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Adding attachments in mail

When i click the paperclip icon in mail to add an attachement, it allows me to search for and select the file as normal. However, after selecting the file and pressing ok, nothing happens. It does not attach the file at all. There's no indication that a file is attached and it is not on the sent email either. The only way seems to be dragging the file into the email body, but I do not want to do it this way.

MacBook Pro 16″, macOS 14.0

Posted on Oct 22, 2023 2:51 AM

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Question marked as Top-ranking reply

Posted on Oct 22, 2023 3:17 AM

Follow on


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).


2 replies
Question marked as Top-ranking reply

Oct 22, 2023 3:17 AM in response to sbridgephoto

Follow on


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).


Oct 22, 2023 3:01 AM in response to sbridgephoto

Running Sonoma 14.0 on M2 Apple Computer


To Test, I have just composed and e-mail from myself to myself


Using the Attach ( Paper Clip ) attach file


Yes can choose a file.


In this Test from my Desktop


The .png files become embedded into the Body of the e-mail


Effectively, this is what you have done by Drag and Drop method


refer image below






Adding attachments in mail

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