How to send a file or document in Messages on a Mac

To send a file in Messages on a Mac, drag it from Finder into the text field at the bottom of the conversation, add a note if you like, and press Return. You can also copy the file in Finder with Command-C and paste it into the field with Command-V, or Control-click it and choose Share, then Messages. In an iMessage conversation, most kinds of file travel this way, not only photos.

Drag it into the conversation

1. Open Messages and select the conversation, or start a new one with the New Message button at the top of the sidebar.
2. In Finder, find the file. Arrange the windows so you can see both, or start the drag and press Command-Tab to bring Messages forward while you are still holding the file.
3. Drop the file on the text field at the bottom of the conversation. It appears in the field as a preview or an icon. Nothing has been sent yet.
4. Type a message alongside it if you want, then press Return.

To send several files, select them all in Finder first and drag them as a group. Shift-click selects a run of files; Command-click picks ones that are not next to each other, as described in how to drag files that are not next to each other. Each file arrives as its own attachment.

If you change your mind before sending, click the file in the text field and press Delete.

Paste it, or use Share

Dragging is not the only way in.

• Copy and paste. Select the file in Finder, press Command-C, click in the Messages text field and press Command-V. The file itself is pasted, not its name.
• Share from Finder. Control-click the file and choose Share, then Messages. A sheet opens where you type the recipient, add a note and click Send. This route is useful when Messages is not open and you do not want to arrange windows.
• Share from other apps. Preview, Photos and many other apps have a Share button in their toolbar or a Share command in the File menu, with the same Messages option. That saves a trip to Finder when the document is already open in front of you.

Why a file did not go through

When a file will not send, it is usually one of these.

The conversation is green. Blue bubbles are iMessage. Green bubbles are carrier messages relayed through your iPhone, and they are much less dependable for documents. Photos and short videos usually make it; PDFs, spreadsheets and zip files may not arrive, or may not open at the other end. For documents in a green conversation, Mail is the safer route.

The file is very large. Long videos and big archives can fail and show Not Delivered under the message. Trim the video first (select it in Finder, press the Space bar and use the Trim button in Quick Look), or send it another way, such as AirDrop to someone nearby.

It is a folder. Messages sends files, not folders. Control-click the folder in Finder and choose Compress, which makes a zip file beside it, and send the zip. How to send a whole folder from a Mac covers the other options.

Messages is not signed in. Choose Messages > Settings, click iMessage and check that your Apple Account is signed in and enabled.

If a send fails, Messages marks it with a red alert icon. Click the icon and choose Try Again once you have fixed the cause.

Send a file to yourself

Messages is one of the quickest ways to move a file from your Mac to your own iPhone. Start a conversation with your own phone number or email address, drop the file in, and it shows up on every device signed in to your Apple Account. On the iPhone, open the attachment and use the Share button to save it to Files. How to get files from a Mac onto an iPhone by dragging has other routes for the same job.

The reverse, keeping something someone sent you, is covered in how to save a photo or file from Messages on a Mac.

Have the files ready before you open the chat

The friction with Messages is rarely the send itself. It is that the file is in one window, Messages is in another, and the conversation you need is buried in a long list. By the time you have found the chat, the Finder window has slipped behind something else.

Ledge takes the window juggling out of it. Drag the file up to the notch and let go; it lands on a shelf that drops from the notch and stays there. Collect anything else that belongs in the same message from other folders and apps. Then open Messages, pick the conversation, open the shelf with Option-Space or a click on the notch, and drag the files down into the text field. A chat app gets the file itself rather than a path, so it attaches the way you expect.

You can also add Messages as a routing destination in Ledge’s Settings, so it stays on the shelf even when Messages is closed. Ledge has no account and no cloud: it hands the file from one app to another on your Mac, and the sending is left to Messages.

Questions

Does the other person need a Mac to open the file?

No. They need an app that can open that kind of file on whatever device they use. A PDF or a JPEG opens almost anywhere. A file made in an app that only runs on a Mac may need exporting to a common format first.

Can I send a file to a group conversation?

Yes. Drop it into the group conversation the same way, and everyone in the group receives it.

Does Messages keep a copy of files I send?

Yes. Your original stays where it was, and Messages keeps its own copy as part of the conversation, which counts toward the space Messages uses on your Mac. Deleting the conversation removes that copy, not your original.