Forum Thread

Tracing path of an email message sent from a Office 365 email account

627 52 October 27, 2017 at 03:56 PM
We installed Hmail server application on a computer which is connected to other devices. When those devices encounter a fault or malfunction, Hmail server sends out an email and text message to few of our office users. Hmail server is able to send an email
message to the user's personal email account like user@aol.com, user@outlook.com but not to their work email account. We are on Office 365 for work email accounts. Hmail server can also send text messages to user's cell phones and our users get the text.

Hmail server sends messages from an Office 365 email account hmailinfo@ourdomain.com It uses SMTP server smtp.office365.com and TLS port 587 as mentioned in the first option
at https://support.office.com/en-us/...05d654b4c4

Our server admin has whitelisted the hmailinfo@ourdomain.com email address and also whitelisted the IP address of the computer
on which Hmail server is running. Still, no emails are received to our user's work email accounts. He cannot see any emails received from hmailinfo@ourdomain.com passing via our firewall or in server logs. Port 25 is not blocked for our email server according to our server admin.

Our email server admin does not have more time to help us, but our users want to know why emails can be received to their personal email addresses but not work email accounts.

The error message in Hmail server logs when Hmail server tries to send email to our user's work email account is

------------------------------------------------------------------------------------------

"DEBUG" 2616 "2017-09-27 07:03:37.728" "AWStats::LogDeliveryFailure"
"SMTPD" 2616 747 "2017-09-27 07:03:37.735" "A.B.C.D" "SENT: 550 Unknown user"
"DEBUG" 2596 "2017-09-27 07:03:37.738" "The read operation failed. Bytes transferred: 0 Remote IP: A.B.C.D, Session: 747, Code: 2, Message: End of file"
"DEBUG" 2596 "2017-09-27 07:03:37.742" "Deleting message file."
"DEBUG" 2596 "2017-09-27 07:03:37.745" "Ending session 747"
"DEBUG" 2616 "2017-09-27 07:03:37.865" "Creating session 749"


A.B.C.D stands for IP address of computer on which Hmail is running
------------------------------------------------------------------------------------------

We have SPF records for our DNS, but our server admin claims it is not needed for this since many printers in our area send a scanned document as email attachment to the user's work email account. Those printers have a static IP address but those printers use a Gmail account and not a Office 365 email account like this Hmailserver application.


1. Where could the Hmail server messages be blocked and how can I trace it?

2. Which server logs do I need to look to find out why the messages are getting blocked?

Any suggestions would be appreciated.

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#2
I am not familiar with hmail server myself. My first thought was that it may be trying to route mail locally but doesnt have any record of those accounts. Could you need to create a route to the office 365 server as implied in this post?
https://www.hmailserver.com/forum...hp?t=31432
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#3
It sounds like you have hmail configured with the same dns namespace as your office 365 domain. I.e. if hmail is configured for 123.com and o365 is also setup for 123.com, that is probably your issue. Hmail thinks it's the primary mail server for 123.com. So when an email comes to it destined for user@123.com, it checks it's mailbox store for that user, and if it doesn't exist it rejects it as an invalid user as it has no where to deliver to.

If this is the case you can fix a few ways:
If hmail has no mailboxes on it, change the namespace or setup a universal forwarder for 123.com to forward to o365's smtp server.

If it does have mailboxes it gets trickier. You'll have to see if hmail has a "if local delivery not possible forward to" like option and configured that accordingly, or see if it has a"use mx records" override.

If hmails only purpose in your environment is to essentially be an smtp relay, it might be easier to install a free smtp relay in it's place, make an 0365 account for said relay, then have the relay forward all mail to 0365 using said account.
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Last edited by edrock200 October 29, 2017 at 06:01 PM.
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#4
Quote from mrt419
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I am not familiar with hmail server myself. My first thought was that it may be trying to route mail locally but doesnt have any record of those accounts. Could you need to create a route to the office 365 server as implied in this post?
https://www.hmailserver.com/forum...hp?t=31432
Thanks, but emails are sent to aol.com addresses so something at our domain is blocking those emails.

I appreciate your help.
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#5
Quote from edrock200
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It sounds like you have hmail configured with the same dns namespace as your office 365 domain. I.e. if hmail is configured for 123.com and o365 is also setup for 123.com, that is probably your issue. Hmail thinks it's the primary mail server for 123.com. So when an email comes to it destined for user@123.com, it checks it's mailbox store for that user, and if it doesn't exist it rejects it as an invalid user as it has no where to deliver to.

If this is the case you can fix a few ways:
If hmail has no mailboxes on it, change the namespace or setup a universal forwarder for 123.com to forward to o365's smtp server.
Thanks, but how do I change the namespace or setup a universal forwarder? Hmail does not have mailboxes on it.

Quote from edrock200
:
If hmails only purpose in your environment is to essentially be an smtp relay, it might be easier to install a free smtp relay in it's place, make an 0365 account for said relay, then have the relay forward all mail to 0365 using said account.
Thanks, but our system admin doesn't have time to configure the smtp relay for us.

I appreciate your help.
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Quote from p_s_92
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Thanks, but how do I change the namespace or setup a universal forwarder? Hmail does not have mailboxes on it.



Thanks, but our system admin doesn't have time to configure the smtp relay for us.

I appreciate your help.
Sounds like thats a business requirement thought to get your stuff working. This is why you have managers to get this type of thing done when someone is too busy, or hire a contractor.
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Quote from p_s_92
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Thanks, but how do I change the namespace or setup a universal forwarder? Hmail does not have mailboxes on it.



Thanks, but our system admin doesn't have time to configure the smtp relay for us.

I appreciate your help.
I'm not very familiar with hmail but basically somewhere in the config it's been setup to think it's controls the same namespace as O365. You need to change that to something else, ie if your namespace is office.com change it to office.local.
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Actually looks pretty easy. Open your hmail admin console, click on domains, highlight your domain and click edit, rename. Here's a screenshot of adding a domain, not renaming, but notice the edit button to the right:
http://gopalthorve.com/wp-content/uploads/2012/02/hmailserver-add-new-domain-2.png
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Quote from LiquidRetro
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Sounds like thats a business requirement thought to get your stuff working. This is why you have managers to get this type of thing done when someone is too busy, or hire a contractor.
Thanks, but managers don't have budget for hiring a contractor. Places like us have less people and even lesser budget.
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#10
Quote from edrock200
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Actually looks pretty easy. Open your hmail admin console, click on domains, highlight your domain and click edit, rename. Here's a screenshot of adding a domain, not renaming, but notice the edit button to the right:
http://gopalthorve.com/wp-content...main-2.png
Thanks, I will try that.
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