Hi all,

I've had security/openssl31 installed for many months, and all dependent ports 
rebuilt against it, (with ssl=openssl31 in DEFAULT_VERSIONS) so that I could 
keep an eye on what might have issues with it, assuming an
eventual change to the 3-series in base.  And maybe it's more secure, given 
that it's had a pile of extra work done to it, while 1.1.1... is in 
maintenance.  Up to this weekend, everything has been great.

One of the applications that I use that depends on openssl is mail/fetchmail, 
which I use to retrieve mail from my ISP's IMAP server at imap.telstra.com:993.

Coincident with updating the security/ca_root_nss port, fetchmail started to 
complain that the imap server was using a self-signed certificat in its chain:

Oct  7 09:09:52 zen fetchmail[3770]: Server certificate verification error: 
self-signed certificate in certificate chain
Oct  7 09:09:52 zen fetchmail[3770]: Missing trust anchor certificate: 
/C=US/O=DigiCert Inc/OU=www.digicert.com/CN=DigiCert Global Root CA
Oct  7 09:09:52 zen fetchmail[3770]: This could mean that the root CA's signing 
certificate is not in the trusted CA certificate location, or that c_rehash 
needs to be run on the certificate directory. For details, please see the 
documentation of --sslcertpath and --sslcertfile in the manual page. See 
README.SSL for details.
Oct  7 09:09:52 zen fetchmail[3770]: OpenSSL reported: error:0A000086:SSL 
routines::certificate verify failed
Oct  7 09:09:52 zen fetchmail[3770]: imap.telstra.com: SSL connection failed.

After some head-scratching, I rebuilt fetchmail manually so that it was 
configured to use the openssl1.1.1w in base, rather than the port, and now it 
works again.  I haven't been able to figure out why.

I've tried rebuilding openssl31 with all of the optional (deprecated) pieces 
turned on, on the suspicion that Telstra must be using something dodgy, but 
their certificate does not seem to have changed recently, and does
not look especially dodgy to me: it seems to be signed by the DigiCert Global 
CA.

Looking at the timing of the failure and what changed at that point, I can now 
see that it was not openssl31 as such, but security/ca_root_nss that changed, 
and it did not change by upstream version, just by port version,
due to a change in the way that it is installed: 
https://reviews.freebsd.org/D42045

Does anyone have any thoughts about why this change would have broken this very 
specific thing, and perhaps what I can do about it?

Cheers,

Andrew


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