On Wed, Jul 08, 2020 at 09:03:52AM +0200, Rainer Ruprechtsberger wrote:

> this is not my only problem with TLS verification - and I'm struggling
> to debug this:
> 
> *mail.mail.protection.outlook.com cannot be verified by postfix:
> posttls-finger: certificate verification failed for
> blahblahommited.mail.protection.outlook.com[104.47.14.36]:25: untrusted
> issuer /C=BE/O=GlobalSign nv-sa/OU=Root CA/CN=GlobalSign Root CA
> 
> But I do trust this CA:
> smtp_tls_CAfile = /etc/ssl/certs/ca-certificates.crt

The posttls-finger(1) utility does not use the "smtp_tls_CAfile"
parameter, which is specific to the smtp(8) delivery agent.  Its
CAfile has to be set explicitly via the "-F" command-line option.

> Which I did verify by:
> openssl s_client -CAfile
> /var/spool/postfix/etc/ssl/certs/ca-certificates.crt -connect
> blahblahommited.mail.protection.outlook.com:25 --starttls smtp

    /var/spool/postfix/etc/ssl/certs/ca-certificates.crt !=
    /etc/ssl/certs/ca-certificates.crt

Why are you running s_client with that particular choice of filename?
Along with any private keys, DH parameters, ...  the CAfile is loaded by
Postfix *before* it drops privileges and enters the chroot jail.

-- 
    Viktor.

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