Hello:

I have been receiving a "mailer-daemon" reply when I try to send emails to addresses ending in a specific domain (in this case it is 'microplay.ca'). The error message is this:

Hi. This is the qmail-send program at yahoo.com.


I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.

<******@microplay.ca>note: I edited address for privacy)
Connected to 207.96.250.22 but connection died. Possible duplicate! (#4.4.2) I'm not going to try again; this message has been in the queue too long

The domain name is related to my business. I have spoken both with my Head Office and also with my provider (Rogers), and both believe the problem lies with outlook. I can send email to addresses ending in microplay.ca if I use Rogers web mail. I have tried using Outlook 2007 on a laptop I own, and it will not send to microplay.ca either. All other email seems to work fine. However, I can receive mail from microplay.ca addresses; I just can't send it to them. I am at a loss on how to proceed. How can one single domain mess things up? It worked fine for years and then just stopped.

You're trying to send through a Yahoo account? Can you log into Yahoo's web interface and try to send the message from there? Perhaps your microplay.ca server is bouncing Yahoo mail?

Thanks for commenting. It appears that all my mail is routed through 'yahoo'; that is how Rogers mail seems to be set up. But my mail goes through fine if I'm use Rogers web mail, so it can be a rejection from Yahoo. That is how Rogers determined that it must be Outlook, because the mail goes through fine when I use webmail instead of outlook.

It takes about a day for the rejected message to get returned to me. It stays 'in the queue' a long time. I really hate the thought of abandoning Outlook because of this, but I'm running out of ideas to try.

Any other thoughts or information I can provide to troubleshoot this?

Wait...so Rogers Mail is sending THEIR mail through Yahoo? That's sort of odd - they don't have their own servers?

Rogers/Yahoo are joint companies, at least here in Canada. Google Roger/yahoo and you will see. Anyway, I have been advised by Rogers that the problem does not lie with them. Perhaps they are mistaken, but as I stated previously, both my own IT dept as well as Rogers think the problem must lie in Outlook.

Well I just tried using another email client (Post Office 2) and lo and behold it does not send email to microplay.ca either. So I think either Rogers or HO is mistaken after all; perhaps the problem is not Outlook after all.

Do you have any other e-mail accounts - like maybe a GMail account?

If not, maybe you could get one, just for testing purposes - with any ISP *OTHER* than Rogers/Yahoo. Then set Outlook to use that new ISP for sending mail and see if you can send to your microplay.ca account.

Good idea...i have a hotmail account which I just added to Outlook. I sent a test email to a microplay.ca address along with another rogers.com address of my own. I got the test email back on my rogers.com address, but the microplay.ca one did not go thru. I tried it from Windows live and I CAN email to microplay.ca. Very confusing. Any more light?

Are you using SMTP to send through Hotmail?

Not sure it would help, but it probably won't hurt. Try scanning your PST file for errors. See if this helps: http://www.officeforlawyers.com/outl...ol.htm#SCANPST

It looks like I'm using MAPI for the hotmail account, not SMTP. And coincidently, I did do a PST scan just last weekend. Outlook had encountered errors and wouldn't work it all (this had never happened before), so I ran SCANPST and it fixed things.

Oh, you have the Hotmail Connector installed. O.K. When SCANPST fixes errors you need to make sure and run it again (and again maybe) until it comes back clean. Sometimes it requires multiple passes to completely clean the PST file.

I re-ran the SCANPST fix several times, and you were correct, it took about 3 times before a zero error report came back. I tried emailing again but it did not seem to work. I thought I'd mention a detail that might not be significant at all, but it just occured to me that all the email addresses affected are store numbers, ie the email address all in the form 00854@microplay.ca. Is it possible that some filter does not like email addresses that begin with numbers? Just a thought.....I'm still scratchin my head...

Interesting question. Do you have an e-mail address there that does NOT start with numbers? Maybe "postmaster@"?

Also, who hosts your microplay.ca server? Is that Rogers also or do you have a 3rd party hosting?

I'm not sure if there are any addresses without numbers. I will check into that furher. Below I've included part of the header for a successful email using webmail, and below that an example of a problem one using an email client. The key must be in there somewhere...What does webmail do differently? Thanks again for your help....

Part of the header to a successful email to microplay.ca domain using webmail:

X-Apparently-To: encoregames@rogers.com via 206.190.37.189; Thu, 10 Feb 2011 14:36:08 -0800
X-YahooFilteredBulk: 207.96.250.22
Received-SPF: none (mta1012.rog.mail.sp1.yahoo.com: domain of 00749@microplay.ca does not designate permitted sender hosts)
X-YMailISG: Bz6D_TccZArZd3X6XCs8b8RhI64QCj8OTDQdRUzOKDvqrNKW
bd0F9ETuvwXgDGP72HDu6uc7gfyX7x2IBUgIbRKzVJUZjzDzkw p7eCtSOr25
8j6VtnhTY4Cii_uCCdU.gKTpoOpYrZB3zITmBAdY4kYD85mK2W nSV80G8M3C
pfAceN1.fdHhVpYV1xwX.b0j_ahV0bAeUc_NZS7XRDu0FCiTZU oPsG04PTfr
YwXJJz.Gd3m0Li9UflaLz60f.NkycqTbczezHTpCxqa0N1Yzjh _H7qG_Ssyg
EqSpOGkao8sh_ghHr08oTloBSN4FaG6PK3nxgdOIYjG_nSuaVJ iUtr1HBJHQ
2xbEvJ8Pt5ypMcl.F81g.ILeKIjRrTrOd5z3p74E2JBXmeYnr8 C3ZEtKdhjZ
sh6jXqIWc3nv7WRYdXzJ6ABq4AM4A6j_ZWMMNIxYUwt_gfKirI tA14TJJqr3
4FOovSpsOPEENpDief97SsjaqJ186iEfN68WSxe03Ko2vxejpk VVZOzE5w4h
ymo28F2InZhW1o5zq_ki585UVUs5z9EMpnS7ftZ7Rc0q4ILA_h j56RXzldTa
93A-
X-Originating-IP: [207.96.250.22]
Authentication-Results: mta1012.rog.mail.sp1.yahoo.com from=rogers.com; domainkeys=pass (ok); from=rogers.com; dkim=pass (ok)
Received: from 207.96.250.22 (EHLO mail.lesuperclub.ca) (207.96.250.22)
by mta1012.rog.mail.sp1.yahoo.com with SMTP; Thu, 10 Feb 2011 14:36:07 -0800

Part of header for problem email:

Hi. This is the qmail-send program at yahoo.com.
I'm afraid I wasn't able to deliver your message to the following addresses.
This is a permanent error; I've given up. Sorry it didn't work out.

<00750@microplay.ca>:
Connected to 207.96.250.22 but connection died. Possible duplicate! (#4.4.2) I'm not going to try again; this message has been in the queue too long.

--- Below this line is a copy of the message.

Return-Path: <encoregames@rogers.com>
Received: (qmail 76431 invoked from network); 9 Feb 2011 23:35:59 -0000
DomainKey-Signature: a=rsa-sha1; q=dns; c=nofws;
s=s1024; d=rogers.com;
h=DKIM-Signature:Received:X-Yahoo-SMTP:X-YMail-OSG:X-Yahoo-Newman-Property:From:To:Subjectate:Message-ID:MIME-Version:Content-Type:X-Mailer:Thread-Index:Content-Language;
b=0Eh/g4kmpZ3CVHfordOLmk9LXtSK4YPK0x5dk3anaSvak5E9IQv5Q7 O9ihddF9r76rthI3qgCqpZaN5z4tku3k7RmwEnao6peCXXkJ1o mPFChW/SzeRYtP+iWSm3ZMAdMGsMbNRjDkVsIHfm16epGR6teto54SrSs 7N3CjC2NVA= ;
DKIM-Signature: v=1; a=rsa-sha256; c=relaxed/relaxed; d=rogers.com; s=s1024; t=1297294559; bh=6yP1pKJ4JbMpIYfWH5PKknlQzGucXmkpPX2UllXROuk=; h=Received:X-Yahoo-SMTP:X-YMail-OSG:X-Yahoo-Newman-Property:From:To:Subjectate:Message-ID:MIME-Version:Content-Type:X-Mailer:Thread-Index:Content-Language; b=z4b3mnmjrE3vvHSQKpie9NVKx5eFk0qEET4/atGB5bsqFo90vofUx247NCejgWXaWBTmOzjgWbW9+nxaoUFZVO 0ro7A2VlZ9TeGOVP0sSvk/oznq5b0IY+yD2GQ9TzmSkV/M/pv4kKGRCo/OozUkX0rcYE7vGwIEvSACHV4zPak=
Received: from BrianInthofPC (encoregames@99.254.168.226 with login)
by smtp107.rog.mail.re2.yahoo.com with SMTP; 09 Feb 2011 15:35:56 -0800 PST
X-Yahoo-SMTP: cfGCsk2swBCPx347qTCdvaZ5FeTQjjnNMd_iC9TrxoLeJpI-
X-YMail-OSG: 7OkBWpsVM1n_8jIKTsr7wvWbZyhvbPeDtIBGVdJ5nbIPRfN
CaJX.JCIoPwhcFCmKG9MxW6Wpxuo1zfvoiEKtol2772CbfG5Ap q.k2A60VIO
h4ZAhnvcpyDrqQTQt3xGXa2ZVl7mjzTDmqRtU4tFegMiVh8TlW ylUWcK_1hn
.Zj2k6Kf1PUEOwzSmCjJOiU73URwE88txGLCdwD92s3J9eU6iQ ZpfmLibc8F
aV7w4gT20JQ--
X-Yahoo-Newman-Property: ymail-3
From: "Encore Games \(Microplay\)" <encoregames@rogers.com>
To: "'Microplay Kitchener'" <00750@microplay.ca>
Subject: test
Date: Wed, 9 Feb 2011 18:35:54 -0500
Message-ID: <000001cbc8b2$1872ed30$4958c790$@com>
MIME-Version: 1.0
Content-Type: multipart/alternative;
boundary="----=_NextPart_000_0001_01CBC888.2F9CE530"
X-Mailer: Microsoft Office Outlook 12.0
Thread-Index: AcvIshgdQC/mLmF+SxafYx1uM+99VQ==
Content-Language: en-ca

This is a multi-part message in MIME format.

------=_NextPart_000_0001_01CBC888.2F9CE530
Content-Type: text/plain;
charset="us-ascii"
Content-Transfer-Encoding: 7bit

A little hard to tell from those headers - and they apparently aren't complete - but it looks like it's actually your ISP (Superclub?) who is rejecting the message. Maybe their SMTP queues aren't configured correctly?

Also, who hosts your microplay.ca server? Is that Rogers also or do you have a 3rd party hosting?