For the future readers of the thread - solution suggested by Christian 
Herget works like a charm!

Regards,
Bartek

On Tuesday, October 12, 2021 at 6:26:07 PM UTC+2 Christian Herget wrote:

> Hello,
> I searched for a workaround for this issue and the following worked for me 
> (Windows 10).
> Go to https://letsencrypt.org/certificates/ and get the active Let’s 
> Encrypt R3 certificate (https://letsencrypt.org/certs/lets-encrypt-r3.der
> ).
> Add this certificate to your Windows certificate store. For this you just 
> need to right click the file and select Install Certificate.
>
> Best regards,
> Christian
> Tony Rietwyk schrieb am Montag, 4. Oktober 2021 um 04:47:48 UTC+2:
>
>> 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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