On 9/05/2025 9:08 am, Dan Mahoney wrote:
There’s only one certificate in your chain, you need to send the intermediate 
cert as well.

The cert you’re signing with isn’t trusted by browsers.

Certificate chain
  0 s:CN = rollcage13.aboc.net.au
    i:C = US, O = Let's Encrypt, CN = R10

Arguably, this is even worse than being self-signed.

Compared with my sendmail (stop laughing) server:

Not laughing at all, many -many- years ago I did a lot of work with Sendmail (before the m4 stuff, that long ago!) - very valuable lesson was learned; Don't leave your email address in a sendmail config file as a "I did it this way" note, or for -decades- you will get "help!" emails! If you did enough Sendmail stuff, perl's line noise didn't seem so bad.

But - I don't really understand what you're saying here. I think I need to RTFM on this again.



Certificate chain
  0 s:CN = prime.gushi.org
    i:C = US, O = Let's Encrypt, CN = E5
  1 s:C = US, O = Let's Encrypt, CN = E5
    i:C = US, O = Internet Security Research Group, CN = ISRG Root X1

I believe if you just point postfix at your cert chain, it will do the right 
thing as long as the certs are in the correct order.

-Dan

On May 8, 2025, at 15:34, Carl Brewer via Postfix-users 
<postfix-users@postfix.org> wrote:


Hi,

I've been running postscript on a FreeBSD 13.x server with Letsencrypt running 
as a cron job to keep SSL certs up to date automagically :


in main.cf :


smtpd_tls_security_level = may
smtpd_tls_cert_file = 
/usr/local/etc/letsencrypt/live/rollcage13.aboc.net.au/cert.pem
smtpd_tls_key_file = 
/usr/local/etc/letsencrypt/live/rollcage13.aboc.net.au/privkey.pem

As best I can tell, this has worked for a number of years without issue.

I've noticed this error of late :

May  9 08:15:44 rollcage13 postfix/smtpd[88039]: warning: TLS library problem: 
error:14094412:SSL routines:ssl3_read_bytes:sslv3 alert bad 
certificate:/usr/src/crypto/openssl/ssl/record/rec_layer_s3.c:1621:SSL alert 
number 42:

And some mail isn't making it through - I guess it's possible that the above 
config never worked and I didn't notice, but I suspect this is a new thing.


When I check the SSL config using the ssl-tools.net checks, I'm seeing "Unknown 
Authority" as the error, but also seeing a cert that looks ok :

 From : https://ssl-tools.net/mailservers/rollcage13.aboc.net.au

Certificates
First seen at: a day ago
CN=rollcage13.aboc.net.au
Certificate chain

    rollcage13.aboc.net.au
        40 days remaining
        2048 bit
        sha256WithRSAEncryption
        Unknown Authority
        R10

Subject
Common Name (CN)

        rollcage13.aboc.net.au

Alternative Names

        rollcage13.aboc.net.au


Apart from the "Unknown Authority" it looks fine.

Permissions in the cert directory are all ok, or at least, all the same, so if 
it can read one bit it can read them all :

rollcage13:/usr/local/etc/letsencrypt/live/rollcage13.aboc.net.au # ls -la
total 16
drwxr-xr-x  2 root  wheel        7 Mar 18 05:08 .
drwxr-s---  3 root  readcirts    4 Sep 19  2021 ..
-rw-r--r--  1 root  wheel      692 Sep 19  2021 README
lrwxr-xr-x  1 root  wheel       47 Mar 18 05:08 cert.pem -> 
../../archive/rollcage13.aboc.net.au/cert23.pem
lrwxr-xr-x  1 root  wheel       48 Mar 18 05:08 chain.pem -> 
../../archive/rollcage13.aboc.net.au/chain23.pem
lrwxr-xr-x  1 root  wheel       52 Mar 18 05:08 fullchain.pem -> 
../../archive/rollcage13.aboc.net.au/fullchain23.pem
lrwxr-xr-x  1 root  wheel       50 Mar 18 05:08 privkey.pem -> 
../../archive/rollcage13.aboc.net.au/privkey23.pem



any suggestions, I'm no wizz when it comes to SSL setups, and am pretty rusty 
here.




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