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Catalina Mail Attachments Embed Issues

My wife is a mail user, she is trying to simply send pdf attachments to windows users gmail, outlook.

The documents are now embedding within the email and are not going out as attachments.

If i zip up the pdf files they are handled correctly both ends. Whats going on? everything Iread says oh its recipients client issues. Its not it OSX mail i need to stop it.

What makes things worse my mail client works properly attaching documents correctly.

I have tried the inline viewing option but this is just viewing I want / need an email client that plays well with others. We have moved away from MS Windows for over 5 years but this could drive us back.

I have run out of ideas Help

MacBook

Posted on Jun 17, 2020 12:46 PM

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Question marked as Top-ranking reply

Posted on Jun 17, 2020 1:00 PM

Nothing is going on. If the PDF is a single page document it is displayed in the sender's message but is still going out as an attachment. Multi-page PDFs, however, are shown as an attachment.


I recommend always sending documents from a Mac to Windows as a ZIP archive to avoid unwanted translation problems. A safety precaution, you might say.


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Question marked as Top-ranking reply

Jun 17, 2020 1:00 PM in response to ukgreenman

Nothing is going on. If the PDF is a single page document it is displayed in the sender's message but is still going out as an attachment. Multi-page PDFs, however, are shown as an attachment.


I recommend always sending documents from a Mac to Windows as a ZIP archive to avoid unwanted translation problems. A safety precaution, you might say.


Jun 17, 2020 12:56 PM in response to ukgreenman

Outlook doesn't know how to process real email properly. It never has and I doubt it ever will. Microsoft only considers Exchange to be real email, so everything else is just something they don't want to bother with.


The best way to overcome the problems with Outlook is to send the message as plain text (Format menu), and set these two options in the Edit > Attachments menu:

Send Windows friendly Attachments

Insert Attachments at End


You can set those as defaults by setting them from the Message Viewer window and not have a new message open. They then appear with "Always…" prepended on the command names.


Until Microsoft decides it should follow email standards, people who use real email clients will have to make adjustments when sending messages to recipients who use Outlook.

Catalina Mail Attachments Embed Issues

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