Apple Mail 2.0.5, Sending Windows Friendly Attachments From A Mac OS X System

Apple Mail 2.0.5 which ships with Mac OS X 10.4 Tiger, now comes with a built-in feature that simplifies sending Windows friendly attachments through email.

‘Windows-friendly’ refers to the removal of resource files in attachments sent from a Mac system. Mac systems are based on UNIX file systems which uses forked files whilst Windows systems don’t. The result of this difference is the apparent duplication of attachments on Windows systems, of attachments that are emailed from Mac systems.

In truth, the duplicated file, which is usually abbreviated with an underscore (_) or period (.) is a resource file that is used on Mac systems (but cannot be opened on Windows systems). This duplication is often the cause for confusion rather than harm, leading the Windows receipient to believe that your attachment is a dud.

Apple Mail 2.0.5 provides 2 ways to get around the sticky ‘Windows-friendly’ attachment issue:

  • a global setting that ensures all attachments emaied through Apple Mail are stripped of their forked files or;
  • a temprorary setting that does a similar action but restricted to the intended email only

Toggling The Global Windows-Friendly Attachment Settings

Click on the Edit menu in Apple Mail, select Attachments followed by ‘Always Send Windows Friendly Attachments’ (see: Diagram 1.0). This toggles a global setting that will apply to all subsequent emails until this setting is turned off by repeating the above mentioned process.

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Making Individual Email Attachments Windows Friendly

To attach a file when composing a new email, click on the Attach button in the toolbar of the email composition window.

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Click on ‘Send Windows Friendly Attachments’ in the attachment selection window which appears. In so doing, you have made the attachment for the individual email sent Windows friendly but subsequent emails will continue to include forked files and this process has to be repeated to ensure that future attachments are Windows friendly. Unfortunately, Mail offers no convenient way to toggle Windows friendliness for attachments added to your message by drag & drop or copy & paste.

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When Windows Friendly Settings Fail

When all else fails and despite toggling the Windows friendly attachments setting, the Windows receipient on the receiving end still cannot open your attachment; a suggested remedy is to Zip the attachment before including it in your outgoing email. This is the generally recommended solution for users of versions of Mac OS X prior to Max OS X 10.4 Tiger which, shipped with versions of Apple Mail that does not include the ability to strip resource files.