Tatay, It doesn't look like you missed something. did you try telnet from the MS to smtp.office365.com, port: 587? and send a simple test mail (lookup the exact protocol which involves the commands helo, mail rcpt and data).
On Fri, Jul 4, 2025 at 5:34 PM Chi vediamo <tatay...@gmail.com> wrote: > > Hello Community > > We just upgraded to Cloudstack 4.20.1 > > > we just found an issue with the email sender not working from cloudstack > specifically: > > > there are no issues with the firewalls: > > telnet smtp.office365.com 587 > Trying 52.96.36.130... > Connected to mira-ooc.tm-4.office.com. > Escape character is '^]'. > 220 BN8PR03CA0003.outlook.office365.com Microsoft ESMTP MAIL Service ready at > Fri, 4 Jul 2025 15:01:26 +0000 [08DDBA8812A96531] > quit > 221 2.0.0 Service closing transmission channel > Connection closed by foreign host. > > > 2025-07-04 15:01:57,332 ERROR [o.a.c.u.m.SMTPMailSender] > (qtp1404565079-345:[ctx-80979faa]) (logid:0e1f5dee) Unable to send mail > [Password Reset Request] to the recipcients > [[{"mailAddress":"ta...@mymail.com"}]]. javax.mail.MessagingException: Could > not connect to SMTP host: smtp.office365.com, port: 587; > at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1961) > at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:654) > at javax.mail.Service.connect(Service.java:295) > at javax.mail.Service.connect(Service.java:176) > at javax.mail.Service.connect(Service.java:125) > at > org.apache.cloudstack.utils.mailing.SMTPMailSender.sendMail(SMTPMailSender.java:175) > at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:527) > at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:332) > at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:234) > at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1927) > 2025-07-04 15:01:57,336 DEBUG [o.a.c.u.UserPasswordResetManagerImpl] > (qtp1404565079-345:[ctx-80979faa]) (logid:0e1f5dee) User password reset email > for user UserAccount {"accountName":"domain1","id":5,"username":"tatay"}. > account id: 5 domain id: 3 sent to o...@321communications.com with token > expiry at 2025-07-04T15:31:57.243+0000 > 2025-07-04 15:08:28,663 WARN [c.c.c.ConfigurationManagerImpl] > (qtp1404565079-447:[ctx-7d09367d, ctx-af7db5cb]) (logid:37392271) > Configuration user.password.reset.email.sender no found. Perhaps moved to > ConfigDepot > 2025-07-04 15:08:28,675 WARN [c.c.c.ConfigurationManagerImpl] > (qtp1404565079-447:[ctx-7d09367d, ctx-af7db5cb]) (logid:37392271) > Configuration user.password.reset.mail.template no found. Perhaps moved to > ConfigDepot > > > I have the > User password reset smtp useAuth enabled > User password reset enabled enabled > user.password.reset.email.sender Is filled correctly > user.password.reset.smtp.username is the same email sender > Password was confirmed its working. > user.password.reset.email.Template > Hello {{username}}! > You have requested to reset your password. Please click the following link to > reset your password: > http://{{{resetLink}}} > If you did not request a password reset, please ignore this email. > > Regards, > The Tatay Team > > Is there something else that needs to be done ? > > Please help us > > Thank you > > Tatay > > > >