Voicemail to Email not reaching 3 users due to gmail smtp authentication error

[rcm87]

I am an IT guy, who is just dangerous enough with PBX systems.  I  finally thought I had everyone working by using Gmail as an SMTP relay for the  Mitel  5000.  I set up a 3rd party password in Gmail on the voicemail@domainname.com account as well as allow less secure apps and everyone started working except for 3 users.  I am using forward and copy for all of the users. 

The 3 users get this error message:
Jan 28 11:12:58 KUMC exim[1893]: 1nDUnx-0000UX-FP <= Voicemail@dominaname.org U=root P=local S=208279 T="[0:10] Message for MB 118 from a caller at 16362369543"
Jan 28 11:13:13 KUMC exim[1896]: 1nDUnx-0000UX-FP ** user1@domainname.org R=smarthost T=remote_smtp: SMTP error from remote mail server after MAIL FROM:<Voicemail@domainname.org> SIZE=212725: host smtp.gmail.com [173.194.207.108]: 530-5.7.0 Authentication Required. Learn more at\n530 5.7.0  https://support.google.com/mail/?p=WantAuthError r14sm3968943qkp.85 - gsmtp

Jan 28 12:44:56 KUMC exim[12052]: 1nDWEx-00038O-B3 <= Voicemail@domainname.org U=root P=local S=154491 T="[0:08] Message for MB 115 from a caller at 18174376900"
Jan 28 12:45:11 KUMC exim[12055]: 1nDWEx-00038O-B3 ** user2@domainname.org R=smarthost T=remote_smtp: SMTP error from remote mail server after MAIL FROM:<Voicemail@domainname.org> SIZE=158055: host smtp.gmail.com [173.194.66.109]: 530-5.7.0 Authentication Required. Learn more at\n530 5.7.0  https://support.google.com/mail/?p=WantAuthError bq33sm3884005qkb.64 - gsmtp

Everyone else, which is probably 15-20 other users get this:

Jan 28 12:46:06 KUMC exim[12219]: 1nDWG4-0003B5-Sf <= Voicemail@domainname.org U=root P=local S=188319 T="[0:09] Message for MB 105 from a caller at 18646085887"
Jan 28 12:46:20 KUMC exim[12221]: 1nDWG4-0003B5-Sf => user3@domainname.org R=smarthost T=remote_smtp H=smtp.gmail.com [173.194.66.108] X=TLSv1:AES128-SHA:128 C="250 2.0.0 OK  1643395580 h9sm802194qkn.121 - gsmtp"
Jan 28 12:46:20 KUMC exim[12221]: 1nDWG4-0003B5-Sf Completed

The 3rd party password has to be working for the majority of the people, I just am not sure what is different about these 3 users.  Any help would be great.

Administrator E-Mail Address - Voicemail@domainname.org
Email Address - Voicemail@domainname.org
Email Real Name - Voicemail
E-mail SMTP port - 587
Email SMTP Server - smtp.gmail.com
Email System - SMTP
Email Username - voicemail@domainname.org
Gateway Password -  Gmail  3rd Party Password

I did check the  DNS Search List and that is set correctly to our internal DNS Server (From other post)
Thanks for the help.   

[Tech Electronics]

rcm87,

Have you tried performing these steps manually via console or another SMTP client test application?

My guess is that the problem is not with the MiVO-250, but with those individual accounts not being setup the same way as the other 15-20 people or not in the same domain.

Thanks,

TE

[rcm87]

Well, I did test sending emails to my personal email account (yahoo.com account) and the same people failed.  With the people that always have worked, even when I change to my yahoo account, they still work, so I feel it is something the Mitel 5000 is sending differently for these few users.  What would I change via the console?

[rcm87]

==Update==
Ran into an issue where I needed to update the App password again in my voicemail Gmail account because all users were bouncing with authorization needed.   

To fix the 3 users, I had to delete the mailbox and then just recreate them.  I believe they were set it integrated before, and even just changing the setting from integrated to "Forward and Copy" did not fix the issue.  Delete the mailbox, set up "Forward and Copy" they were working as they should.  Hope that helps.