If I use SMTPS, I get a different error:
2020-08-27 18:42:10,370 ERROR [Thread-6531] GoSmtpMailSender:56 - Sending 
failed for email [Go Email Notification] to [gocd@***.**]
javax.mail.AuthenticationFailedException: 451 4.3.2 Internal server error

at 
com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:965)
at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:876)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:780)
at javax.mail.Service.connect(Service.java:388)
at 
com.thoughtworks.go.config.GoSmtpMailSender.send(GoSmtpMailSender.java:51)
at 
com.thoughtworks.go.config.BackgroundMailSender.lambda$send$0(BackgroundMailSender.java:48)
at java.base/java.lang.Thread.run(Unknown Source)


On Thursday, 27 August 2020 at 17:46:48 UTC+2 [email protected] wrote:

> From the logs looks like the GoCD server is not able to connect to the 
> SMTP server that's configured. May be check the firewall settings? 
>
> The relevant section is the SocketTimeoutException from the logs. 
>
> On Thu, 27 Aug, 2020, 20:35 Jeroen Oortwijn, <[email protected]> 
> wrote:
>
>> Hello,
>>
>> I'm trying to set up the Email server on the GoCD server (
>> http://localhost:8153/go/admin/config/server#!email-server), but I can't 
>> get it to work.
>>
>> When I fill in all the details and click the Send Test Email button, 
>> after a while the following message appears:
>> There was an unknown error performing the operation. Possible reason (Not 
>> Acceptable)
>>
>> In the server log (go-server.log) appears the following:
>> 2020-08-27 16:51:18,460 ERROR [Thread-5048] GoSmtpMailSender:56 - Sending 
>> failed for email [Go Email Notification] to [gocd@***.**]
>> javax.mail.MessagingException: Exception reading response
>> at 
>> com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2460)
>> at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2187)
>> at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:740)
>> at javax.mail.Service.connect(Service.java:366)
>> at 
>> com.thoughtworks.go.config.GoSmtpMailSender.send(GoSmtpMailSender.java:51)
>> at 
>> com.thoughtworks.go.config.BackgroundMailSender.lambda$send$0(BackgroundMailSender.java:48)
>> at java.base/java.lang.Thread.run(Unknown Source)
>> Caused by: java.net.SocketTimeoutException: Read timed out
>> at java.base/sun.nio.ch.NioSocketImpl.timedRead(Unknown Source)
>> at java.base/sun.nio.ch.NioSocketImpl.implRead(Unknown Source)
>> at java.base/sun.nio.ch.NioSocketImpl.read(Unknown Source)
>> at java.base/sun.nio.ch.NioSocketImpl$1.read(Unknown Source)
>> at java.base/java.net.Socket$SocketInputStream.read(Unknown Source)
>> at com.sun.mail.util.TraceInputStream.read(TraceInputStream.java:126)
>> at java.base/java.io.BufferedInputStream.fill(Unknown Source)
>> at java.base/java.io.BufferedInputStream.read(Unknown Source)
>> at com.sun.mail.util.LineInputStream.readLine(LineInputStream.java:106)
>> at 
>> com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2440)
>> ... 6 common frames omitted
>>
>> Above messages aren't really helpful in debugging the problem, so I want 
>> to view the SMTP log, but couldn't find it.
>> Is there a way to enable the SMTP log and where is it then located?
>>
>> Kind regards,
>>
>> Jeroen Oortwijn
>>
>

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