Now that a lot of our IBM i customers are moving to the cloud for their email servers (ie, Google, Microsoft Office 365, Godaddy, etc) we are finding that some "tricks" have been played up until now that just won't cut the mustard with these new email services.

The main trick we're seeing is that of email address "spoofing".  This means the FROM address you are specifying doesn't match the Account (AUTHUSER) parameter on the MAILTOOL command.

When using a cloud service you're required, in most cases, to provide an account ID and password.  In most cases this should match the FROM address (ie, FROMADDR should be the same as AUTHUSER).  

Examine this scenario:

You just set up your new cloud server through GMail.  You supply an account id of joe@yourcompany.com along with the associated password.  But, for the "from" address you specify "replytome@yourcompany.com".  With most cloud providers one of two things will happen:

1. The "from" address will automatically get changed to the account id, overriding the specified "from" address.
2. The email will not be delivered because the "from" address and the account ID do not match.

I ran a couple of examples and am including the results of the SMTP debug file created by MAILTOOL to show exactly how this works:

Test 1: Using GMail

​The following command was run to perform this test:

MAILTOOL TOADDR(bvstone@yahoo.com) FROMADDR(notme@bvstools.com) 
SUBJECT(Test) MESSAGE('Test Email') CONFIG('/bvstools/bvstools_test2.json') 
DEBUG(*YES)

The following configuration file settings were used:

{
	"variables": [
	{
		"name":"send_with_server_type",
		"default":"*MAILTOOL"
	},
	{
		"name":"mail_router",
		"default":"smtp.gmail.com"
	},
	{
		"name":"use_mail_router",
		"default":"*ONLY"
	},
	{
		"name":"use_ssl",
		"default":"*YES"
	},
	{
		"name":"smtp_port",
		"default":"465"
	},
	{
		"name":"smtp_auth_user",
		"default":"bvstone@bvstools.com"
	},
	{
		"name":"smtp_auth_password",
		"default":"*********"
	}	]
}

The resulting email headers are as follows:

From: bvstone@bvstools.com
X-Google-Original-From: notme@bvstools.com
MIME-Version: 1.0
To: bvstone@yahoo.com
Subject: Test

  As you can see, in the case of GMail the From address is overridden.  Google does add it's own header showing what actually was used as the From address, though.

Test 2:  Using Outlook and Office 365

​The following command was run to perform this test:

MAILTOOL TOADDR(bvstone@yahoo.com) FROMADDR(notme@outlook.com) 
SUBJECT(Test) MESSAGE('Test Email') 
CONFIG('/bvstools/bvstone_outlook_test.json') DEBUG(*YES)

The following configuration file settings were used:

{
	"variables": [
	{
		"name":"send_with_server_type",
		"default":"*MAILTOOL"
	},
	{
		"name":"mail_router",
		"default":"smtp-mail.outlook.com"
	},
	{
		"name":"use_mail_router",
		"default":"*ONLY"
	},
	{
		"name":"perform_mx_lookup",
		"default":"*NO"
	},
	{
		"name":"use_ssl",
		"default":"*TLS"
	},
	{
		"name":"smtp_port",
		"default":"587"
	},
	{
		"name":"smtp_auth_user",
		"default":"bvstone@outlook.com"
	},
	{
		"name":"smtp_auth_password",
		"default":"*************"
	}	]
}

The resulting email headers are as follows:

From: Brad Stone <bvstone@outlook.com>
To: "bvstone@yahoo.com" <bvstone@yahoo.com>
Subject: Test

So, as you can see the outlook also does allow the email through but again it updates the From address to the same as the account used.

I have also run into the following error from a customer trying to use a different From address and Office 365:

03/16/2016 17:06:07 <SMTP.OFFICE365.COM says:> 550 5.7.60 SMTP; Client does not have permissions to send as this sender

In this case it is pretty obvious what the error is.  Either this can't be done or somewhere in Office 365 there are settings to allow different senders for different accounts.

UPDATE:  Here is another example from Office 365:

<SMTP.OFFICE365.COM says:> 554 5.2.0 STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied; Failed to process message due to a permanent exception with message Cannot submit message. 

In the end, it's best to set up accounts for email and use the appropriately instead of trying to take the quick and easy way out.  Normally this just results in spending 3 or 4 times more resources on the project that just doing it right the first time.

Feel free to contact us with any questions regarding these issues.  Thanks!

Brad
www.bvstools.com