SMTP OAuth email account connection failed Issue <!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } span { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } h2 { font-size: 24pt; font-family: Lato; color: var(--now-color--text-primary, black); } h3 { font-size: 18pt; font-family: Lato; color: var(--now-color--text-primary, black); } h4 { font-size: 14pt; font-family: Lato; color: var(--now-color--text-primary, black); } a { font-size: 12pt; font-family: Lato; color: var(--now-color--link-primary, #00718F); } a:hover { font-size: 12pt; color: var(--now-color--link-primary, #024F69); } a:target { font-size: 12pt; color: var(--now-color--link-primary, #032D42); } a:visited { font-size: 12pt; color: var(--now-color--link-primary, #00718f); } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } The issue occurs when configuring the email account with SMTP + OAuth, resulting in a connection error to the SMTP server (outlook.office365.com) with the message: 'Could not connect to SMTP host: outlook.office365.com, port: 587'. The error includes a nested exception: 'javax.net.ssl.SSLException: Unsupported or unrecognized SSL message'. The user has MFA enabled but no mailbox configured, and the issue persists despite attempting configurations from referenced articles. Release<!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } span { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } h2 { font-size: 24pt; font-family: Lato; color: var(--now-color--text-primary, black); } h3 { font-size: 18pt; font-family: Lato; color: var(--now-color--text-primary, black); } h4 { font-size: 14pt; font-family: Lato; color: var(--now-color--text-primary, black); } a { font-size: 12pt; font-family: Lato; color: var(--now-color--link-primary, #00718F); } a:hover { font-size: 12pt; color: var(--now-color--link-primary, #024F69); } a:target { font-size: 12pt; color: var(--now-color--link-primary, #032D42); } a:visited { font-size: 12pt; color: var(--now-color--link-primary, #00718f); } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } All Cause<!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } span { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } h2 { font-size: 24pt; font-family: Lato; color: var(--now-color--text-primary, black); } h3 { font-size: 18pt; font-family: Lato; color: var(--now-color--text-primary, black); } h4 { font-size: 14pt; font-family: Lato; color: var(--now-color--text-primary, black); } a { font-size: 12pt; font-family: Lato; color: var(--now-color--link-primary, #00718F); } a:hover { font-size: 12pt; color: var(--now-color--link-primary, #024F69); } a:target { font-size: 12pt; color: var(--now-color--link-primary, #032D42); } a:visited { font-size: 12pt; color: var(--now-color--link-primary, #00718f); } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } The connection failure was caused by an SSL/TLS configuration mismatch. Switching to STARTLS resolved the 'Unsupported or unrecognized SSL message' error, as outlined in the Microsoft reference link: https://support.microsoft.com/en-us/office/pop-imap-and-smtp-settings-for-outlook-com-d088b986-291d-42b8-9564-9c414e2aa040. Resolution<!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } span { font-size: 12pt; font-family: Lato; color: var(--now-color--text-primary, #000000); } h2 { font-size: 24pt; font-family: Lato; color: var(--now-color--text-primary, black); } h3 { font-size: 18pt; font-family: Lato; color: var(--now-color--text-primary, black); } h4 { font-size: 14pt; font-family: Lato; color: var(--now-color--text-primary, black); } a { font-size: 12pt; font-family: Lato; color: var(--now-color--link-primary, #00718F); } a:hover { font-size: 12pt; color: var(--now-color--link-primary, #024F69); } a:target { font-size: 12pt; color: var(--now-color--link-primary, #032D42); } a:visited { font-size: 12pt; color: var(--now-color--link-primary, #00718f); } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } 1. Update the email account connection security to STARTLS instead of SSL/TLS. 2. Verify the SMTP server settings (host: outlook.office365.com, port: 587) and ensure they align with Microsoft's recommended configurations for Office 365.3. Confirm the user account used for SMTP authentication has the required mailbox license and permissions and test the connection.