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:

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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