Exchange 2007 pop connector smtp smart host outlook connection issues

pjnutt
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I am trying to install a new server using the pop connector and smtp smart host.  When I run retrieve now on the pop connector, it's errors out with the following information in the popconnector log:
[t 0] 07/05/10, 17:23:00: (SMTP) [RX] 554 5.1.0 Sender denied
[t 0] 07/05/10, 17:23:00: Failure hrResult (0x800ccc6f) trying to deliver message id 1:
[t 0] 07/05/10, 17:23:00: SMTPRESPONSE:    * * *   !Failed!   * * *
[t 0] 07/05/10, 17:23:00:                  * * *              * * *
[t 0] 07/05/10, 17:23:00:                  * * *  0x800ccc6f  * * *
[t 0] 07/05/10, 17:23:00:       Command: [SMTP_DOT]
[t 0] 07/05/10, 17:23:00:     Completed: Yes.
[t 0] 07/05/10, 17:23:00:     IxpResult:
[t 0] 07/05/10, 17:23:00:   ---> ---> --->  hrResult: 0x800ccc6f
[t 0] 07/05/10, 17:23:00:                pszResponse: 554 5.1.0 Sender denied
[t 0] 07/05/10, 17:23:00:              uiServerError: 554
[t 0] 07/05/10, 17:23:00:              dwSocketError: 0
[t 0] 07/05/10, 17:23:00:                pwszProblem: <none>
[t 0] 07/05/10, 17:23:00: Unfamiliar error delivering mail: 554
[t 0] 07/05/10, 17:23:00: Full response details:
[t 0] 07/05/10, 17:23:00: SMTPRESPONSE:    * * *   !Failed!   * * *
[t 0] 07/05/10, 17:23:00:                  * * *              * * *
[t 0] 07/05/10, 17:23:00:                  * * *  0x800ccc6f  * * *
[t 0] 07/05/10, 17:23:00:       Command: [SMTP_DOT]
[t 0] 07/05/10, 17:23:00:     Completed: Yes.
[t 0] 07/05/10, 17:23:00:     IxpResult:
[t 0] 07/05/10, 17:23:00:   ---> ---> --->  hrResult: 0x800ccc6f
[t 0] 07/05/10, 17:23:00:                pszResponse: 554 5.1.0 Sender denied
[t 0] 07/05/10, 17:23:00:              uiServerError: 554
[t 0] 07/05/10, 17:23:00:              dwSocketError: 0
[t 0] 07/05/10, 17:23:00:                pwszProblem: <none>
[t 0] 07/05/10, 17:23:00: (SMTP) [TX] QUIT
[t 0] 07/05/10, 17:23:00: (POP3) [TX] QUIT
[t 0] 07/05/10, 17:23:00: (SMTP) [RX] 221 2.0.0 Service closing transmission channel
[t 0] 07/05/10, 17:23:00: (AsyncConn[ localhost:25 ]) Connection to 'localhost' closed.
[t 0] 07/05/10, 17:23:00: EVENT: Because of transient or unknown failures, one or more messages (1) could not be delivered to 'DeAnn@XXX.com' on the SMTP server 'localhost'. The messages will be left on the POP3 server. If these failures continue to occur, you can either connect to the POP3 account and retrieve or delete the messages manually, or resolve the problem causing the errors. For more information, see the log file at "C:\Program Files\Windows Small Business Server\Logs\pop3connector\pop3service.log".
[t 0] 07/05/10, 17:23:00: (POP3) [RX] +OK server signing off.
[t 0] 07/05/10, 17:23:00: (AsyncConn[ pop.bizmail.yahoo.com:995 ]) Connection to 'pop.bizmail.yahoo.com' closed.

Also, I can connect my users to the exchange server, however; it doesn't appear as though it's maintaining a connection with the server.  When I launch outlook, it prompts for a user name and password to remote.mydomain.com.  I can cancel out and eventually send and receive e-mail, but something seems amiss.  The sending and receiving is intermittent and one of my users gets an error: The operation failed. An object cannot be found. error!

Any input would be great.

Thanks!
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Distinguished Expert 2018

Commented:
First, get your server up-to-date. That includes Exchagne service packs and rollups.
Second, run the entire set up internet setup wizards. They set up the external domain names that Exchange can accept, so right now it looks like Exchange is not aware of those.

Author

Commented:
Ok, I ran all the updates for the server OS.  I upgraded to SP2 for Exchange 2007.  Didn't change anything.  Do I need to have my own certificate purchased to run Exchange?  This client is converting from a workgroup to a nice new SBS server.  They thought they wanted to keep Yahoo as their e-mail provider, and seem reluctant to change.  I can get their e-mail from yahoo through the pop connector and configure smtp, those things seem to be working.  However, Outlook is not working at all with this configuration.  There HAS to be something I am missing.  Should I just convince them to host their own e-mail and purchase a certificate through godaddy for their domain?  Right now yahoo owns everything and they pay an annual fee to yahoo for e-mail and the domain.  As always, any help is appreciated!
Distinguished Expert 2018

Commented:
The official MS position (and one I agree with) is that the pop3 connector is a transitional device to help migrate businesses from hosted to in-house email. So yes, I would recommend planning a migration from yahoo to in-house migration plans as a long term strategy. An inexpensive SSL certificate could be part of that strategy if outlook, OWA, or activesync will be used for outside email access, but is not necessary at all if email is strictly accessed on the LAN.
With that said, none of that should impact how Outlook connects to Exchange The only thing that changes is that mail is no longer "pulled" from another server via pop3 first, but is delivered (pushed) to the exchange server directly. The data, once in exchange, is still stored the same way, and outlook connects to exchange the same way.
So now that pop3 is working, we should look at your oulook issues and resolve them.
Unfortunately your recent reply gives no indication of what errors you are seeing or what steps you've taken to troublehsoot.
Also, because we've solved the pop3 issue and that was the question raised, I'd recommend closing thsi problem (as pop3 now works) and anybody looking for a similar solution can easily see what worked for you wnad what didn't. Noew problems, such as outlook not working, should probably be asked as a new question, as some people familiar with Outlook may not be looking at this question due to its SBS/POP3 nature. Just some advice to get the most help possible.

Author

Commented:
I disagree.  POP works intermittently and I am still seeing the exact same errors in the pop3connector log that I was seeing before.  There has to be a configuration issue that needs to be addressed.

FWIW I didn't change anything other than running updates on the server and upgrading exchange to service pack 2.

Here's an excerpt from the system logs:
Because of transient or unknown failures, one or more messages (1) could not be delivered to 'DeAnn@XXX.com' on the SMTP server 'localhost'. The messages will be left on the POP3 server. If these failures continue to occur, you can either connect to the POP3 account and retrieve or delete the messages manually, or resolve the problem causing the errors. For more information, see the log file at "C:\Program Files\Windows Small Business Server\Logs\pop3connector\pop3service.log".
Distinguished Expert 2018

Commented:
Aye. I wasn't trying to push you to close a problem prematurely. In your last reply, you wrote as follows:
I can get their e-mail from yahoo through the pop connector and configure smtp, those things seem to be working.
....I took the "those things seem to be working" as an indication that the problem posted was resolved. If you are still seeing this error after the updates then I'd recommend three things:
1) Make sure you've installed SBS update-rollup 4.
2) Run the SBS BPA.
3) You've posted the system event logs twice now, but have made no indication (or have not posted) the log it indicates that you should check to further pinpoint the problem. You should look at the log it indicates:
C:\Program Files\Windows Small Business Server\Logs\pop3connector\pop3service.log
And see if it reveals anything to you. If not, you can always post those errors back to see if we can shed some light on the situation.
Commented:
Well.  I logged into the customers web interface for e-mail.  Turns out there was a message "stuck" in the inbox causing the pop connector issue.  Once that problem was solved, I could successfully receive via the pop connector without issues.  Outlook started working without problems once this issue was solved with the "stuck" e-mail.  Thanks for your response, I believe this one was an anomaly.

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