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Outlook won't send to some addresses, message stays in Outbox

Posted on 2011-04-28
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Last Modified: 2012-05-11
Hi - we have a user who has a handful of people they cannot get an email to. The message sits in the outbox, and if there are multiple recipients on the message, the other recipients will receive the message, but those few will not. There is no error message generated, the message just sits in the outbox until the user deletes it. They have triple-checked that the addresses are correct, and there's never a bounce-back message. It happens regardless of how the address was entered - hand-typed, nickname file, or contact record.

We're using Outlook 2007 in cached mode with Exchange 2007. They're not Working Offline. This user's machine was recently upgraded to Windows 7 from XP, so it's a fresh install of Office 2007 and a recently rebuilt .ost file. I've spent hours googling this issue and can't find another example with the same parameters. Any help would be greatly appreciated.
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Question by:gtrapp
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LVL 18

Expert Comment

by:Netflo
ID: 35488552
Create a new profile and instead of cached mode make it online, try to send an email to those recipients if the problem does not happen create the user a new profile in cached mode and then try to send an email to those recipients.

Let me know how you get along
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Expert Comment

by:zazagor
ID: 35500188
Hi,

To me this looks like a grey-list/reverse-dns problem.

1) Check that your external-IP for the Exchange has revers DNS
2) Verify if the recipiants are using grey-lists.

//zazagor
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Expert Comment

by:Netflo
ID: 35500544
zazagor, your solution is incorrect. Once the message is submitted is leaves Outlook and Exchange would queue the message. The same would be for rDNS.

If it was a resisting issue the message would deliver after 5min (depending on the recipients mail server) and rDNS may cause an NDR or be placed in the recipients spam mailbox.

Nevertheless, try to avoid commenting on solutions unless you exactly how technology works and how it can help on a scenario like this.

Gtrapp have you tried my solution, let me know how you get on.
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Author Comment

by:gtrapp
ID: 35515037
We use group policy to set cached mode, so I may not be able to set the user's profile to online. However, we also use Citrix in online mode. Would test sending from Citrix work as well? I have not had a chance to reconnect with this user to test your solution yet, but thanks.
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Accepted Solution

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Netflo earned 1500 total points
ID: 35515072
Yes please try from Citrix as this will be on online mode, let me know how you get on.
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Author Comment

by:gtrapp
ID: 35517805
a little more information just came in - the user has at least 3 people at the same domain that she sends emails to. One of them receives her messages with no problem. Two of them just sit in her outbox and never go out. We will be trying to send from Citrix tomorrow.

thanks
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Author Comment

by:gtrapp
ID: 35708750
So when this user sent a message to one of the recipients using Citrix, she got a bounceback message from our exchange server that shows the email address (which she typed into the to: field, so it wasn't copied/pasted or added from a contact list) with extra information attached. Here's what it looks like:

IMCEAMAILTO-[UserfirstUserlast]+40[company]+2E[com]@[ourdomain].com
#550 5.4.4 ROUTING.NoNextHop; unable to route ##

the brackets and generalizations are mine. so somehow it's changing the address and appending the domain of our company onto it. if the user just typed the address "UserfirstUserlast@company.com" into her to: field, what would be causing Exchange 2007 to change it like this?
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LVL 18

Expert Comment

by:Netflo
ID: 35708899
I think we need to cover the basics here, is the Exchange 2007 box up to date?

You should be on SP3 rollup 3 v2
http://www.microsoft.com/downloads/en/details.aspx?FamilyID=17615f50-8a56-428c-bc1a-629795692da1&displaylang=en
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Author Comment

by:gtrapp
ID: 35725107
I'm not sure what service pack that server is on, I'll have to check. In the meantime, it would appear that there were messages sitting in the user's outbox on Citrix that finally sent when she logged on to Citrix for the first time. Not sure how they got stuck there, and the recipient was mighty confused when he got an email from December, but now it seems that the user can successfully send messages to all of the people she was having issues with. It's still a bit of a mystery, but seems to be resolved for the time being. Thanks for taking the time to help.
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Author Closing Comment

by:gtrapp
ID: 35725114
The issue wasn't really resolved, but the suggestion to try a non-cached version of Outlook was helpful.
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