How to review and delete iMessage attachments on your Mac, one by one

How we checked

The Apple steps on this page come from Apple’s support guides, checked Oct 16, 2026. The Super Duper Space steps match the screens in the current app. On our development Mac, the app found 22,225 Messages attachments, 18.71 GB of videos, and 218 videos (2.2 GB) already saved in Photos. Your Mac will be different.

Where the folder sits, and why Messages grows, is in the Messages storage guide.

What does System Settings > Storage > Messages do?

This list is built in. You do not install anything. macOS already shows Messages as its own category.

Apple’s find-and-delete guide says to choose Apple menu > System Settings, click General, then click Storage. Click the Info button on a category that has one. Messages “contains content from Messages conversations, including attachments” (Apple Support, and the same line on the Storage settings page). To delete a file, select it, then click Delete. Show in Finder opens that file in the Finder.

For Documents, the same guide says you can view large files or downloads, and sort by Name, Kind, Last Accessed, or Size. For Messages, the description is conversation content, including attachments.

Apple’s Storage pages do not say the Messages list sorts by size, and they do not say you can play the video in that list. They also do not say whether the Delete button there removes the file from your iPhone. For that, use delete on your Mac and keep the iPhone copy.

How do I delete attachments inside one Messages conversation?

Use this when you know which chat. You are looking at the photos and videos from that conversation, and you pick the ones to delete.

Apple’s Messages guide for viewing photos and videos says you can view the photo or play the video in the conversation, or click the Info button, scroll to Photos, and double-click a file to open it. The Save Photo button next to a photo or video saves it in your photo library (Apple Support).

Apple’s current Messages user guide gives these delete steps (Apple Support):

1. Select a conversation, then click the contact or group icon at the top.
2. Scroll to a category, such as Photos, then click Show more.
3. Shift-click the items, Control-click the selection, and choose Delete.

Apple’s iCloud storage article, published September 14, 2026, describes the same area with an Info button: open the conversation, click Info, scroll to Photos, click an attachment, hold Command to add more, Control-click, choose Delete, then click Delete Attachment (Apple Support). The two pages name different clicks. Use the steps that match the buttons on your Mac.

Deletes made in the Messages app go to Recently Deleted for up to 30 days. After 30 days, Apple says the messages are removed from all your devices. After 40 days, they are permanently deleted from iCloud. If Messages in iCloud is on, deleting a message or conversation on your Mac deletes it from all your devices where Messages in iCloud is on (Apple Support).

Apple does not describe a list of the largest videos from every chat, and it does not describe a match against the Photos library on this Mac.

Can I delete files in ~/Library/Messages/Attachments?

The attachment files on a Mac live in ~/Library/Messages/Attachments. In Finder, choose Go > Go to Folder and paste that path. They sit in nested folders, so finding one video by hand is slow. More on the layout is in the Messages storage guide.

Apple’s support pages do not document deleting that folder. The Library guide says not to use the Library folder to store files and folders you create (Apple Support). The Attachments folder is inside Library. The delete steps Apple published are in Messages and in Storage.

A few things can go wrong if you delete files there anyway:

• Recently Deleted, the 30-day recovery Apple describes, is for messages and attachments you delete in the Messages app. Apple does not describe that recovery for a Finder delete in this folder.
• Leave chat.db and the other files in ~/Library/Messages alone. The attachment files are the ones in Attachments. chat.db is the Messages database.
• Apple documents a Download button at the bottom of Info view when photos and videos for a conversation are in iCloud and not on the Mac yet (Apple Support). We have not finished a test of deleting the local file while Messages in iCloud is on. If the copy is still in iCloud, the Mac may download it again later.

If you delete files in Finder anyway, back up with Time Machine first and quit Messages. The iPhone question for Apple’s own Delete buttons is in delete on your Mac and keep the iPhone copy.

How do these ways of deleting Messages attachments compare?

Apple pages checked Oct 16, 2026.

Start in Storage when you want the built-in list. Open the conversation when you know the chat. Leave the Attachments folder alone unless you already have a Time Machine backup. Apple’s pages do not include a delete procedure for that folder. Super Duper Space is for playing the large videos and choosing Keep or Remove from this Mac.

How do I review attachments one by one in Super Duper Space?

Super Duper Space is a Mac app in private beta. It lists the Messages attachments already on this Mac. You decide file by file. Nothing is deleted when you first choose.

1. On the Messages screen, Biggest videos first says to play each one, largest first, and choose what stays. Click Start.
2. Play the video. Choose Keep or Remove from this Mac. The note under those buttons says removing only adds it to your list, and nothing is deleted until you confirm. Undo clears that choice.
3. Review and delete opens Review what you selected. That screen says nothing is deleted yet. Then Move to Ready to delete. The app moves those local files out of Messages. They still use disk space.
4. Put them back, or Delete for good. The button includes the count and the size. Deleting can’t be undone after that.
5. The app then checks whether those files are gone. It does not scan the Messages folder again on its own. Refresh, on the Messages screen, scans that folder when you click it.

Browse attachments is the grid. Each card’s button is Select, and it changes to Selected. A file marked In iCloud only cannot be selected, because that copy is not on this Mac. The sort menu starts at Largest first. You can change it to Conversation, which orders chats from A to Z and puts the larger file first inside a chat. There is also Review these one at a time, and that pass uses Keep and Remove from this Mac.

Messages by conversation lists your chats, largest first, and you open one to see the attachments you have not decided on. The list keeps up to 250 chats. If you have more than that, the smaller ones are not on this list.

Already in Photos is marked Safest. It is photos and videos that match an item in the Photos library on this Mac: an exact copy, or a file that looks the same. The check uses Photos data already on this Mac and does not download originals from iCloud.

Exact duplicates are identical copies. The app says to keep the newest one. Keep newest · select extras, or Remove extra copies, adds the other copies to your list. Clear group undoes that selection. Selecting a group does not remove anything. Those files still go through Ready to delete, then Delete for good.

The conversation label is the chat display name. If the display name is empty, the app uses the room name, then the chat identifier. It does not edit chat.db, so it does not delete conversations or message text. A removed file can show up as a missing attachment in that conversation on this Mac.

It removes the copy stored on your Mac. Your other devices keep their copies. If Messages in iCloud is on, a file may download again later, and we’re still testing that setup. It needs macOS 14 or later, and Full Disk Access to read the Messages folder. Scanning, Photos checks, and Messages deletion stay on your Mac. There is no account and no analytics. We never upload your scan or send your photos anywhere. The app reads attachment filenames, dates, and conversation labels. It does not read your message text. If you confirm a cleanup that runs npm, pnpm, or Homebrew, that tool may contact its own servers.

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Is a disk map the same as reviewing Messages attachments?

We have not tested DaisyDisk for this page. The CleanMyMac page lists DaisyDisk and GrandPerspective as ways to see what is big on the whole disk. A map can show a large Messages folder. Reviewing the attachments means opening each file and deciding, with Keep or Remove from this Mac.

Related: Messages storage, Delete on Mac, keep iPhone, FAQ, CleanMyMac alternative.