OL2002: SMTP E-mail Sent Through Internet Account Goes Through Exchange Account Instead (281030)

SYMPTOMS

When you send a message to someone in your Exchange Server organization, addressing it to that person's Internet mail or Simple Mail Transfer Protocol (SMTP) address and specifying an Internet account as the account from which to send the message, the message is sent from your Exchange Server account instead. When you receive a reply, the To field displays your Exchange Server address, not the specified Internet account address.

CAUSE

This behavior occurs because Outlook resolves the recipient's Internet address against the entry that exists for that person in the Exchange Server global address list, replacing the SMTP address with an Exchange Server (EX) address. For example, Outlook replaces the SMTP address user@microsoft.com with an EX address such as Firstname Lastname.

When you try to send the message from the specified Internet account, Outlook searches for an SMTP address but finds only the replacement EX address. Because the Internet mail account cannot handle EX addresses, the message is marked for delivery by the next account in the Outlook account list. If that is the Exchange account, Outlook sends the message to the recipient's EX address.

This behavior occurs only when you use the SMTP address of someone who is also in your Exchange Server address book.

WORKAROUND

To work around this behavior, create another user profile in Outlook, one that points to a Hotmail, IMAP, or POP3 account that is not connected to your Exchange Server, and then log on to that profile to send messages to users within your Exchange Server organization.

MORE INFORMATION

For POP3 accounts, click the Advanced tab in the Internet E-mail Settings dialog box, and then click to select the Leave a copy of messages on the server check box so that mail is not inadvertently delivered to this new profile.