How to fix Office 365 SMTP connection errorsIssue <!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: #000000; } span { font-size: 12pt; font-family: Lato; color: #000000; } h2 { font-size: 24pt; font-family: Lato; color: black; } h3 { font-size: 18pt; font-family: Lato; color: black; } h4 { font-size: 14pt; font-family: Lato; color: black; } a { font-size: 12pt; font-family: Lato; color: #00718F; } a:hover { font-size: 12pt; color: #024F69; } a:target { font-size: 12pt; color: #032D42; } a:visited { font-size: 12pt; color: #00718f; } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } When testing your Office 365 SMTP connection, you may receive a connection error even though authorization tokens exist. The error appears as: "Email sender connection invalid.: Cannot connect to SMTP server: smtp.office365.com, as: <user name>, message: failed to connect." Release<!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: #000000; } span { font-size: 12pt; font-family: Lato; color: #000000; } h2 { font-size: 24pt; font-family: Lato; color: black; } h3 { font-size: 18pt; font-family: Lato; color: black; } h4 { font-size: 14pt; font-family: Lato; color: black; } a { font-size: 12pt; font-family: Lato; color: #00718F; } a:hover { font-size: 12pt; color: #024F69; } a:target { font-size: 12pt; color: #032D42; } a:visited { font-size: 12pt; color: #00718f; } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } All supported releases Cause<!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: #000000; } span { font-size: 12pt; font-family: Lato; color: #000000; } h2 { font-size: 24pt; font-family: Lato; color: black; } h3 { font-size: 18pt; font-family: Lato; color: black; } h4 { font-size: 14pt; font-family: Lato; color: black; } a { font-size: 12pt; font-family: Lato; color: #00718F; } a:hover { font-size: 12pt; color: #024F69; } a:target { font-size: 12pt; color: #032D42; } a:visited { font-size: 12pt; color: #00718f; } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } This issue occurs when you authorize the email account while logged in to the instance using single sign-on (SSO). The browser uses the current SSO session and fetches the token as your logged-in user rather than the SMTP account user. Resolution<!-- /*NS Branding Styles*/ --> .ns-kb-css-body-editor-container { p { font-size: 12pt; font-family: Lato; color: #000000; } span { font-size: 12pt; font-family: Lato; color: #000000; } h2 { font-size: 24pt; font-family: Lato; color: black; } h3 { font-size: 18pt; font-family: Lato; color: black; } h4 { font-size: 14pt; font-family: Lato; color: black; } a { font-size: 12pt; font-family: Lato; color: #00718F; } a:hover { font-size: 12pt; color: #024F69; } a:target { font-size: 12pt; color: #032D42; } a:visited { font-size: 12pt; color: #00718f; } ul { font-size: 12pt; font-family: Lato; } li { font-size: 12pt; font-family: Lato; } img { display: ; max-width: ; width: ; height: ; } } Go to the Manage tokens table and delete the existing refresh and access tokens.Open an incognito browser window and log in to the instance as a local admin (non-SSO user).Open the SMTP account and select Authorize email account access.On the Microsoft authentication page, enter the credentials for the account specified in the User name field of the SMTP account form.Verify this account has permission to fetch tokens. If you are unable to fetch tokens, contact your Microsoft Azure admin for assistance. The test connection succeeds after the tokens are fetched correctly.