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




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