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I get mail forwarded to my OS X Mail from an Outlook account at work. I use my Mac to reply to messages directly from Mail.app and now I want to forward all my sent mails from Mail to my Outlook account for filing.

Is there any way to do this that's easier than individually forwarding all the messages manually? I want to keep all the messages separate.

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You can set Rules in Mail.app preferences to take actions on emails. What should work is a rule configured like this:

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You would just need to fill in the to: field with the account that should be receiving all email.

Another option is to forward mail from the source. If the source is iCloud, you can Forward all messages automatically. If you use Gmail, Gmail can do it too.

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  • Thanks for your answer Adam, it answers my question perfectly, which makes me realise I have written it badly. I should have made it clear that I have this arrangement: work outlook (on pc in workplace) out of office forwarding to gmail which is retrieved by Mail.app. The gmail account is used purely for this purpose and receives no other email, therefore the gmail inbox and sent items are identical and match what is received in my work outlook. Mail.app is on my laptop which I use out and about and so the sent items are stored locally and do not pass back through gmail. – Murdoch Mar 27 '12 at 20:25
  • Its these items which I want to sync back to Outlook on my workplace pc. I hope you can follow that! – Murdoch Mar 27 '12 at 20:29

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