Hit Command + A to select all folders and drag them to the Trash. Go into the "Messages" directory and then the "Attachments" directory. In the Go To Folder popup window, enter: ~/Library I would recommend caution in this approach, as there could be unexpected consequences, but it has worked for me. Note that this process bypasses the trash and deletes the image(s) immediately. Click on a photo, (optionally select all of them by pressing Command + A), then right click (or control click) and select delete. If you click on “Details” (in the top right corner) in a particular thread, you can see all of the photos that have been sent and received. (which of course is the key to the syncing), and then identifying at which places (email addresses and iPhone number) you want to. In the Messages application, select one of your text threads. Now scroll down and click on Send & Receive: Here you are presented with the same options as in the Messages account settings on your Mac, starting with entering your Apple i.d. On the Mac, launch Messages and select Preferences from the Messages menu. Note that this setting is specific to your computer and will NOT delete Messages on other devices, including on your iPhone. To sync iMessage to a Mac, open your iPhone and go to Settings > Messages > Send & Receive. Go to Messages -> Preferences -> General -> Keep Messages and change this setting to 30 days or 1 year. Turn on automatic deletion of your text messages on your Mac.Here are options for recovering storage space that is being used by your text messages and photo attachments: If you send and receive a lot of text messags, especially ones with images and photographs, you may find that your Mac Messages application is taking up a LOT of precious space.
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