Hello Dahn,

We used the msmtp ubuntu to test from the Management server, and works with no 
problem.

You mean the Java mail client ?

Whould we disable this functionality for now ? As seems is a bug.

Thank you


Tata Y.





> On Jul 7, 2025, at 2:44 AM, Daan Hoogland <d...@apache.org> wrote:
> 
> ok, I didn't realise that, yes, it might well be so. But this seems to
> be an issue with the mail client, not with reset password. The same
> issue would occur for alert mails and any other mails the system would
> send. Do you use any of those as well?
> 
> On Sun, Jul 6, 2025 at 4:11 PM Chi vediamo <tatay...@gmail.com> wrote:
>> 
>> 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
>>>> 
>>>> 
>>>> 
>>>> 
>> 

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