Sending Attachments to AOL and MAC recipients

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Outlook version
Outlook 2010 32 bit
Email Account
When I attempt to send an email using Outlook with a pdf or jpg attached to somebody with an AOL address or a MAC user, they say that they can't open the file.

The only way I can get around this is to send the same letter to the same recipient using my online email client. Then, the recipient can open the same file that he can't open when I sent it using Outlook.

Is there an explanation or a fix so that I don't have to go online to send certain files?

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