Exchange messages departing via SMTP server from prior account

We've just deployed Exchange 2010 in our organization, replacing a hosted POP/IMAP/SMTP solution. The hosted solution remains available so that IMAP users are able to access their pre-Exchange messages. Consequently, iOS4 users have both an Exchange account and either a POP or IMAP account with a corresponding SMTP server.
The problem we're encountering involves which mail server is used when replying to messages with iOS4 devices. The president of our company has an iPhone 4 and an iPad 2: any message he replies to goes out via the SMTP server in use with our old solution.
So if I send him a message which arrives in his Exchange mailbox, if he replies to me with either of those devices, the reply ends up in my POP/IMAP mailbox on the previous mail server. This is a problem as people are not monitoring their old account inboxes now that the bulk of mail is received via Exchange, and this has resulted in a number of important messages missed or ignored.
I have been able to reproduce this.
Once again in a nutshell:
I send a message is to president. Arrives in his Exchange inbox. He replies via iPad or iPhone. Message arrives in old POP/IMAP inbox.
I can verify this behavior via message headers.
As a workaround, we've attempted to reconfigure the SMTP settings associated with the old account to use the SMTP service on the Exchange server. This works fine inside our firewall, but remote performance has been very inconsistent . And we really would like to block SMTP at the firewall.
I believe this issue has been discussed before, but in my review of the pertinent discussions, it doesn't look like there has been a solution.
Has anyone found a solution for this problem?

users will remain on the domain. decommissioning or altering access to the old mailboxes until some point post-migration would be unwanted so there's a fallback method in case anything goes wrong. until testing reveals a better method, the strategy
for Exchange 2003 / Server 2003 environment will remain as is for now using ldifde export of select user object attributes followed by ldifde import of select attributes to contact objects, followed by admodify.net / admodcmd updating of the necessary mail/exchange
attributes via %’mailNickName’% similar to what's described below to forward internal mail to the external host.
Using ADModify to Change Exchange Specific AD User Attributes in Bulk
Using ADModify – A real world example

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for Exchange 2003 / Server 2003 environment will remain as is for now using ldifde export of select user object attributes followed by ldifde import of select attributes to contact objects, followed by admodify.net / admodcmd updating of the necessary mail/exchange
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I have a grandfathered free google apps account and use [email protected] to handle my personal email. Under this same user in google apps, I also have an alias setup using the name [email protected] (I use the alias for non-personal correspondence). Per a discussion over on google's forums (thanks Warren Chang and Goldy Arora) when I set up the alias under the 'Accounts' tab on google, I deselected 'Treat as an alias' and selected 'Send through mydomain.com SMTP servers' for outgoing mail. I then filled in the SMTP server settings with 'smtp.gmail.com' instead of 'smtp.mydomain.com'. For username and password I used [email protected] and its corresponding password.
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