This message seems to be generated by Outlook itself. However I found a
solution.
In Outlook 2003 at least (don't know about other versions): Open the message
from System Administrator, subject Undeliverable, that lists the recipients
who "could not be reached", with "452 too many recipients, send more in a
second session" after each.
Under the Actions menu at the top is the option to Send Again. If you click
that, you will see that your original message reappears, ready to be sent.
But the recipients listed after TO, CC, or BCC are only the ones the System
Administrator listed as 'could not be reached'--NOT all the addresses in the
original list of recipients.
(Depending on how many you initially had, you will notice that the original
message was sent to some of the recipients you wanted but not those listed
in the System Administrator error message.)
Send that message.
You may find that it now is received by all the addresses. Or you may get
the same error message from the System Administrator again. However there
will be considerably fewer undeliverable addresses listed.
You may repeat the 'Resend Message' process as many times as necessary to
get your message to all its intended recipients.
Essentially, when Outlook is telling you "send more in a second session" it
really is smart enough to do most of the work for you. That is, you don't
have to manually break up your mailing list into limited chunks to send a
small batch at a time.
I'd guess that this feature works the same way or at least as easily in
Outlook 2007--although we have seen MS programmers sometimes remove formerly
useful features in supposed application 'upgrades.'