Read Receipts in "Failed Mail" folder

There are very few settings for the POP connector, a single POP3 login (which must work or there would be no mail), no routing rules, a schedule (every 15 min), logging level(Medium) and the undeliverable box which is set to one of the Cust Service Reps and seems to work.

I've never thought of the POP3 connector as transitional -- I use it in all small sites.  Its especially useful where some of the email addresses need to be forwarded elsewhere (eg this customer has a non-employee agent who gets her mail only on her blackberry-- she has no access to the company's systems) or to make use of spam filtering by the ISP (mark and forward).

In any event, the problem seems to be after the POP3 connector, isnt it Exchange that puts mail into "failed mail"?  And if Outlook Express can open the message, what could be so failed about it that made it not go to an exchange folder?

Am I the only person with this problem?  I see it on several sites but there is little mention of it anywhere else.  Someone must know how to set Exchange to not reject read receipts!?

Thanks for your help.  I understand the BCC problem but I still find the read receipts issue to be counterintuitive - there is nothing that in the header would normally be hidden like a bcc sender would be.  I still have the sense that its an error in the connector not a feature of the protocol.  
I really wish there was a way to switch from the POP3 connector and address all the other issues around it -- E.g. users who have a pop3 account and who will not have a domain account, easily offloading spam filtering to an external full service provider, etc.  Anyhow, thanks.

Since grading comments aren't shown to all, I am reposting them in order to be able to respond:

"Thanks for your help. I understand the BCC problem but I still find the read receipts issue to be counterintuitive - there is nothing that in the header would normally be hidden like a bcc sender would be. I still have the sense that its an error in the connector not a feature of the protocol.
I really wish there was a way to switch from the POP3 connector and address all the other issues around it -- E.g. users who have a pop3 account and who will not have a domain account, easily offloading spam filtering to an external full service provider, etc. Anyhow, thanks. "

It's not an error.  The POP3 Connector totally rewrites the headers in order to be able to deliver the email internally.

There is a way to switch from the POP3 Connector and address all the other issues around it.  You can certainly have users which keep a POP3 Account and do not have a domain account.  See "How to share an SMTP address space in Exchange 2000 Server or in Exchange Server 2003"  http://support.microsoft.com/kb/321721

Offloading of SPAM filtering is also quite easy.  Check out www.exchangedefender.com for an example of one service that does this quite well.

Your situation isn't really that unique.

Jeff
TechSoEasy

The problem with distribution lists has been around since 2003's POP3 connector and is well understood.

However I agree with the OP's comments that the problem with delivery and read receipts isn't clear. Technically these receipts are just standard emails with a from and to address just like every other email. So why will 2008's POP3 connector not deliver them to the mailboxes?

I have one client site with SBS 2003 POP3 Connector which has been working for around 4 years now (client won't move from dynamic IP broadband so can't securely setup SMTP - not my choice) and works without any problems with delivery and read receipts. So why the change in 2008?

"won't move from dynamic IP broadband so can't securely setup SMTP - not my choice"

I have many clients that have dynamic IP addresses that we use SMTP without a problem.  So that's no reason to keep using POP3, and POP3 is definitely not a secure solution.

There was no change to the POP3 Connector with SBS 2008, so I would suspect it has something to do with the Anti-Virus software that's installed.  When I look back on this question, it seems as though that may have been the issue as well... but the fact remains that using the POP3 connector really isn't ideal for permanent solution in most any situation.

Jeff
TechSoEasy

"I have many clients that have dynamic IP addresses that we use SMTP without a problem.  So that's no reason to keep using POP3, and POP3 is definitely not a secure solution."

Jeff, how are you setting those up?

" ...but the fact remains that using the POP3 connector really isn't ideal for permanent solution in most any situation"

I have to disagree with you. It has it's drawbacks and it's not an alternative to SMTP but when it's needed a business can happily run on it, permanently, if they understand the limitations.

"Jeff, how are you setting those up?"

Using www.dyndns.org and pointing the MX record to whatever host you create at dyndns.

"when it's needed a business can happily run on it"

Why would it be needed?

Jeff
TechSoEasy

"Why would it be needed?"

Running an SMTP server on a dynamic IP is never a good idea. When that IP changes then systems will continue to send mail to the old IP. If there is a new SMTP server on the old IP then it will receive the new mail (if configured to do so) destined for the old system until the DNS cache at the remote location refreshes or is updated. Not exactly a secure solution and not a solution for any business who that has security in mind.

Which is why you would set the TTL very low on that host name.  (to something like 330).  That way it expires in any cached DNS.

Jeff
TechSoEasy

"Which is why you would set the TTL very low on that host name.  (to something like 330).  That way it expires in any cached DNS."

You're relying on all DNS servers (that the senders mail system would use) to behave properly which is something you have no control over. There are many supposed 'DNS caching' software that don't obey those rules.

What you are suggesting will work, but isn't insecure, isn't recommended (from anywhere official I've seen) and I'm actually surprised at it being suggested. In the current climate of hacking and malware all for the purposes or stealing your identity this just isn't a good idea. Period.

I'm not prepared to put the one client (who is a solicitor / lawyer but that's not the issue) I have who is dynamic into that situation. Their IP changes on average three times per month.