5000 Voicemail to email issue

[Viktar]

Hello all,
Spend a quite a bit of time trying to resolve an issue with sending Voicemail to email. Hopefully will get some suggestions here.
Here is my complete story:
The feature been working for about 2 years since the phone system been installed. About 1 year ago the feature stopped working  but our IT administrator did not care much about it. Now he is gone and Im trying to fix it. First blamed on the new firewall that was installed about a year ago. Crossed it out when temporary connected the old firewall. Tried to use third-party email client (Sylpheed if anybody curious) to send the email over SMTP, got the message on Gmail account that we use for VM about third-party application login has been blocked. Went through gmail setup proccess generating unique password for third-party applications. Now email client can send the emails over SMTP using following settings:
SMTP server: smtp.gmail.com
SMTP port: 465
SSL enabled
SMTP Authentication enabled
At this point I can say it's not a firewall issue. Even tried to disconnect Mitel controller and use it's internal IP address on my desktop with email client - still ok.
Got access to firewall logs and I can see 465 port requests when sending by email client but I can not see any requests when Mitel is trying to send VM to email.
Here is my Mitel settings related to VM to email feature:
IP Settings:
Module IP address: 10.238.203.50 (internal network)
Module subnet mask: 255.255.255.0
Module gateway: 10.238.203.2 (firewall, the same on all computers computers within our network)
DNS Primary IP: 10.238.203.3 (Windows server,the same on all computers within our network)
DNS Secondary IP: 8.8.8.8 (Google public DNS server, just in case)
DNS Search list: the same from internal DNS server
E-mail Gateway:
Administrator e-mail address: donotreply@ourserver.com (shouldn't matter as long as valid format?)
E-mail real name: Mitel VoiceMail (shoudn't matter as long as no special characters)
E-mail SMTP port: 465
SMTP server: smtp.gmail.com
E-mail System: SMTP
E-mail username: ***@gmail.com
Gateway Password: *** (the same as for third-party app)
Mailbox E-mail Sync settings:
Sync level: Forward & Copy
Enable SSL for Server Connection: Yes
E-mail Account folder: INBOX
E-mail Address for Voice Messages: ***@gmail.com
Synchronize MWI with E-mail Client: Yes

Here is the log from mail.mainlog file:
Sep  7 13:08:54 Tri-Way exim[4563]: 1kFKdR-0001Bb-Qx <= XXX@gmail.com U=root P=local S=158817 T="[0:08] Message for MB 233 from a caller at (XX) XXX-XXXX"
Sep  7 13:08:57 Tri-Way exim[4568]: 1kFKdR-0001Bb-Qx smtp.gmail.com [173.194.204.108] No route to host
Sep  7 13:08:58 Tri-Way exim[4566]: 1kFKdR-0001Bb-Qx == XXX@destination.com R=smarthost T=remote_smtp defer (113): No route to host
Sep  7 13:08:58 Tri-Way exim[4566]: 1kFKdR-0001Bb-Qx ** XXX@destination.com: retry timeout exceeded
Sep  7 13:08:58 Tri-Way exim[4577]: 1kFKdW-0001Bp-7Z <= <> R=1kFKdR-0001Bb-Qx U=mail P=local S=107948 T="Mail delivery failed: returning message to sender"
Sep  7 13:08:58 Tri-Way exim[4566]: 1kFKdR-0001Bb-Qx Completed
Sep  7 13:08:58 Tri-Way exim[4579]: 1kFKdW-0001Bp-7Z ** XXX@gmail.com R=smarthost T=remote_smtp: retry time not reached for any host after a long failure period
Sep  7 13:08:58 Tri-Way exim[4579]: 1kFKdW-0001Bp-7Z Frozen (delivery error message)

Please, let me know if I missed anything or you have any further questions.
Thanks in advance.

[Travis]

Hey Viktar,

I would make sure the pbx can get to gmail's email servers first. Open up ssh to the system and go to "command line". You should see OLM> On the screen. Type "ping smtp.gmail.com" and press enter. You should get return messages. Press CTRL + C to stop and then type "email_retry -a clear"
try leaving another message.

Also make sure allow less secure app access is enabled on the gmail account.

-Travis

[Viktar]

Thanks Travis,
I'll try your recommendation as soon as I get to the office. Working mostly from home now days and don't have access from outside of our firewall. Will let you know how did it go.

[Viktar]

Hello Travis,
Ping command went ok.
Ran "email_retry -a clear" old messages got cleared but Gmail server rejected the connection on port 465.
Switched to port 587, tried another message and it worked.
Magic command "email_retry -a clear" goes to my knowledge spreadsheet now.
Thanks for your help.

[Travis]

No problem dude! you can also do email_retry -a show to show current messages in queue. Type help in the olm for a bunch of helpful commands. mp = shows message print, netstat -ant = shows all active tcp connections with the system, top = shows process stats, kinda like task manager. these are all pretty safe but be careful in here. Mitel support didn't even know about message print. That works for older systems too!