Email Not Sent Encrypted

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Email Not Sent Encrypted

Postby Gfw » Wed Jan 11, 2017 3:42 pm

I am using Pro version 9.52 with domian set to yyyZLtd.com. I have a valid SSL cert (yyyzltd.com) registered under localhost. Under Services and Connectors -> SMTP on [General] I have Enable Inbound TLS checked and under [Outbound] I have send using TLS if remote server supports checked.

If I send an email from my outlook client (configured for port 587 and SSL) the email is marked by GMail as "yyyzltd.com did not encrypt this message".

Any suggestions?

MailEnable-Ian
Site Admin
Posts: 8439
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Email Not Sent Encrypted

Postby MailEnable-Ian » Fri Jan 20, 2017 4:24 am

Hi,

MailEnable does not encrypt the message contents. It only encrypts the connection between the client and server when sending the data over SSL.
Regards,

Ian Margarone
MailEnable Support

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Re: Email Not Sent Encrypted

Postby Gfw » Fri Jan 20, 2017 3:08 pm

Maybe I am misstating the issue.

If I send message to my GMail acccount, the message from GMail on the account in question... "encryption: yyyzltd.com did not encrypt this message Learn more".

I have the standard version of MailEnable on a second VPS account with the identical settings and if a message is sent to my GMail account by that ail server it is treated by GMail as "encryption: Standard (TLS) Learn more".

Suggestions/links as to how to resolve appreciated.

Thanks.

MailEnable-Ian
Site Admin
Posts: 8439
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Email Not Sent Encrypted

Postby MailEnable-Ian » Sun Jan 22, 2017 11:56 pm

Hi,

On the server that is not encrypting the connection have you enabled the outbound TLS option within the SMTP properties under the "Outbound" tab? Navigate within the Standard administration console to: servers > localhost > services and connectors > SMTP. Right click on SMTP and select properties. Navigate to the "Outbound" tab and tick the option for "Send using TLS if remote server supports it" and then restart the SMTP service.
Regards,

Ian Margarone
MailEnable Support

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Re: Email Not Sent Encrypted

Postby Gfw » Tue Jan 24, 2017 12:10 pm

Thanks for your response. I already had the items that you mentioned configured as you outlined.

As I previously mentioned, I have the standard version on a second VPS account and it works as it should. To the extent possible, I placed each version on the screen side-by-side and compared the settings. I also changed the SSL certificate to make sure that it was a good cert.

Using CheckTLS and checking sender, I get "Your email was sent, however it was NOT SENT SECURELY using TLS.".

Any more suggestions?

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

Re: Email Not Sent Encrypted

Postby mosta2 » Mon Aug 21, 2017 6:11 pm

I am having the same issue,
this is important because all users who receive emails from server now gets a red alerts on gmail make them look suspicious
not sure why gmail made this ridiculous thing

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Re: Email Not Sent Encrypted

Postby Gfw » Tue Aug 22, 2017 10:40 am

I'm still having the same issue. I posted the original message back in January... Now in august the problem still exists with no additional response from support. Kind of feel deserted... :(

MailEnable-Ian
Site Admin
Posts: 8439
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Email Not Sent Encrypted

Postby MailEnable-Ian » Tue Aug 22, 2017 11:57 pm

Hi,

I'm still having the same issue. I posted the original message back in January... Now in august the problem still exists with no additional response from support. Kind of feel deserted... :(


If you require a managed response to your problems then the best way forward is to lodge a support ticket via our support ticketing system. We will require more detail and access to the server to troubleshoot the problem in more detail.
Regards,

Ian Margarone
MailEnable Support

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Re: Email Not Sent Encrypted

Postby Gfw » Wed Aug 23, 2017 12:43 am

You mean that after we follow all of your directions and it still fails that you now want us to spend $80 to $100 an hour because your documentation isn't complete? What is your hourly charge for what you are suggesting

MailEnable-Ian
Site Admin
Posts: 8439
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Email Not Sent Encrypted

Postby MailEnable-Ian » Wed Aug 23, 2017 12:54 am

Hi,

If you have a second server running Standard edition with identical settings as your problematic server which works, then it's not a MailEnable configuration issue and more so an environmental problem to that server. Have you checked that TLS 1.1 and TLS 1.2 are enabled on the problematic server? Please see: https://technet.microsoft.com/en-us/library/dn786418(v=ws.11).aspx#BKMK_SchannelTR_TLS12

The forum is a discussion board and therefore we cannot provide managed support that requires investigation on your server without lodging tickets. Perhaps lodge the ticket under "Upgrade" or "Installation" so we can take a look at the server and advise.
Regards,

Ian Margarone
MailEnable Support

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Re: Email Not Sent Encrypted

Postby Gfw » Wed Aug 23, 2017 1:08 am

I only have the one server. And if I send a message from my server to Gmail, I get the following...

from: Gfw@yyyz.com
to: gordonweis@gmail.com
date: Tue, Aug 22, 2017 at 8:04 PM
subject: test
mailed-by: yyyz.com
signed-by: yyyz.com
security: yyyzltd.com did not encrypt this message Learn more

And, Gmail give the recipient a red flag indicating a non-safe email. Even if I send from gw@yyyzltd.com, I get the same message.

from: Gw@yyyzltd.com <Gw@yyyzltd.com>
to: gordonweis@gmail.com
date: Tue, Aug 22, 2017 at 8:07 PM
subject: test
mailed-by: yyyzltd.com
signed-by: yyyzltd.com
security: yyyzltd.com did not encrypt this message Learn more

What is the real solution?

MailEnable-Ian
Site Admin
Posts: 8439
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Email Not Sent Encrypted

Postby MailEnable-Ian » Wed Aug 23, 2017 1:16 am

Hi,

In your previous posts you mentioned:

As I previously mentioned, I have the standard version on a second VPS account and it works as it should.


This is why I assumed you had a second server.

What is the real solution?


We don't know without performing tests on your server and inspecting the configuration in more detail.
Regards,

Ian Margarone
MailEnable Support

Gfw
Posts: 18
Joined: Thu Mar 31, 2016 12:52 pm

Re: Email Not Sent Encrypted

Postby Gfw » Wed Aug 23, 2017 1:37 am

And now I'm back to one of my previous questions... What is the charge?

MailEnable-Ian
Site Admin
Posts: 8439
Joined: Mon Mar 22, 2004 4:44 am
Location: Melbourne, Victoria, Australia

Re: Email Not Sent Encrypted

Postby MailEnable-Ian » Wed Aug 23, 2017 2:01 am

Hi,

I've sent you a private message.
Regards,

Ian Margarone
MailEnable Support

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