I write in Arial - It arrives as Times New Roman

Barney is completely correct. I ran a few tests through Apple Mail and Outlook, composing in various different ways and sending with both. The results are just a disaster. The bottom line is that you are never going to get an e-mail to display exactly the same way you composed it. Even if you installed Windows and used Outlook, you could still pick some non-default font and the sender would see it differently. Plus, as others have said, there are any number of other systems that are going to delete or rearrange your message before the recipient ever sees it.

Try your best, but don't assume anything. If you must have it in a particular format, use PDF. That, at least, is much easier to do on a Mac.

Now, for those that are interested, here are the ugly details...

Apple Mail in Leopard and the accompanying documentation makes frequent references to "Rich Text". This is not the "text/richtext" or "text/enriched" format as specified in the the MIME e-mail RFCs (See RFC 2045 for one example, out of many.) It is just an HTML attachment inside your message. For the record, anything other than a "Plain Text" e-mail message is just a sequence of attachments. An e-mail client is free to decide what to do with all those attachments and they can display them inline (as with HTML and images) or represent them as an attachment (via a download link or icon). But internally, they are all the same thing.

Outlook give you the option of creating either "Rich Text" or "HTML" messages. But, in fact, they are lying to you. Regardless of which one you choose, your "rich" messages are in HTML. I checked this inside my Mac's POP e-mail server just to make sure Apple Mail didn't convert something on the fly.

The "Rich Text" HTML that Apple Mail creates is just awful. It uses deprecated font tags instead of style sheets. It only includes the specific font you used and no fallback fonts like "serif" or "sans-serif". This would help a great deal.

On the bright side, I still think Apple Mail is a very powerful and competent e-mail client. The bad HTML is generates is clearly labeled "webkit", so that is where the problem is. I bet Apple Mail could still compose true MIME richtext if you knew how to enable it. I send a true "richtext" message and received it using both Outlook and Apple Mail. Outlook completely failed and displayed only the plain text alternative with a bunch of attachments. Apple Mail properly displayed the richtext and the appropriate attachments inline. Regardless of market share, Apple Mail is a fundamentally better e-mail client - and I've proved it!

From what I have seen so far, I could (and will) write two bugs against Apple Mail.
1) Apple Mail uses the deprecated "font" tag instead of style sheets.
2) Apple Mail doesn't provide alternate fonts in font tags. If I compose a message in Palatino, it shouldn't just say face="Palatino" or font-family: Palatino, it should say font-family: Palatino, serif. At least get the serifs right.

From what I have seen so far, I could (and will) write two bugs against Apple Mail.

You may a well include the one that requires the font chosen in New Message to be different from what is in the Preferences in order to appear in the outgoing html code. Have you been able to verify that one?

The actual bug is that if you don't change anything, it sends a plain text email, regardless of your preference settings.
I personally don't consider this a bug but a feature. If I don't specifically make a message that requires html, it doesn't clutter the 'interwebs' with useless bs. However, for those that don't espouse my beliefs in email's simplicity and brevity, I can see where this is not only confusing, but also inconsistent.

The actual bug is that if you don't change anything, it sends a plain text email, regardless of your preference settings.

The fact that Font/Color Preferences do not affect the outgoing is not a bug. They are not intended to do that. The bug is that if you do change something in New Message, like size or color, making your outgoing Rich Text, but do not choose a different font than what you have in Preferences, there will be no font specified in the outgoing html code.

I wrote the following bugs against Apple Mail.
Apple Mail should use CSS for HTML messages instead of deprecated HTML tags - Enhancement
Apple Mail should specify fallback fonts in HTML messages - Enhancement
Apple Mail does not specify font style when sending HTML messages - UI/Usability
Apple Mail "Rich Text" is confusing - UI/Usability

I wrote the following bugs against Apple Mail.

Thanks!

Apple Mail does not specify font style when sending HTML messages

What is that one exactly -- bold, italic, etc. not indicated with proper code?

It is actually the font face. I was in a hurry. I went back and updated the title. That is the one where you change the size or something else and it doesn't specify a font face, leaving it entirely up to the client.

I think all of Mail's problems are from WebKit. I don't quite understand it. Usually, it is easier to compose something into a particular format and much more difficult to parse someone else's random code. Apple Mail is the opposite. It has trouble composing but can display just about anything. Clearly, that WebKit composition code is brand new.

I would have preferred to have come up with a solution rather than writing bug reports. I think in this case all we can do is wait for Apple to improve it. At least I think they switched to HTML-only precisely to improve how messages look in Outlook because that is the only "enriched" format that Outlook can understand. Once again, Microsoft's limitations define a new standard. Sigh.

I think all of Mail's problems are from WebKit. I don't quite understand it. Usually, it is easier to compose something into a particular format and much more difficult to parse someone else's random code. Apple Mail is the opposite. It has trouble composing but can display just about anything. Clearly, that WebKit composition code is brand new.

What I find somewhat discouraging is that I think these same bugs have been in Mail for 3 years now. The only significant thing Leopard changed as far as I know is the mixed encodings in html messages.

Tom Gewecke wrote:
What I find somewhat discouraging is that I think these same bugs have been in Mail for 3 years now. The only significant thing Leopard changed as far as I know is the mixed encodings in html messages.

I can see how Apple would consider these issues to be relatively lower in priority. How much effort should a company put forth so that another company's bug-filled product works? If I were in charge of Mail at Apple, I would have the bug-fix bar set pretty high on these items. On the question "is it broken?" the answer would have to be "definitely" and the corresponding "how hard is it to fix?" would have to be "very easy".

Yes, these bugs may be 3 years old, but how many people have complained about them? Most people just send attachments and don't try fancy fonts. Those who do are likely to be people with many Mac friends where they show up fine on the other end. I wouldn't get my hope up that these bugs will be fixed. I think fixing the "default font" and "fallback font" bugs have the greatest chance (relatively speaking) of being done. They are easy to do and would have a measurable improvement in the product's quality.

The mixed encoding bug sounds like something very similar. It wasn't a "bug" at all. Apple actually changed code to accommodate a bug in Outlook. They did the same thing with the entire HTML "Rich Text" format. From my point of view, Apple has been bending over backwards to ensure compatibility with Outlook.

I can see how Apple would consider these issues to be relatively lower in priority.....The mixed encoding bug sounds like something very similar. It wasn't a "bug" at all. Apple actually changed code to accommodate a bug in Outlook.

I agree totally. In the end, Apple is primarily a hardware company, and Mail.app is a tiny part of what matters. If it doesn't meet a particular user's requirements, there are several alternatives available.

Folks, I'm pretty sure this is a Mac flaw, not Windows!!!

1) Email sent from Mac to Outlook -- you get font substitution (Arial to Times).

2) Email sent from Mac to Firefox browser -- you get font substitution (Verdana to Times).

In this case #2, the email never hit any settings in Outlook. (Yes, in both cases I set the font specifically for each new message in Mail.)

An email in Arial, Verdana, whatever font, from a Windows to Windows machine (created in HTML) will show up correctly. THIS HAS NOTHING TO DO WITH THE SETTINGS IN OUTLOOK FOR HTML MAIL. (Sorry for my shouting.)

The issue is that Mac mail doesn't properly send common (to Windows) coding. It doesn't play nice.

Yes, in both cases I set the font specifically for each new message in Mail.

And in both cases, was the font you set in New Message different than what was set in Mail Preferences? That is required for the html generated by Mail.app to contain any font info. You can check whether the html had font info in it or not by doing View > Message > Raw Source on the messages in your Sent folder.

In the case with the Firefox Browser, are you sure that you had Preferences > Content > Fonts and Colors > Advanced set so that pages choose their fonts rather than the user?

The issue is that Mac mail doesn't properly send common (to Windows) coding.

So you are saying Outlook cannot correctly read the font info contained in the html generated by Mail.app? That's interesting if true -- I had thought that Outlook could do that OK.

When you send an email from Mail, and you don't change the font, it does not set a font face in the coding. Therefore, Outlook uses it's default font of Times New Roman (which I could find no possible way to change).

I have done exactly what you have tried to do, sending to my Outlook account, and can reproduce these results 100% of the time.

If you set the font in Mail to something other than your default font (yes, this is a bug/feature), that font face will be encoded in the message. It displays correctly in Outlook. It's there. I see it displayed, and the raw source of the message includes the encoding.

Look at the source of the messages in Outlook (right-click in the message body and choose source) and see if it has all the encoding for the font. If it does not have the encoding, your Outlook exchange server (or whatever server is being used) is stripping the HTML code out of the message. If it does contain the encoding and it is not displaying correctly, you have other issues with your Outlook setup.

If you set the font in Mail to something other than your default font (yes, this is a bug/feature), that font face will be encoded in the message. It displays correctly in Outlook. It's there. I see it displayed, and the raw source of the message includes the encoding.

Thanks for confirming this.

Look at the source of the messages in Outlook (right-click in the message body and choose source) and see if it has all the encoding for the font. If it does not have the encoding, your Outlook exchange server (or whatever server is being used) is stripping the HTML code out of the message. If it does contain the encoding and it is not displaying correctly, you have other issues with your Outlook setup.

That's an interesting point -- I wonder how often this is the case?

Our Outlook is set up to not display HTML and cannot be changed. You can click in the header on one of those non-intuitive windows sort of text, sort of button, bars and choose to show the HTML.

This may be the case with people you correspond with. The admins can set it up that way to prevent malicious code from executing in the HTML. Our admins still allow us to view the HTML if we choose to after the message arrives.

It could be the case that the Exchange server has been set up to strip the html for the same protection idea, but more drastic.