Apple Event: May 7th at 7 am PT

Looks like no one’s replied in a while. To start the conversation again, simply ask a new question.

Switchers beware - email from Mail is not processed by Outlook properly

I was furious to learn yesterday that many of the emails I have sent over the past few months to Customers / Suppliers / Colleagues and friends just haven't been read properly. The reason for this due to Mail's failing to send a compatible format which can easily be read on outlook!!! Either the email is not able to be processed by Outlook properly, or Mail sends it in an unexpected format removing text from the message, unexpectedly. Just be very careful not to assume your email is being read in a way Mail presents it to you by your Outlook recipients!

This is absolutely unforgivable, IMHO, from such a basic application which is apparently part of the "most advances operating system in the world"! Apple like to keep crowing about the compatibility with Microsoft applications, but they cant even claim this for their basic bundled email client!

I have a few examples, here is one: create a new mail; type some text; leave 3 line spaces; type some more text; leave 3 more line spaces; type some text to sign off. Insert two photos by drag and drop into the two spaces you left between the text. The mail looks great doesn't it? Address it to a friend who uses Outlook (certainly Outlook 2008) on Windows (or an address which can be set-up on a Windows Outlook client), press send. Check out how it looks in your sent items, still looks great! Now check it on Outlook. The first piece of text is in the message body. The photos are there as attachments. The rest of your message has been shifted to two separate text attachments which look too innocuous to be bothered with. I wonder how this would look on a blackberry???

The point is, depending on how the mail is worded can mean the actual message can be completely lost and you would never know why?

This is a massive failing for Mail which I don't see many people discussing, so am I alone? Other examples include inserted line breaks in messages once they are read on Outlook. I dread to think how the mail appears on a blackberry?

If I knew how to include screen shots here I would.

iMac intel, Mac OS X (10.6.2), iPhone 3GS 16GB, macbook

Posted on Dec 5, 2009 5:44 AM

46 replies

etresoft

Level 8

46,560 points

Dec 6, 2009 8:50 AM in response to Robert Borley

Tom Gewecke wrote:
I think at one point Apple said they did not consider this behavior a bug or intend to move in that direction (and they certainly have not done so). Let us know what kind of reaction you get to your reports this time around.

Don't hold your breath. I have gotten very poor responses from Apple on my Mail.app bug reports. I think it does make sense to keep plugging away at it. I'm starting to think about writing my own Mail program. Ten years ago I thought it was a waste of time because I could never compete with the likes of AOL, Outlook, Eudora, and Apple. I'm not so sure anymore. They have all either gone downhill or gone out of business. I don't think Thunderbird is much competition. Complaining about Apple Mail will get a very small amount of interest. Not complaining because you're not using it will get much more interest.

Robert Borley wrote:
I am really sorry that I am coning across as adversarial, I truly don’t mean to.

Barney-15E’s comments aren’t helpful though, and rather than address the issue seem too give the message, “Apple have it right, if you don’t like it just go and use some other software”. I really do not want to use that as a solution.

Mail issues are particularly difficult. One can usually only reproduce the problem with e-mail and people very reluctant to supply examples. In such cases I try to feed both sides. I will sincerely offer to help while also engaging in the fight/rant just to see which direction the original poster prefers to take. They almost always choose fighting and ranting. I'm glad you didn't 🙂

I am taking the plunge with my business switching to all macs and mac OSX server, (against the advice of my IT support guy). It’s going to be a battle I am sure and some of the systems we run just have to use Windows.

I wish you good luck, but I'm not sure it is a wise choice. You are making an enemy of the IT support guy because reducing his importance. Macs just don't need as much support. Everyone knows that. But for people in IT support, that is literally food on the table.

I stopped trying to be an Apple evangelist years ago. I find a haughty disdain for PCs and their users to be a more effective method. People who are "Mac people" probably already have one. If a PC users asks me if they should buy a Mac I'll just respond "Oh no! Macs are for creative people." To publicly embrace a minority status takes a special kind of person. If people truly want a Mac, they will get one on their own and be happy with it.

I really appreciate your helpful response in recognizing the problem and reporting it to Apple. I am sure they will listen to you much more than my feedback lodged last week.

They may listen "more" but that is still "very little".

I totally agree with your comments about Outlook. It is shockingly bad for an email client so widely used.

Outlook still has an option to send uuencoded attachments. <shudder>

Eventually employers will come to realise just how unproductive it is as a productivity solution.

Not a chance! We still use Lotus Notes.

Tom Gewecke

Level 10

115,970 points

Dec 6, 2009 9:33 AM in response to Robert Borley

I will not use this forum to vent frustration at Apple in future as it clearly upsets some people here.

The most important reason to not use it for that is because you are only talking to other users like yourself here, not Apple.

I will have users on my case asking me why Mail doesn’t send email properly to our customers who use Outlook. They will hate Entourage and it will drive them back towards Outlook on Windows, which I don’t want because I believe superior productivity can be achieved with Mail, Address Book, iCal etc.

Yes, understood. But to be realistic, nothing significant is going to change in Mail for a year or two, and, as I mentioned, 5 years have gone by without Apple changing the requirement to set the font for each outgoing message individually in order to ensure html mail is sent and the recipient sees the font you want him to (which many business users find an intolerable burden). Whether switching to a different email app makes sense depends on the priorities of the specific user, and for many that turns out to be the best course of action in the end.

The same holds for other Apple apps: Pages reads and creates .doc stuff, but people who need complete compatibility with Windows Word should use Word for Mac instead. Firefox can do things that Safari cannot. Apple's iWeb is no replacement for Adobe Dreamweaver when you need a professional web site. And if your business happens to need to write documents in the languages of India and SE Asia, there are some good reasons to keep Windows running somewhere for that purpose.

Dec 6, 2009 9:53 AM in response to etresoft

etresoft wrote:
I'm starting to think about writing my own Mail program. Ten years ago I thought it was a waste of time because I could never compete with the likes of AOL, Outlook, Eudora, and Apple. I'm not so sure anymore. They have all either gone downhill or gone out of business. I don't think Thunderbird is much competition. Complaining about Apple Mail will get a very small amount of interest. Not complaining because you're not using it will get much more interest.

Go for it. If it's half as good as BusyCal's version of iCal, it'll be a hit. There are loads of great things about Mail and it's simplicity and clean interface is one of them. If you manage to produce something that embraces or replicates Mail Acton and Mail tags at the same time, you could well be in with a hit. Maybe Mail plug-ins are the way to go?

Eventually employers will come to realise just how unproductive it is as a productivity solution.

Not a chance! We still use Lotus Notes.

This made me laugh, I nearly wrote "What ever happened to Lotus Notes?" on my last post but thought it would be getting off topic! Can't believe your business is still using it! I have never used it, but many colleagues, suppliers and customers complain bitterly about it.

It amazes me how little importance businesses and software companies place on productivity applications surrounding email, calendars and contacts! Surely someone should do a study on just how much time users spend on their PC's, Mac's and laptops using these programs. For many of us at work, poor use of email and poor organization almost takes over our lives. Using Apple Mail, MailActon and Mailtags has revolutionised my life (along with a GTD system).

Dec 6, 2009 10:02 AM in response to Tom Gewecke

I'm beginning to think it better to just let my business stick to Windows. This just seems defeatist when the real reason is just because too many other companies use Windows.

Barney-15E

Level 10

112,818 points

Dec 6, 2009 6:58 PM in response to etresoft

I will try to figure out what version of Exchange server we are running. I am connected to a DoD server, which must handle requests from the Mac OS, so I don't know if I can determine if there are some Mac specific extensions loaded or if I can determine what they are.

Dec 7, 2009 3:17 AM in response to Barney-15E

Hi Barney,

I just sent my test mail to a friend who works at the OUP (Oxford University Press) to see how it was received on his PC Outlook Client vs. Blackberry vs. Mac at home. Whilst the mail looked fine on his Mac, both the Blackberry and Outlook emails missed off the second two paragraphs of the email. They were both removed to separate attachments.

Not sure what versions of each client they use, I could find out, but not sure if it's worth it.

Don't know what to do from here. I could complain to Apple again, or as you suggest to the other "real" culprit, MS. Both would probably be a waste of time and now I'm beginning to feel as though I'm in a minority being upset about this? Like you say, maybe users should just be trained to be aware that email is primarily a text only medium, and mixing anything else risks the recipients ability to easily view and read important text content.

What a blow!

Thanks for your inputs.

etresoft

Level 8

46,560 points

Dec 7, 2009 8:11 AM in response to Robert Borley

Robert Borley wrote:
I just sent my test mail to a friend who works at the OUP (Oxford University Press) to see how it was received on his PC Outlook Client vs. Blackberry vs. Mac at home. Whilst the mail looked fine on his Mac, both the Blackberry and Outlook emails missed off the second two paragraphs of the email. They were both removed to separate attachments.

Did you try my trick of selecting all the message content and changing the font to something non-default? The result is a message very similar to what Thunderbird creates.

Like you say, maybe users should just be trained to be aware that email is primarily a text only medium, and mixing anything else risks the recipients ability to easily view and read important text content.

The only real problem is Apple's assumption that other e-mail programs are adhering to e-mail standards that have been in place for 20 years. If you force your message to be rich text (via changing the font) you will send both a plain text and an HTML version of the same message. In theory, clients that cannot understand the HTML can still see the text version, followed by lots of gibberish.

You will probably just make the situation worse by trying "plain text". Very few people (including Apple, Inc. Mail programmers) really know what "plain text" means. It text, plain text, and nothing else. As soon as you add any attachment, you've created a complex message. If you add an attachment and leave the message type as "plain text", you've created a standards-compliant, perfectly valid e-mail message that Outlook can't display properly. If you want to send such messages to Outlook users, you must be aware of Apple's behavior and Microsoft's bugs and work around them both.

Dec 7, 2009 9:53 AM in response to etresoft

etresoft wrote:
Did you try my trick of selecting all the message content and changing the font to something non-default? The result is a message very similar to what Thunderbird creates.

No. I wanted to do the same test but with a well respected professional organisation as the recipient. Not that that means they are cutting edge with the latest software, often it means the opposite, but the real world nonetheless.

The only real problem is Apple's assumption that other e-mail programs are adhering to e-mail standards that have been in place for 20 years. If you force your message to be rich text (via changing the font) you will send both a plain text and an HTML version of the same message. In theory, clients that cannot understand the HTML can still see the text version, followed by lots of gibberish.

I have just tried the workaround, but I am not prompted to select, change or make the mail Rich Text. I select the font from the toolbar and am just presented with a font dialogue box. When I change the font, the font changes but nothing else happens. I then close the font dialogue box, press send and the mail goes.

I am doing this on my Macbook running 10.5 so I will try again later on my iMac running 10.6.

etresoft

Level 8

46,560 points

Dec 7, 2009 9:58 AM in response to Robert Borley

Robert Borley wrote:
I have just tried the workaround, but I am not prompted to select, change or make the mail Rich Text. I select the font from the toolbar and am just presented with a font dialogue box. When I change the font, the font changes but nothing else happens. I then close the font dialogue box, press send and the mail goes.

You must have your default set to be "rich text". It doesn't matter. You still need to change the font for force it to be "rich text".

I am doing this on my Macbook running 10.5 so I will try again later on my iMac running 10.6.

I only checked on 10.6.

Tom Gewecke

Level 10

115,970 points

Dec 7, 2009 9:59 AM in response to Robert Borley

When I change the font, the font changes but nothing else happens.

Make sure the font you have changed it to is not the same as the font listed in your Mail > Preferences.

Dec 8, 2009 3:32 PM in response to Tom Gewecke

OK. Done. I selected Tahoma instead of Helvetica, which is set in System preferences. I sent another test mail to OUP. I'll report back when I get a reply.

Thanks again.

Dec 8, 2009 6:23 PM in response to Robert Borley

This is a long standing issue, and easily solved by sending in Plain Text vs Rich Text Format. Outlook makes a mess of RTF when sending to others, and does badly receiving that sent from Apple's Mail. In general it is best to send in Plain Text -- see:

http://email.about.com/cs/netiquettetips/qt/et070103.htm

Ernie

etresoft

Level 8

46,560 points

Dec 9, 2009 6:57 AM in response to Ernie Stamper

Ernie Stamper wrote:
This is a long standing issue, and easily solved by sending in Plain Text vs Rich Text Format.

No. Sending in "plain text" has no effect. If you send a message in "plain text" with attachments, Outlook cannot display it properly.

I always use "plain text" in quotes because it isn't really plain text. If you compose a "plain text" message in Apple Mail, and add an attachment, you get a complex MIME document with one or more "text/plain" parts and one or more attachments. That is what Outlook cannot display.

If, on the other hand, you force Apple Mail to generate a true HTML "rich text" message by setting a non-default font for the entire message, then you will create a complex MIME document with one part being an HTML segment that Outlook can display properly.

I verified this myself. I can give you a screen shot if you don't believe me.

Dec 9, 2009 7:11 AM in response to etresoft

You are simply incorrect based upon many, many people who have found this works! Experience proves the theory. In fact, Mail itself will convert RTF to Plain Text when sending messages with attachments when only a single font has been used in composing the message, for this exact reason.

It is the dual copies (once in Plain Text, and once in RTF/limited HTML) that causes Outlook (and Outlook Express) users to think the files are embedded.

Let's don't clutter the topic to display, but feel free to send me a screenshot via email -- my address can be found in my Profile. I am fully aware of the creation of the plain text portion of the message with header to that effect you mention, but it does not matter. It is the creation of the second portion in RTF/HTML that is problematic.

Ernie

direwolf8

Level 4

1,280 points

Dec 9, 2009 8:41 AM in response to Robert Borley

It's true that Windows users often assume that the world is compatible with them even if they use software in non-standard ways. Here are a few things that all users need to understand:

Web pages and e-mail messages may look different in every client, browser, and computer. If you need something to look exactly as it does on your screen, send a pdf with embedded fonts. Mail is not the way to send a document that needs to look exactly a certain way.

You may be able to send unlimited size enclosures with your e-mail, but the recipient may not be able to receive them. So your users may have to learn about ftp. It's not the fault of the mail program. You're trying to use it for something other than mail, as it was originally intended.

Switchers beware - email from Mail is not processed by Outlook properly