How to fix IMAP connection issues with Outlook 365 inbound email accountsIssue <!-- /*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 you test IMAP email accounts for Outlook 365 servers using the STARTTLS protocol, you may see the error message: "Connection failed: * BYE Jakarta Mail Exception: java.net.SocketTimeoutException: Read timed out" 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: ; } } Microsoft has made changes that prevent the STARTTLS protocol from working. This affects all email accounts that use IMAP and connect to outlook.outlook365.com servers. 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 All > System Mailboxes > Administration > Email Accounts.Open the email account record that is failing with the error.Make these two changes: For the Security Connection, select SSL/TLS from the drop-down menu.Update the port to 993. Go to All > System Definition > X509 Certificate.Check for expired certificates. If you find any, remove or deactivate them.Return to the email account, and under Related links, select Test Connection.