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Avoid wrapped text in messages from Mail to Outlook Apps
I recently began getting complaints from people I emailed (mostly work-related) that the messages I was sending came out wrapped at a certain width, which was annoying to them especially as I often mail long messages.

I figured out that what these people had in common is that they were using Outlook or Outlook Express. I did some research and realised that uses a recent SMTP extension, the format=flowed parameter to the plain/text Content-type. Without getting into details that would scare those of you with little knowledge of SMTP and MIME, this is essentially a way of sending plain text that is wrapped at a fixed width for transport, but can be reassembled as long lines on the receiving end. Apparently, neither Outlook nor Outlook Express (and, unsurprisingly, a rather old version of Lotus Notes my biggest customer uses) supported this extension.

Now what weirded me out completely is that I use Rich Text (i.e. text/html) to send e-mails. Without wanting to get into a religious flamewar, even though I've been e-mailing long enough to know what UUCP is, I'm a convert to Rich Text e-mail. Although I stay clear of patterned backgrounds and pink 72-point type for aesthetic reasons, I do appreciate the ability to make something italic or underlined, or insert a table or a bulleted list here and there. And yet my messages were being sent as Plain Text.

No more than a couple of clicks through Mail's help system and I had found the cause: if there is no special formatting in your message (no italics, bold type, different fonts or sizes etc.), as there often isn't in my messages, then Mail sends the message as Plain Text -- even if you've selected Rich Text. This has the unfortunate side effect of making your mail wrap at a fixed column (72, as a matter of fact) for those of your recipients unfortunate enough to be using some version of Outlook, either through ignorance or employer requirement.

So, what, I see you ask, dear reader, did you do to rectify this? Did you abandon Mail for another application (shock! horror!)? Make sure every message had some formatting (as if I would ever remember to do that)?. Au contraire, dear reader, there is a simple and elegant solution: If you don't already have a signature, create one, and make sure it has some formatting in it. If, like me, you think signatures are a waste of bits, you can do what I did: create a signature consisting solely of a period "." and make that bold, or italic. Now your outgoing messages will always be Rich Text, and wrap beautifully on Outlook readers, with the sole blemish being a tiny dot at the end.

And yes, dear reader, I did try using a space, and even some weirder invisible Unicode characters like the non-breaking space, which naive HTML coders are so fond of, or the less well known but equally useful em quad, but unfortunately, Mail won't let you have a signature consisting solely of non-printing characters. So I'm stuck with the dot. But still, at least I'm not stuck with my customers' complaints.
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Avoid wrapped text in messages from Mail to Outlook
Authored by: gullevek on Nov 16, '05 07:02:26AM

even more worse is the bug that adds a "space" to the end of each line. Worse because Thunderbird that makes it "not line breaked" breaks URLs then. So all long urls I send around in office ... are not working. I reported this 3 times to apple, its still in "working on" state. And That since 10.4.1. *sigh*

I wished could do the "hard line break" way of Thunderbird and actually _ANY_ other Mail application. This tricky "flow" breaking in the background is a pain. Really. Thunderbird, mutt, etc, have just long long lines, not break, difficult to read and Outlook just breaks it down hard and it just looks stupid. Especially because you don't see the issue on your side. Its not line breaks where it will put it, so you know what will happen. No it does it behind your back.

*sight* These are one of the small things that make life with a Mac really difficult.

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Avoid wrapped text in messages from Mail to Outlook
Authored by: greed on Nov 16, '05 09:03:35AM

Space-Newline is the sequence used by "format=flowed" to indicate a soft line break, that is, one that can be removed to re-flow the paragraph for the display.

It should NOT be sending long words broken in the middle, including URLs. Yell at Apple if it does. (For best protection of URLs in transport, surround with angle brackets. Still won't guarantee that some MUA or Exchange won't mess with it, though.)

Is your URL problem on transmit or receive? I haven't had anyone say that URLs I sent them are unusable--unless I've sent them to someone on the far side of an old Exchange server, which will re-wrap all text/plain messages. I've seen URLs displayed broken in, but clicking on them re-assembles them correctly (or right-click and Copy Link).

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Avoid wrapped text in messages from Mail to Outlook
Authored by: gullevek on Nov 16, '05 04:40:50PM

I yelled at apple for the URLs. I just did (after 10.4.3) a new bug report with showing that even the angel brackets don't help to save the URL. I hope apple listens to me.

Actually I encourage all who have the same URL issue to yell - file a bug report - at apple. The more they know, the more likely it is that it get fixed.

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Avoid wrapped text in messages from Mail to Outlook
Authored by: jaysoffian on Nov 16, '05 05:50:24PM
Specifically, from RFC 3676, Section 4.2 (Generating Format=Flowed) Apple is going against the following recommendation:
Regardless of which technique is used, a generating agent SHOULD NOT insert a space in an unnatural location, such as into a word (a sequence of printable characters, not containing spaces, in a language/coded character set in which spaces are common). If faced with such a word which exceeds 78 characters (but less than 998 characters, the [SMTP] limit on line length), the agent SHOULD send the word as is and exceed the 78-character limit on line length.
Technically they are not violating the RFC since it says "SHOULD NOT" and not "MUST NOT" but it is highly annoying to have to use TinyURL all the time... I filed this bug under 10.2, so I'm not hopeful that they have any plans to fix it.

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Avoid wrapped text in messages from Mail to Outlook
Authored by: Roquentin on Nov 17, '05 12:01:46AM
My understanding is that the relevant part of RFC 3676 is actually paragraph 4.3, in which it is written:
[Quoted-Printable] encoding SHOULD NOT be used with Format=Flowed unless absolutely necessary (for example, non-US-ASCII (8-bit) characters over a strictly 7-bit transport such as unextended [SMTP]). In particular, a message SHOULD NOT be encoded in Quoted-Printable for the sole purpose of protecting the trailing space on flowed lines unless the body part is cryptographically signed or encrypted.
Apparently does send 8-bit characters over a 7-bit transport, so technically its behavior is correct. Not that that's any confort to those who are on the receiving end of broken URLs (not users, natch). I remember first hearing about this behavior over three years ago, so my bet is that you won't see it change in, but will eventually see other email clients improve their handling of email sent from clients observing this requirement of RFC 3676. 2 cents.

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Avoid wrapped text in messages from Mail to Outlook
Authored by: iggybird on Nov 16, '05 08:11:33AM

Can't you make the period white (or whatever color your background is)?

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Set the dot to white
Authored by: stephanos on Nov 17, '05 01:22:19AM

Yes! You can! <HOMER>Woohoo!</HOMER> I knew posting this on would make someone improve on it :)

Thanks iggy.

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Bullets and tiny text
Authored by: interlard on Nov 16, '05 08:43:56AM

Great hint. Now how to I make 10 point text (which is readable for Windows users) readable by me in Mail when I'm either reading or writing emails? I normally write emails in plain text so the displayed font is set by me to be readable, then I switch to rich text to add the formatting. A real pain.

We need a zoom function, or just a way to increase the displayed size of text on a Mac. With screen resolutions increasing, text on Macs is getting smaller and smaller. When will the madness end??

Another thing: the hint mentions using rich text to get bullets. I don't see how Mail supports bullets, which I find really annoying. What's the trick?

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when reading 10pt text: use [command]-+...
Authored by: nick on Nov 16, '05 09:04:55AM the message-window. it does the zoom-trick for me.

is this a hint on its own? but i'm pretty shure one of the 8034 hints covers this already.


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Sorry, it doesn't help me
Authored by: interlard on Nov 16, '05 11:06:19AM

Thanks for the tip (everyone) but it doesn't help me when I'm writing emails. I know, I should have said this in the original message but I'm just a very flawed person. :-)

Anyway, tips on tiny text are still appreciated.

Or these mysterious bullets.

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Bullets and tiny text
Authored by: greed on Nov 16, '05 09:12:50AM

There's a problem with point sizes from Windows.

The problem is, Windows doesn't use point sizes. Anytime a font size is specified as "points", Windows interprets it as "pixels".

Every other system currently in use treats "points" as "1/72 of an inch", which is ever so slightly wrong, but close enough for practical use. The display resolution (pixels-per-inch) is then used to convert points to pixels. You can't use the Windows completely incorrect definition of "points" without messing everything else up. I, personally, don't think design bugs should be copied into other systems.

The fix is, as far as I'm concerned, to ignore absolute point sizes and obey only relative sizes from stylesheets and the like. (So, font-size: 10pt or 10px is ignored, but font-size: 1.5em, or 150%, and so on are accepted.) And implement Minimum Font Size like Mozilla and friends have had for a bit now, and has been added to the latest Safari.

For practical use, I hit Cmd-Option-P (I think) to get the Plain Text alternative. If there isn't a Plain Text alternative, and I really can't read it, I tell the sender to re-send without messing with the font size.

Hmmm, maybe I can figure out how to make the Mozilla stylesheet parser Do What I Want....

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Bullets and tiny text
Authored by: lar3ry on Nov 16, '05 10:56:43AM

Technically, font sizes (height) shouldn't be specified in "em" units, since those units measure width. Instead, use "ex" to specify height. ("1.5ex" means 150% the height of the base font.)

CSS allows the use of silly units for any measurement, which gets confusing. The reason, though, is for uniformity: setting a margin top, bottom, width, and height all at "1.5em" would describe a uniform margin around a block.


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Bullets and tiny text
Authored by: AndySpry on Nov 16, '05 10:10:13AM

I use [Command]-+ (increase font size) and [Command]-- (decrease font size) when I have my hands on the keyboard. But most often when using, I am moving around opening and closing messages with the mouse.

To get the decrease/increase font size into's reader window, open any e-mail message and select View->Customize Toobar and put the button with the little and big "A" onto the toolbar. This gives you the option of changing the font size with the mouse.

You can also do this on the's main window and on the compose message window. They have separate toolbar configurations.

The first thing I do when upgrading OS X across major versions is update my tool bars to include the set of actions that maximize my e-mail workflow.

My biggest gripe with is that there is no action (command or button) to step to the next unread message in a mailbox. You can get this action by typing [Command]-w to close the current message, pressing the Up or Down arrow to go to the next unread message in the mailbox (depending on how you sort your mail), then pressing return. I'd like a single keystroke or button press for this action.

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Bullets and tiny text
Authored by: Unsoluble on Nov 16, '05 02:42:34PM
If you view your mail in the mail pane instead of opening them up into their own windows, you can just hit the arrow keys to cycle through messages...

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Bullets and tiny text
Authored by: timgaden on Nov 16, '05 06:08:43PM
You could try this tip, which shows you how to set a minimum font size for displaying HTML messages.

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Bullets and tiny text
Authored by: interlard on Nov 17, '05 09:50:35PM

timgaden, I LOVE YOU. This is freaking perfect! Now I can read everyone's emails, AND my own. I can't believe I had to apply a hack just to make email easy to read. Apple, what are you THINKING??

Time, I'm going to be really helpful to 10 people tomorrow. They in turn will be really really nice to 10 other people. And so on. Eventually the wave of goodwill should get back to you. Oh wait, I live in New won't get far.

OK, so how do I get bullets in emails? Where's the toolbar button for that? C'mon Apple, M$ gave us this DECADES ago. ;-)

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Authored by: ottonomy on Nov 17, '05 11:30:59PM

I assume you want to do something more sophisticated with bullets in your emails than simply inserting bullet characters by typing option-8. But in case you're not...

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Authored by: stamaknox on Nov 23, '05 08:57:55PM

Thank you, thank you, thank you! I have been trying to figure out how to avoid cut and paste for bullets in mail. A real help.

One thing I hope someone can help with --- when I use the option/8 combo, the font style "jumps" to monaco. I noticed it does this with any option key combo when I am typing an email. I can highlight the text and revert back to my preferred font (which obviously is not monaco) but this makes it more time consuming. I use bullets alot. Any ideas on why -- &/or how to stop this "reverse default setting"?


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Tiny text
Authored by: narya on Dec 08, '05 03:36:42AM

Tim, you made my day! Thank you!


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Avoid wrapped text in messages from Mail to Outlook
Authored by: fds on Nov 16, '05 10:40:15AM

Actually, recent versions of Outlook Express seem to support format=flowed. Only the delsp=yes extension isn't understood by it. Or by Thunderbird or others, hence those "broken" long URLs in them.

And Office Outlook doesn't seem to support any of it.

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Avoid wrapped text in messages from Mail to Outlook
Authored by: Spartacus on Nov 16, '05 03:16:23PM

You think signatures are a waste of bits but you send rich text e-mails? :-D

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Avoid wrapped text in messages from Mail to Outlook
Authored by: rlicata on Nov 17, '05 12:01:33AM

I think the bigger problem here is that you can't send a concise email. ;-)

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Avoid wrapped text in messages from Mail to Outlook
Authored by: 5chm31din6 on Nov 17, '05 12:23:49PM

Why are email clients still wrapping text, even if it is plain text, for cryin' out loud? I want to know how to send plain text (my format of choice) without the limitations of a 72 or 80 character wrap. I hate that. It's stupid. It's unnecessary -- just like Daylight Wasting Time.

Power corrupts. PowerPoint corrupts absolutely.

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