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Sending Windchill notification with SMTP server using TLS

adawkins-2
10-Marble
10-Marble
‎Apr 14, 2016 08:07 PM
‎Apr 14, 2016 08:07 PM

Sending Windchill notification with SMTP server using TLS

There' are a few discussions on this already but I was not able to get things working after following them so hoping someone can point me in the right direction.

I want to configure Windchill to use an SMTP server that uses TLS.  I wasn't successful in getting this to work and don't have access to the SMTP server so I switched to trying to use gmail SMTP since it looks like others have gotten this to work in the past. 

I have:

1) Enabled IMAP in the gmail account

2) Enabled less secure access in the gmail account

3) Exported a certificate for smtp.gmail.com and imported it into the JRE keystore using keytool.

4) Emailed my corporate account from the gmail account to make sure it doesn't get caught as spam

5) Set the following Windchill properties:

  • wt.mail.from=<gmail address>
  • wt.notify.notificationSenderEmail=<gmail address>
  • wt.mail.mailhost=smtp.gmail.com:587
  • wt.mail.properties=$(wt.home)$(dir.sep)mail.properties
  • wt.mail.smtp.starttls.enable=true
  • wt.mail.starttls.enable=true  (I'm pretty sure the line above is the correct property but saw it called out this way a few times so set this as well just in case)
  • wt.mail.smtp.starttls.required=true
  • wt.mail.smtp.ssl.trust=smtp.gmail.com
  • wt.mail.smtp.username=<-> - this is stored in mail.properties file
  • wt.mail.smtp.password=<gmail password> - this is stored in mail.properties file

6) Tried to send email from Windchill.  The email stays in the queue and never gets sent.

I turned on the verbosity in Windchill.  In the method server log it appears to connect but not using TLS (my IP XXXX out for security) :

2016-04-14 16:41:57,589 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-smtp.gmail.com at your service, [XXXXXX]

2016-04-14 16:41:57,589 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-SIZE 35882577

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-8BITMIME

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-STARTTLS

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-ENHANCEDSTATUSCODES

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-PIPELINING

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-CHUNKING

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 SMTPUTF8

2016-04-14 16:41:57,590 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SIZE", arg "35882577"

2016-04-14 16:41:57,591 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "8BITMIME", arg ""

2016-04-14 16:41:57,591 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "STARTTLS", arg ""

2016-04-14 16:41:57,591 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""

2016-04-14 16:41:57,591 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "PIPELINING", arg ""

2016-04-14 16:41:57,591 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "CHUNKING", arg ""

2016-04-14 16:41:57,591 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SMTPUTF8", arg ""

2016-04-14 16:41:57,633 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: use8bit false

2016-04-14 16:41:57,633 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - MAIL FROM:<adawkins@fitbit.com>

2016-04-14 16:41:57,647 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 530 5.7.0 Must issue a STARTTLS command first. d12sm60264283pfj.85 - gsmtp

2016-04-14 16:41:57,647 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: got response code 530, with response: 530 5.7.0 Must issue a STARTTLS command first. d12sm60264283pfj.85 - gsmtp

Any suggestions for what I'm missing highly appreciated!

Abby

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4 REPLIES 4
BineshKumar1
13-Aquamarine
13-Aquamarine
(To:adawkins-2)
‎Apr 14, 2016 11:40 PM
‎Apr 14, 2016 11:40 PM

I am using google apps email with test system, here are my settings.

wt.mail.png

I have enabled wt.mail.verboseTransport verbose and here is the  snippet from the logs.

2016-04-14 22:02:53,392 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: useEhlo true, useAuth true


2016-04-14 22:02:53,392 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false


2016-04-14 22:02:53,526 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 220 smtp.gmail.com ESMTP 43sm19562986qgh.28 - gsmtp


2016-04-14 22:02:53,526 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: connected to host "smtp.gmail.com", port: 587


2016-04-14 22:02:53,526 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 


2016-04-14 22:02:53,527 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - EHLO tbwcapp08.domain.local


2016-04-14 22:02:53,575 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-smtp.gmail.com at your service, [73.253.247.146]


2016-04-14 22:02:53,575 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-SIZE 35882577


2016-04-14 22:02:53,575 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-8BITMIME


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-STARTTLS


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-ENHANCEDSTATUSCODES


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-PIPELINING


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-CHUNKING


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 SMTPUTF8


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SIZE", arg "35882577"


2016-04-14 22:02:53,576 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "8BITMIME", arg ""


2016-04-14 22:02:53,577 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "STARTTLS", arg ""


2016-04-14 22:02:53,577 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""


2016-04-14 22:02:53,577 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "PIPELINING", arg ""


2016-04-14 22:02:53,577 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "CHUNKING", arg ""


2016-04-14 22:02:53,577 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SMTPUTF8", arg ""


2016-04-14 22:02:53,577 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - STARTTLS


2016-04-14 22:02:53,616 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 220 2.0.0 Ready to start TLS


2016-04-14 22:02:53,873 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - EHLO tbwcapp08.domain.local


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-smtp.gmail.com at your service, [73.253.247.146]


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-SIZE 35882577


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-8BITMIME


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-ENHANCEDSTATUSCODES


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-PIPELINING


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250-CHUNKING


2016-04-14 22:02:53,912 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 SMTPUTF8


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SIZE", arg "35882577"


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "8BITMIME", arg ""


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH"


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "PIPELINING", arg ""


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "CHUNKING", arg ""


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SMTPUTF8", arg ""


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM 


2016-04-14 22:02:53,913 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: AUTH LOGIN command trace suppressed


2016-04-14 22:02:54,137 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: AUTH LOGIN succeeded


2016-04-14 22:02:54,157 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: use8bit false


2016-04-14 22:02:54,157 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - MAIL FROM:<mail@bineshkumar.me>


2016-04-14 22:02:54,193 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 2.1.0 OK 43sm19562986qgh.28 - gsmtp


2016-04-14 22:02:54,193 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - RCPT TO:<mail@bineshkumar.me>


2016-04-14 22:02:54,229 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 2.1.5 OK 43sm19562986qgh.28 - gsmtp


2016-04-14 22:02:54,229 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Verified Addresses


2016-04-14 22:02:54,229 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP:   mail@bineshkumar.me


2016-04-14 22:02:54,229 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DATA


2016-04-14 22:02:54,331 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 354  Go ahead 43sm19562986qgh.28 - gsmtp


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - Date: Fri, 15 Apr 2016 02:02:54 +0000 (GMT)


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - From: mail@bineshkumar.me


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - To: mail@bineshkumar.me


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - Message-ID: <1254670415.0.1460685774157@tbwcapp08.domain.local>


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - Subject: Approve Promotion Request


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - MIME-Version: 1.0


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - Content-Type: text/html; charset="UTF-8"


2016-04-14 22:02:54,334 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - Content-Transfer-Encoding: 7bit

Thank you

Binesh Kumar

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adawkins-2
10-Marble
10-Marble
(To:BineshKumar1)
‎Apr 15, 2016 06:43 PM
‎Apr 15, 2016 06:43 PM

These look pretty much like what I have but went through and reset them all again without any luck.   Our servers are all in the cloud so we are using SSL. Using openssl: openssl s_client -connect smtp.gmail.com:587 -starttls smtp  I'm able to submit an email without the STARTTLS issue so my guess it's something to do with the java certificate.  I've tried redownloading and reimporting the smtp.google.com certificate into the keystore but still no luck...

Abby

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BineshKumar1
13-Aquamarine
13-Aquamarine
(To:adawkins-2)
‎Apr 15, 2016 08:30 PM
‎Apr 15, 2016 08:30 PM

I suspect a syntax error in the wt.properties, it is firing the connection without TLS. If I comment my TLS enable line in wt.properties I get the same error as yours. Stating 10.1 TLS is enabled, so you are good.

2016-04-15 20:27:08,972 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 SMTPUTF8


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SIZE", arg "35882577"


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "8BITMIME", arg ""


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "STARTTLS", arg ""


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "PIPELINING", arg ""


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "CHUNKING", arg ""


2016-04-15 20:27:08,973 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: Found extension "SMTPUTF8", arg ""


2016-04-15 20:27:09,047 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: use8bit false


2016-04-15 20:27:09,047 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - MAIL FROM:<mail@bineshkumar.me>


2016-04-15 20:27:09,095 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 530 5.7.0 Must issue a STARTTLS command first. f139sm9572095qke.43 - gsmtp


2016-04-15 20:27:09,095 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: got response code 530, with response: 530 5.7.0 Must issue a STARTTLS command first. f139sm9572095qke.43 - gsmtp


2016-04-15 20:27:09,095 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 


2016-04-15 20:27:09,095 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - RSET


2016-04-15 20:27:09,133 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 250 2.1.5 Flushed f139sm9572095qke.43 - gsmtp


2016-04-15 20:27:09,135 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - DEBUG SMTP: MessagingException while sending, THROW: 


2016-04-15 20:27:09,136 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. f139sm9572095qke.43 - gsmtp


2016-04-15 20:27:09,136 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - 


2016-04-15 20:27:09,136 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2203)


2016-04-15 20:27:09,136 INFO  [EMailQueue.SchedulingThread] wt.system.out Administrator - at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1694)


2016-04-15 20:27:09,136 INFO  [EMailQueue.Sche

I know you would have done that, but scan through wt.properties again wt.mail properties

Thank you

Binesh Kumar

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adawkins-2
10-Marble
10-Marble
(To:BineshKumar1)
‎Apr 15, 2016 07:29 PM
‎Apr 15, 2016 07:29 PM

Maybe the issue is my version of Windchill?  I'm on 10.2 M020.  I know PTC doesn't support TLS with the SMTP server but since others had gotten it to work, I was hopeful I could figure it out...

Abby

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