Outlook issue when creating offline emails

I am webmaster for a client who is having repeated issues with his emails being shown as sent but they are not received in Outlook.

His version is Microsoft Office Outlook 12.0.

Best I can isolate when this happens is when he writes a lot of emails in the offline mode and then signs on and they all get queued automatically to go out at once.

His emails show as successfully sent in his Outlook mailbox and are being sent to employees within his company's domain with cc's to multiple other domains. No error or bounce messages are ever received. He just finds out at a later date no one received the emails at any of the domains.

Our site is hosted by midphase... they always tell me that all messages are being shown as delivered but I can confirm that the emails he forwards to me when this issue arises are not in the mailboxes of the recipients he has addressed them to.

There does not appear to be a problem if he is sending emails in any mode other than OFFLINE.

I appreciate any help or insight anyone may have regarding this issue.

 

Yes to both.

He also can forward the original email to all recipients after he learns they did not get the first one and everyone receives it.

 

Have a feeling mails will send just fine

You're right. I would love to be able to tell him "just don't use the OFFLINE mode" but he says he has to because he is writing these emails while commuting on a train. When he gets to an area where he can pickup a wireless access, he signs on and they queu to send all at once. He assumes all is fine and then I get bombarded with forwards on the emails no one has received when he finds out they aren't getting through.