Problem setting up account in outlook windows (SMTP) Server only on Windows
Problem reported by Marlon Toro - 5/22/2024 at 6:31 AM
Regards Community,  i'm new using smartermail and i'm having problem adding some accounts to outlook on windows. the message is "We couldn't connect to the outgoing (SMTP) server. Please check the outgoing (SMTP) server settings and try again"
This only happens when configuring my users accounts on Windows, who use Mac are configured correctly.
Maybe somebody can guide me to solve this error. Thank you for the support.

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Tan Replied
Are you the end user or sysadmin of smartermail?
Kyle Kerst Replied
Employee Post
The most common cause of this type of error is having the SSL/TLS settings, port number, or hostname settings incorrect. It's also possible your computer doesn't support the right versions of TLS and may be rejecting connectivity because of that. Do other email clients fail with the same settings?
Kyle Kerst System/Network Administrator SmarterTools Inc. (877) 357-6278 www.smartertools.com
Douglas Foster Replied
In Outlook, you need to check the box for "my outgoing server requires authentication", with the sub-option to "use the same credentials as for incoming".  This is my most common mistake.

Ports:   If you use SSL/TLS encryption option in Outlook, the matching SmarterMail port needs to be configured for "SSL", which means mandatory encryption.   This is best.  

If you use the STARTTLS option in Outlook, the matching SmarterMail port needs to be configured for "TLS", which means optional encryption.

Marlon Toro Replied
Thank you everyone for your answer and support,  I still can't add the account to outlook, my windows server is fully updated, Smartermail is well configured, i have the same configuration for all users and the problem only occurs with email users who use OS Windows Outlook, all OS Macos Outlook users work without problem. 
In Windows, I updated the Framework to version 4.8 and reviewed the firewall configuration. I also tried to configure different versions of Outlook and I still have not been able to configure the email for Windows users. I dont know what more do. 

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