Hello Dahn,
Several tests same error, does the Password reset supports TLS, seems that is
the issue. Also Microsoft is forcing to move to TLS1.3
I see TLS configuration options up to TLS 1.2 for Quota and For alerts, but
none for Password Reset.
openssl s_client -starttls smtp -connect smtp.office365.com:587 -tls1_2
No client certificate CA names sent
Client Certificate Types: RSA sign, DSA sign, ECDSA sign
Requested Signature Algorithms:
RSA-PSS+SHA256:RSA-PSS+SHA384:RSA-PSS+SHA512:RSA+SHA256:RSA+SHA384:RSA+SHA1:ECDSA+SHA256:ECDSA+SHA384:ECDSA+SHA1:DSA+SHA1:RSA+SHA512:ECDSA+SHA512
Shared Requested Signature Algorithms:
RSA-PSS+SHA256:RSA-PSS+SHA384:RSA-PSS+SHA512:RSA+SHA256:RSA+SHA384:ECDSA+SHA256:ECDSA+SHA384:RSA+SHA512:ECDSA+SHA512
Peer signing digest: SHA256
Peer signature type: RSA-PSS
Server Temp Key: ECDH, secp384r1, 384 bits
Thank you
Tata Y.
> On Jul 5, 2025, at 10:01 AM, Daan Hoogland <d...@apache.org> wrote:
>
> 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
>>
>>
>>
>>
