While Messages for macOS allows for the deletion of individual photos from a conversation, the photos are not deleted on other iMessage clients so they have to be deleted off of each client that was open at the time. This is a problem when my girlfriend decides to text me risqué photos over the weekend and I left Messages running on my work machine. I guess I have some careful deleting to do tomorrow!

Anyway, I am unable to find out how to delete a photo from a conversation on iOS Messages at all. Is it even possible? The only way to do it appears to be to delete the entire conversation which I do not want to do. Anyone have any clues?

  • I will note that even with my mixed bag of El Cap and Sierra hosts, all 3 MacOS iMessage clients synced the deleted files. It is only on iOS 10 that the photos do not get removed. – Darf Nader Oct 31 '16 at 5:34

Go into the conversation on your iOS device (assuming iOS10). In the top right corner you should see an information symbol ("i" in a circle). Click on it. Then scroll down to the picture you want to delete. Then tap and hold the picture. Three options will come up: copy, delete, more. Select delete. If you're using an iPhone 6s or newer, be careful not to force touch the image instead of tapping and holding.

  • Thank you! The problem was I was force touching the image which prevent the delete options from showing. – Darf Nader Oct 31 '16 at 4:18

iMessage operates like SMS or old-school email, not like webmail or FB messenger where what you're viewing is basically a real-time mirror of the server. Once a message has been delivered to your devices the server is done with it, so no, there are no take-backs of the way you're hoping for.

Basically, tell your girlfriend to send you sensitive stuff through another medium in the future.

  • Thanks for the explanation... and noted. I still am not sure when I am going to delete those things! – Darf Nader Oct 31 '16 at 4:22
  • Just realized you basically stated as much haha, and didn't ask about that particular aspect, sorry. – tolgraven Oct 31 '16 at 4:24
  • Sounds like you've got a bigger issue, tbh. Everyone needs a 24/7 backdoor to their work machine(s), hey. Get on it! – tolgraven Oct 31 '16 at 4:27
  • I actually have JumpDesktop to it so I'm good. Thanks! – Darf Nader Oct 31 '16 at 4:28
  • Odd, for whatever reason, pictures in the MacOS version of iMessage must allow for the photos to be deleted as they were not there! – Darf Nader Oct 31 '16 at 4:33

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