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
>
>
>
>

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