Thanks for the assistance with this issue.  As it turns out I had added *hosts_avoid_tls = *.example.com* to the *remote_smtp **transport *when this domain would only accept clear text connections some time ago.  It had been so long ago that I forgot that the entry had been added.  The exim -bt u...@example.com command revealed the transport which helped me track down the entry.  I commented out the hosts_avoid_tls config and everything is back to normal.  Appreciate the assistance and as always am glad to learn more about Exim.

-Patrick

On 10/18/2022 8:56 AM, Cyborg via Exim-users wrote:
Am 18.10.22 um 14:58 schrieb Patrick Porteous via Exim-users:
I've recently started receiving the following message in my log files when sending to one host:

2022-10-18 07:12:45 H=example.com [###.###.###.199]: a TLS session is required, but an attempt to start TLS failed 2022-10-18 07:12:45 H=example.com [###.###.###.196]: a TLS session is required, but an attempt to start TLS failed 2022-10-18 07:12:45 H=example.com [###.###.###.198]: a TLS session is required, but an attempt to start TLS failed 2022-10-18 07:12:46 H=example.com [###.###.###.197]: a TLS session is required, but an attempt to start TLS failed 2022-10-18 07:12:46 H=example.com [###.###.###.194]: a TLS session is required, but an attempt to start TLS failed 2022-10-18 07:12:46 someu...@example.com R=dnslookup T=remote_smtp defer (-38) H=example.com [###.###.###.194]: a TLS session is required, but an attempt to start TLS failed

The error is causing email addressed to this host to hang in my queue and then fail to be delivered after the time out period. My exim.config is setup with the following options enabled:

Thats exactly what should happen, if you enforce TLS and the other side can't offer it, it fails.

You used:

hosts_require_tls = ....
tls_tempfail_tryclear = false

in your transport . Ergo, it fails, if it's not possible. And I go 10:1 whatever is used in:

tls_require_ciphers = ...

is not been offered in the external mailserver tls offer i.e. because it's a malconfigured exchange server.

To not block your queue, you can do this:

begin retry
# Address or Domain    Error       Retries
# -----------------    -----       -------

*                      refused
*                      quota
*                      tls_required
*                      *           F,2h,15m; G,16h,1h,1.5; F,4d,6h

which instantly sends a delivery-message to the sender, if TLS fails.

best regards,
Marius

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