Exchange SMTP TLS - Do I need to setup 587?

[mscott]

Hello,

 

At the moment we are still running a local exchange, this isn't a school network so its not as easy to upgrade our equipment as time isn't something that comes easy.

 

Anyways, we're currently running Exchange 2013 and mail flow works fine for the most part except we're having an issue with personal Microsoft accounts and when we send emails to lets say a hotmail.com email address, it goes straight into the recipients junk folder.

 

After doing a mxtoolbox.com test, It said this -> [TABLE=class: table table-striped table-bordered table-condensed tool-result-table, width: 2181]

[TR]

[TD=class: table-column-Name]SMTP TLS[/TD]

[TD=class: table-column-Response]Warning - Does not support TLS.[/TD]

[/TR]

[/TABLE]

Any ideas?

 

Thanks

[3s-gtech]

So you have a certificate bound to your send connector? You’ll have to use Powershell to query it to see. If not, it’ll send mail in plaintext (IIRC).

[georgeescott]

I’d start here https://techcommunity.microsoft.com/t5/exchange-team-blog/exchange-server-tls-guidance-part-1-getting-ready-for-tls-1-2/ba-p/607649 following the official guidance on making sure TLS is enabled.

 

Look at setting up SPF/DKIM/DMARC too as this lowers the chances of emails being detected as spam.

[mscott]

Well. After I did another mxtoolbox.com test it then got rid of the smtp tls not supported and instead came up with this ->

 

[TABLE=class: table table-striped table-bordered table-condensed tool-result-table, width: 2181]

[TR=bgcolor: #F9F9F9]

[TD=class: table-column-Name]SMTP Banner Check[/TD]

[TD=class: table-column-Response]Reverse DNS does not match SMTP Banner[/TD]

[/TR]

[/TABLE]

 

- - - Updated - - -

 

Will take a look at this now actually, I cant remember whether this was setup eek!

[PaddyNewman]

Make sure there is a valid PTR record in public DNS for your advertised mailserver name, otherwise people will get unhappy! It will be held by the people that look after your IP addresses applied to that, not your own public DNS.