On Mon, Dec 09, 2024 at 08:28:55AM +0100, Tobi via Postfix-users wrote:

> since this weekend we have the issue that our postfix seems to be
> unable to verify TLS certs presented by Microsoft. We get
> 
> > Server certificate not verified

Is that preventing mail delivery, or just noise in the logs?

> openssl verify -verbose <(echo | openssl s_client -connect \
>       52.101.73.19:25 -starttls smtp 2>/dev/null)

This does not set the "servername" (SNI extension hostname), so you'll
get the defaUlt certificate, which may not be the "right one".

> > C = US, ST = Washington, L = Redmond, O = Microsoft Corporation, CN = 
> > mail.protection.outlook.com
> > error 20 at 0 depth lookup: unable to get local issuer certificate
> > error /dev/fd/63: verification failed

It would have been more useful if you had posted the certificate chain
instead.  Assuming you were actually tryign to get to something like:
"<some-customer-com.mail.protection.outlook.com>.  Probing that we
see a chain with an EE and issuer certificate:

    $ posttls-finger -cC -lverify -Lsummary 
"nist-gov.mail.protection.outlook.com" 2>/dev/null
        > /tmp/msft-chain.pem

    $ openssl crl2pkcs7 -nocrl -certfile /tmp/msft-chain.pem |
        openssl pkcs7 -print_certs -noout
    subject=C = US, ST = Washington, L = Redmond, O = Microsoft Corporation, CN 
= mail.protection.outlook.com
    issuer=C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-1

    subject=C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-1
    issuer=C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert 
Global Root CA

This verifies against the Fedora 41 system trust store, via the "Digicert
Global Root CA" trust anchor:

    $ openssl verify -show_chain -untrusted /tmp/msft-chain.pem 
/tmp/msft-chain.pem
    /tmp/msft-chain.pem: OK
    Chain:
    depth=0: C = US, ST = Washington, L = Redmond, O = Microsoft Corporation, 
CN = mail.protection.outlook.com (untrusted)
    depth=1: C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-1 
(untrusted)
    depth=2: C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert 
Global Root CA

The certs in question are below my signature.  Unless the problem was
fixed between your post and my reply.  Things seem OK on the MSFT end.

-- 
    Viktor.

$ openssl crl2pkcs7 -nocrl -certfile /tmp/msft-chain.pem |
    openssl pkcs7 -print_certs

subject=C = US, ST = Washington, L = Redmond, O = Microsoft Corporation, CN = 
mail.protection.outlook.com
issuer=C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-1
-----BEGIN CERTIFICATE-----
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1P98W5eP3I2YWc5VxfaEbL9RDA==
-----END CERTIFICATE-----

subject=C = US, O = DigiCert Inc, CN = DigiCert Cloud Services CA-1
issuer=C = US, O = DigiCert Inc, OU = www.digicert.com, CN = DigiCert Global 
Root CA
-----BEGIN CERTIFICATE-----
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-----END CERTIFICATE-----
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