Probs with OS X Mail App

March 3, 2006 8:59 AM

This is driving my family bonkers: Mom is on OS X (Tiger) using Mail APP. Mom sends X an email. X replies to email. X's reply comes back to X. (ie, My mom's emails substitute the email address of the person she's emailing in the reply-to field.)

This doesn't matter who she is mailing or which account she's mailing from (her ISP account or her own domain). It also doesn't matter which ISP she uses (she's switched, thinking the prob was with one of them).

I've searched through Mail App for a possible switch or field regarding the reply to variable. Found nothing. This has been going on for six months and I'm ready to throw the computer out the window.

posted by dobbs to computers & internet (21 comments total)

Dobbs, have you looked at the headers? Is this actually inserting a reply-to: header line?

I've been using mail.app for years, and have never run into anything like this. Weird.
posted by alms at 9:37 AM on March 3, 2006

Is her email account through gmail by any chance? its reply / cc of reply behaviors for pop are kind of weird by default, but not exactly what you are describing.
posted by luriete at 9:41 AM on March 3, 2006

This page provides a set of terminal commands to examine/change the default mail headers.
posted by bachelor#3 at 9:43 AM on March 3, 2006

When you say "X's reply comes back to X," do you mean it *bounces* (with all the bounce header info), or that it seems to be a normal email received by X?

My theory, based on your little information, is that your mom's email address is input wrongly and that mail sent back to her is simply bouncing.

To see if this is the case, in Preferences go to Accounts, click on the account, and TRIPLE-check that the address in the "Email Address" field is correct. Best way to do it is to highlight it, delete it, and re-enter it.

Other questions:

--What happens to mail your mom sends to herself?

--What does the "reply-to" field show of messages your mom sends you?

--Do you have a sample of the mail received by people after they try to reply to your mom's messages?

--Can you share headers from several messages?
posted by Mo Nickels at 9:49 AM on March 3, 2006

(Of course, switching addresses and ISPs should mean my theory doesn't hold water, but I would still check if I were you. Also, seeing the headers is really, really important to solving this problem. Any chance you can send me an email from your mom's account?)
posted by Mo Nickels at 9:51 AM on March 3, 2006

One other thing: your mom can set what the reply-to is before sending.

Open a new message. At the left is a little icon that looks like three parallel, horizontal lines with a downward-pointing triangle. Click on it. You should see an option for "Reply-To Address Field." Selecting it will put a check next to it and add a blank reply-to field to the fields at the top of that message and all subsequent messages.
posted by Mo Nickels at 9:54 AM on March 3, 2006

Thanks, all.

Okay, some more explanation:

No, I didn't mean it bounces. It actually gets sent to whoever's sending it. In addition, when I hit reply to one of her messages, I SEE my own address in the TO field before I hit send. So, I'm aware of it and can change the TO field, but it's a nightmare for new correspondances.

It is not a gmail account that's in question.

Open a new message. At the left is a little icon that looks like three parallel, horizontal lines with a downward-pointing triangle.

Mo, is there a way to set this as a default?

I don't know much aboout headers, but here's everything:

From: [e-mail]
Subject: Fwd: webstuff
Date: March 1, 2006 4:59:33 PM EST (CA)
To: [e-mail]
Reply-To: [e-mail]
Return-Path:
X-Original-To: [e-mail]
Delivered-To: [e-mail]
Received: from BAYC1-PASMTP06.BAYC1.HOTMAIL.COM (bayc1-pasmtp06.bayc1.hotmail.com [65.54.191.166]) by worm.dreamhost.com (Postfix) with ESMTP id 2A97A14D862 for ; Wed, 1 Mar 2006 13:59:27 -0800 (PST)
Received: from [64.228.1.112] ([64.228.1.112]) by BAYC1-PASMTP06.BAYC1.HOTMAIL.COM over TLS secured channel with Microsoft SMTPSVC(6.0.3790.1830); Wed, 1 Mar 2006 14:00:32 -0800
Message-Id:
Message-Id:
X-Originating-Ip: [64.228.1.112]
X-Originating-Email: [[e-mail]]
Mime-Version: 1.0 (Apple Message framework v746.2)
References:
Content-Type: multipart/alternative; boundary=Apple-Mail-5--265583878
X-Mailer: Apple Mail (2.746.2)
X-Originalarrivaltime: 01 Mar 2006 22:00:34.0296 (UTC) FILETIME=[909A9780:01C63D7B]
posted by dobbs at 11:10 AM on March 3, 2006

arrgh. Crap, I meant to change my mom's email address in the X-Originating-Email: line to [e-mail]. Crap crap.
posted by dobbs at 11:11 AM on March 3, 2006

And why the hell is hotmail mentioned in the headers? Neither of us has a hotmail account.
posted by dobbs at 11:13 AM on March 3, 2006

I know nothing about Mail.app, but I know people using computers. After reading Mo Nickels' message and dobbs' headers, here's what I think is happening:

Every time your mother goes to send a message, she is filling out both the To: and Reply-To: fields with the recipient's email address. Because she thinks she has to. (Her reply is going to [e-mail], so she fills out the Reply-To: with [e-mail]....)

Walk her through her process of sending an email, or stand over her shoulder when she does it.

As to why Hotmail, check the SMTP settings of Mail.app and make sure they are for her current ISP and email account.
posted by jellicle at 11:53 AM on March 3, 2006

Mo, is there a way to set this as a default?

Just selecting it for a single new message will make the Reply-To field appear for all subsequent new messages.

Do this: look in this folder

/Users/usernamehere/Library/Mail/Bundles/

and see if your mom has any Mail.app bundles (which add features). Is it possible you have a version of the "httpmail plugin" which permits accessing Hotmail from within Mail.app? If so, try disabling it and see if that helps.

Also, double-check your mom's Outgoing Mail Server (SMTP) settings in her accounts. Click on the "server settings" button there and see what's being used. If it's an IP address and not a host name, see if it matches any in the headers above--or better, do a nslookup on it to see who it belongs to. (You can also just go to Arin an use the "search WHOIS" field to look up any IP address.)

In any case, double-check with your mom's ISP to see what the correct STMP server should be and see if it matches what you have. I think it should be "smtp.sympatico.ca," based on the IP address given above.

(Email Jessamyn about your mom's email address being in the clear above.)
posted by Mo Nickels at 11:57 AM on March 3, 2006

Every time your mother goes to send a message, she is filling out both the To: and Reply-To: fields

The Reply-To field is not usually visible. It sounds as if it is not currently visible to Dobbs's mom.

Dobbs: what happens if you set her account up in a completely different program, just as a test?
posted by Mo Nickels at 12:00 PM on March 3, 2006

Oh, duh! Sympatico is an MSN service--that's why it has Hotmail host names in the mail headers.
posted by Mo Nickels at 12:02 PM on March 3, 2006

jellicle, thanks, but that can't be it. The reply-to thing that mo mentioned is kind of hidden (I've been using mail app for years and have never seen it before). I don't think she's doing that but I will check tomorrow when I see her. If it's this, I'm going to be pissed. :)

Also, I'm positive her incoming and outgoing mail servers are set to the right things (no hotmail) as I set them up with her over the phone.

My mom is extremely computer illiterate and would only enter what I tell her to enter--she doesn't know what any of the pref fields are or do and probably hasn't even heard of hotmail.

Mo, I'm not at her house now but will be tomorrow so will check some of this stuff. However, I doubt she has a hotmail plugin thing as I set up the computer (from scratch) for her.

And yes, symptico is the isp and those settings are correct.

I am very familiar with my own mail stuff and for her own domain, I am sure all the settings are correct as I've set up dozens of email programs for clients.

Dobbs: what happens if you set her account up in a completely different program, just as a test?

I haven't tried this yet. I suppose I could bring up entourage (my mom lives in another city) and try.
posted by dobbs at 12:04 PM on March 3, 2006

Unfortunately, the Sympatico web site stupidly requires a Sympatico email address before accessing help so I can't verify the SMTP address.
posted by Mo Nickels at 12:05 PM on March 3, 2006

Here's another header from an email direct from her domain (not sympatico account) to my domain:

From: [e-mail]
Subject: test
Date: February 13, 2006 5:07:23 PM EST (CA)
To: [e-mail]
Reply-To: [e-mail]
Return-Path:
X-Original-To: [e-mail]
Delivered-To: [e-mail]
Received: from [216.209.15.73] (unknown [216.209.15.73]) by toby.dreamhost.com (Postfix) with ESMTP id D207615E64A for ; Mon, 13 Feb 2006 14:07:28 -0800 (PST)
Mime-Version: 1.0 (Apple Message framework v746.2)
Content-Type: text/plain; charset=US-ASCII; format=flowed
Message-Id: <1 [e-mail]>
Content-Transfer-Encoding: 7bit
X-Mailer: Apple Mail (2.746.2)
posted by dobbs at 12:07 PM on March 3, 2006

To test, just download the demo of Gyaz or simply log into another OS X user account and setup Mail.app from scratch.

Also, this sounds like a good use for Bosco's screen share. I've used it before. It's basically VNC, but it makes it very, very easy to use for at least one of the users.
posted by Mo Nickels at 12:09 PM on March 3, 2006

Interesting! Return-Path shouldn't be empty, and WTF with your address in the Reply-To field?

Drastic but guaranteed solution: backup all of your mom's mail to another folder. Delete all Mail.app prefs and folders--ALL of it--except the backed-up mail. Re-setup Mail.app from a virgin state. Reimport the backed up mail. All done.

You could also fool with the stuff on bachelor#3's link, but the original hint is several years old.
posted by Mo Nickels at 12:15 PM on March 3, 2006

Yeah, I'll have to go that route, probably. What a pain in the ass. It's such a bizarre issue.

Thanks everyone for help! I will check back here tomorrow from my mom's place to see if there are any more solutions.
posted by dobbs at 12:39 PM on March 3, 2006

I'm not sure if this is related, but I had this same problem on a Windows 2000 machine with Outlook 2003 on an Exchange 5.5 server. If I clicked "Reply to All" on any email received from someone not on the Exchange server (someone outside of the company), my email address would be added to the To: field and I would get a copy of it delivered to my inbox. I figured that it was just some strange quirk with Outlook 2003, and never bothered looking it up.

I just got in the habit of removing my address when replying. Are the people who respond to yermoM's email messages all on OSX using Mail, or are some of them on Windows using Outlook Express or Outlook?
posted by Jim T at 12:51 PM on March 3, 2006

Jim, my family is all on Mac. All her friends are on Windows (not sure particulars), but it happens to anyone she mails.
posted by dobbs at 1:58 PM on March 3, 2006