yuuvis® RAD Q&A

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by (120 points)

We are trying to configure email for the Core Service on a server hosted in AWS EC2.

We have the AWS SMPT sever setup with the below settings.

email-smtp.us-east-1.amazonaws.com
Port - have tried 25 also 587
Security - Have tried with StartTLS - accepted by AWS SMTP also 'None'

When attempting to send test emails getting the below exception in the core-service log

2023-07-17 19:40:11,166 ERROR [com.os.ecm.mail.MailManagerImpl] (default task-2) MessageError: Unable to send message. [jakarta.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587;
nested exception is:

javax.net.ssl.SSLException: Unsupported or unrecognized SSL message]

Have tried this same setup using GMAIL SMTP on port 587 and having the same error.

I have verified connection to the SMTP server can be established using the below powershell command and result

PS C:\Windows\system32> Test-NetConnection -Port 587 -ComputerName email-smtp.us-east-1.amazonaws.com

ComputerName : email-smtp.us-east-1.amazonaws.com
RemoteAddress : 52.86.209.58
RemotePort : 587
InterfaceAlias : Ethernet 3
SourceAddress : 172.17.153.9
TcpTestSucceeded : True

PS C:\Windows\system32> Test-NetConnection -Port 587 -ComputerName smtp.gmail.com

ComputerName : smtp.gmail.com
RemoteAddress : 142.251.167.108
RemotePort : 587
InterfaceAlias : Ethernet 3
SourceAddress : 172.17.153.9
TcpTestSucceeded : True

1 Answer

0 votes
by (19.6k points)

The problem is OAuth2 and/or 2FA which was not supported until version 9.12.
With the current version 9.16 LTS this is supported and can be configured as described here:
https://yuuvisdevelop.atlassian.net/wiki/spaces/onpremise/pages/538902548/Sending Emails via OAuth2 Authentication for Microsoft Office 365

Best regards
Nicolai

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