Re: Trouble with SMTP, TLS and dovecot.org.

2023-09-07 Thread Aki Tuomi via dovecot


> On 07/09/2023 20:46 EEST Ralph Seichter via dovecot  
> wrote:
> 
>  
> * Aki Tuomi via dovecot:
> 
> > I updated the settings a bit on the server as well. Maybe it works
> > better now?
> 
> Yes, it does indeed:
> 
>   Sep  7 19:33:23 ra postfix/smtp[14429]: Trusted TLS connection established 
> to talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25: TLSv1.3 with 
> cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange ECDHE (prime256v1) 
> server-signature RSA-PSS (2048 bits) server-digest SHA256 client-signature 
> ECDSA (secp384r1) client-digest SHA384
>   Sep  7 19:33:24 ra postfix/smtp[14429]: 1989FBE002A: 
> to=, 
> relay=talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25, delay=4.3, 
> delays=0.01/0.01/3.6/0.73, dsn=2.0.0, status=sent (250 2.0.0 Ok: queued as 
> D22D55DEF4)
> 
> Thank you, Aki. Would you be willing to share what was changed in your
> server's settings and/or certificates? I am still wondering what exactly
> caused the issue. By the way, I have reverted all TLS-related changes
> previously used for testing on my end, returning to Postfix's defaults.
> 
> -Ralph

Mostly just disabled older TLS stuff and in particular enabled TLSv1.3.

Aki
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Re: Trouble with SMTP, TLS and dovecot.org.

2023-09-07 Thread Ralph Seichter via dovecot
* Aki Tuomi via dovecot:

> I updated the settings a bit on the server as well. Maybe it works
> better now?

Yes, it does indeed:

  Sep  7 19:33:23 ra postfix/smtp[14429]: Trusted TLS connection established to 
talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25: TLSv1.3 with 
cipher TLS_AES_256_GCM_SHA384 (256/256 bits) key-exchange ECDHE (prime256v1) 
server-signature RSA-PSS (2048 bits) server-digest SHA256 client-signature 
ECDSA (secp384r1) client-digest SHA384
  Sep  7 19:33:24 ra postfix/smtp[14429]: 1989FBE002A: 
to=, 
relay=talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25, delay=4.3, 
delays=0.01/0.01/3.6/0.73, dsn=2.0.0, status=sent (250 2.0.0 Ok: queued as 
D22D55DEF4)

Thank you, Aki. Would you be willing to share what was changed in your
server's settings and/or certificates? I am still wondering what exactly
caused the issue. By the way, I have reverted all TLS-related changes
previously used for testing on my end, returning to Postfix's defaults.

-Ralph
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Re: Trouble with SMTP, TLS and dovecot.org.

2023-09-07 Thread Aki Tuomi via dovecot


> On 07/09/2023 03:49 EEST Ralph Seichter via dovecot  
> wrote:
> 
>  
> * Marc Schiffbauer via dovecot:
> 
> > Wild guess: you need to explicitely allow for example DEFAULT@SECLEVEL=0 
> > ciphersuite in postfix to make *your* openssl accept this remote sslv3 
> > connection
> 
> Thanks, Marc. I had thought about this, and have tried various Postfix
> parameters related to TLS ciphers and protocols. So far, no dice. In the
> meantime, I also ran tests using Swaks, and this resulted in a possible
> different route of investigation: Postfix uses a certificate issued by
> Let's Encrypt (secp384r1) for both in- and outbound connections with
> STARTTLS. If I use the same certificate with Swaks, I see the same error
> as I do with Postfix. If I use Swaks *without* specifying a local TLS
> certificate, the STARTTLS handshake works:
> 
>   === Trying talvi.dovecot.org:25...
>   === Connected to talvi.dovecot.org.
>   <-  220 talvi.dovecot.org ESMTP Postfix (Debian/GNU)
>-> EHLO ra.horus-it.com
>   <-  250-talvi.dovecot.org
>   <-  250-PIPELINING
>   <-  250-SIZE 104857600
>   <-  250-ETRN
>   <-  250-STARTTLS
>   <-  250-ENHANCEDSTATUSCODES
>   <-  250-8BITMIME
>   <-  250-DSN
>   <-  250 CHUNKING
>-> STARTTLS
>   <-  220 2.0.0 Ready to start TLS
>   === TLS started with cipher TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256
>   === TLS no local certificate set
>   === TLS peer DN="/CN=talvi.dovecot.org"
> 
> Looks the combination of certificate ciphers and OpenSSL library
> versions on my end and on the talvi.dovecot.org end is causing some
> bother. The original error message points to a protocol issue, not a
> cipher problem, and how SSLv3 gets into the mix is anybody's guess.
> Perhaps I'll see clearer after some much needed sleep.
> 
> -Ralph

I updated the settings a bit on the server as well. Maybe it works better now?

Aki
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Re: Trouble with SMTP, TLS and dovecot.org.

2023-09-06 Thread Ralph Seichter via dovecot
* Marc Schiffbauer via dovecot:

> Wild guess: you need to explicitely allow for example DEFAULT@SECLEVEL=0 
> ciphersuite in postfix to make *your* openssl accept this remote sslv3 
> connection

Thanks, Marc. I had thought about this, and have tried various Postfix
parameters related to TLS ciphers and protocols. So far, no dice. In the
meantime, I also ran tests using Swaks, and this resulted in a possible
different route of investigation: Postfix uses a certificate issued by
Let's Encrypt (secp384r1) for both in- and outbound connections with
STARTTLS. If I use the same certificate with Swaks, I see the same error
as I do with Postfix. If I use Swaks *without* specifying a local TLS
certificate, the STARTTLS handshake works:

  === Trying talvi.dovecot.org:25...
  === Connected to talvi.dovecot.org.
  <-  220 talvi.dovecot.org ESMTP Postfix (Debian/GNU)
   -> EHLO ra.horus-it.com
  <-  250-talvi.dovecot.org
  <-  250-PIPELINING
  <-  250-SIZE 104857600
  <-  250-ETRN
  <-  250-STARTTLS
  <-  250-ENHANCEDSTATUSCODES
  <-  250-8BITMIME
  <-  250-DSN
  <-  250 CHUNKING
   -> STARTTLS
  <-  220 2.0.0 Ready to start TLS
  === TLS started with cipher TLSv1.2:ECDHE-RSA-AES256-GCM-SHA384:256
  === TLS no local certificate set
  === TLS peer DN="/CN=talvi.dovecot.org"

Looks the combination of certificate ciphers and OpenSSL library
versions on my end and on the talvi.dovecot.org end is causing some
bother. The original error message points to a protocol issue, not a
cipher problem, and how SSLv3 gets into the mix is anybody's guess.
Perhaps I'll see clearer after some much needed sleep.

-Ralph
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Re: Trouble with SMTP, TLS and dovecot.org.

2023-09-06 Thread Marc Schiffbauer via dovecot
* Ralph Seichter via dovecot schrieb am 06.09.23 um 22:43 Uhr:
> Hello,
> 
> I cannot seem to send STARTTLS protected mail to talvi.dovecot.org, and
> I was wondering if anybody else sees similar problems:
> 
> Sep  6 22:29:10 ra postfix/smtp[15748]: SSL_connect error to 
> talvi.dovecot.org[94.237.105.223]:25: -1
> Sep  6 22:29:10 ra postfix/smtp[15748]: warning: TLS library problem: 
> error:0A000417:SSL routines::sslv3 alert illegal 
> parameter:../openssl-3.0.9/ssl/record/rec_layer_s3.c:1586:SSL alert number 47:
> Sep  6 22:29:10 ra postfix/smtp[15748]: 1AAE4BE0031: Cannot start TLS: 
> handshake failure
> Sep  6 22:29:10 ra postfix/smtp[15748]: SSL_connect error to 
> talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25: -1
> Sep  6 22:29:10 ra postfix/smtp[15748]: warning: TLS library problem: 
> error:0A000417:SSL routines::sslv3 alert illegal 
> parameter:../openssl-3.0.9/ssl/record/rec_layer_s3.c:1586:SSL alert number 47:
> Sep  6 22:29:10 ra postfix/smtp[15748]: 1AAE4BE0031: 
> to=, 
> relay=talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25, delay=1.6, 
> delays=0.02/0.01/1.6/0, dsn=4.7.5, status=deferred (Cannot start TLS: 
> handshake failure)
> Sep  6 22:30:05 ra postfix/smtpd[15616]: timeout after END-OF-MESSAGE from 
> localhost[127.0.0.1]
> Sep  6 22:30:05 ra postfix/smtpd[15616]: disconnect from localhost[127.0.0.1] 
> ehlo=1 xforward=1 mail=1 rcpt=1 data=1 commands=5
> 
> The originating server uses Postfix 3.8.2 and OpenSSL library
> 3.0.9. To be able to send messages to dovecot.org at all, I had to use
> Postfix's "smtp_tls_policy_maps" setting to explicitly disable TLS for
> this destination domain.

Your openssl-3.0.9 (I suppose gentoo stable?) will not allow TLSv1 or 
sslv3 connections bei default anymore.

Wild guess: you need to explicitely allow for example DEFAULT@SECLEVEL=0 
ciphersuite in postfix to make *your* openssl accept this remote sslv3 
connection

Cheers
-Marc

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Trouble with SMTP, TLS and dovecot.org.

2023-09-06 Thread Ralph Seichter via dovecot
Hello,

I cannot seem to send STARTTLS protected mail to talvi.dovecot.org, and
I was wondering if anybody else sees similar problems:

Sep  6 22:29:10 ra postfix/smtp[15748]: SSL_connect error to 
talvi.dovecot.org[94.237.105.223]:25: -1
Sep  6 22:29:10 ra postfix/smtp[15748]: warning: TLS library problem: 
error:0A000417:SSL routines::sslv3 alert illegal 
parameter:../openssl-3.0.9/ssl/record/rec_layer_s3.c:1586:SSL alert number 47:
Sep  6 22:29:10 ra postfix/smtp[15748]: 1AAE4BE0031: Cannot start TLS: 
handshake failure
Sep  6 22:29:10 ra postfix/smtp[15748]: SSL_connect error to 
talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25: -1
Sep  6 22:29:10 ra postfix/smtp[15748]: warning: TLS library problem: 
error:0A000417:SSL routines::sslv3 alert illegal 
parameter:../openssl-3.0.9/ssl/record/rec_layer_s3.c:1586:SSL alert number 47:
Sep  6 22:29:10 ra postfix/smtp[15748]: 1AAE4BE0031: to=, 
relay=talvi.dovecot.org[2a04:3545:1000:720:acc1:5bff:fe5e:459]:25, delay=1.6, 
delays=0.02/0.01/1.6/0, dsn=4.7.5, status=deferred (Cannot start TLS: handshake 
failure)
Sep  6 22:30:05 ra postfix/smtpd[15616]: timeout after END-OF-MESSAGE from 
localhost[127.0.0.1]
Sep  6 22:30:05 ra postfix/smtpd[15616]: disconnect from localhost[127.0.0.1] 
ehlo=1 xforward=1 mail=1 rcpt=1 data=1 commands=5

The originating server uses Postfix 3.8.2 and OpenSSL library
3.0.9. To be able to send messages to dovecot.org at all, I had to use
Postfix's "smtp_tls_policy_maps" setting to explicitly disable TLS for
this destination domain.

-Ralph
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