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?

O.K., so you send with Outlook through Hotmail and the message goes through fine?

Who hosts your microplay.ca account?

Sorry, my last post might have been confusing. The test email to a microplay.ca address from my hotmail account using Outlook did NOT go through. So there still seems to be a problem with outlook...?

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?