Error: "Failed to connect to SMTP server" and "Failed to read TLS record" when sending Test E-mail from Company Maintenance

Solution Properties

Solution ID:

225924450087394

Last Modified Date:

Fri Jul 17 22:49:04 UTC 2026

Taxonomy Path:

Category//Integration//Microsoft 365

Author:

Error: "Failed to connect to SMTP server" and "Failed to read TLS record" when sending Test E-mail from Company Maintenance

Description

Cause

Port blocked by Windows Firewall (or other firewall) resulting in connection time out.

SSL setting selected for SMTP encryption in Sage 100 Company Maintenance - Email - but TLS is required for connection.

Resolution

Select TLS option for SMTP Encryption selection in Sage 100 Company Maintenance - Email.

Allow access thru Windows Firewall for ports specified (Chilkat log mentions 2 ports).

Steps to duplicate