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Hi Terry,

definitelly it is not expected...

could you check please the value stored in setting:  /Globalsettings/System/MailServer/DoNotUsePickup

In Settings -> System -> Global settings

Best regards,
Vladimir

Here is the setting:

situation not become clear! Lets look error details, it should be a log file:

Monitoring -> Logs -> EmailHandler -> 2020_07.log

or

Files -> System -> Log -> EmailHandler -> 2020_07.log

Hi Vladimir,

The log snippet above is from that log. For every email sent, it first logs the Pickup Directory failure, then the sent successfully using SMTP protocol part of the log. Here are some additional log lines:

[7/31/2020 9:33:40 AM]: Send using Pickup Directory Service failed. Trying SMTP protocol.
[7/31/2020 9:33:40 AM]: Mail sent successfully using SMTP protocol. Recipients: 'D*r@n*c.com' - CC Recipients: - BCC Recipients:

[7/31/2020 9:45:16 AM]: Send using Pickup Directory Service failed. Trying SMTP protocol.
[7/31/2020 9:45:16 AM]: Mail sent successfully using SMTP protocol. Recipients: 'e*5@gmail.com' - CC Recipients: - BCC Recipients:

[7/31/2020 9:45:16 AM]: Send using Pickup Directory Service failed. Trying SMTP protocol.
[7/31/2020 9:45:17 AM]: Mail sent successfully using SMTP protocol. Recipients: 'r*s@gmail.com' - CC Recipients: - BCC Recipients:

[7/31/2020 9:45:17 AM]: Send using Pickup Directory Service failed. Trying SMTP protocol.
[7/31/2020 9:45:17 AM]: Mail sent successfully using SMTP protocol. Recipients: 'y*c@gmail.com' - CC Recipients: - BCC Recipients:

[7/31/2020 9:51:06 AM]: Send using Pickup Directory Service failed. Trying SMTP protocol.
[7/31/2020 9:51:07 AM]: Mail sent successfully using SMTP protocol. Recipients: 'a*t@gmail.com' - CC Recipients: - BCC Recipients:

[7/31/2020 10:11:29 AM]: Send using Pickup Directory Service failed. Trying SMTP protocol.
[7/31/2020 10:11:30 AM]: Mail sent successfully using SMTP protocol. Recipients: 'c*3@gmail.com' - CC Recipients: - BCC Recipients:

Hi Terri,
I suppose your version DW below 9.6...  
We improved a logging in DW9.6 - it now has a detail log for exceptions.

Could you try to install a Dynamicweb.Mailing package at least 3.0.1 (or newer)?

The solution is running 3.0.8. 

Hi Terry,
well, this sounds very strange for me - because such text in error log was only in Dynamicweb.Mailing versions below 3.0.1. Also I indeed was able to reproduce such weird log in v2.2.3 but not in 3.08

Fortunately, there is a simple check - if you really has Dynamicweb.Mailing 3.0.8 - all detailed error logs should be shown in Monitoring area -> Event viever. Try to filter events here by category "Application/SMTP"

Hi Vladimir,

Packages shows something different than solution settings. I'll try the dll update and see if that resolves the logging. Thanks for your help.