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

46,960 points

Dec 9, 2009 10:36 AM in response to Ernie Stamper

Ernie Stamper wrote:
You are simply incorrect based upon many, many people who have found this works! Experience proves the theory.

I put my trust in my own eyes.

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.

No it doesn't. I've got just such a message sitting in /var/mail right not that proves it.

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.

No, that is the format that Outlook understands. The one that gives Outlook problems is a "multipart/mixed" containing plain text parts and image parts.

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.

It is sitting in your inbox. My ISP is having a DDOS right now, so it is from my work e-mail address instead of "etresoft".

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.

My experiments indicate the exact opposite. I admit that I don't know what happens when you put Exchange into the mix. But sending from my local SMTP to my local POP indicates that using "rich text" and "making sure" with a font change is the way to go. I'm quick to shoot down people making unsubstantiated and illogical claims about Apple Mail. In this case, the original poster is 100% correct.

Dec 9, 2009 4:49 PM in response to etresoft

I am pleased to report that your workaround worked perfectly! It worked! You are absolutely correct. The email was received in perfect condition on both Outlook and Blackberry.

Even with the pictures in-line on Outlook (I have asked for whether this is also the case on the Blackberry and am waiting for a reply).

I am so pleased this worked, it's now a question of training users to do this every time they feel the need to send mails with picture attachments. Crazy, but at least Mail can be forced to communicate properly with Outlook with this simple combination of text and photo attachments.

However, don't you think this also highlights that it is a failing of Mail as an email client? How come changing the font forces Mail to send the email in a format Outlook and Blackberry users can read without removing text from the mail body and keeping the attached pictures in-line? Surely there should be a more straightforward way of doing this, or even that Mail should do this automatically!

I also tried the advice posted by Ernie Stamper and it did not work. It had the same effect as doing nothing. The pictures were removed to attachments along with the more crucial 2nd and last paragraphs. I really don't understand why he is so adamant that it works. I will reply to him separately.

Many thanks once again for the work around, but it would be great if Mail could just cope with this simple email as do so many other email clients.

Dec 9, 2009 5:20 PM in response to Ernie Stamper

Hi Ernie,

Thanks for your post.

It may be a long standing issue, but it most likely isn't something known to many who are coming over to use Mail from Outlook, or switching from Windows.

Also, your workaround doesn't work, I tested it today. It has no effect on the net result. The email arrived mutilated by Outlook in the same way it does by performing the composition with the default settings.

Even if it did work, the article you pointed me to on About.com is not that relevant to this post. If you read this post closely you will notice that I am not trying to send "Fancy HTML" emails. That might be the net result of what Mail is creating, following my simple actions, but it is not what I want to do.

I am simply adding 1 or 2 picture attachments to an email with a method Apple encourages one to use. By dragging the pictures into the message body. In fact I'm pretty sure that leaving the curser in the middle of the message body and clicking the attach button in the toolbar has the same effect.

In this scenario of attaching two pictures to make a simple text, picture email combination your article in About.com should be entitled "When in Doubt, Send Rich Text Email, not Plain Text Email or Fancy HTML, but remember to change the font".

It would even be nice if Mail would just send the text complete in the message body and the pictures as attachments not in line, but it doesn't.

Thank you for replying though and trying to help out. I understand where you are coming from and understand that fancy HTML email should always be accompanied by an alternative way to view the message for the recipient or not sent at all.

What I am trying to highlight here though is that Mail has a major drawback for users trying to communicate with recipients using MS Exchange / Outlook and Blackberries (Most commercial recipients?). Text only, OK, but adding one picture results in Outlook pulling the mail to pieces removing important text?? Crazy!

Dec 9, 2009 5:32 PM in response to direwolf8

Hi,

Thanks for your comments but Apple encourage it's customers to use it in this way. They should adequately warn us if what you say is correct. I do not agree that the things you mention such as ftp is something users should know all about. All I am trying to do here is attach 2 pictures to an email and expecting the TEXT in the email at the very least to turn up in the body and not as attachments.

If I'm using Mail for something it is not intended for, then all it is intended for is sending text only email. I can't believe Apple nor most of it's users would settle for that. Mail is working properly and in accordance to internet standards, I have learned that much. But it isn't Outlook friendly, thats my point here, that it should be. Other email clients cope with this as does mail when the font is changed just before pressing send!

Barney-15E

Level 10

112,992 points

Dec 9, 2009 7:30 PM in response to Robert Borley

All I am trying to do here is attach 2 pictures to an email and expecting the TEXT in the email at the very least to turn up in the body and not as attachments.

Then don't send mixed part messages to Outlook. Separate all of the text from the attachments and it can usually handle it. Outlook cannot handle properly formatted messages where text is interspersed with attachments.

But it isn't Outlook friendly, thats my point here, that it should be. Other email clients cope with this as does mail when the font is changed just before pressing send!

Other clients don't cope with this. Outlook will even mangle Outlook Express and Entourage messages formatted correctly. Those are both written by Microsoft.

Dec 10, 2009 2:44 AM in response to Barney-15E

Barney-15E wrote:
Then don't send mixed part messages to Outlook. Separate all of the text from the attachments and it can usually handle it. Outlook cannot handle properly formatted messages where text is interspersed with attachments.

Hi Barney. Thanks, I've worked out another workaround based on your advice. I still think Mail should warn you that adding an attachment just 1 character into a message will mean the rest of the text will not be viewable on a blackberry or Outlook Client. Or even better, it should just work the way it does when you do the change font thing.

How should I separate all the text from the attachments anyway...?
This is what I did, it this the best way...?
Attach all attachments while the cursor is blinking right at the beginning of the message body or right at the end, before and after any other characters you want in the body text, or the cursor is in the subject or address fields, then click attach, or drag and drop with extreme care?

I have tried it this way, seems a bit cumbersome but it does work.

Other clients don't cope with this. Outlook will even mangle Outlook Express and Entourage messages formatted correctly. Those are both written by Microsoft.

OK. What I mean is other clients on a Mac like Thunderbird. What about Entourage? Eudora? Opera?, anyone?

I still think Mail should be Outlook friendly, no matter what the internet protocols say. It it possible, proved by the 'change the font' work around. Or is that a bug in mail which has the effect of sending Outlook friendly messages? Could be I suppose?

Anyway, still disappointed with Apple Mail because of this, fact remains, it cant send Outlook friendly emails without a lot of messing about when you need to attach a picture or pdf. Should be simple, should "Just Work"!

Dec 10, 2009 2:53 AM in response to etresoft

Got a reply from my friend over at OUP...

Yes, saw it all (3 paras and 2 pics) in the body of the email (not as attachments) for both OUtlook and blackberry. You've obviously cracked it!

Cheers

Thanks again. At last, Outlook friendly emails from Mail with inline attachments! Should it really be this hard? At least there is a way to achieve it. The 'change font' workaround is the way to go.

AnttiS

Level 1

6 points

Dec 10, 2009 3:27 AM in response to Robert Borley

Does not work with PDF:s though. The only way to get a correctly showing message in to outlook with a pdf attachment is to make a plain text message and put the attachment in last, after your signature. I tested many variations. See http://discussions.apple.com/thread.jspa?messageID=10714785#10714785

Antti

Dec 10, 2009 4:10 AM in response to AnttiS

You are right. The change font trick here actually makes things worse too, as it removes the text from the body of the mail and puts it in a .htm file instead of a .txt file.

However, I don't find that you have to use plain text as you say in your post...

If you put the pdf attachment right at the start or the end of the message (body text), then it turns up fine (albeit as a separate attachment) in Outlook and the body text remains in the mail.

Barney-15E

Level 10

112,992 points

Dec 10, 2009 5:41 AM in response to Robert Borley

How should I separate all the text from the attachments anyway...?
This is what I did, it this the best way…?

There is an option in Edit>Attachments to always place attachments at end of message.

Other clients don't cope with this. Outlook will even mangle Outlook Express and Entourage messages formatted correctly. Those are both written by Microsoft.

OK. What I mean is other clients on a Mac like Thunderbird. What about Entourage? Eudora? Opera?, anyone?

Entourage is on the list of known issues.

I still think Mail should be Outlook friendly, no matter what the internet protocols say. It it possible, proved by the 'change the font' work around. Or is that a bug in mail which has the effect of sending Outlook friendly messages? Could be I suppose?

Some people think that is a bug. I'm not so sure. I'm not sure of the correct term for the message, but unless you do something that drives RTF or HTML-type formatting, it essentially sends plain text with attachments.

Anyway, still disappointed with Apple Mail because of this, fact remains, it cant send Outlook friendly emails without a lot of messing about when you need to attach a picture or pdf. Should be simple, should "Just Work"!

As long as you put attachments at the end, it seems to be able to handle it, and is not that difficult with the option in the Edit>Attachments submenu. I've got a couple more tests going to my Outlook account, but it seems the Remote Desktop server is down, so I can't check until I go to work. Gmail does a better job, but similar to outlook in that a plain text with attachments at the end will display the plain text alternative, and then attachments. However, with Attachments at end of message, Gmail displays them inline--even without any font formatting. That is what I want to look at on Outlook.

The "Always send Windows friendly Attachments" was Apple's attempt to make Outlook compatible emails. I'm not sure it works as well as putting the attachments at the end. However, if you want to send an attachment that they can save from Outlook, you must use plain text only.

direwolf8

Level 4

1,280 points

Dec 10, 2009 7:29 AM in response to Robert Borley

I think you misunderstood some of my comments. Apple Mail doesn't set the limitations. Even if Apple Mail accepts a 20 GB attachment, it's not likely that every hop along the way will pass it intact. Your own outgoing mail server will have a limit. And the incoming mail server will have a limit beyond your control. If your users need to send large attachments and don't know how to use anything but email, then they won't be able to do their jobs.

You said yourself that "Mail works in accordance to internet standards... but it isn't Outlook friendly." Shouldn't you be encouraging Microsoft to adhere to internet standards instead of forcing everybody to let Microsoft set the defacto standards?

etresoft

Level 8

46,960 points

Dec 10, 2009 8:23 AM in response to AnttiS

AnttiS wrote:
Does not work with PDF:s though.

PDF is completely different. While the Mac treats PDFs as any other image, on Windows, PDFs are just another file. This is not a bug on either end. It is just an extra capability that the Mac has that Windows does not.

Barney-15E

Level 10

112,992 points

Dec 10, 2009 3:20 PM in response to Barney-15E

I goofed up my test, but discovered something else.

I tried every combination of Attachments at end and Windows Friendly and each one showed up fine in Outlook 2007. Perplexed, I looked closer and noticed that I had used an account that had a default signature with font formatting, Color, and hyperlink. Apparently that was enough to make Outlook display the message correctly. I forgot to check if I could download the attachments, though.

Dec 10, 2009 3:54 PM in response to direwolf8

direwolf8 wrote:
I think you misunderstood some of my comments. Apple Mail doesn't set the limitations. Even if Apple Mail accepts a 20 GB attachment, it's not likely that every hop along the way will pass it intact. Your own outgoing mail server will have a limit. And the incoming mail server will have a limit beyond your control. If your users need to send large attachments and don't know how to use anything but email, then they won't be able to do their jobs.

Sorry, I missed your point about large attachments. You are right of course, but this is not relevant to me. I always encourage users to send email attachments smaller than a couple of Mb. I am only talking about attaching 2 - 3 pictures to a mail on this post. Drop box and such like are much better tools for large files.

You said yourself that "Mail works in accordance to internet standards... but it isn't Outlook friendly." Shouldn't you be encouraging Microsoft to adhere to internet standards instead of forcing everybody to let Microsoft set the defacto standards?

I did indeed say that and in an ideal world I would agree with your comments. However, we all know that what you are suggesting here is a complete waste of time, for now anyway. I mentioned in an earlier post in this thread that this would be futile. Almost as futile as me filing a bug report on the Apple feedback link about this problem. MS has proved time and again that it doesn't care about it's own customers, let alone users of competitive products.

At least there is some small chance that if a high status forum member agrees with the fact that Apple and Mail as a product is missing out on providing the right service to it's users, they may be able to get Apple Mail developers to listen to reason. MS is losing its grip on its monopoly, but slowly. Outlook is still ubiquitous enough to care only about it's de facto standards and if the rest of us want to communicate effectively with it's users then we have to fall in line for now. Not completely, but for simple mail like this surely?

Dec 12, 2009 6:47 PM in response to etresoft

Hi,
You know you were considering writing your own email client, well write the first Google Wave client for the Mac instead and get it to work with iCal and Address Book. We can forget all about this entire post very quickly. Oh, and by the way, Outlook will be dead very soon!
Rob

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