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Prevent odd characters in emails from Mail to Outlook Apps
There seems to be a problem where emails composed using RTF in Mail.app adds in characters that are unrecognized by Outlook (2000, in my test case). Outlook therefore just puts a question mark in those characters' places. To get rid?of the seemingly random?question marks, don't ever format your text "inline." Instead, do your formatting when you are finished composing the message.

In other words, don't use Command-I to enable italics before you type the word, and then hit Command-I again to turn off italics. Instead, just type your email all the way through to the end, and then go back and change what you want to change by hitting Command-whatever. For some reason, when you format your text while you're typing, Mail.app adds =A0 to the "end" of the emphasis in the RTF/HTML part. This can be seen from reading the raw info of the email -- I can verify this from within my Sent items in Mail by viewing the raw source! check this out:
  I need a test email to see if I can get it to =
  produce <i>weird</i>=A0characters,=A0within the email from apple's =
  mail To ANOTHER client EMAIL ACCOUNT. <b>LET'S</b>=A0see if this does it =
  ok.
All of those =A0 characters become question marks to Outlook users (at least, in Outlook 2000). This holds true even if you turn bold on and back off without typing anything, but then continue on composing, it seems. So, just wait till you're finished composing the email to emphasize your words -- and pray this is resolved in Leopard. BTW, I wound up looking into this due to this really old thread on the macosxhints forums.
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Prevent odd characters in emails from Mail to Outlook
Authored by: thg on Jul 19, '07 09:29:50AM
There's nothing wrong with having A0's in text. They are just "no-break spaces." The ? results because Outlook reads them using the wrong encoding. It's part of a more general problem where Outlook bugs cause certain kinds of rich text (= html, not .rtf) sent by Mail to display with Chinese or other garbled characters. For details of how this happens and other possible fixes see

http://homepage.mac.com/thgewecke/woutlook.html

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Related question
Authored by: hamarkus on Jul 19, '07 11:26:53AM

Very detailed explanation, thanks. A stupid question, how does any application opening a pure text file know which text encoding was used. I guess .doc .rtf and other formats have headers, tags and other metadata for that. But a pure text file? I sometimes have the feeling the app can only guess (or do these checks what the first two bytes are).



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Related question
Authored by: thg on Jul 19, '07 11:53:26AM

There may be programs that can guess at the encoding of plain text by analysing the bytes they contain, but generally there is no way to know what the encoding is. So most apps let you select an encoding in the Open dialogue. An exception to this is plain text which has a Byte Order Mark (BOM) as the very first character. All modern apps will know that this is a form of Unicode and should interpret it correctly.



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Prevent odd characters in emails from Mail to Outlook
Authored by: Fairly on Jul 20, '07 10:11:20PM

Exactly. A0 is simply &nbsp;. Don't ever count on Outlook being compatible with anything. This isn't your problem - it's Microsoft's. As always.



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Prevent odd characters in emails from Mail to Outlook
Authored by: strike3 on Jul 19, '07 10:33:15AM
This may be a slightly different issue, but I resolved the "question marks in Outlook" problem by setting my outgoing messages to UTF-8 format. Use the following terminal command:

defaults write com.apple.mail NSPreferredMailCharset "UTF-8"

Haven't had any problems since.

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Prevent odd characters in emails from Mail to Outlook
Authored by: Coumerelli on Jul 19, '07 03:33:55PM
Interesting. I HAD that chosen from within mail's (Message > Text Encoding... > Unicode (UTF 8)) but it isn't persistent between launches. Maybe THAT's part of it. I'll have to write it into the pref file with default and see what happens. And with what the first commenter said (thg), yes, I agree, but that doesn't mean MS does it the right way. After all, the home page for IE on microsoft.com doesn't validate because of over 200 errors!

---
"The best way to accelerate a PC is 9.8 m/s2"

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Prevent odd characters in emails from Mail to Outlook
Authored by: thg on Jul 19, '07 05:10:13PM

Did you read the note I linked to? It certainly does NOT imply that MS does anything the right way. In fact it says this whole issue is caused by bugs in MS Outlook (which of course should have been fixed ages ago).



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Prevent odd characters in emails from Mail to Outlook
Authored by: Coumerelli on Jul 20, '07 09:16:07AM

no...I didn't :-|. But I will now. :)

---
"The best way to accelerate a PC is 9.8 m/s2"



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Similar problem with Exchange?
Authored by: anandman on Jul 20, '07 08:24:48PM

I have a problem where I get question marks added to an email I send through my company's Exchange server if I attach a file to a reply. It doesn't happen all the time and I haven't figured out the reason it happens yet. And it looks like the question marks are only at the end of sentences, added after the period character. The interesting thing is Outlook isn't necessariily involved since Mail.app just sends it to the Exchange server and I will see the question marks in Mail.app if I cc: myself. I'll have to try this UTF-8 thing and see if that fixes this problem too.



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Similar problem with Exchange?
Authored by: Fairly on Jul 22, '07 09:50:50AM

Exchange == M$ Horse Manure. Expect anything. AFAIK Exchange will also mess up properly formatted (format=flowed) messages and turn them into a typical M$ mess. Solution is to get away from all things Microsoft. Let's face it: we have to do it sooner or later. So sooner causes less pain even if it's still a lot of pain.



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