Email PDF in outlook from a MAC seperates pdf file into seperate .ai files

Sorry if this is in the wrong thread!
I'm not an adobe user. However I have many Adobe users on my network who create pdf files (using a variety of adobe products such as photoshop, illustrator, acrobat) and email them to other employees, customers, vendors, etc...
When the email is received on the other end the single pdf attachment has been broken down into separate files.
example: 9-6-11.pdf     will become: 9-6-11.pdf; 9-6-11.ai; 9-6-11.ai
The pdf file still opens as it should however this is starting to cause some confusion in the office. Any idea why this is happening and how i can make it stop?

Thread moved to correct forum.

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    Log Name:      Application
    Source:        ASP.NET 2.0.50727.0
    Date:          4/15/2014 5:47:10 PM
    Event ID:      1309
    Task Category: Web Event
    Level:         Warning
    Keywords:      Classic
    User:          N/A
    Computer:      CGC-SBS2008.cgclaw.local
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    Event code: 3001
    Event message: The request has been aborted.
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    Event time (UTC): 4/16/2014 12:47:10 AM
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    Event detail code: 0
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        Trust level: Full
        Application Virtual Path: /EWS
        Application Path: C:\Program Files\Microsoft\Exchange Server\ClientAccess\exchweb\EWS\
        Machine name: CGC-SBS2008
    Process information:
        Process ID: 7528
        Process name: w3wp.exe
        Account name: NT AUTHORITY\SYSTEM
    Exception information:
        Exception type: HttpException
        Exception message: Request timed out.
    Request information:
        Request URL:
    https://mail.cgclaw.com:443/EWS/Exchange.asmx
        Request path: /EWS/Exchange.asmx
        User host address: 71.104.101.181
        User: CGCLAW\ScottGrossberg
        Is authenticated: True
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        Thread account name: NT AUTHORITY\SYSTEM
    Thread information:
        Thread ID: 44
        Thread account name: NT AUTHORITY\SYSTEM
        Is impersonating: False
        Stack trace:
    Custom event details:
    Event Xml:
    <Event xmlns="http://schemas.microsoft.com/win/2004/08/events/event">
      <System>
        <Provider Name="ASP.NET 2.0.50727.0" />
        <EventID Qualifiers="32768">1309</EventID>
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        <TimeCreated SystemTime="2014-04-16T00:47:10.000Z" />
        <EventRecordID>1420339</EventRecordID>
        <Channel>Application</Channel>
        <Computer>CGC-SBS2008.cgclaw.local</Computer>
        <Security />
      </System>
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        <Data>4/16/2014 12:47:10 AM</Data>
        <Data>de0e4dd0fe794e7ca055e3436d6648eb</Data>
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        <Data>
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        <Data>w3wp.exe</Data>
        <Data>NT AUTHORITY\SYSTEM</Data>
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        <Data>https://mail.cgclaw.com:443/EWS/Exchange.asmx</Data>
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        <Data>CGCLAW\ScottGrossberg</Data>
        <Data>True</Data>
        <Data>NTLM</Data>
        <Data>NT AUTHORITY\SYSTEM</Data>
        <Data>44</Data>
        <Data>NT AUTHORITY\SYSTEM</Data>
        <Data>False</Data>
        <Data>
        </Data>
      </EventData>
    </Event>
    Jay Doyle

    any more? anything you can find...
    is SBS 2008? what you do, then the error occurred?
    -->Persistent Email crash in Outlook on a MAC
    all emails crash? can't send and receive?
    those may be helpful...
    https://www.eventid.net/display-eventid-1309-source-ASP.NET%202.0.50727.0-eventno-8159-phase-1.htm
    http://blogs.msdn.com/b/crm/archive/2008/11/20/asp-net-2-0-50727-0-warning-event-id-1309-due-to-request-time-out.aspx
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    Howtodo

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