Sendmail 'Authentication failed' error at office365.com

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Hi all:
I'm trying to configure sendmail to send me an email when something breaks. I am having a hard time getting it to work with Office365.com. I've been up and down the web and have found similar problems (with gmail, not office365) and have been learning a lot about java email settings, but have not been successful.
I have verified that I'm seeing the server, I get replies when I ping and see the server when I telnet over to smtp.office365.com. I set up the account on Thunderbird and it sends mail just fine. I've verified that 'authorized SMTP' is enabled at office365.com. Running out of ideas on what else to try or how else to debug.
Here is what I am using:
mail = 'name@domain.org';
password = 'xxx';
server = 'smtp.office365.com';
port = '587';
setpref('Internet','E_mail', mail);
setpref('Internet','SMTP_Server', server);
setpref('Internet','SMTP_Username', mail);
setpref('Internet','SMTP_Password', password);
props = java.lang.System.getProperties;
props.setProperty( 'mail.smtp.ssl.trust', server);
props.setProperty( 'mail.smtp.user', mail );
props.setProperty( 'mail.smtp.password', password );
props.setProperty( 'mail.smtp.host', server );
props.setProperty( 'mail.smtp.port', port );
props.setProperty( 'mail.smtp.starttls.enable', 'true' );
props.setProperty( 'mail.smtp.auth', 'true' );
sendmail('recipent@domain.org','Subject','Message')
It returns:
Error using sendmail (line 175)
Authentication failed.
Anyone have any ideas or thoughts on how to debug?
Thanks, Rob
  3 Comments
Markus Hohlagschwandtner
Markus Hohlagschwandtner on 26 Nov 2022
I found the problem. SMTP AUTH hast to be disabled.
props.setProperty( 'mail.smtp.auth', 'false' );

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Answers (1)

Mehmet Ali
Mehmet Ali on 3 Oct 2023
When I am using this code I am getting an error :
Error using sendmail
530 5.7.57 Client not authenticated to send mail. [VI1PR0102CA0080.eurprd01.prod.exchangelabs.com
2023-10-03T15:12:54.961Z 08DBC367B59984EF]
Do you have any suggestion for this?

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