On Thu, 28 Nov 2019, Gary Dale via Exim-users wrote:

On 2019-11-28 2:40 a.m., Graeme Fowler via Exim-users wrote:
On 27 Nov 2019, at 20:44, Gary Dale via Exim-users <exim-users@exim.org> wrote:
The test message sent by swaks (in the testing section of the howto) again simply sits in the mailq.
I know this should be a *really* obvious question, but?

What do the logs say for each attempt to deliver the message? Are there any attempts to deliver?

Graeme


Apart from lots of "frozen" messages, I found this and some similar entries:

If you run something like:
   exigrep dental logfile
you will get your log sorted by message, which may make things clearer.

removing the dentaloffice from the domain name, which is how I used to have it before going through the smtps howto, and sending a new message to garyd...@rogers.com, I got this:

[ Reformatted by AA using grepmail. Has long lines. ]
2019-11-28 07:39:45 1iaJ5F-00053v-JS <= root@rossland.dental U=root P=local 
S=791
2019-11-28 07:39:46 1iaJ5F-00053v-JS ** garyd...@rogers.com R=smarthost T=remote_smtp_smarthost H=rossland.dental [104.171.30.152] X=TLS1.2:ECDHE_RSA_AES_256_GCM_SHA384:256 CV=no DN="C=US,postalCode=70002,ST=Louisiana,L=Metaire,street=3500 N. Causeway Blvd Suite 160,O=DNC Holdings Inc.,OU=Support,OU=Hosted by DNC Holdings\, Inc.,OU=PremiumSSL Wildcard,CN=*.dnchosting.com": SMTP error from remote mail server after RCPT TO:<garyd...@rogers.com>: 550-Please turn on SMTP Authentication in your mail client.\n550-cpe0018e7d3134a-cm00195ed9bd6e.cpe.net.cable.rogers.com\n550-(molar.dentaloffice.rossland.dental) [99.248.179.149]:51442 is not\n550 permitted to relay through this server without authentication.
2019-11-28 07:39:46 1iaJ5F-00053v-JS Completed

+++ 1iaJ5G-00053y-5k has not completed +++
2019-11-28 07:39:46 1iaJ5G-00053y-5k <= <> R=1iaJ5F-00053v-JS U=Debian-exim 
P=local S=2748
2019-11-28 07:39:52 1iaJ5G-00053y-5k ** root@rossland.dental R=smarthost 
T=remote_smtp_smarthost H=rossland.dental [104.171.30.152] 
X=TLS1.2:ECDHE_RSA_AES_256_GCM_SHA384:256 CV=no 
DN="C=US,postalCode=70002,ST=Louisiana,L=Metaire,street=3500 N. Causeway Blvd Suite 
160,O=DNC Holdings Inc.,OU=Support,OU=Hosted by DNC Holdings\, Inc.,OU=PremiumSSL 
Wildcard,CN=*.dnchosting.com": SMTP error from remote mail server after end of data: 
550 This message was classified as SPAM and may not be delivered
2019-11-28 07:39:52 1iaJ5G-00053y-5k Frozen (delivery error message)


It looks like the remote smarthost thinks I'm not using TLS.

No. TLS is about encryption. The 1iaJ5F-00053v-JS log says that the remote smarthost thinks you are not *authenticating* (which should, but may or may not be, encrytped).

--
Andrew C. Aitchison                                     Kendal, UK
                        and...@aitchison.me.uk


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