On 2025-07-16 12:04, Frank Bures wrote:
On 2025-07-16 11:51, Frank Bures wrote:
Recently I have not been able to send root system mail from my Fedora 42 machine using Sendmail via gmail SMTP relay.  It worked reliably since I built this machine more than a year ago.

Any attempt to send mail either from cron or from CLI returns:

relay=smtp.gmail.com. [142.251.185.109], dsn=4.4.1, stat=Deferred: Connection timed out with smtp.gmail.com.

I generated a new app password for my sendmail and appropriately changed and regenerated /etc/mail/authinfo*.

No cigar.

Does anyone have any idea where to look at?

E-mail from Thunderbird works normally as this message proves.

An additional info:

If smtp.gmail.com resolves to an IPv6 address, relaying works.  If it resolves into IPv4 address, the above error ensues.

I checked my firewall, there is nothing relevant to the smtp.gmail.com IPv4 addresses.

More info:

openssl s_client -connect smtp.gmail.com:587 -6

returns:

C0A22B281F7F0000:error:80000065:system library:BIO_connect:Network is unreachable:crypto/bio/bio_sock2.c:178:calling connect() C0A22B281F7F0000:error:10000067:BIO routines:BIO_connect:connect error:crypto/bio/bio_sock2.c:180:
connect:errno=101

If I force sendmail to use IPv6 address for smtp.gmail.com by adding

 2607:f8b0:4023:1427::6d smtp.gmail.com

to /etc/hosts

and try to send a test mail from CLI, I get

relay=smtp.gmail.com., dsn=4.4.1, stat=Deferred: smtp.gmail.com.: Network is unreachable

I tried to restart the network with no effect.

Any help, please?
Frank

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