Http send report errors / duplicati-monitoring

TL;DR I “think” this is a poor interaction between Let’s Encrypt default cert chain, OS certs, and mono.
This leaves multiple ways to fix, but the controllable one (though limited) is the certs that server sends.

I’m not a certificate wizard (but learning some), but the default one appears to be the cross signed one.
Wireshark shows that an Edge access to https://www.duplicati-monitoring.com gets the below:

Certificate: 3082056030820448a00302010202104001772137d4e942b8ee76aa3c640ab7300d06092a… (id-at-commonName=ISRG Root X1,id-at-organizationName=Internet Security Research Group,id-at-countryName=US)
    signedCertificate
        version: v3 (2)
        serialNumber: 0x4001772137d4e942b8ee76aa3c640ab7
        signature (sha256WithRSAEncryption)
            Algorithm Id: 1.2.840.113549.1.1.11 (sha256WithRSAEncryption)
        issuer: rdnSequence (0)
            rdnSequence: 2 items (id-at-commonName=DST Root CA X3,id-at-organizationName=Digital Signature Trust Co.)
                RDNSequence item: 1 item (id-at-organizationName=Digital Signature Trust Co.)
                RDNSequence item: 1 item (id-at-commonName=DST Root CA X3)
        validity
            notBefore: utcTime (0)
            notAfter: utcTime (0)
        subject: rdnSequence (0)
        subjectPublicKeyInfo
        extensions: 7 items
    algorithmIdentifier (sha256WithRSAEncryption)
    Padding: 0
    encrypted: 0a73006c966eff0e52d0aedd8ce75a06ad2fa8e38fbfc90a031550c2e56c42bb6f9bf4b4…

Note that the issuer is DST ROOT CA X3. The two versions of their certificate are described on page
Extending Android Device Compatibility for Let’s Encrypt Certificates showing default is cross-signed.
DST Root CA X3 Expiration (September 2021) talks about an Android exception. It doesn’t care about
DST Root CA X3 being expired. Other implementations do, such as older OpenSSL, and BoringSSL, which forked from it in 2014. mono uses BoringSSL. See the (oddly quiet) issue on it I mention earlier.

https://usage-reporter.duplicati.com/ suggests vast majority of Duplicati users use Windows not mono.

Resources for Certificate Chaining Help has a Workarounds for OpenSSL 1.0.2. link with three options.

1 is to remove the expired certificate as some are doing here, but I’m not sure how to keep it removed.
Ubuntu seems to have that problem solved by recently removing it from their ca-certificates packages.

2 is to ask the client to prefer the trust store certificates over the chain that the server sends. Without it, presumably the cross-sign of DST ROOT CA X3 is found and (except on Android) the access is failed.
The mono issue I cite asks them to do the change by using the X509_V_FLAG_TRUSTED_FIRST flag.

3 is for web server to get and use the alternative certificate chain that doesn’t go to DST ROOT CA X3.
It simply ends at ISRG Root X1 (self-signed) which presumably is trusted by most systems these days.

This breaks old Android, but that might not matter, and it probably solves the failures with current mono.
The limitation of this is that the server-side Let’s Encrypt workaround might need to be done elsewhere.
The procedure for asking for the alternative chain seemingly varies by ACME client (if it can even do it).

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