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Article - CS288408

Email notification fails with error "Could not connect to SMTP host" when Office 365 is configured in Windchill PDMLink

Modified: 03-Dec-2025   


Applies To

  • Windchill PDMLink 10.2 M030-CPS08 to 13.0
  • FlexPLM 12.0

Description

  • How to configure Windchill to integrate with mail which works with SMTPS?
  • Configure Windchill mail integration referring CS46949, but it doesn't work.
  • After changing the email server to Office 365 emails from Windchill are not being generated.
  • Error in MethodServer log: 
    [EMailQueue.SchedulingThread] wt.system.out Administrator - EMailMessage message submission failed
[EMailQueue.SchedulingThread] wt.system.err Administrator - javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;
  • Email fails when Office 365 is configured with SSL.
  • Failed to send Email by Quick Links > Email Page when using Office 365 SMTP server
  • Method Server logs: 
    INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2 
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: mechanism LOGIN not supported by server
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: mechanism PLAIN not supported by server
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: mechanism DIGEST-MD5 not supported by server
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Using mechanism NTLM
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG NTLM: type 1 message: 4E 54 4C 4D 53 53 50 00 01 00 00 00 03 A2 00 00 00 00 00 00 26 00 00 00 06 00 06 00 20 00 00 00 70 6C 6D 70 72 6F 
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: AUTH NTLM command trace suppressed
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG NTLM: type 3 message: 4E 54 4C 4D 53 53 50 00 03 00 00 00 18 00 18 00 60 00 00 00 18 00 18 00 78 00 00 00 00 00 00 00 40 00 00 00 14 00 14 00 40 00 00 00 0C 00 0C 00 54 00 00 00 00 00 00 00 90 00 00 00 01 82 00 00 70 00 6C 00 6D 00 40 00 68 00 79 00 63 00 2E 00 63 00 6E 00 70 00 6C 00 6D 00 70 00 72 00 6F 00 3C 68 C3 90 A0 A8 24 32 2B B6 45 C8 53 25 35 61 84 78 49 60 1A 8E F4 9F B5 B9 AF B4 D3 B9 99 EB 1F 48 D2 A3 46 D3 6F A7 84 8B 6F 73 D4 B4 4F 8B 
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: AUTH NTLM failed
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - EMailMessage message submission failed
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - EMailMessage 535 5.7.3 Authentication unsuccessful
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - EMailMessage subject: 审核
INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - EMailMessage not submitted to: <user email address>
INFO  [EMailQueue.SchedulingThread] wt.system.err Administrator - javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful
  • Method Server logs:  
    INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "SIZE", arg "157286400"
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "PIPELINING", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "DSN", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "AUTH", arg "LOGIN XOAUTH2"
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "8BITMIME", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "BINARYMIME", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "CHUNKING", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Found extension "SMTPUTF8", arg ""
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: protocolConnect login, host=smtp.office365.com, user=<user email address>, password=<non-null>
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2 
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: Using mechanism LOGIN
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: AUTH LOGIN command trace suppressed
INFO  [ajp-nio-127.0.0.1-8010-exec-1] wt.system.out Administrator - DEBUG SMTP: AUTH LOGIN failed
  • Failed to send Email by Quick Links > Email Page 
  • Error in MethodServer log: 
    2025-11-25 13:26:50,884 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - DEBUG SMTP: use8bit false
2025-11-25 13:26:50,885 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - MAIL FROM:<xxxxx>
2025-11-25 13:26:50,899 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 250 xxxx sender accepted
2025-11-25 13:26:50,900 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - RCPT TO:<xxxx>
2025-11-25 13:26:52,915 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 571 xxxxx prohibited. We do not relay
2025-11-25 13:26:52,915 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - RCPT TO:<xxxx>
2025-11-25 13:26:54,929 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 571 xxxxx prohibited. We do not relay
2025-11-25 13:26:54,930 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - DEBUG SMTP: Invalid Addresses
2025-11-25 13:26:54,930 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - DEBUG SMTP:   xxxx
2025-11-25 13:26:54,930 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - DEBUG SMTP:   xxxxx
2025-11-25 13:26:54,930 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - DEBUG SMTP: Sending failed because of invalid destination addresses
2025-11-25 13:26:54,930 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - RSET
2025-11-25 13:26:54,946 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 250 SMTP state reset
2025-11-25 13:26:54,946 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - DEBUG SMTP: MessagingException while sending, THROW: 
2025-11-25 13:26:54,946 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - jakarta.mail.SendFailedException: Invalid Addresses;
2025-11-25 13:26:54,946 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator -   nested exception is:
2025-11-25 13:26:54,946 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 	org.eclipse.angus.mail.smtp.SMTPAddressFailedException: 571 xxxxx prohibited. We do not relay
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - ;
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator -   nested exception is:
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 	org.eclipse.angus.mail.smtp.SMTPAddressFailedException: 571 xxxxx prohibited. We do not relay
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 	at org.eclipse.angus.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:2097)
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 	at org.eclipse.angus.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1291)
2025-11-25 13:26:54,947 INFO  [ajp-nio-127.0.0.1-8010-exec-4] wt.system.out Administrator - 	at com.infoengine.webject.msg.SendMail.invoke(SendMail.java:501)
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