I am using HelpScout and sending through SendGrid (in order to track opens, bounces etc). I am having issue because eBay, which sends member messages to our customer support HelpScout app, rejects our replies with messages such as:
bounces+544081-5160-me=example.org#sendgrid.info
is not a registered email address...
add to whitelist etc..
Here are some of the headers from a HelpScout reply sent through SendGrid. As you can see it has this bounces... email address everywhere.
Delivered-To: me#example.org
Return-Path: <bounces+544081-5160-me=example.org#sendgrid.info>
Received: from o1638913x156.outbound-mail.sendgrid.net (o1638913x156.outbound-mail.sendgrid.net. [163.89.13.156])
by mx.google.com with ESMTPS id ly8si1461978wjb.40.2015.05.19.16.22.21
for <me#example.org>
(version=TLSv1.2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
Tue, 19 May 2015 16:22:22 -0700 (PDT)
Received-SPF: pass (google.com: domain of bounces+544081-5160-me=example.org#sendgrid.info designates 163.89.13.156 as permitted sender) client-ip=163.89.13.156;
Authentication-Results: mx.google.com;
spf=pass (google.com: domain of bounces+544081-5160-me=example.org#sendgrid.info designates 163.89.13.156 as permitted sender) smtp.mail=bounces+544081-5160-me=example.org#sendgrid.info;
dkim=pass header.i=#sendgrid.me
Received: by filter0448p1mdw1.sendgrid.net with SMTP id filter0448p1mdw1.14711.555BC5AB1
2015-05-19 23:22:20.183545946 +0000 UTC
Received: from secure.helpscout.net (unknown [10.100.60.108])
by ismtpd-019 (SG) with ESMTP id 14d6e7c27b3.1336.1b3f18
for <me#example.org>; Tue, 19 May 2015 23:22:19 +0000 (UTC)
From: Customer Support <help#oursite.com>
To: me#example.org
Subject: Fwd: Your message to ebayuser123 was blocked, because it wasn't sent from your registered email address.
Message-Id: <reply-8673-92216597-234152896-1432077739-1043083945#helpscout.net>
Why is SendGrid creating this address and is there a way to prevent it - I need an address that doesn't change so that I can whitelist.
Related
I created an instance on AWS Amazon an installed Plesk trial for a month
First problem that I discovered is that I coulnd't register my DNS on the plesk panel, cause I had just one IP and my domain provider (registro.br) requires 2 ips for dns (I know that Route53 is an option, but I have so many domains, it'd be expensive), so I had to duplicate all dns records generated by plesk to my registro.br dns manager
Second problem is that all my e-mails is going to spam on gmail and been rejected by outlook, I searched on the gmail headers message to find out why, first I solved an DKIM that wasn't passing, but now, SPF, DKIM and DMARC pass but it still with the same problem
Here is my gmail message header
Delivered-To: andreluismonteiro33#gmail.com
Received: by 2002:a5d:43cb:0:0:0:0:0 with SMTP id v11csp5983036wrr;
Wed, 27 Mar 2019 04:35:17 -0700 (PDT)
X-Google-Smtp-Source: APXvYqzW3R3CzTzXlriAjBGdijdyPfwAG3wrCpYA0ZCMDWW/unHc0BcyC6cgpv207SK3aOu5rLYz
X-Received: by 2002:a37:7b02:: with SMTP id w2mr254415qkc.225.1553686516947;
Wed, 27 Mar 2019 04:35:16 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1553686516; cv=none;
d=google.com; s=arc-20160816;
b=ewYQPERXxFgaiVzPRplhOFb8IOtrKS/E+YiLV4q07h/wNKMVZ2RTowMacTmSs9hxS2
7K0tIavCxfCHJpGXbVKe7d20DHQPeO2X2RV763F3zoLdfmunK4xiEL2itH6n60VJBi10
OPrM7g7v2p/boWL2gr29m20hxkOv2TYvYNLS27N4Bx3u0pmha4LwpmeLupOlVshQPlL1
OrEFCYqa92s4goJSun31OuzKK18r4qivvHpk/9Ntln76mE9oAj/66Zti/9DULljXm9tQ
bRs+QTgu7SqFc8qAQ/rZ80otgaIOmihI6K3Eh+UeeeRl//T33Y1udZXCtz3tc1b9RoeS
mjTw==
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
h=user-agent:message-id:subject:to:from:date
:content-transfer-encoding:mime-version:dkim-signature;
bh=IZzGk5hdbwv1XsfTE2Dngp1hMDfBwbnO3RaSFfeDt+k=;
b=VM37h+XoHJK20uNPocaVd4DkXTBDvFA2kSPWQbw0E9YVjKS12PcHLq4cbXaxj4zMsr
ZHW5jlLFkdfAl/x66rY7u8NozQy3jNMXWxgL5fEs7i5PP4G20icV4r4Wy0Vkf4IFKINp
0xN7ytoI2XnIyC6gKO1UAnqoAGjc/KYPfgdEmfYr8UBAHTwNXI4WmR4CJAkr8K1Q+i8Z
dCq9ZcpqBND40dPavJ6+cw5+RuD04pTN/Py4OY1pUbTdNPQ4aSsBMrgijvjtgwc5p2Mj
N9KYHo8a3bxruORfAhGXWuJa/uMRuJc8Drqd34i58YdXe0ws3551ZhXFAdIxB4K6gsAb
2GAg==
ARC-Authentication-Results: i=1; mx.google.com;
dkim=pass header.i=#naifersistemas.com.br header.s=default header.b=jZvGchWi;
spf=pass (google.com: domain of contato#naifersistemas.com.br designates 3.209.102.205 as permitted sender) smtp.mailfrom=contato#naifersistemas.com.br;
dmarc=pass (p=NONE sp=NONE dis=NONE) header.from=naifersistemas.com.br
Return-Path: <contato#naifersistemas.com.br>
Received: from naifersistemas.com.br (ec2-3-209-102-205.compute-1.amazonaws.com. [3.209.102.205])
by mx.google.com with ESMTPS id y27si3573136qth.174.2019.03.27.04.35.16
for <andreluismonteiro33#gmail.com>
(version=TLS1_2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
Wed, 27 Mar 2019 04:35:16 -0700 (PDT)
Received-SPF: pass (google.com: domain of contato#naifersistemas.com.br designates 3.209.102.205 as permitted sender) client-ip=3.209.102.205;
Authentication-Results: mx.google.com;
dkim=pass header.i=#naifersistemas.com.br header.s=default header.b=jZvGchWi;
spf=pass (google.com: domain of contato#naifersistemas.com.br designates 3.209.102.205 as permitted sender) smtp.mailfrom=contato#naifersistemas.com.br;
dmarc=pass (p=NONE sp=NONE dis=NONE) header.from=naifersistemas.com.br
Received: from webmail.naifersistemas.com.br (localhost.localdomain [IPv6:::1]) by naifersistemas.com.br (Postfix) with ESMTPSA id 8FECF8BFD0 for <andreluismonteiro33#gmail.com>; Wed, 27 Mar 2019 11:35:16 +0000 (UTC)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=naifersistemas.com.br; s=default; t=1553686516; bh=IZzGk5hdbwv1XsfTE2Dngp1hMDfBwbnO3RaSFfeDt+k=; l=7; h=From:To:Subject; b=jZvGchWishigWIDTPn07tRDJTCnWVyMo45TbK1VACsi2uqHNBhA38iJqKtQuxRKfG
QFAdtdy25lJONMIMkmMjL8A29wjkUN2Cg7kjgpbm6UP5QNqVKGIJYwoxRNtb5vd3da
Wi4M/PHk3P4vcjKKGfg4Cq1JPC/e4+6dLr0TqkZU=
MIME-Version: 1.0
Content-Type: text/plain; charset=US-ASCII; format=flowed
Content-Transfer-Encoding: 7bit
Date: Wed, 27 Mar 2019 08:35:16 -0300
From: "André Luis Monteiro" <contato#naifersistemas.com.br>
To: andreluismonteiro33#gmail.com
Subject: teste
Message-ID: <5b66270df1b5aebef561a898e2c8c4d3#naifersistemas.com.br>
X-Sender: contato#naifersistemas.com.br
User-Agent: Roundcube Webmail/1.3.6
teste
Here is my outlook reject message
This is the mail system at host naifersistemas.com.br.
I'm sorry to have to inform you that your message could not
be delivered to one or more recipients. It's attached below.
For further assistance, please send mail to postmaster.
If you do so, please include this problem report. You can
delete your own text from the attached returned message.
The mail system
<andre_luis_monteiro1998#hotmail.com>: host
hotmail-com.olc.protection.outlook.com[104.47.46.33] said: 550 5.7.1
Unfortunately, messages from [3.209.102.205] weren't sent. Please contact
your Internet service provider since part of their network is on our block
list (S3140). You can also refer your provider to
http://mail.live.com/mail/troubleshooting.aspx#errors.
[BN3NAM04FT044.eop-NAM04.prod.protection.outlook.com] (in reply to MAIL
FROM command)
Reporting-MTA: dns; naifersistemas.com.br
X-Postfix-Queue-ID: 8FC9A8BFD1
X-Postfix-Sender: rfc822; contato#naifersistemas.com.br
Arrival-Date: Wed, 27 Mar 2019 11:33:09 +0000 (UTC)
Final-Recipient: rfc822; andre_luis_monteiro1998#hotmail.com
Original-Recipient: rfc822;andre_luis_monteiro1998#hotmail.com
Action: failed
Status: 5.7.1
Remote-MTA: dns; hotmail-com.olc.protection.outlook.com
Diagnostic-Code: smtp; 550 5.7.1 Unfortunately, messages from [3.209.102.205]
weren't sent. Please contact your Internet service provider since part of
their network is on our block list (S3140). You can also refer your
provider to http://mail.live.com/mail/troubleshooting.aspx#errors.
[BN3NAM04FT044.eop-NAM04.prod.protection.outlook.com]
Assunto teste
De André Luis Monteiro
Para andre_luis_monteiro1998#hotmail.com
Data Hoje 08:33
teste
You can try couple of more thing:
1.Publish PTR for 3.209.102.205 to naifersistemas.com.br (or the value you're sending in EHLO) instead of ec2-3-209-102-205.compute-1.amazonaws.com.
Since this IP belongs to an Ec2 instance, Outlook may have blacklisted this (It does stupid things until you build the reputation).
https://support.microsoft.com/en-us/supportrequestform/8ad563e3-288e-2a61-8122-3ba03d6b8d75
You can see if you can whitelist the IP using above link.
With Gmail, try to add some good message body and test it again , you can use this to check the score:
https://www.mail-tester.com/
I am using Plesk (Onyx) in combination with external DNS.
I configured mail and everything seems to be ok, but I am not sure if my mail configuration is correct, because sometimes a DMARC-report states, that a SPF / DKIM verification did not pass.
My configs:
DNS-Records for domain - mydomain.com AND mail.mydomain.com (created the same dns entries twice, for mydomain.com and subdomain mail.mydomain.com, except MX-entry, which is only configured for mydomain.com):
Reverse DNS: 123.456.1.1 -> mail.mydomain.com
MX: mail.mydomain.com
SPF: v=spf1 +a +mx -all
_dmarc: v=DMARC1; p=none; pct=100; rua=mailto:mailerror#mydomain.com; ruf=mailto:mailerror#mydomain.com; fo=1; adkim=s; aspf=r
domainkey: o=-
default._domainkey: v=DKIM1; p=SIGNATUREHERE;
PLESK/Server related:
Hostname: zeus.mydomain.com
Mailname: mail.mydomain.com
Mail-headers of test mail:
Delivered-To: test-email#gmail.com
Received: by 10.31.48.86 with SMTP id w83csp1454833vkw;
Fri, 6 Oct 2017 01:39:44 -0700 (PDT)
X-Google-Smtp-Source: AOwi7QAKFeawe3fGhxawUkAdVvaqjrBGMTZvJ466CoQNxwFGRk6xInOapHBRt14rI+zpCQmcl4z4
X-Received: by 10.223.184.246 with SMTP id c51mr1352887wrg.250.1507279184077;
Fri, 06 Oct 2017 01:39:44 -0700 (PDT)
ARC-Seal: i=1; a=rsa-sha256; t=1507279184; cv=none;
d=google.com; s=arc-20160816;
b=SignatureHERE
ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
h=content-transfer-encoding:mime-version:subject:to:from:date
:dkim-signature:message-id:arc-authentication-results;
bh=4lLj3bndoJBX1fsz99dGcUZLZyWwVlQLXwB3uGl3sKs=;
b=SignatureHERE
ARC-Authentication-Results: i=1; mx.google.com;
dkim=pass header.i=#mydomain.com header.s=default header.b=RUVEDlBN;
spf=pass (google.com: domain of info#mydomain.com designates 123.456.1.1 as permitted sender) smtp.mailfrom=info#mydomain.com;
dmarc=pass (p=NONE sp=NONE dis=NONE) header.from=mydomain.com
Return-Path: <info#mydomain.com>
Received: from mail.mydomain.com (mail.mydomain.com. [123.456.1.1])
by mx.google.com with ESMTPS id k10si874730wrg.550.2017.10.06.01.39.43
for <test-email#gmail.com>
(version=TLS1_2 cipher=ECDHE-RSA-AES128-GCM-SHA256 bits=128/128);
Fri, 06 Oct 2017 01:39:44 -0700 (PDT)
Received-SPF: pass (google.com: domain of info#mydomain.com designates 123.456.1.1 as permitted sender) client-ip=123.456.1.1;
Authentication-Results: mx.google.com;
dkim=pass header.i=#mydomain.com header.s=default header.b=RUVEDlBN;
spf=pass (google.com: domain of info#mydomain.com designates 123.456.1.1 as permitted sender) smtp.mailfrom=info#mydomain.com;
dmarc=pass (p=NONE sp=NONE dis=NONE) header.from=mydomain.com
Message-Id: <59d74150.0ac7df0a.a9cd2.2856SMTPIN_ADDED_MISSING#mx.google.com>
Received: from mydomain.com (unknown [188.93.221.133]) by mail.mydomain.com (Postfix) with ESMTPSA id 6821B3C00CF for <test-email#gmail.com>; Fri,
6 Oct 2017 10:39:43 +0200 (CEST)
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=mydomain.com; s=default; t=1507279183; bh=4lLj3bndoJBX1fsz99dGcUZLZyWwVlQLXwB3uGl3sKs=; l=26539; h=From:To:Subject; b=RUVEDlBNkO7PgHEEmuAlCSgG+batl5Ple/8O94GKLu7StZJLLa01k4rbjlnKX+3R9
mWt8+kOAPthM6lro4Z23B7LMk2ueWDpkFJZX3zRnOUC9E7LiIIQXNz83s8N640T6e7
7a4nFVAWgS9bIu/+TyyInPHOsnbe0/IKZKAyJw9k=
Authentication-Results: zeus.mydomain.com;
spf=pass (sender IP is 188.93.221.133) smtp.mailfrom=info#mydomain.com smtp.helo=mydomain.com
Received-SPF: pass (zeus.mydomain.com: connection is authenticated)
Date: Fri, 06 Oct 2017 10:39:43 +0200
From: MyDomain <info#mydomain.com>
To: test-email#gmail.com
Subject: mydomain.com: Test Subject
MIME-Version: 1.0
Content-Type: text/html; charset="utf-8"
Content-Transfer-Encoding: quoted-printable
What do I have to change, if I want to use f. e. "info#mydomain.com" as from-address/sender address? Do I need to change the mailname to"mydomain.com"? Can I safely delete DNS entries for mail.mydomain.com, if I change mailname to "mydomain.com"? Is there a way to configure the mailname in PLESK/make sure PLESK does not overwrite it, if a new update/upgrade is made?
EDIT: Test of unlocktheinbox: https://www.unlocktheinbox.com/mail-tester/9YBYhi8wpqo=/
#mfuesslin,
You should run your email through this email tester, it's recognized as the #1 email authentication and configuration testing platform. All you have to do is send an email to mailtest#unlocktheinbox.com and it will auto-respond in minutes.
Once you get the results and if you need help fixing any of the items it points you, everyone will be able to help you more because it's more specific.
mydomain.com is the from domain you're using, right? You should make sure to have SPF, DKIM, and perhaps DMARC with domain alignment with the envelope from.
As a side note, is this all that's in your SPF record? What services do you want to be able to send email out on your behalf? Why not get more specific?
v=spf1 +a +mx -all
We've configured SPF, DKIM and DMARC records for our domain and they're working fine. Our DMARC reports from Gmail, Hotmail, Yahoo also confirm the same.
However, just last week, one of our (Gmail) users brought to our attention a fraudulent email sent from a spoofed email address on our domain.
After looking at the email headers, we realised Gmail didn't initiate a DMARC check at all and the email landed in user's inbox. Gmail had only performed an SPF check which had passed because the check was performed on the envelop FROM header domain.
The email header (with identifying details redacted) looked like the following:
Delivered-To: redacted#gmail.com
Received: by 10.28.167.23 with SMTP id q23csp326872wme;
Mon, 20 Feb 2017 23:53:04 -0800 (PST)
X-Received: by 10.36.147.1 with SMTP id y1mr22192213itd.34.1487663583976;
Mon, 20 Feb 2017 23:53:03 -0800 (PST)
Return-Path: <redacted#fraudulentdomain.net>
Received: from server2.fraudulentdomain.net (server2.fraudulentdomain.net. [144.X.Y.Z])
by mx.google.com with ESMTP id i196si19658513ioi.78.2017.02.20.23.53.03
for <redacted#gmail.com>;
Mon, 20 Feb 2017 23:53:03 -0800 (PST)
Received-SPF: pass (google.com: domain of redacted#fraudulentdomain.net designates 144.X.Y.Z as permitted sender) client-ip=144.X.Y.Z;
Authentication-Results: mx.google.com;
spf=pass (google.com: domain of redacted#fraudulentdomain.net designates 144.X.Y.Z as permitted sender) smtp.mailfrom=redacted#fraudulentdomain.net
Received: by server2.fraudulentdomain.net (Postfix, from userid 330)
id 385716C165; Tue, 21 Feb 2017 08:53:03 +0100 (CET)
To: redacted#gmail.com
Subject: Some Subject
From: My Service <spoofed#mydomain.com>,
"MIME-Version:1.0"#server2.fraudulentdomain.net
Content-type: text/html; charset=iso-8859-1
Message-Id: <20170221075303.385716C165#server2.fraudulentdomain.net>
Date: Tue, 21 Feb 2017 08:53:03 +0100 (CET)
Why did Gmail not initiate a DMARC check and just performed an SPF check? Is it got to do something with the Display FROM header having 2 values?
That's a bug, I reported it to Google, they have fixed it now.
My website, all written in PHP, has an automatic system to notify users via email. Everything worked perfectly until i moved everything on a new less expensive dedicated server (new IP, also). Now, from the new server, all the emails are sent to the spam folder. Why? What happened? Gmail says it's marked as spam because it violates these guidelines about the sender. Here is the message header of one of the emails
Delivered-To: fontanavideostudios#gmail.com
Received: by 10.64.224.200 with SMTP id re8csp1701580iec;
Sun, 1 Feb 2015 07:30:19 -0800 (PST)
X-Received: by 10.140.22.5 with SMTP id 5mr1380826qgm.72.1422804619177;
Sun, 01 Feb 2015 07:30:19 -0800 (PST)
Return-Path: <noreply#racebooking.net>
Received: from ns362512.ip-91-121-174.eu ([2001:41d0:1:ef28::1])
by mx.google.com with ESMTP id e3si21772874qaf.113.2015.02.01.07.30.18
for <fontanavideostudios#gmail.com>;
Sun, 01 Feb 2015 07:30:19 -0800 (PST)
Received-SPF: none (google.com: noreply#racebooking.net does not designate permitted sender hosts) client-ip=2001:41d0:1:ef28::1;
Authentication-Results: mx.google.com;
spf=none (google.com: noreply#racebooking.net does not designate permitted sender hosts) smtp.mail=noreply#racebooking.net
Received: by ns362512.ip-91-121-174.eu (Postfix, from userid 504)
id DFE0916074; Sun, 1 Feb 2015 16:28:52 +0100 (CET)
To: fontanavideostudios#gmail.com
Subject: Qualcuno ha commentato il tuo post
X-PHP-Originating-Script: 504:new_notification.php
From: Racebooking <noreply#racebooking.net>
Reply-To: no-reply
MIME-Version: 1.0
Content-Type: text/plain; charset=utf-8
Message-Id: <20150201152852.DFE0916074#ns362512.ip-91-121-174.eu>
Date: Sun, 1 Feb 2015 16:28:52 +0100 (CET)
The domain, racebooking.net, has a good reputation and MX, mail, smtp point to the same ip: 91.121.174.40 which is the same IP of racebooking.net (here is a test)
Any idea?
Check this line in the header:
Received-SPF: none (google.com: noreply#racebooking.net does not designate permitted sender hosts) client-ip=2001:41d0:1:ef28::1;
Authentication-Results: mx.google.com;
spf=none (google.com: noreply#racebooking.net does not designate permitted sender hosts) smtp.mail=noreply#racebooking.net
I think you have not correctly configured the SPF entries in your DNS.
See this Google Products thread about this: https://productforums.google.com/forum/#!topic/apps/nvGcYDjONfc
I can see that you have no SPF entries defined for "racebooking.net":
$ dig +short racebooking.net txt
"1|www.racebooking.net"
You need to define an SPF entry like:
"v=spf1 mx a:mail0.racebooking.net -all"
You also need to include any other host from which you might be sending email (ie web applications sending email from #racebooking.net).
More info about what SPF is: http://en.wikipedia.org/wiki/Sender_Policy_Framework
We have an application sending mail with reply-to addresses in the form of NNN#email.example.com. The mail is sent via Sendgrid and replies are parsed using Sendgrid's Parse API. The problem is some email doesn't get back to us because the reply-to address has been changed to NNN#sendgrid.net. Sendgrid support says they never touch the reply-to and we've confirmed by a Gmail logging account that our application sends mail out correctly. So that leaves me suspecting certain mail servers are switching the domain name with that of the MX host. Our MX records for email.example.com are:
mx3.sendgrid.net 20
mx4.sendgrid.net 20
mx5.sendgrid.net 20
mx.sendgrid.net 10
mx2.sendgrid.net 20
Are there any mail servers or clients that are known to modify reply-to addresses? Or is there any other possible explanation?
Edit Headers from an email send by our app and logged with a Gmail account (sanitized to remove client information):
Delivered-To: logger#company.com
Received: by 10.112.62.41 with SMTP id v9csp143404lbr;
Tue, 31 Jul 2012 04:25:29 -0700 (PDT)
Received: by 10.182.51.37 with SMTP id h5mr22717342obo.35.1343733928944;
Tue, 31 Jul 2012 04:25:28 -0700 (PDT)
Return-Path: <Editors#domain.com>
Received: from o1.email.domain.com (o1.email.domain.com. [208.117.48.105])
by mx.google.com with SMTP id m6si10752851oec.6.2012.07.31.04.25.27;
Tue, 31 Jul 2012 04:25:28 -0700 (PDT)
Received-SPF: pass (google.com: domain of Editors#domain.com designates 208.117.48.105 as permitted sender) client-ip=208.117.48.105;
Authentication-Results: mx.google.com; spf=pass (google.com: domain of Editors#domain.com designates 208.117.48.105 as permitted sender) smtp.mail=Editors#domain.com; dkim=pass header.i=#Domain.com
DKIM-Signature: v=1; a=rsa-sha1; c=relaxed; d=Domain.com; h=date
:from:reply-to:to:message-id:subject:mime-version:content-type
:content-transfer-encoding; s=smtpapi; bh=+VZlU9LWGUpMR4neAk/JMo
1DD2E=; b=T3Be3k1Gp+shIGgQZPJ1vtx1kUCRMCRAqRgf8LxVUdvQ1/7YWRKnls
+zrXi6dhJXaLrEyVmt7MyYgxvkVvnJqWYy4tAQABtANQHdLSle4AK1+BY+/m2h4E
fj91rMgQySNbrVV+mhaiE5Q7NxvIa35azUUO0/zRYpluDUt6UBEcQ=
Received: by 10.16.69.117 with SMTP id mf20.27729.5017C0A66
Tue, 31 Jul 2012 06:25:26 -0500 (CDT)
Received: from email.domain.com (unknown [10.60.208.17])
by mi15 (SG) with ESMTP id 5017c0a6.202a.a5e396
Tue, 31 Jul 2012 06:25:26 -0500 (CST)
Date: Tue, 31 Jul 2012 07:25:25 -0400
From: Editors <Editors#domain.com>
Reply-To: 5005#email.domain.com,
Editors <Editors#domain.com>
To: user#example.com
Message-ID: <5017c0a5d4365_e294729d8c86360#app02.manuscripts.domain.com.mail>
Subject: Invitation
Mime-Version: 1.0
Content-Type: text/html;
charset=UTF-8
Content-Transfer-Encoding: 7bit
X-Sendgrid-EID: lcSu+eeYyj7byVT4rUR8IwFlWv7xwmQ9mjigbpHftFWQeg+HlxpNd7F1nbL2uoqLRAg4sHwj57Rrx78FZhDo2L2DCVfamQm0+wEFzkMnensGOv19JFRIAeDMZY53SVpKMwm4Klqcm6L6s9+UaFtqnRUE3/jexZ6uJAFc5x57JG4=
So you see the reply-to is set properly in these headers, but when the recipient replied we saw the reply-to address change to 5005#sendgrid.net.
We have the exact same issue. I'm no Exhange guru so I can't validate this - but I'm willing to bet the company you are sending mail to has a configuration flag that states to NOT use a 'reply to' command. Our application sends out as ourcompany#appmail.com with the reply to address set to user#mycompany.com. I can test with gmail and yahoo and it works great!
But certain companies we email always come back t the 'ourcompany#appmail.com' address as if there was no reply to set. Think about all the junk mail you get where the reply address is your own email address. I can only imagine MS and Novell have flags to force replies to the actual sender.
Now if we could just get clarification from a real expert as to whether or not this flag is out there.