SMTP Server on Domain
We have a SMTP server setup on a server on our internal domain to relay emails from our internal reporting systems and multi function machines. The SMTP server forwards the emails out to our Office 365 mail server using an existing office 365 user. We are upgrading our security for all users to multi factor login and although I could use a app specific password, we are starting to use SendGrid instead of our 365 server for these. Plus we have people all the time reply to those emails when we specifically have it as part of the body of the email to not reply. I am using mailto:noreply@domain.com now on the SMTP configuration of our internal server but it seems that the SMTP server is still relaying mailto:admin@domain.com instead of noreply. I don't see any settings on the STMP configuration for this. So why would it still be using admin and where would it get that? I have the login for the SendGrid to apikey and the apikey password.
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ASKER
So on the internal SMTP I have the admin email setup for failed emails. If I change that to noreply, that would resolve it you think?
you are using the hardest path.
You have put an authenticated user on the SMTP server, hence from the address will be the user you had authenticated.
To make a smooth transition, you should install exchange 2016. Yes, it might a bit complicated, but the exchange 2016 is complementary for any office 365 subscriptions.
Alternatively, you will need to add the mailto:noreply@domain.com into your authenticated user's proxy address.
You have put an authenticated user on the SMTP server, hence from the address will be the user you had authenticated.
To make a smooth transition, you should install exchange 2016. Yes, it might a bit complicated, but the exchange 2016 is complementary for any office 365 subscriptions.
Alternatively, you will need to add the mailto:noreply@domain.com into your authenticated user's proxy address.
Instead of using authenticated submission to O365, presuming that you are only delivering to internal addresses, just use normal delivery to O365 and create a suitable connector.
ASKER
I am trying to prevent recipients from replying to these emails and if they do, they will get an delivery failure. The admin account is constantly getting replies when the emails specifically state not to reply. I would assume a connector would not require a "real" email address?
If you want replies to the emails to "bounce", then there cannot be a mailbox associated with the address, so I would suggest using a receive connector in O365 as a "relay" connector, secured with either a certificate, or using the exit address.
ASKER
It does appear that when I create the connector, using a noreply as the email, does not allow the email to get delivered. I was sure I read that you can put anything in as the from email address, but that does not seem to be working. The only way I was able to get it to work was putting noreply as an alias or use an actual licensed email box.
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ASKER
I did just as you instructed and emails will not get delivered unless a use a valid email address or an alias. Which is not what I wanted to do because that email will get their replies. I am not sure what I am missing.
Well, The technique works when the connetcor and the on premises part is set correctly.
Are the emails leaving the on premise SMTP gateway?
Things to check
1. That the on premises server is sending on TCP/25 (not TCP/587) to the O365 MX record
2. That the noreply@ address is using a domain that is in O365
3. That the correct exit IP address is set on the O365 connector
If teh emails are leaving the on premises SMTP gateay, are they visiable in Message Trace in O365?
Are the emails leaving the on premise SMTP gateway?
Things to check
1. That the on premises server is sending on TCP/25 (not TCP/587) to the O365 MX record
2. That the noreply@ address is using a domain that is in O365
3. That the correct exit IP address is set on the O365 connector
If teh emails are leaving the on premises SMTP gateay, are they visiable in Message Trace in O365?
ASKER
So what should the SMTP server address be? I have two documents that shows two different ones:
XXX-com.mail.protection.outlook.com (where XXX would represent our domain in this example )
or
smtp.office365.com
XXX-com.mail.protection.outlook.com (where XXX would represent our domain in this example )
or
smtp.office365.com
Use the MX record that O365 shows
admin.microsoft.com > Settings > Domains > public domain DNS Records > MX
The format that you have looks good, but always worthwhile checking.
smtp.office365.com is what one would use for authenticated submission instead of smtp delivery.
admin.microsoft.com > Settings > Domains > public domain DNS Records > MX
The format that you have looks good, but always worthwhile checking.
smtp.office365.com is what one would use for authenticated submission instead of smtp delivery.
Email Servers
Within Internet message handling services (MHS), a message transfer agent or mail transfer agent (MTA) or mail relay is software that transfers electronic mail messages from one computer to another using a client–server application architecture. A MTA implements both the client (sending) and server (receiving) portions of the Simple Mail Transfer Protocol (SMTP). The terms mail server, mail exchanger, and MX host may also refer to a computer performing the MTA function. The Domain Name System (DNS) associates a mail server to a domain with mail exchanger (MX) resource records containing the domain name of a host providing MTA services.
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if you have a look at the message headers - you should be able to track where the address changes from noreply to admin - and thats the relay point you need to look at (has to be your internal relay i would have thought)