Because Outlook and Outlook Express both use the same underlying technology, the cause and Select Log on using and enter the username and password that can send using this SMTP server. I get the error message "Establishing an encrypted connection to your outgoing (SMTP) server failed.
Sep 19, 2010 · To connect to Outlook Web App users must authenticate first. The OWA virtual directory can be secured using different authentication settings depending on the network environment. Exchange Server 2010 Outlook Web App Authentication Types. There are four authentication methods available for Exchange Server 2010 OWA. They are: If the problem persists, verify your mail server address and other important settings: My Sent folder is not updated in Webmail when I send messages from my email program. You may need to change your email program's server settings to IMAP for the Sent folder to sync properly. Before you start, remove your current email profile.