slack_outages/

On Sunday, 3 October 2021 at 22:40:25 UTC+11 [email protected] wrote:

> lördag 2 oktober 2021 kl. 22:11:55 UTC+2 skrev Walter Hop:
>
>> On 2 Oct 2021, at 20:44, Matthew Trescott via TortoiseSVN <
>> [email protected]> wrote:
>>
>> I don't believe anything changed on its own since yesterday; TortoiseSVN 
>> was still giving errors this morning. However, I completed the certificate 
>> chain switch (certbot renew --preferred-chain 'ISRG Root X1' --force-renew) 
>> and Tortoise is now satisfied, although my old Android now complains :)
>>
>>
>> That is great! It’s a fair trade-off. I’m pretty sure that SVN clients on 
>> old Android phones are extremely rare. I am definitely going to try the 
>> alternate chain. Sadly our ACME client (acme_tiny) does not support it yet, 
>> but we created a PR for it - it was rejected then, on the premise that it 
>> wouldn’t be necessary. But now that the DST expiration has finally 
>> happened, it turns out there are various corner cases where a sysop would 
>> want to choose the alternate chain.
>>
>> So indeed the problem is that Tortoise is only checking whether the 
>> highest certificate in the chain is a trust anchor, and not considering 
>> that an intermediary could be a trust anchor as well.
>>
>>
>> That is important information. thank you. I don’t know the TortoiseSVN 
>> source, but this MIGHT be caused by the way that the bundled OpenSSL is 
>> configured. The OpenSSL version is new enough, and this behavior is 
>> switchable. A patch was circulated on FreeBSD-security to change OpenSSL’s 
>> default behavior so that it should succeed at the first verified 
>> certificate and no longer bother looking at the expired DST root.
>>
>> --- crypto/openssl/crypto/x509/x509_vpm.c.prev  2021-10-01
>> 09:16:51.753533000 -0400
>> +++ crypto/openssl/crypto/x509/x509_vpm.c       2021-10-01
>> 09:19:39.708106000 -0400
>> @@ -537,7 +537,7 @@
>>       "default",                 /* X509 default parameters */
>>       0,                         /* Check time */
>>       0,                         /* internal flags */
>> -     0,                         /* flags */
>> +     X509_V_FLAG_TRUSTED_FIRST, /* flags */
>>       0,                         /* purpose */
>>       0,                         /* trust */
>>       100,                       /* depth */
>>
>> Perhaps (but this is absolutely above my pay grade) a similar 
>> configuration in TortoiseSVN’s build makes OpenSSL fail, and a change to 
>> OpenSSL’s configuration might be a structural solution for TortoiseSVN.
>>
>
> Unless I'm mistaken, this flag is already set, at least in the "default" 
> parameter section (as in the patch). It is not set in the "ssl_client" 
> section but I don't know which section might be used by the TortoiseSVN 
> connection.
>
> However as far as I understand the workaround is only required on OpenSSL 
> 1.0.2. TortoiseSVN is, AFAIK, using OpenSSL 1.1.1. 
>
> Kind regards,
> Daniel Sahlberg
>

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