Image as attachment to email

This is unchanged in Lion. "View image as icon" only applies to how it appears on your machine. All images are sent as "inline" images. You can use Attachment Tamer to get more control over this.

Check the lower, right-hand corner of your e-mail and verify the size of your images. If Mail thinks your image is too big, it may try to reduce the size.

Not being able to save the image is entirely a problem with the PC. Have your recipient's try a right click on the image or perhaps some menu selection.

You can always turn the attachment into a zip file; then it will appear in a pretty predictable way on any platform.

charlie

Your'e welcome!

pepa_u wrote:

Thanks for quick response. I came across this attachment tamer, however, it seems to me ridiculous to pay $15 for something that should be handled by the mail.app. Espectially because the "view as icon" trick used to work in Snow Leopard.

No. It never did. View as icon never did anything more than change how the image was displayed before you sent it. You'll have to trust me on this 🙂

I have set the settings in the lower right corner to "actual size". No help.

That control actually does do something. It isn't going to help with how the image is displayed, but it will help with the "tiny image" problem you mentioned before.

We are unfortunately surrounded by PCs. There is 95% probability that on the other side of wires is receiving the email a Windows client. So I have the problem, not them. For them there is something wrong with Mac, because between Windows machines, there are no such troubles with email attachments.

Please define "Windows machine". Are you talking about Windows 95, or Windows 7 with Outlook 2010, or something in between? Apple Mail is designed to send e-mails that recent versions of Outlook can read - and I mean that specifically. It was designed for Outlook. But it was designed for recent versions of Outlook, not old ones.

There is no way how to save the file in outlook if this problem occurs. I have explored that.

That is fundamentally, categorically, 100% an Outlook problem. There is no physical way to get an image from machine A to machine B without it becoming an attachment. If Outlook won't let you save the attachment, that is Outlook's problem. That is not a problem for Eudora, Lotus, Thunderbird, or any other PC e-mail client.

Strange is that if I attach the file, chose "view as icon" and do not write anything to the message, it is correctly visible as attachment in Outlook.

That is because of bugs in various versions of Outlook. If you want, you may have good luck with Apple Mail's "Always insert attachment at end of message" setting. This was designed for old versions of Outlook that get confused at the first attachment. You will no longer be able to format e-mail with text and images interspersed, but that's life.

The "Actual size" has unfortunately no effect on the attachment if "view as icon" was selected.

It has the same effect as with "view in place". People are often confused because the file size displayed under the icon is not updated, but the image will actually be resized before sending. (Just keep in mind that the "view as icon" option does not have any effect on the sent message, except if you use Attachment Tamer.)

Definition of Windows machine is in my case WinXP to Win7 with MS Office 2003 or MS Office 2007 (I haven't tested the issue with Office 2010).

I wouldn't say it is entirely an Outlook problem. The images that you can't extract in Outlook technically aren't sent as attachments, but as "related mime parts" (or embedded images), which is way to sent files which the recipient is not meant to extract from the message as opposed to attachments. (On the other hand it's true that most email software can extract them anyway.)

One way to avoid sending embedded images, is to use only plain text (which is also what happens if you don't include any text in your message, a special case you have mentioned), but there's a lot of other things you will need to set up and keep in mind to get correct results in Outlook. See this older post for more details.

Adam Nohejl wrote:

I wouldn't say it is entirely an Outlook problem. The images that you can't extract in Outlook technically aren't sent as attachments, but as "related mime parts" (or embedded images),

A related MIME part is an attachment. As soon as you "attach" a file or image, turn on boldface or italic, or do anything that makes your e-mail the least bit fancy, you are creating one or more attachments.

The only difference is how Outlook interprets a multipart/related attachment whose first part is a text/html attachment. That multipart/related item is then treated as an encapsulated web page. I have no doubt that Outlook will allow the user to save the images. The people using it just don't know how and find it easier to blame the Mac than to right click or explore that mystical and magical area known as the Outlook menubar.

One way to avoid sending embedded images, is to use only plain text (which is also what happens if you don't include any text in your message, a special case you have mentioned), but there's a lot of other things you will need to set up and keep in mind to get correct results in Outlook.

Initial indications are that it is much more difficult to get Lion to create plain text messages with attachments. Such messages aren't plain text at all and will be problematic for a different set of users.

Fundamentally, the problem is with PC users who expect e-mail to look a certain way because that is how it has always looked since 1994. They blame the Mac and are completely oblivious to the fact that the software they are using is the one that constructs HTML messages that way and invented the entire concept. They have never sent an HTML message so they don't know how to deal with it. It is not an Apple Mail problem. It is not an Outlook problem. It is a PC user problem.

etresoft wrote:

Adam Nohejl wrote:

I wouldn't say it is entirely an Outlook problem. The images that you can't extract in Outlook technically aren't sent as attachments, but as "related mime parts" (or embedded images),

A related MIME part is an attachment. As soon as you "attach" a file or image, turn on boldface or italic, or do anything that makes your e-mail the least bit fancy, you are creating one or more attachments.

This may be a terminological misunderstanding. Here's what I mean by attachments and MIME parts:

Turning on boldface or italic usually results in an creation of two "alternative" MIME parts. Attaching files results in additional "mixed" mime MIME parts (usually with an "attachment" content disposition), which are attachments. But embedded images sent as "related" mime parts form an "aggregate object" together with the HTML part (see RFC 2387), although Apple Mail counts them as attachments.

The terminology is explained in this two RFCs:

http://www.faqs.org/rfcs/rfc2387.html

http://www.faqs.org/rfcs/rfc1806.html

The only difference is how Outlook interprets a multipart/related attachment whose first part is a text/html attachment.

My reading of the RFCs is that if you want an email client to interpret images as separate entities (attachments) you should put them in a multipart/mixed parent part, not in a multipart/related parent part.

When you send rich text (HTML) email using Mail, which contains images (and no non-images attachments) all images are sent as embedded images (using the HTML img element) using multipart/related.

Initial indications are that it is much more difficult to get Lion to create plain text messages with attachments. Such messages aren't plain text at all and will be problematic for a different set of users.

I haven't noticed any problems yet: I can change the format via the Format menu or permanently in the preferences. If I choose rich text and the message contains no formatting, it will be sent as plain text, but if you choose plain text, the message is always sent as plain text.

Anyway, for sending plain text with attachments that displays correctly in Outlook I recommend the aforelinked post.

It is a PC user problem.

Most of my work revolves around email and mutual incompatibilities of various email software products. Some things are done right in Apple Mail, some in Thunderbird, and some (believe it or not) in Outlook. And none of the email clients is perfect. Outlook sure has a lot of flaws (interpreting multiple mixed text parts, interpreting CSS and HTML formating, interpreting HTML without any font specification, sending the nonstandard WINMAIL.DAT files, etc.), but I see the problem with embedded images mainly as an Apple Mail problem. Of course, it is just a matter of point of view as with any compatibility issues.

Adam Nohejl wrote:

etresoft wrote:

Initial indications are that it is much more difficult to get Lion to create plain text messages with attachments. Such messages aren't plain text at all and will be problematic for a different set of users.

I haven't noticed any problems yet: I can change the format via the Format menu or permanently in the preferences. If I choose rich text and the message contains no formatting, it will be sent as plain text, but if you choose plain text, the message is always sent as plain text.

My bad, I was wrong: It seems that in Lion, Mail will send any message containing more than one image and no text or text with any number of images as rich text regardless your settings. (With non-image attachments plain text fortunatelly still means plain text.) I am going to reporth this as a bug too.

There is a fundamental flaw in your analysis - you are using logic. You can't just read RFCs and code to that. Those are just "Requests for Comment" and are not standards that anyone has agreed to follow. Apple Mail has been refined over the years to be as compatible as possible with the widest range of PC e-mail clients as possible. Many of your suggestions are actually the way Apple Mail used to work in 2003 or so. They aren't "bugs" per se - they are doing that on purpose.

Windows-friendly attachments, Insert attachments at end of message, HTML e-mail, and the demise of plain text are all changes that Apple put into place specifically to address bugs in various PC e-mail clients.

I have only seen a single instance where Apple ever encoded anything incorrectly. That was specifically with CSV attachments and Apple fixed that fairly quickly. The whole "cannot save embedded image" problem is a documented bug in Outlook.

etresoft wrote:

There is a fundamental flaw in your analysis - you are using logic. You can't just read RFCs and code to that. Those are just "Requests for Comment" and are not standards that anyone has agreed to follow.

I will just review the facts: Apple Mail seems to be the only email software that sends (some) attachments in multipart/related. Outolook doesn't, Thunderbird doesn't, Lotus Notes doesn't, Gmail doesn't. (Do you know any other software that sends image attachments in mutlipart/related?) Incidentally, the RFCs, which are the only "standard" we have for this, specify that multipart/related is meant for compound objects.

If we ignore RFCs and say that what Outlook and other PC software does on purpose are bugs, it's easy to claim that Apple Mail is "refined over the years" to be "compatible" etc. Don't get me wrong: I really like Apple Mail and appreciate many of its features that other email software doesn't have. I just want to avoid being one-sided.

Adam Nohejl wrote:

I will just review the facts: Apple Mail seems to be the only email software that sends (some) attachments in multipart/related. Outolook doesn't, Thunderbird doesn't, Lotus Notes doesn't, Gmail doesn't. (Do you know any other software that sends image attachments in mutlipart/related?)

Yes, I do. I just tested them. They are: Outlook Express 6, Outlook 2003, Thunderbird, and Lotus Notes. The default rich text format for all of these e-mail clients is multipart/related, just like Apple Mail. I don't have a gmail account, so I couldn't test that one.

etresoft wrote:

Yes, I do. I just tested them. They are: Outlook Express 6, Outlook 2003, Thunderbird, and Lotus Notes. The default rich text format for all of these e-mail clients is multipart/related, just like Apple Mail. I don't have a gmail account, so I couldn't test that one.

These clients allow you to insert an embedded picture, which of course creates a multipart/related message, consequently they do not display such embedded picture as an attachment. But if you attach an image file (using the Attach command) in Outlook, Thunderbird or Lotus Notes, they send it in a multipart/mixed message, unlike Apple Mail which sends embedded images even if you add them using the Attach command.

To sum it up:

• Outlook, Thunderbird, and Lotus Notes allow you both to send images as attachments (in the same way as you would attach any other files), which results in a multipart/mixed message, and to send embedded images (using a separate menu command or button), which results in a multipart/related message
• Gmail's web interface only sends attachments (there's no way to insert embedded images), which results in a multipart/mixed message.
• Apple Mail sends image files as embedded images, which results in a multipart/related message, even if you use the Attach. Consequently, Outlook, Thunderbird, Lotus Notes and Gmail's web interface do not recognize these images as attachments. (The current version of Apple Mail sends images in a multipart/mixed only if you add non-image attachments too.)