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Tweak Mail to always send to Hotmail/MSN accounts Apps
It seems that emails sent from Mail.app are not being received by Hotmail/MSN accounts, ostensibly due to the way headers are formatted in Mail. There are workarounds (CC'ing yourself, or setting the Priority of the message to Low or High), but the easiest solution seems to be this one (from this thread in Apple Discussions)
  1. Quit Mail
  2. Open Terminal
  3. Type or paste this text into Terminal: defaults write com.apple.mail UserHeaders '{"X-Priority"="3";}', and then hit Return
  4. Quit Terminal
When you relaunch Mail, you should be able to send away to your friends on Hotmail/MSN.
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Tweak Mail to always send to Hotmail/MSN accounts | 10 comments | Create New Account
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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: computerdude33 on Nov 02, '05 07:01:01AM

Or, just send them a Gmail invite.



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: EddEdmondson on Nov 02, '05 08:11:39AM

Testing indicates Hotmail may have fixed this, or that Apple have with 10.4.3 and that this is no longer an issue. Still worth using the hint if you have important mail to send however.



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: simbalala on Nov 02, '05 08:37:53AM
Testing indicates Hotmail may have fixed this, or that Apple have with 10.4.3
I made my tests with 10.4.3 and the problem exists.

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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: simbalala on Nov 02, '05 08:33:09AM

This seems like a common sense fix that everyone should make.

I sent a series of emails from Mail at different priority settings to another account and there was no X-Priority: setting at all with the "normal" priority setting before I made the fix.

High was 1, low was 5, normal was completely absent.

After the fix normal is X-Priority: 3

I use Mail to respond to customer email and I figured that I'll probably forget to set a priority to an MSN account without the fix so I made the tweak.



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: callefjant on Nov 02, '05 12:12:57PM

why on earth can't the standard five years old mail app from the worlds second biggest os developer not speak with the world leading webmail service from the worlds biggest software company? how come that it should be any problems at all? when was email invented? the seventies?



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: simbalala on Nov 02, '05 04:07:27PM

To be fair, lots of email programs don't set the Priority Level.

My ISP email account, which I only ever use via webmail does not and has no options for doing so even though it does have a field for the priority in the received message display. So I can send it an email and it will tell me what priority level the message has but it won't let me send a priority rated one.

The issue with HotMail was more likely an effort to cut down on spammers by throwing up roadblocks. I can see no reason not to set priorities myself.



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: bradleyd1971 on Nov 02, '05 08:45:31PM

This problem is news to me.... I send myself several messages everyday from my max using Mail.app to my msn account (and have been since i bought my PB in May), and I never had any problems at all.

This hint might fix the problem if it is occuring, but I don't believe that the missing header is the cause.



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: macteam on Nov 03, '05 12:34:06AM

I have also send email to hotmail without problems (that I know of) and has newer use priority in Mail (strange enough as I sometimes uses priority in Entourage :) )



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Tweak Mail to always send to Hotmail/MSN accounts
Authored by: gxw on Nov 03, '05 06:03:49PM

Hummm weird....

According to the mail RFC, any mail header begining with X- is a user defined header. The receiving system needs to just ignore these (or add some of their own). Somebody's out of RFC spec if this fix actually works.



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Appreciation
Authored by: piper on Nov 08, '05 05:53:04AM

I want to give public thanks to you, gxw, for posting this solution. I am a computer consultant and I have a client who has been having this exact problem for a while. It's been killing me (and driving her NUTS). I had tried fixing permissions, we thought it might be a problem with her email server (the system admin was having trouble believing it, though). I just sent an email having run this fix so we'll see if this does it. Thank you!



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