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Avoiding the automatic embedding of RGB JPEG attachments sent from Mac to PC via Mail

For some reason RGB JPEG files attached to an email in Mail and sent to a PC user automatically embed their end, which is a real nuisance. There are only two ways I have found around it: attach a simple Word document as well as the image or use an FTP service instead. Neither is convenient, but they do work. The issue seems to be a compatibility issue between Mail and Outlook. Is there a setting in Mail that can prevent this from happening? If not, there should be.

iMac 24″, macOS 13.6

Posted on Nov 29, 2023 9:01 PM

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Posted on Dec 3, 2023 8:22 AM

Quenda-71 wrote:

when I send an email attachment of a JPEG from Mail to a client using a PC the file appears to them to be part of the body of the email (embedded) rather than a separate email attachment

OK. That makes sense. This is probably the #1 Apple Mail complaint over the past 25 years. It isn't going to change. I recommend you give up the effort. You may find any number of "solutions" on the internet that are entirely fake. You can't change this.

the image cannot be downloaded

It can be. Your recipients probably just don't know how. This is 100% a problem with Microsoft Outlook. The difference between an e-mail with an attachment and an e-mail with an embedded image is just a single word. That word is either "inline" or "attachment". So you have to ask yourself. Why does a single word make something impossible in Outlook? Of course, you could ask a similar question to Apple. Why not allow this one word to be changed? I can't answer either question.


All I can suggest is to give up. This hasn't changed in 25 years, so it is unlikely to be changed in the future. Apple will eventually discontinue the Mail app and replace it with the iOS version. But I don't think you can control this setting on the iPad either.


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Question marked as Top-ranking reply

Dec 3, 2023 8:22 AM in response to Quenda-71

Quenda-71 wrote:

when I send an email attachment of a JPEG from Mail to a client using a PC the file appears to them to be part of the body of the email (embedded) rather than a separate email attachment

OK. That makes sense. This is probably the #1 Apple Mail complaint over the past 25 years. It isn't going to change. I recommend you give up the effort. You may find any number of "solutions" on the internet that are entirely fake. You can't change this.

the image cannot be downloaded

It can be. Your recipients probably just don't know how. This is 100% a problem with Microsoft Outlook. The difference between an e-mail with an attachment and an e-mail with an embedded image is just a single word. That word is either "inline" or "attachment". So you have to ask yourself. Why does a single word make something impossible in Outlook? Of course, you could ask a similar question to Apple. Why not allow this one word to be changed? I can't answer either question.


All I can suggest is to give up. This hasn't changed in 25 years, so it is unlikely to be changed in the future. Apple will eventually discontinue the Mail app and replace it with the iOS version. But I don't think you can control this setting on the iPad either.


Nov 30, 2023 5:00 AM in response to Quenda-71

Apple can fix Apple Applications, Operating Systems and Accessories 


Apple Can not fix Third Party Applications and how that Applications renders Image File attachments when used & sending via Apple Mail Application


That falls clearly Out-Side the Domain of Apple and rests with the Third Party Application Developers


User wrote " Is there a setting in Mail that can prevent this from happening? If not, there should be."


By all means do send your Feedback to Apple Requesting some Feature Addition


Though to be honest. It is doubtful Apple will make any Feature changes in macOS 13 Ventura as there are still working on bug fixes and any potential feature addition in macOS 14 Sonoma


They could also be Developing a successor to Sonoma.


So would not hold my breath for anything New in Ventura

Nov 30, 2023 2:34 AM in response to Quenda-71

Send attachments to Windows users in Mail on Mac


Try these suggestions for sending email attachments to Windows users.

Open Mail for me

  • To send Windows-friendly attachments for all messages, choose Edit > Attachments, then select Always Send Windows-Friendly Attachments.
  • To send Windows-friendly attachments for a single message, click the Attachment button in the toolbar of the new message window, then select Send Windows-Friendly Attachments (if the checkbox isn’t shown, click Show Details).
  • Send documents as PDFs instead of in their original format.
  • Use filename extensions (such as .docx for a Microsoft Word document).

If a Windows user receives two attachments (such as “MyFile” and “._MyFile”), they can ignore the file with the underscore.


Nov 30, 2023 6:25 PM in response to PRP_53

Thanks for the suggestion P. Phillips, but I already have 'Always Send Windows-Friendly Attachments' selected. I can't sent a RGB photo as a PDF to a client as it defeats the purpose (image for web use, not print use. I always use the .jpg extension for the file.


I have been a professional Mac user for over thirty years, but I am not a programmer. I am well aware that Apple can't fix issues that are Microsoft related. The problem is I don't know if it is occurring at the Mail sending end or the Outlook receiving end. Although I am a Mac user most of my clients use PCs and some, but not all, are encountering this issue when I send them RGB JPEGS. I first encountered this embedding issue many years ago and the Mac model and OS seem to make no difference whatsoever. The only constant is that the Apple Mail program is being used, which leads me to suspect it is a Mail issue.

Dec 1, 2023 2:00 AM in response to Quenda-71

Quenda-71 wrote:

Thanks for the suggestion P. Phillips, but I already have 'Always Send Windows-Friendly Attachments' selected. I can't sent a RGB photo as a PDF to a client as it defeats the purpose (image for web use, not print use. I always use the .jpg extension for the file.

I have been a professional Mac user for over thirty years, but I am not a programmer. I am well aware that Apple can't fix issues that are Microsoft related.

Welcome


Pleased you acknowledge that Apple can not fix that which they do not control.


The problem is I don't know if it is occurring at the Mail sending end or the Outlook receiving end.


It is the interaction between the two different e-mail clients.


Neither is at Fault as per se as that is just how each works.


My wife using a MS Windows machine with a old 2012 MS E-mail Client that sends e-mails in html format


When I receive and e-mail with text and image from her in Apple Mail, when it looks, be be polite, a real mess and almost impossible to read


Although I am a Mac user most of my clients use PCs and some, but not all, are encountering this issue when I send them RGB JPEGS. I first encountered this embedding issue many years ago and the Mac model and OS seem to make no difference whatsoever.


Then suggest using a Non Apple E-mail Client that is more MS Windows friendly


The only constant is that the Apple Mail program is being used, which leads me to suspect it is a Mail issue.


Sorry but wrong assumption



Dec 1, 2023 6:43 AM in response to Quenda-71

Quenda-71 wrote:

For some reason RGB JPEG files attached to an email in Mail and sent to a PC user automatically embed their end, which is a real nuisance. There are only two ways I have found around it: attach a simple Word document as well as the image or use an FTP service instead. Neither is convenient, but they do work. The issue seems to be a compatibility issue between Mail and Outlook. Is there a setting in Mail that can prevent this from happening? If not, there should be.

Can you explain what you mean by "embed their end"? And can you also explain what you mean by "a real nuisance"? Please be specific. Your description of what you are actually seeing, and what you actually have to do on the other end might help explain the problem you are having.


Without that information, I can't say any more than basic e-mail answers. That's the way it works. Outlook has been a nuisance for pretty much everyone for 30 years. All e-mail vendors have to been over backwards to try to construct e-mail messages that will be visible and useable on the majority of the many, many different versions of Outlook that exist.


Additionally, there can be any number of other issues involved. When you say it works if you add another file or "an FTP service (???), that suggests that you have one of those very poor e-mail filtering systems that completely disassembles e-mail, scans it all for viruses, and then reassembles it, corrupting it in the process. That's nothing that Apple can fix.

Dec 3, 2023 2:32 AM in response to etresoft

By ‘embedding their end’ I mean simply that when I send an email attachment of a JPEG from Mail to a client using a PC the file appears to them to be part of the body of the email (embedded) rather than a separate email attachment, therefore the image cannot be downloaded which defeats the purpose of sending it and is therefore ‘a nuisance’. I don’t have any ‘email filtering system’ you refer to nor would I. FTP is File Transfer Protocol (such as WeTransfer, Dropbox etc.) which are used for sending huge image files you can’t send via email. This to me is the only viable solution to the issue.

Dec 3, 2023 4:49 AM in response to Quenda-71

FWIW I usually use gmail to send mail attachments via Safari. But sometimes I deliberately use Mail.app when I want to attach images inline with the message text. (I have gmail and iCloud accounts added to Mail.app but I very rarely send via iCloud account, usually only mail with largish attachments).


For me, gmail shows those attachments below the message while Mail.app shows them inline. I have not tested whether sending via Safari-gmail or Mail.app-gmail-account behaves identically anyway because I send via the gmail account anyway.


I do not, however, know how each recipient happens to receive the attachment. But that is their problem. So far nobody has complained.

Dec 3, 2023 6:05 AM in response to Quenda-71

Quenda-71 wrote:

By ‘embedding their end’ I mean simply that when I send an email attachment of a JPEG from Mail to a client using a PC the file appears to them to be part of the body of the email (embedded) rather than a separate email attachment, therefore the image cannot be downloaded which defeats the purpose of sending it and is therefore ‘a nuisance’.

Tell them to right-click on the image and choose “Save as Picture.” (Or some similar words to that effect)

Microsoft has chosen that method to render “inline” attachments. To my knowledge, no other email client works that way.


I don’t have any ‘email filtering system’ you refer to nor would I.

They might, or their network might.

Avoiding the automatic embedding of RGB JPEG attachments sent from Mac to PC via Mail

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