TLS issue

Question asked by Russ Michaels - 3/15/2016 at 1:08 PM

Unanswered

I am trying to set smartermail to allow TLS but am having problems.

I have enabled TLS on ports 25 and 587, and if I do a test from mxtoolbox it says TLS is supported.

But any app which sends mail through this server fails as soon as I tell it to use TLS.

why ?

6 Replies

Reply to Thread

Russ Michaels Replied

3/15/2016 at 2:03 PM

same issue here

Karl Jones Replied

3/15/2016 at 4:21 PM

I think we need more info to answer that question...
Do you have a SSL cert. Is it self signed or CA created, have you bound IIS to smartermail. Have you bound imap, pop3 ports to SSL also.
Did you enable TLS on the server registry..????
These 2 links were useful to me. https://portal.chicagonettech.com/kb/a54/configure-ssl-tls-to-secure-smartermail.aspx

http://portal.smartertools.com/kb/a2671/configure-ssl-tls-to-secure-smartermail.aspx

Russ Michaels Replied

3/16/2016 at 3:32 AM

Karl,

yes I have a CA wildcard SSL cert that we use on several websites.
yes smartermail is bound to IIS, this is not a new server, it has been in use a few years,
TLS is enabled, the server gets an "A" on the qualys ssllabs

Hari Murugan Replied

3/16/2016 at 3:42 AM

You could use IIS Crypto to enable or disable TLS in the registry.

"www.nartac.com/Products/IISCrypto/Download"

Karl Jones Replied

3/16/2016 at 2:31 PM

Can you look in the SMTP logs... what are the SMTP logs saying when negotiating a TLS connection.
Also check and make sure that authentication on the client is enabled on port 587 connections.
I had a problem where all the mxtoolbox, IIScrypto and autodiscover smtp/imap tests etc all passed. I used this tool https://slproweb.com/products/Win32OpenSSL.html to show that there was a error and i had to re-export the SSL cert and everything worked after that.

Russ Michaels Replied

3/16/2016 at 2:48 PM

Hari, as stated TLS is already enabled and has been for a long time, and I already use the nartac product.
Turned out that all that was required was a reboot and then it started working.

Back to Community Threads

Please leave this box unchecked

6 Replies

Reply to Thread

Tags

Related Knowledge Base Articles