Message Breaks when Sending to Outlook

I've found that my messages are getting split in very strange ways when received by Outlook clients. The email body will stop at some point and the remaining message gets inserted into an attachment.
I can repeat this behavior anytime by including attachments -- if the attachment appears on Mail in the body, the message breaks at the point the file appeared in the email and the remaining body shows up in a second attachment.
While I can rectify that by ensuring that my attachments always appear at the end (why does mail show them in the body that way if they're really just attached?), I've also had this happen in circumstances where there is no attachment and I've been unable to identify what triggered the message break.
This is a huge problem for me, since my business clients mostly use Outlook and my emails to them are showing up all screwy.
Has anyone seen this before? It doesn't happen on other clients -- gmail web client doesn't do this, for example. So it's probably an Outlook problem. I'm just trying to understand why it happens so I can be certain to work around it in professional email.
PowerMac G5, MacBook Pro Mac OS X (10.4.8)

Actually, just for an update, if I turn off MMS I can send to multiple contacts. But with MMS on, I can't. Am I the only person having this issue?
I've tried a restore, and set-up as new phone. But still having no success.

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Based upon my research, I imagine people will say the problem is on the Outlook end of things -- but I still want to know if there's a way to solve my "attachment vs. signature" problem better than the wonky workaround I've developed.
FYI: we're running Mac OS X 10.6.6, and therefore have Mail 4.4.
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Message was edited by: BAField

Read the attached link and the link to the microsoft site to better understand what may be happening.
http://docs.info.apple.com/article.html?artnum=304245
If the attachment is plain text it should not be sent as a windows friendly attachment.
If the attachment is recognized as having rich text content it should be sent a as a windows friendly attachment.
The linked Microsoft document in the attached link has a Common Scenarios section which shows the Solution settings for Outlook based on the Problem experienced by the recipient.

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Staffs have their own private mailbox (as you would expect) but also share common mailboxes like "Support" and "Info". When an email came
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Location/Ubicacion: Arizona USA
Time Zone/Hora Local: UTC/GMT -7
If this message has adequately addressed your issue, please click on the “Accept as Solution” button. If you found a post useful then please "Give Kudos" at the bottom of my post, so that this information can benefit others.
Si esto mensaje le ha ayudado, por favor haga clic en "Aceptar como solución". Si encuentra un mensaje útil, por favor "Da Kudos" al final del mensaje, por lo que esta información puede beneficiar a otros.
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Message Breaks when Sending to Outlook

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