javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful [SG2PR06CA0118.apcprd06.prod.outlook.com]

Question

I have tried changing the password but nothing worked. Please provide an update. 

Email log from my Java application is below.

DEBUG: setDebug: JavaMail version 1.4.7

Current processing batch no:1

Sending BCC e-mail.

Sending to SMTP server ....

DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]

DEBUG SMTP: useEhlo true, useAuth true

DEBUG SMTP: useEhlo true, useAuth true

DEBUG SMTP: trying to connect to host "smtp.office365.com", port 587, isSSL false

220 SG2PR06CA0118.outlook.office365.com Microsoft ESMTP MAIL Service ready at Mon, 13 Aug 2018 03:07:08 +0000

DEBUG SMTP: connected to host "smtp.office365.com", port: 587

EHLO <IP>

250-SG2PR06CA0118.outlook.office365.com Hello [IP]

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-STARTTLS

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8

DEBUG SMTP: Found extension "SIZE", arg "157286400"

DEBUG SMTP: Found extension "PIPELINING", arg ""

DEBUG SMTP: Found extension "DSN", arg ""

DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""

DEBUG SMTP: Found extension "STARTTLS", arg ""

DEBUG SMTP: Found extension "8BITMIME", arg ""

DEBUG SMTP: Found extension "BINARYMIME", arg ""

DEBUG SMTP: Found extension "CHUNKING", arg ""

DEBUG SMTP: Found extension "SMTPUTF8", arg ""

STARTTLS

220 2.0.0 SMTP server ready

EHLO 192.168.5.141

250-SG2PR06CA0118.outlook.office365.com Hello [115.42.245.38]

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-AUTH LOGIN XOAUTH2

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8

DEBUG SMTP: Found extension "SIZE", arg "157286400"

DEBUG SMTP: Found extension "PIPELINING", arg ""

DEBUG SMTP: Found extension "DSN", arg ""

DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""

DEBUG SMTP: Found extension "AUTH", arg "LOGIN XOAUTH2"

DEBUG SMTP: Found extension "8BITMIME", arg ""

DEBUG SMTP: Found extension "BINARYMIME", arg ""

DEBUG SMTP: Found extension "CHUNKING", arg ""

DEBUG SMTP: Found extension "SMTPUTF8", arg ""

DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM 

AUTH LOGIN

334 VXNlcm5hbWU6

dGVzdC13c2hjQHRhbC5zZw==

334 UGFzc3dvcmQ6

RGFqMTc3NjM=

535 5.7.3 Authentication unsuccessful [SG2PR06CA0118.apcprd06.prod.outlook.com]

javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful [SG2PR06CA0118.apcprd06.prod.outlook.com]

Going to sleep for 1min(s)

at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:826)

at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:761)

at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:685)

at javax.mail.Service.connect(Service.java:317)

at javax.mail.Service.connect(Service.java:176)

at javax.mail.Service.connect(Service.java:125)

at javax.mail.Transport.send0(Transport.java:194)

at javax.mail.Transport.send(Transport.java:124)

Answer 1

HI, Which service are you using? Are you configuring SMTP relay?

Answer 2

Hi,

Thanks for the prompt reply. We don't use any relay server and just send direct email using smtp.office365.com.

Answer 3

Thanks, Does it work before? There are three ways to configure it. Which one are you using?

I added a link as a reference.

https://support.office.com/en-us/article/how-to...

Answer 4

We are testing it for the first time and configured option 1.

Answer 5

The first one required an Office 365 account. Did you purchase an Office 365 subscription? Office 365 must include exchange online service.