Guys,
I used the dbgView.exe and I got this from the log. It is failing because of an authentication problem. Thing is I don't know to what the IPO is authenticating. If I hit check in the SMTP set-up in Control Panel Icon, It works fine as seen in the stunnel logs. I hope you guys will see something here.
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Receive OPEN for session 00000083, call-id 84
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Access = ACCESS_LEAVE_VOICEMAIL:
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Mailbox: Extn3150
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Calling Party: 4662
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Display String: Extn4662>Extn3150
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Target Party: 3150
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Greeting Modifier:
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Language: enu
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Call Ident: 84
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Call Status: No Answer (1)
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Call Type: Internal
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Call Direction: Incoming
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Called Party: 3150
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - DDI Number: 3150
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Calling Party Name: Extn4662
30/09 14:56:08.494 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Called Party Name: Extn3150
30/09 14:56:08.508 vmprov5s (06,5) 10c0,27d8: VMClient::RxOpen - Created dialog 04D8CB38
30/09 14:56:08.508 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - - Internal: !Internal!=Y
30/09 14:56:09.491 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Configuring for reliable disconnect, IDLE time is 300.000s
30/09 14:56:09.491 vmprov5s (06,5) 10c0,27d8: VMClient::RxOpen 04DA3E80 Extn3150 (1), session=00000083
30/09 14:56:09.491 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Receive OPEN for session 00000083, call-id 84
30/09 14:56:09.491 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Check flags[13] 128 for advising recording
30/09 14:56:09.493 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Configuring for reliable disconnect, IDLE time is 300.000s
30/09 14:56:09.493 vmprov5s (06,5) 10c0,27d8: VMClient::RxActive 04DA3E80 (session=00000083)
30/09 14:56:09.493 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Receive ACTIVE for session 00000083, call-id 84
30/09 14:56:09.674 vmprov5s (23,5) 10c0, b28: Succeeded in loading sound bite C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\Extn3150_1.WAV [uLaw]
30/09 14:56:19.409 vmprov5s (23,5) 10c0, b28: Succeeded in loading sound bite C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Wavs\enu\MC_01.WAV [uLaw]
30/09 14:56:19.409 vmprov5s (24,5) 10c0, b28: Successfully determined fragments for announcement 1146 using language enu, fragments are "1440"
30/09 14:56:19.479 vmprov5s (23,5) 10c0, b28: Succeeded in loading sound bite C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Wavs\enu\1440.WAV [uLaw]
30/09 14:56:19.479 vmprov5s (09,4) 10c0, b28: Session: 00000083 - VoiceMailDialog::ChangeNode: Node "IntuityRecordNode" took 125 milliseconds to Initialise.
30/09 14:56:19.854 vmprov5s (09,4) 10c0, b28: Session: 00000083 - StartRecording C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\MSG00423.WAV
30/09 14:56:40.030 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Configuring for reliable disconnect, IDLE time is 300.000s
30/09 14:56:40.030 vmprov5s (06,5) 10c0,27d8: VMClient::RxClose 04DA3E80 (session=00000083)
30/09 14:56:40.030 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - Receive CLOSE for session 00000083, call-id 84
30/09 14:56:40.030 vmprov5s (09,4) 10c0,27d8: Session: 00000083 - EndRecording
30/09 14:56:40.061 DbgOut (01,5) 4288,9312: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_ATTACH)
30/09 14:56:40.063 vmprov5s (09,4) 10c0,2460: Background saving "C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\MSG00423.WAV" to 1 mailboxes
30/09 14:56:40.073 vmprov5s (23,5) 10c0,27d8: Succeeded in loading sound bite C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Wavs\enu\MC_01.WAV [uLaw]
30/09 14:56:40.073 DbgOut (01,5) 4288,10200: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)
30/09 14:56:40.097 vmprov5s (09,4) 10c0,2460: Wave file C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\MSG00423.WAV, maximum energy was 6.337233, factor used to normalize 1.574073, took 32 ms
30/09 14:56:40.098 vmprov5s (09,4) 10c0,2460: Wave file C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\MSG00423.WAV, rewritten at 0.180000 FS
30/09 14:56:40.099 vmprov5s (09,4) 10c0,2460: Background saving message "C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\MSG00423.WAV" to 3150 [entry 1 of 1]
30/09 14:56:40.119 DbgOut (01,5) 11876,11720: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)
30/09 14:56:40.119 DbgOut (01,5) 11876,9744: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)
30/09 14:56:40.140 vmprov5s (13,5) 10c0,2460: Renaming message file "Extn3150/C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Accounts\Extn3150\MSG00019.WAV" to "C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Accounts\Extn3150\ceac3c92f01b4979b04a68025c61b6c5.WAV"
30/09 14:56:40.142 vmprov5s (06,5) 10c0,2460: NotifyMessageEventToPhoneManager Message ID = MSG00019
30/09 14:56:40.157 vmprov5s (09,5) 10c0,2460: EMailerRequest::Send: Queued email request for dperfetti42@gmail.com, subject is Voicemail Message (Extn4662 > Extn3150) From:4662, use EMAPI=false
30/09 14:56:40.162 vmprov5s (09,4) 10c0,2460: IntuityRecordNode - Sent recording to mailbox: "3150" <Private: 0> <Priority: 0>
30/09 14:56:40.164 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Receive buffer size is 0x10000 bytes (64K)
30/09 14:56:40.164 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Send buffer size is 0x10000 bytes (64K)
30/09 14:56:40.173 vmprov5s (09,4) 10c0,2460: Background saved message "C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Greetings\MSG00423.WAV" to at least 1 mailboxes and took 110 milli-seconds
30/09 14:56:40.174 DbgOut (01,5) 4288,9312: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)
30/09 14:56:40.338 vmprov5s (23,5) 10c0, b28: Succeeded in loading sound bite C:\Program Files (x86)\Avaya\IP Office\Voicemail Pro\VM\Wavs\enu\MC_01.WAV [uLaw]
30/09 14:56:40.339 vmprov5s (0a,5) 10c0, b28: OSThreadFunc exited[VMClient, 04DA3E98]
30/09 14:56:40.339 vmprov5s (09,5) 10c0, b28: Session: 00000083 - ~IClient [Connections 0 - 0] [Buffer pool(0:1000 1:250 2:2500 3:546) allocated:4, in use (here:0, total:0) seq:0] [Links:11631 from 12000] [CMMsg:2 left from 2] [VM:0 NODES:0 SN:0 SBL:0 TASKS:7 FILES:0 Msgs:16]
30/09 14:56:40.340 DbgOut (01,5) 4288,2856: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)
30/09 14:57:40.195 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::ReadResponse: Timed Out waiting for response from SMTP server.
30/09 14:57:40.195 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::Connect: An unexpected SMTP login response was received.
30/09 14:57:40.206 vmprov5s (14,2) 10c0,19d8: CSMTPConnection:

isconnect: An unexpected QUIT response was received.
30/09 14:57:40.257 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Receive buffer size is 0x10000 bytes (64K)
30/09 14:57:40.257 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Send buffer size is 0x10000 bytes (64K)
30/09 14:57:40.749 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::AuthLogin: AUTH LOGIN authentication was unsuccessful.
30/09 14:57:40.749 vmprov5s (14,2) 10c0,19d8: CSMTPConnection:

isconnect: An unexpected QUIT response was received.
30/09 14:57:40.750 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::Connect: An unexpected HELO/EHLO response was received.
30/09 14:59:30.484 vmprov5s (09,5) 10c0,19d8: EMailerRequest::Send: Queued email request for dperfetti42@gmail.com, subject is Voicemail Message (Extn4662 > Extn3150) From:4662, use EMAPI=false
30/09 14:59:30.497 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Receive buffer size is 0x10000 bytes (64K)
30/09 14:59:30.497 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Send buffer size is 0x10000 bytes (64K)
30/09 14:59:58.392 DbgOut (01,5) 11876,2884: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_ATTACH)
30/09 14:59:58.662 DbgOut (01,5) 11876,2864: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_ATTACH)
30/09 15:00:30.510 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::ReadResponse: Timed Out waiting for response from SMTP server.
30/09 15:00:30.510 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::Connect: An unexpected SMTP login response was received.
30/09 15:00:30.522 vmprov5s (14,2) 10c0,19d8: CSMTPConnection:

isconnect: An unexpected QUIT response was received.
30/09 15:00:30.573 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Receive buffer size is 0x10000 bytes (64K)
30/09 15:00:30.573 vmprov5s (09,3) 10c0,19d8: CMailSocket::Create: Send buffer size is 0x10000 bytes (64K)
30/09 15:00:31.080 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::AuthLogin: AUTH LOGIN authentication was unsuccessful.
30/09 15:00:31.080 vmprov5s (14,2) 10c0,19d8: CSMTPConnection:

isconnect: An unexpected QUIT response was received.
30/09 15:00:31.080 vmprov5s (14,2) 10c0,19d8: CSMTPConnection::Connect: An unexpected HELO/EHLO response was received.
30/09 15:01:08.159 DbgOut (01,5) 11876,2864: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)
30/09 15:01:08.159 DbgOut (01,5) 11876,2884: DllMain(hinstDLL=0x10000000, fdwReason=DLL_THREAD_DETACH)