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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

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46 replies

Dec 5, 2009 6:39 AM in response to Robert Borley

If you are actually using 10.6, you have posted your message in the wrong forum. This one is for 10.5. The 10.6 Mail forum is here:

http://discussions.apple.com/forum.jspa?forumID=1338

I think many people for whom compatibility with Windows Outlook is of primary importance choose to use the MS app Entourage which is designed for that.

To have screenshots in your message, you need to put them on a server and then put a link to that here.

Dec 5, 2009 12:12 PM in response to Tom Gewecke

Hi,

The reason I posted it under 10.5 is because I use 10.5 on my Macbook which is where I have been testing this problem. The problem is exactly the same using Mail under 10.6, so I suppose this post can stay here under 10.6 with no issues.

I would have thought almost anyone (certainly a vast majority) using Mac Mail would consider compatibility with Windows Outlook is of primary importance. Who would want messages being sent which weren't going to be received and read in the way they are supposed to look. Especially with missing text from the main body of the email?

Dec 5, 2009 12:43 PM in response to Robert Borley

I suppose this post can stay here under 10.6 with no issues.


It is certainly much better to have it here, since no one is going to pay any attention to or produce fixes for problems like this in 10.5 at this point.

I would have thought almost anyone (certainly a vast majority) using Mac Mail would consider compatibility with Windows Outlook is of primary importance.


Whether that's true you can judge by searching to see how many other people have raised Outlook problems here compared to other things. Personally I haven't seen a lot of changes in Mail over the last 5 years aimed at Outlook compatibility, aside from changing a behavior that produced mixed encodings in rich text messages (to accommodate a very stupid bug in Outlook that generated gibberish text).

The place to tell Apple directly what you need is here:

http://www.apple.com/feedback/macosx.html

Dec 5, 2009 12:47 PM in response to Barney-15E

Barney-15E wrote:
Which is unforgivable? Writing an email program that does not comply with internet email standards or writing one that does?


That depends greatly on your interpretation of what matters to most users.

I have no idea which email program between Mail and Outlook doesn't comply with the internet email standards you refer to, but I assume you are referring to Outlook in defense of Mail?

That said, it doesn't really matter. The fact remains that email sent from Mail looks messed up on Outlook which is used by a huge number of people, especially in the commercial arena. That matters. I have sent the same test message I mentioned from Gmail (web) and Thunderbird (client) and the mail turns up in Outlook exactly as expected.

Thunderbird even asks if you want the mail sent in HTML, Plain text or both and the mail still turns up in Outlook as you would expect whichever option you choose. Mail is the only client I have used which messes it up.

I think it is important for any user of Mail to know this because they could be expecting recipients to see and read their mails as they were intended and not with chunks of text removed to separate attachments without their knowledge. I was shocked to find this out. This is something that I feel strongly that Apple should take note of and address (I've left feedback).

Using a Mac is great and a great experience in general. I don't want to use another email client. Even Thunderbird isn't as nice to use, and as for Entourage, it's like Microsoft have purposely made it hideous to temp people back to Windows. Outlook is streets ahead, but still clunky and full of MS overkill. But Mail is just the best client out of any I have tried so far, on lots of fronts (IMHO). So to discover that it has this major flaw is simply distressing.

Dec 5, 2009 3:22 PM in response to Robert Borley

Robert Borley wrote:
Barney-15E wrote:
Which is unforgivable? Writing an email program that does not comply with internet email standards or writing one that does?


That depends greatly on your interpretation of what matters to most users.

I have no idea which email program between Mail and Outlook doesn't comply with the internet email standards you refer to, but I assume you are referring to Outlook in defense of Mail?

That said, it doesn't really matter. The fact remains that email sent from Mail looks messed up on Outlook which is used by a huge number of people, especially in the commercial arena. That matters. I have sent the same test message I mentioned from Gmail (web) and Thunderbird (client) and the mail turns up in Outlook exactly as expected.

I send Mail to my Outlook account at work and it shows up exactly as I sent it, after I enable HTML in Outlook. My exchange server turns off HTML by default and I must specifically select it in each message. I have tried various methods including "Windows friendly," and I actually got better results by not using that option.
Thunderbird even asks if you want the mail sent in HTML, Plain text or both and the mail still turns up in Outlook as you would expect whichever option you choose. Mail is the only client I have used which messes it up.

Well then, just use Thunderbird.
I think it is important for any user of Mail to know this because they could be expecting recipients to see and read their mails as they were intended and not with chunks of text removed to separate attachments without their knowledge. I was shocked to find this out. This is something that I feel strongly that Apple should take note of and address (I've left feedback).

What every person should know is that there is no standard that prevents an email client from displaying an email any way it wishes. No matter what you do on your end when sending, the recipient's email client decides how to display the email. If you want people to see a document exactly as you prepared it, send a pdf. It is designed for that exact purpose. Email is not.
Using a Mac is great and a great experience in general. I don't want to use another email client. Even Thunderbird isn't as nice to use, and as for Entourage, it's like Microsoft have purposely made it hideous to temp people back to Windows. Outlook is streets ahead, but still clunky and full of MS overkill. But Mail is just the best client out of any I have tried so far, on lots of fronts (IMHO). So to discover that it has this major flaw is simply distressing.

There is no major flaw. It does send internet compatible email. How your recipient sees that message is up to their client. Trying to make your software "Microsoft compliant" is stupid, as they will just change the specification to break your program.

Dec 5, 2009 6:18 PM in response to Barney-15E

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Dec 5, 2009 7:13 PM in response to Robert Borley

First of all, I need to caution you on using such an adversarial tone. That tends to take threads off track real fast. Such threads are usually started by people just looking to complain and start a fight. Usually they find one and everyone leaves angry.

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.


That being said; this is an excellent example and I was able to reproduce your problem.

I looked at the e-mail that Apple Mail is generating and it is perfectly fine. All the data shows up in Outlook, it just isn't very pretty. The fact that Outlook cannot display an e-mail this simple is just shocking. Outlook is worse than I thought.

You have a valid point about Apple-generated mail needing to be viewable in Outlook. Apple knows this. Apple has been actively dumbing down Apple Mail for years to try to improve its interoperability with Outlook. Sadly they still have some work to do.

There does appear to be a workaround for your problem - at least on this simple message.

When you compose an e-mail, the last item in the "Format" menu will be either "Make Plain Text" or "Make Rich Text". Apparently, Outlook has trouble with the plain text. Furthermore, the "Make Rich Text" option might not be enough. Don't even use that menu option. Select all the text in your message. Click the "Fonts" toolbar icon. Change the font to something else, it doesn't matter what. When you do that Mail should ask you if you wan to change to "Rich Text". You do. This is very important, you can't just leave the default at "Rich Text" or just change the message to "Rich text". You must make a an actual "rich text" modification to your message. Then it will show up properly in Outlook. This advice may be different than what most people will give you here in Apple Discussions. I don't care. I just did it and it works.

I am going to file two bug reports with Apple right now.

The first is to improve the format that Apple Mail sends out. Thunderbird does send out a more "pure HTML" than Apple Mail. That is part of the problem.
The second is regarding the "make rich text" option. If I say "rich text", that should override the fact that I haven't really used rich text. Apple clearly agrees with you that "Outlook-compatible" is more important to them than "standards-compatible". Trust me on this one.

So, thanks for the good reproduction steps. But next time, maybe tone it down a bit, eh?

Dec 6, 2009 5:39 AM in response to etresoft

If I say "rich text", that should override the fact that I haven't really used rich text.


Users who want their emails to show up in Outlook in a particular style have been requesting default rich text settings for font, font-size, and color for 5 years now, and there are countless threads in the forums about it. 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.

Dec 6, 2009 6:25 AM in response to etresoft

I am really sorry that I am coning across as adversarial, I truly don’t mean to. I am just finding it hard to suppress my frustration with this issue as it has already caused me a problem at work. But thanks for pointing it out. I’m really not looking for a fight, just clarification that I am not mistaken and not doing something wrong myself.

There are many people in these forums who are extremely helpful to lesser experienced users such as me.

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.

So much so that I am putting myself through he highs and lows of switching to Mac at work. So far the highs outweigh the lows! To me this email flaw is a major disappointment for which I feel compelled to investigate. 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. So I feel I am truly supporting Apple here as I think on balance it will be worth it for staff morale alone (they will all love to have Mac’s and iPhones, and I think iPhone is good for business!).

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. I love Mail and coupled with Mail Act On and Mail Tags, it beats the socks off Outlook and Thunderbird.

Thanks also for your helpful comments and I will indeed tone it down in future. I was really showing my frustration at Apple for missing basics here while advertising Macs as being compatible, not at any users in this Forum. I think Barney took it personal as if he were an Apple employee. I will bear this in mind for future posts and apologise to Barney.

Thanks also for your work around. I will use it as it’s pretty simple, but I hope Apple address this because explaining this to users who just want to type emails, add pictures and for it to “just work” will be a challenge.

I totally agree with your comments about Outlook. It is shockingly bad for an email client so widely used. Eventually employers will come to realise just how unproductive it is as a productivity solution.

Dec 6, 2009 6:48 AM in response to Robert Borley

Robert, can you point me to the Microsoft forums where you ask about Outlook not being able to properly display emails?
I realize completely that you will get no response from Microsoft. However, it is their problem as many email clients produce perfectly fine emails that Outlook cannot display. Even Outlook Express and Entourage suffer this fate. Why is it ok to complain at Apple but not Microsoft?

As I have said before, I can format an email just as you describe, and it displays fine on my Outlook at work. There are probably at least three versions of Outlook running out in the wild, if not more, but on Outlook 2007, formatted emails show up as I format them. However, once converted to html, Outlook 2007 won't allow you to save an attachment for some stupid reason. Add in all the versions of Exchange Server with all the versions of Outlook, and it is silly to try and comply with them all.

Dec 6, 2009 8:04 AM in response to Barney-15E

Hi Barney, I am replying to you to apologise for coming across as adversarial. I didn’t mean to. I was venting frustration at Apple for what I see as causing me a problem using their Mail client as instructed, and the email not showing up in recipients Outlook clients as intended. I will not use this forum to vent frustration at Apple in future as it clearly upsets some people here.

I still feel that this is a major flaw on Apple’s part, especially as most other widely used clients and Webmail don’t present this problem. 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.

Barney-15E wrote:
I send Mail to my Outlook account at work and it shows up exactly as I sent it, after I enable HTML in Outlook. My exchange server turns off HTML by default and I must specifically select it in each message. I have tried various methods including "Windows friendly," and I actually got better results by not using that option.



Communicating this to all our suppliers and customers is impractical.

Well then, just use Thunderbird.



That doesn’t help and is not why I am posting a topic here. I am just pointing out that it must be possible for Apple to address this issue by highlighting that Thunderbird has.

What every person should know is that there is no standard that prevents an email client from displaying an email any way it wishes. No matter what you do on your end when sending, the recipient's email client decides how to display the email. If you want people to see a document exactly as you prepared it, send a pdf. It is designed for that exact purpose. Email is not.



I agree. Every person should know this, but I don’t think they do. I do think users have the right to expect their email, at the very least, to be readable (all text present) in this scenario.

I agree that complex formatting, web publication style columns etc. should be preserved for HTML email and pdf etc. and not expect Mail to produce email readable by other receiving clients.

However, I think expecting users to convert documents to pdf just because they want to attach a photo is impractical, unproductive and unnecessary. Email is evolving from a pure text only way to communicate and users are being encouraged by Apple to use Mail for this purpose. I really don’t think I am expecting too much in this scenario. I think even Apple would agree to this. I could well be wrong though, which is why I’m using their forum.

It does send internet compatible email. How your recipient sees that message is up to their client.


I bow to your expertise here. Your forum status suggests you are more qualified than I on this topic and I am sure Apple are clever enough to ensure their client sends internet compatible email.

It certainly appears that the receiving client is at fault by seemingly not following internet standards as you suggest, in this case Outlook. However, it doesn’t help Mail users because Outlook is used by so many business customers and suppliers, so many family members and friends. Users of Mail should be aware of what is happening to their simple messages upon receipt by Outlook. Or Mail should compensate for this. I strongly feel that this is a major flaw. As mentioned, I don't know of another widely used client that has this problem with Outlook recipients. Surely this is as important to most users as ensuring email is internet compliant.

Outlook is so widely used that MS is powerful enough to ignore that, just because Mail follows certain standards, messages from Mail are pulled to pieces and miss-presented to Outlook users. Complaining to MS is a complete waste of time. Outlook writes it's own standards and as far as I know, Mail is the only email client that cant send this simple mail in a way that can be easily read by Outlook users.

Trying to make your software "Microsoft compliant" is stupid, ...


I think many, including Apple, and most software developers and users think otherwise. Take a look at one post in this forum entitled Snow Leopard with Exchange support not working 33,000+ views and proof that Apple are trying hard to interact properly with MS email products.

...as they will just change the specification to break your program.


I think it’s an unfortunate but necessary evil at the moment. You are probably right to elude to the fact that the industry should be better regulated.

Dec 6, 2009 8:49 AM in response to Barney-15E

Barney-15E wrote:
As I have said before, I can format an email just as you describe, and it displays fine on my Outlook at work. There are probably at least three versions of Outlook running out in the wild, if not more, but on Outlook 2007, formatted emails show up as I format them. However, once converted to html, Outlook 2007 won't allow you to save an attachment for some stupid reason. Add in all the versions of Exchange Server with all the versions of Outlook, and it is silly to try and comply with them all.


I was able to reproduce the problem with Outlook 2007 (12.0.6514.5000) using a local POP server on my Mac. Perhaps Outlook is designed to work better with an Exchange server. That wouldn't surprise me. It is known that Internet Explorer violates the HTTP protocol if it knows it is talking to IIS.

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

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