Windows 10: Windows IIS 6.0 SMTP issues relaying email with particular .docX attachment

Hi,We have a very simple email setup. Emails go to a Cloud Spam/Virus checker, then forwarded/relayed to our external SMTP server, which is Windows 2012 R2, running IIS 6.0 SMTP, which then should forward the email to an internal Exchange Server.We have an external participant who cannt get a particular .docx not all .docx just this particular one to send through. The Cloud Spam provier shows its forwarding to our External SMTP Relay but keeps retrying for 72 hours with error. [SMTP Code: 450, Message: 450 4.4.1 [internal] Connection Timed Out].I can see some entires int he IIS SMTP lo

:)

 

SMTP Relay Service

Forgive me if this is the wrong group;

I Have two mainstream financial programs which have a 'send report via email' option, the mail/report is sent directly from the program, and not added as an attachment to MS Outlook.

In early April the send report failed with a generic 'unable to connect to the server'

At this point nothing other that a program and win update had been installed. (Its not possible to revert the program to the earlier version, as the program will not run without updating

Testing the SMTP Relay Service via PowerShell passed just fine

Testing on another PC gives the same result.

Could it be that the two programs use the same 'win api's' and the problem lies there?

The two program makers are unable to offer anything

 

Trouble opening email attached file (docx)

OK. You're viewing the message in Spectrum webmail, right? When you right-click the docx attachment what options are there?

Do you have another email account (Gmail, Yahoo, outlook.com?) that you could forward the message to?

Don

 

Trouble opening email attached file (docx)

I have trouble opening an email that is attached and is enclosed with < >.docx I am using Windows 10 and my email provider is spectrum (time easrner)

* Moved from: Internet Explorer 8/Other/Unknown