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We have seen this too much in multiple Exchange environments, and need some guidance.

When we email (using simple mail client app) to certain Exchange/Outlook sites, when those sites hit Reply, our email address is mangled, resulting in the reply not getting to us.

It seems to relate to sites running very new Outlook on top of exchange.

Concretely: email is from: But when they hit reply in Outlook, the email is addressed to: sam@

I have examined the mail headers from our mail application closely, and they look fine. (copied below)

What setting in Outlook or Exchange might cause this?

Is there a known fix or solution? (No, we are not switching to Outlook!)

Thank you!

Received: by with SMTP id bw2csp36678ved;
        Thu, 30 Jan 2014 08:39:10 -0800 (PST)
X-Received: by with SMTP id x3mr12306656oec.15.1391099949521;
        Thu, 30 Jan 2014 08:39:09 -0800 (PST)
Return-Path: <>
Received: from ( [])
        by with ESMTPS id v5si3209905oep.7.2014.
        for <>
        (version=TLSv1 cipher=RC4-SHA bits=128/128);
        Thu, 30 Jan 2014 08:39:08 -0800 (PST)
Received-SPF: pass ( domain of designates as permitted sender) client-ip=;
       spf=pass ( domain of designates as permitted sender)
Received: from localhost (localhost.localdomain [])
    by (SMTP Server) with ESMTP id D418A1B81EA
    for <>; Thu, 30 Jan 2014 11:39:07 -0500 (EST)
X-Virus-Scanned: OK
Received: by (Authenticated sender: with ESMTPSA id 8335C1B81C0
    for <>; Thu, 30 Jan 2014 11:39:07 -0500 (EST)
Date: Thu, 30 Jan 2014 08:39:08 -0800
From: Sam Demo <>
Subject: test
To: Sam Demo <>
Mime-Version: 1.0
Organization: Roofers Statewide LLC, (310) 312-8844
Content-Type: text/plain
Content-Transfer-Encoding: quoted-printable
share|improve this question
Never seen this one, but things to try. 1) get the header info from the recipient that actually has the issue (unless you are saying your gmail above had the issue too). 2) Does a reply from that same person work fine if they use OWA instead of an actual Outlook client when replying to you? Or if they use their smartphone? – TheCleaner Jan 30 '14 at 17:14
@TheCleaner great suggestion. I will try to get header from the recipients (not easy). Will try to see how those other questions pan out. – samsmith Jan 30 '14 at 18:05

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