Hi Xavier,

I can't directly answer your question but I had spent quite a bit of time trying to make a Ruby script work with Office 365 SMTP.

This is the script that worked for us - maybe, something here will help?

smtp_host   = 'smtp.office365.com'
smtp_port   = 587
smtp_user   = '[email protected]'
smtp_pwd    = 'whatever-your-password-is'

smtp = Net::SMTP.new(smtp_host, smtp_port)
smtp.enable_starttls_auto

smtp.start("yourdomain.com", smtp_user, smtp_pwd, :login)
smtp.send_message(msg, smtp_user, to_mail)
smtp.finish

For reference, the start method uses this structure:
> start(helo_domain, account, password, authtype)

It was important for us to:
> make sure the smtp host was smtp.office365.com = yours seems OK
> port was 587 = yours seems OK
> STARTTLS was AUTO  = yours seems OK
> make sure that the smtp.start used "yourdomain.com" = not sure if you're doing this
> authentication was LOGIN = yours seems OK

Hope this helps.

Best Regards,
Mohit.



On 6/5/2016 3:07 AM, Xavier Mor-Mur wrote:
Hello

Recently a client has migrated all email accounts to send mail using office365 server. Now my programs can't send email using that server. Always get "Error=535 5.7.3 Authentication unsuccessful"
I tried many options but always get error 553.

< 250-DB5PR04CA0024.outlook.office365.com Hello [2.139.151.187]
< 250-SIZE 157286400
< 250-PIPELINING
< 250-DSN
< 250-ENHANCEDSTATUSCODES
< 250-STARTTLS
< 250-8BITMIME
< 250-BINARYMIME
< 250 CHUNKING
> STARTTLS
< 220 2.0.0 SMTP server ready
Starting SSL handshake
> ...[DataBlock of 132 chars]...
smtpStartTlsRequestDone Rq=12 Error=0
> EHLO XAVIW8
< 250-DB5PR04CA0024.outlook.office365.com Hello [2.139.151.187]
< 250-SIZE 157286400
< 250-PIPELINING
< 250-DSN
< 250-ENHANCEDSTATUSCODES
< 250-AUTH LOGIN
< 250-8BITMIME
< 250-BINARYMIME
< 250 CHUNKING
smtpEhloRequestDone Rq=10 Error=0
> AUTH LOGIN
< 334 VXNlcm5hbWU6
> ZXVyb211c19tYmFAbXVzZW9iaWxiYW8uY29t
< 334 UGFzc3dvcmQ6
> RGFwbzkzOTA=
< 535 5.7.3 Authentication unsuccessful
smtpAuthRequestDone Rq=11 Error=535 5.7.3 Authentication unsuccessful

I configured Outlook and Thunderbird with supplied parameters with no problem.
On that programs can set secure mode to TLS or SSL, but only works TLS.
I don't find how to configure ICS to work with TLS.

I would agree any help about it.
Thanks in advance

Xavi


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