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Mail Decomposes email & Sends Multiple Attachments
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Fresh-Faced Recruit
Join Date: Nov 2003
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I recently abandoned Windows and Office, and bought myself a PowerBook. I'm quite happy with the decision, but there's a problem I'm having with Mail that's driving me batty!
When I compose an email by cutting & pasting an article from a Safari web page, or by simply dragging text from a web page into my browser, the email is 'sometimes' massacred! I'm getting nasty notes back from my email recipients telling me not to send them 15 or 20 attachments!
If I open the sent email, it looks just fine. If I look at the email, as received by someone else, it is nothing but a bunch of attachments. Click on some of them, and they're nothing but a line of text that was in my outgoing note.
I do know that the mail.app does not support HTML, so I'm trying to avoid sending HTML. (THIS, I believe is ludicrous however. Tons of HTML emails are sent around every day. In fact, Apple sends HTML marketing emails to me! But back to the point...) It's a simple need that I have: take text that appears in a browser, and send it in an email. Is Mail.app not capable of doing that? Do I need to switch to Entourage? Or am I doing something wrong?
Thanks for any advice!
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Mac Elite
Join Date: Sep 2000
Location: Canada
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If it's the problem I'm thinking of, it's actually the fault of the Windows email programs.
If you put an attachment in between text in an email, some Windows programs will make the text following the intended attachment attachments themselves. Therefore, a PC user will see some text, the intended attachment, and then a bunch of other attachments containing only text.
How does the intended attachment get there in the first place? Well, if you're dragging and dropping stylized text into an email, that text can be interpreted by the Windows email programs as an attachment (it's rich text instead of plain text), which leads to the above problem with anything you write afterwards.
So, if this is the problem, here are your options: tell your Windows-using friends to get real email clients (lots of luck, right?) or, before you send emails, select from the Format menu, Make Plain Text. This will cause all font, colour and other text attributes to be lost, but you won't upset your email recipients.
Oh, and welcome to the Mac.
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Fresh-Faced Recruit
Join Date: Nov 2003
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Thanks for your advice, dtriska.
As far as I know, this problem has occurred for recipients using either MS Outlook and Outlook Express. But, of course, those are the dominant mail apps :-)
I'll give your suggestion of making my outgoing emails into plain text. The thing that's in the back of my mind is that while I was a Windows/Outlook user, I did in fact copy and paste IE pages into my outgoing emails. Recipients didn't have a problem then? So, if the problem is with the recipient's email client, shouldn't the problem have occurred then as well?
I'll report back in a couple of days,
-Frank
(and happy to be on the Mac :-)
Originally posted by dtriska:
If it's the problem I'm thinking of, it's actually the fault of the Windows email programs.
If you put an attachment in between text in an email, some Windows programs will make the text following the intended attachment attachments themselves. Therefore, a PC user will see some text, the intended attachment, and then a bunch of other attachments containing only text.
How does the intended attachment get there in the first place? Well, if you're dragging and dropping stylized text into an email, that text can be interpreted by the Windows email programs as an attachment (it's rich text instead of plain text), which leads to the above problem with anything you write afterwards.
So, if this is the problem, here are your options: tell your Windows-using friends to get real email clients (lots of luck, right?) or, before you send emails, select from the Format menu, Make Plain Text. This will cause all font, colour and other text attributes to be lost, but you won't upset your email recipients.
Oh, and welcome to the Mac.

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Fresh-Faced Recruit
Join Date: Nov 2003
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Unfortunately, that didn't solve the problem :-( I did switch over to plain text. However, I merely forwarded an HTML email I received, and the recipients claimed that it was a bit of text interspersed with a large number of TIFFs.
I guess I'm at my wit's end on this, as I don't wish to be sending around illegible emails to business associates! Unless anyone else has a thought on this problem, I'm going to have to switch to Entourage...
- Frank
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Forum Regular
Join Date: Apr 2001
Location: Melbourne, VIC, Australia
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I use two different approaches to this problem. If I use drag and drop I always make sure that the added item is the last thing in the email, sitting below my signature.
I prefer to use the dialog box after selcting the last character in the email and attach the file, also selecting the Windows friendly messages box.
Most of my colleagues are Windoze and none of them complain any more.
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 - Earth First - We'll mine the rest of the planets later
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Senior User
Join Date: Jul 2002
Location: Arizona Wasteland
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Originally posted by iFrank:
When I compose an email by cutting & pasting an article from a Safari web page, or by simply dragging text from a web page into my browser, the email is 'sometimes' massacred! I'm getting nasty notes back from my email recipients telling me not to send them 15 or 20 attachments!
Why not just send them the URL?
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Fresh-Faced Recruit
Join Date: Nov 2003
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Thanks Fillman,
Unfortunately, that doesn't seem to solve the problem. I generally do use the dialog box to insert stuff. The real problem, however, is when I want to copy text from a web page, or forward an HTML email that I've received. In both cases, the recipients (who are Windows users with outlook or OE) get garbled emails with a ton of attachments.
- Frank
Originally posted by Fillman:
I use two different approaches to this problem. If I use drag and drop I always make sure that the added item is the last thing in the email, sitting below my signature.
I prefer to use the dialog box after selcting the last character in the email and attach the file, also selecting the Windows friendly messages box.
Most of my colleagues are Windoze and none of them complain any more.
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Fresh-Faced Recruit
Join Date: Nov 2003
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Hi Ganesha,
I generally do send the URL when it's possible (that's new behavior due to this problem). In fact there's a nice Apple Script for Safari that simply creates an email with the URL as the first line.
BUT... if I need to paste text from a web page (perhaps only a sentence is relevant, and I need to highlight it)
OR... if I want to forward an HTML mail that someone else has sent me
OR... if I know someone is travelling and won't have online access
I have this problem. I'm surprised that others don't seem to have this problem? I've probed discussion boards and found scant mention of it.
- Frank
Originally posted by Ganesha:
Why not just send them the URL?
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Professional Poster
Join Date: Jul 2001
Location: New York, NY
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iFrank - one simple question - have you checked the option to send "windows friendly attachments?"
Edit->Attachments->Always Send Windows Friendly Attachments
Also, if you are writing a note about the article, try placing that before anything you paste in from a web page.
As an alternative, I'd suggest printing the page as a .pdf and simply sending that as an attachment (there may well be an applescript available to make this a one-step process)
Lastly - the fact that you are unable to forward HTML emails to windows people is really really bizarre, and definitely suggests a problem with their client (unless you're adding a signature or some other weirdness...)
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cpac
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Fresh-Faced Recruit
Join Date: Nov 2003
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Thanks for the insights CPAC.
Let's see...
1) I do have send Windows Friendly Attachments selected.
2) I also do type notes into emails prior to pasting any text from web pages into emails.
3) I do have an automatic signature entered into emails, so when I choose to forward one, a signature is pasted into the email (I'll try turning that off to see if it makes a difference)
4) sending as a PDF is certainly a possibility as a compromise, though it's also a little annnoying to recipients as they'll need to open a PDF reader (I wonder if I have an HTML mail that's come in, can I simply convert that entire email into a PDF?)
Any other thoughts? Is it worth giving Apple a call on this?
Thanks to all,
- Frank
Originally posted by cpac:
iFrank - one simple question - have you checked the option to send "windows friendly attachments?"
Edit->Attachments->Always Send Windows Friendly Attachments
Also, if you are writing a note about the article, try placing that before anything you paste in from a web page.
As an alternative, I'd suggest printing the page as a .pdf and simply sending that as an attachment (there may well be an applescript available to make this a one-step process)
Lastly - the fact that you are unable to forward HTML emails to windows people is really really bizarre, and definitely suggests a problem with their client (unless you're adding a signature or some other weirdness...)
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Professional Poster
Join Date: Jul 2001
Location: New York, NY
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Originally posted by iFrank:
3) I do have an automatic signature entered into emails, so when I choose to forward one, a signature is pasted into the email (I'll try turning that off to see if it makes a difference)
That could be the problem right there, though when you're pasting text and graphics from a web page, it might still get screwed up.
4) sending as a PDF is certainly a possibility as a compromise, though it's also a little annnoying to recipients as they'll need to open a PDF reader (I wonder if I have an HTML mail that's come in, can I simply convert that entire email into a PDF?)
.pdf is the only way to make sure people are seeing what you send them as you intend them to see it. As for your HTML emails, yes, you can make them (and anything else you can print) into .pdf's using OS X's built-in "save as .pdf" feature from the print dialog.
Any other thoughts? Is it worth giving Apple a call on this?
Not sure if its worth calling the, but you might search their support forums and/or post a question there. They're not always helpful, but it can't hurt.
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cpac
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Fresh-Faced Recruit
Join Date: Nov 2003
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CPAC,
I thought it might be helpful to show you what my emails look like. Since I can't post attachments here, I'd be happy to send a link to anyone -- for the PDF of an HTML email that I forwarded via Mail.app to an Outlook user. This email looked fine in my inbox (and in the outbox after being sent!) but every recipient who got it complained that it looked like this...
- Frank
Originally posted by cpac:
That could be the problem right there, though when you're pasting text and graphics from a web page, it might still get screwed up.
.pdf is the only way to make sure people are seeing what you send them as you intend them to see it. As for your HTML emails, yes, you can make them (and anything else you can print) into .pdf's using OS X's built-in "save as .pdf" feature from the print dialog.
Not sure if its worth calling the, but you might search their support forums and/or post a question there. They're not always helpful, but it can't hurt.
(Last edited by iFrank; Jan 8, 2004 at 05:21 PM.
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Professional Poster
Join Date: Jul 2001
Location: New York, NY
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looked at the .pdf you posted - it appears as though the user is viewing everything in plain text only - everything is the same size courier font...
that might be some of the problem right there. While outlook is certainly capable of displaying nicer email, sometimes users (or admins) have refused to allow anything but plaintext (to avoid the formating problems that can result from more complex email).
[EDIT]
Looking more closely at the .pdf - you can see that indeed the user is viewing the message as plain text - it says so right in the title bar!
[/EDIT]
(Last edited by cpac; Jan 8, 2004 at 06:51 PM.
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cpac
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Forum Regular
Join Date: Sep 1999
Location: Patterson, NY USA
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I have a related problem. An associate sent me an excel attachment from a machine running windows me. I was able to open it with maclink plus converting it into an appleworks spreadsheet. Now, when I forward the original e-mail to another associate running windows xp, when they open the attachment they get nothing but lines of code even though they have excel running on their machines. I tried re-forwarding the e-mail after choosing "always send windows friendly attachments" with the same problem.
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Professional Poster
Join Date: Jul 2001
Location: New York, NY
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When you forwarded, did you add any text after the attachment? (even a signature?)
Some/many windows clients have problems interpreting inline attachments if they're anything but the very last thing in a message.
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cpac
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Forum Regular
Join Date: Sep 1999
Location: Patterson, NY USA
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Originally posted by cpac:
When you forwarded, did you add any text after the attachment? (even a signature?)
Some/many windows clients have problems interpreting inline attachments if they're anything but the very last thing in a message.
Thats what weird about this. I made no changes at all to the original message. The only thing in the original message was the excel attachment. No text at all..........
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Forum Regular
Join Date: Aug 2000
Location: Germany, Europe
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Originally posted by cpac:
iFrank - one simple question - have you checked the option to send "windows friendly attachments?"
Edit->Attachments->Always Send Windows Friendly Attachments
What excactly does this option change about the way an attachment is send?
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Professional Poster
Join Date: Jul 2001
Location: New York, NY
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That option gets rid of the resource fork of a file (the thing that told the OS which program to open it with back when Mac's didn't use file extensions). When the option is checked, a windows user would sometimes see two files for only a single attachment, both with the same name, but one not appearing to be anything.
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Also, after futher investigation, the HTML forwarding problem comes out sometimes if you've got things set to "increase the quote level" of the email. If you turn that off, or decrease the quote level on the relevant text, and get rid of anything you've added at the top, I believe things will work out better.
PS - In Tiger, all the HTML stuff should be resolved, including drag & drop from Safari.
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cpac
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Fresh-Faced Recruit
Join Date: Sep 2005
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We are seeing this behaviour "Mail Decomposes email & Sends Multiple Attachments" on PC's using OUTLOOK. Checking the same email account on the same PC using OUTLOOK EXPRESSS reveals the message as expected - mix of text and images. Interestingly we have had an external user [10.4.2 MAIL] send a file that renders OK in OUTLOOK. He sent to me as well, I redirected it to the PC and OUTLOOK shows it as attachments while OUTLOOK EXPRESS renders correctly. That truly confuses the issue as it implies that OUTLOOK can rende the email correctly at times.
---
We are 20+ Macs running 10.3.9 and 2 Macs running 10.4.2. Also 1 PC on XP Pro and one on W98.
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Mac Elite
Join Date: Jul 2002
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Mail in 10.4 now sends HTML mail when you have "Rich Text" selected as your default message type. I don't know what the other problems in this thread are about, but it's probably Windows' fault.
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Clinically Insane
Join Date: Oct 2000
Location: Los Angeles
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I apparently erroneously thought this issue was solved by Apple long ago. Strangely, I've never had anyone tell me my attachments aren't getting through as intended.
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"The natural progress of things is for liberty to yield and government to gain ground." TJ
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Fresh-Faced Recruit
Join Date: Sep 2005
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The thing that is so nutty about this is that their is apparent inconsistency in the renderings. I'm sending from 10.3.9 Mail and 10.4.2 Mail to a test Win98 box with Outlook and Outlook Express receiving mail - both accounts are newly generated accounts. I have been sending text only, text then an inserted graphic, text then inserted graphic then text then pasted graphic then text. Results are skethcy at best. OE always gets everything OK. O, on the other hand, is generally bad, though sometimes it get sone ok.
So many factors to consider - plain text or rich, signature on or off at new message, cut signature or switch off after new nessage, copy/paste of plain text and graphic, copy/paste of rich text and graphic... It goes on and on. I will need to build some huge array of variables then try all combinations - or - wait for PC users to give up on Outlook and switch to OS X.
:-}
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