The empty EHLO definitely appears to be the issue. I just set up an account on the server to test with using Roundmail and the email never reaches any SMTP server, not just Google’s. The log from exim is below for an email sent to an account on GMX
2020-07-12 14:37:49 1jucAv-0007U9-NT <= [email protected] U=root P=local S=326
2020-07-12 14:37:49 1jucAv-0007U9-NT H=mx01.gmx.net [212.227.17.4]: SMTP error from remote mail server after HELO ;; connection timed out; no servers could be reache: 501 Syntax error in parameters or arguments
2020-07-12 14:37:50 dovecot_login authenticator failed for (User) [46.38.150.153]: 535 Incorrect authentication data ([email protected])
2020-07-12 14:37:50 1jucAv-0007U9-NT H=mx00.gmx.net [212.227.15.10]: SMTP error from remote mail server after HELO ;; connection timed out; no servers could be reache: 501 Syntax error in parameters or arguments
2020-07-12 14:37:50 1jucAv-0007U9-NT ** [email protected] R=dnslookup T=remote_smtp H=mx00.gmx.net [212.227.15.10]: SMTP error from remote mail server after HELO ;; connection timed out; no servers could be reache: 501 Syntax error in parameters or arguments
2020-07-12 14:37:50 1jucAw-0007UI-5G <= <> R=1jucAv-0007U9-NT U=Debian-exim P=local S=1768
2020-07-12 14:37:50 1jucAv-0007U9-NT Completed
2020-07-12 14:37:50 1jucAw-0007UI-5G ** [email protected]: Unrouteable address
2020-07-12 14:37:50 1jucAw-0007UI-5G Frozen (delivery error message)
I then sent an email to mail-tester.com which did get through, and looked at the source
Received: by mail-tester.com (Postfix, from userid 500)
id DD2FBA8746; Sun, 12 Jul 2020 16:26:04 +0200 (CEST)
Authentication-Results: mail-tester.com;
dkim=pass (1024-bit key; unprotected) header.d=XXX.com [email protected] header.b=Ws1KEzae;
dkim-atps=neutral
X-Spam-Checker-Version: SpamAssassin 3.4.2 (2018-09-13) on mail-tester.com
X-Spam-Level:
X-Spam-Status: No/-0.2/5.0
X-Spam-Test-Scores: DKIM_SIGNED=0.1,DKIM_VALID=-0.1,DKIM_VALID_AU=-0.1,
DKIM_VALID_EF=-0.1,SPF_PASS=-0.001,URIBL_BLOCKED=0.001
X-Spam-Last-External-IP: 94.177.XXX.XXX
X-Spam-Last-External-HELO: ???connection?timed?out??no?servers?could?be?reache
X-Spam-Last-External-rDNS: osprey.XXX.com
X-Spam-Date-of-Scan: Sun, 12 Jul 2020 16:26:04 +0200
X-Spam-Report:
* 0.0 URIBL_BLOCKED ADMINISTRATOR NOTICE: The query to URIBL was
* blocked. See
* http://wiki.apache.org/spamassassin/DnsBlocklists#dnsbl-block
* for more information.
* [URIs: XXX.com]
* -0.0 SPF_PASS SPF: sender matches SPF record
* -0.1 DKIM_VALID_EF Message has a valid DKIM or DK signature from
* envelope-from domain
* -0.1 DKIM_VALID_AU Message has a valid DKIM or DK signature from
* author’s domain
* 0.1 DKIM_SIGNED Message has a DKIM or DK signature, not necessarily
* valid
* -0.1 DKIM_VALID Message has at least one valid DKIM or DK signature
Received-SPF: Pass (sender SPF authorized) identity=mailfrom; client-ip=94.177.XXX.XXX; helo=???connection?timed?out??no?servers?could?be?reache; [email protected]; [email protected]
DMARC-Filter: OpenDMARC Filter v1.3.1 mail-tester.com BCD83A0578
Authentication-Results: mail-tester.com; dmarc=pass header.from=XXX.com
Authentication-Results: mail-tester.com;
dkim=pass (1024-bit key; unprotected) header.d=XXX.com [email protected] header.b=Ws1KEzae;
dkim-atps=neutral
Received: from ???connection?timed?out??no?servers?could?be?reache (osprey.XXX.com [94.177.XXX.XXX])
(using TLSv1.2 with cipher ECDHE-RSA-AES256-GCM-SHA384 (256/256 bits))
(No client certificate requested)
by mail-tester.com (Postfix) with ESMTPS id BCD83A0578
for [email protected]; Sun, 12 Jul 2020 16:26:02 +0200 (CEST)
DKIM-Signature: v=1; a=rsa-sha256; q=dns/txt; c=relaxed/relaxed; d=XXX.com;
s=mail; h=Message-ID:Subject:To:From:Date:Content-Transfer-Encoding:
Content-Type:MIME-Version:Sender:Reply-To:Cc:Content-ID:Content-Description:
Resent-Date:Resent-From:Resent-Sender:Resent-To:Resent-Cc:Resent-Message-ID:
In-Reply-To:References:List-Id:List-Help:List-Unsubscribe:List-Subscribe:
List-Post:List-Owner:List-Archive;
bh=r2uoTjB8+0WyaY56vX7vzz3Gp6gjaCFkUrm5xiKb3ZM=; b=Ws1KEzae3IyQuLqpORjVro7hP/
AEJHTpZsT1G2epumRoZezHUAFihQH6YAIeDBNVr9hhecKUyD1ROOOQGEWov1vT4t2wGGNfc0n55Xx
ZXGPCSiOvm6LrJXq5pWfJlB3lRMcS0Ci0iIE9h8lKrVi0dxJP9Qf2WQCsgb0+rlD3HFo=;
Received: from localhost ([127.0.0.1] helo=webmail.XXX.com)
by osprey.XXX.com with esmtp (Exim 4.90_1)
(envelope-from [email protected])
id 1jucvX-0006uD-7l
for [email protected]; Sun, 12 Jul 2020 15:25:59 +0100
MIME-Version: 1.0
Content-Type: text/plain; charset=US-ASCII;
format=flowed
Content-Transfer-Encoding: 7bit
Date: Sun, 12 Jul 2020 15:25:59 +0100
From: [email protected]
To: [email protected]
Subject: Need Headers
Message-ID: [email protected]
X-Sender: [email protected]
User-Agent: Roundcube Webmail
lots of lines containing
“from ???connection?timed?out??no?servers?could?be?reache (osprey.XXX.com [94.177.XXX.XXX])”
which I presume is caused by the lack of server name send by EHLO
So how do I get exim to send the server name with EHLO? Run the update-exim-conf command?
BTW I really appreciate your help on a Sunday. Above and beyond!