TLS Problem with GMail red lock sign

mosta2
Posts: 5
Joined: Mon Aug 21, 2017 6:07 pm

TLS Problem with GMail red lock sign

Postby mosta2 » Mon Aug 21, 2017 10:04 pm

I have configured mailenable with SSL settings, it is working fine but TLS encryption doesn't seem to be working
I have checked the option SMTP >> Outbound >> Send Using TLS when remote server supports
I am sending and receiving using the SSL ports.
But when sending to Gmail it always shows the red lock alert that means the message does not have TLS encryption.
No idea what could be wrong?

MailEnable-Ian
Site Admin
Posts: 8512
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: TLS Problem with GMail red lock sign

Postby MailEnable-Ian » Wed Aug 23, 2017 1:04 am

Hi,

Inspect the MailEnable SMTP log files and locate the SMTP-OU lines for the SMTP transaction with the Gmail server. Do you see the STARTTLS command being successfully issued with the Gmail server? If not, then it's most likely failing TLS and falling back to non-TLS.
Regards,

Ian Margarone
MailEnable Support

mosta2
Posts: 5
Joined: Mon Aug 21, 2017 6:07 pm

Re: TLS Problem with GMail red lock sign

Postby mosta2 » Fri Aug 25, 2017 5:42 pm

Hi Ian,
Thank you for your reply.
I checked the SMTP-OU logs it does not contain STARTTLS commands in any part of its logs,
please advice
Thanks

mosta2
Posts: 5
Joined: Mon Aug 21, 2017 6:07 pm

Re: TLS Problem with GMail red lock sign

Postby mosta2 » Fri Aug 25, 2017 8:09 pm

I have ensured the TLS is enabled on the server, editing the registry keys, etc and on IE it shows TLS 1.1 and TLS 1.2 are enabled. And it works with authentication.
Why would the TLS fail with sending Emails, it does not log any error about TLS seems like ignoring this option
Thank you for your support

mosta2
Posts: 5
Joined: Mon Aug 21, 2017 6:07 pm

Re: TLS Problem with GMail red lock sign

Postby mosta2 » Sat Aug 26, 2017 9:42 am

On your documentation it says I should permit user IME_SYSTEM for SSL certs, I don't find this user on the system, is it old documentation or I am missing something ? I have enabled permissiont for IME_Admin and still the problem exists that Mail enable does not use TLS for outbound messages.

MailEnable-Ian
Site Admin
Posts: 8512
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: TLS Problem with GMail red lock sign

Postby MailEnable-Ian » Mon Aug 28, 2017 2:56 am

Hi,

Try and telnet to the Gmail server via a Windows command prompt on the server. When you connect issue the EHLO command. When the server returns the SMTP advertised extensions do see STARTTLS on the list? If not then you may have a proxy that is masking the STARTTLS extension and thus is causing MailEnabel to fall back to non-TLS when sending the Gmail server.
Regards,

Ian Margarone
MailEnable Support

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