When using Apple Mail, changing format and color options in the body or signature of a plain text email will automatically convert the message to rich text (which Mail treats as HTML). This will cause issues with attachments on a Microsoft Exchange Server 2007 and 2010. The problem is that Apple Mail uses attachment encoding that exchange server does not recognize(Mixed/Alternative). The only way to avoid these issues right now is to make sure the message is Plain Text only with attachments. This involves either creating a new plain text signature or just disabling the signature for files going to particular recipients.
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Permanently deleted user We have found the resolution for this problem. It involves installing a piece of software called attachment tamer. The software is in testing right now and should enable users to send attachments to Outlook users without any attachment issues. It will also allow everyone to re-enable their HTML signature files and reply and forward email with an attachment without failing.
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