Tracking an email message

Hello,
Is there a way to track a message that we send other people outside our company?
I'm not sure what's going on yet but I opened a ticket with my email provider but it will probably take a while to get a response. But my boss was saying that when he sends an email to our client, it does not reach them. We don't get a bounce back or anything. And it's only from this one client. But of course it's always my fault that the emails does not thru, it's never the client's fault.
So if somebody could help, I appreciate it.
Thanks,
Helmut

Hello Helmut.
If a message is successfully sent, it is either accepted or rejected by the recipient's incoming mail server and a sent message will not be copied to the account's sent mailbox if not successfully sent by the account's outgoing mail server.
If a sent message is rejected by the recipient's incoming mail server, a bounce back message is sent from the recipient's incoming mail server indicating why the message was not accepted.
Most, if not all incoming mail servers have spam and virus scans for all received messages and false positives do occur. There is a possibility the messages sent by your boss have been marked as spam by the recipient's incoming mail server and if the messages contain attachments, the attachments may have been flagged as containing a virus.
The Mail.app does not provide a read receipt for received messages without your knowledge when requested by a sender nor does it include a read receipt request for sent messages since this generally does not work with SMTP mail since the recipient's incoming mail server and the recipient's email client must support providing a read receipt. If the recipient's incoming mail server and email client supports providing a read receipt when requested by a sender, the recipient will also have the option to not provide a read receipt when requested by a sender.
You can download a Mail.app plugin called Mail Priority at the following link.
http://www.versiontracker.com/dyn/moreinfo/macosx/14967
MailPriority is a plug-in for Mail.app on 10.2 and 10.3 providing a simple interface to set Priorities for outgoing messages, colorize messages in the message list and to request read receipts. (You only get a receipt, if the receiving mail client supports this feature and the recipient enables this option.)
The MailPriority plugin is not compatible with Tiger Mail and I don't believe using it will resolve your problem.

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