Fix a Problem Sending Screenshots in OS X’s Messages

Kill imagent icon hugeI often send screenshots to friends using OS X’s Messages app by pasting them into the section of the window where you compose text; they can be used to illustrate things, such as problems on my Mac, or show bits of text or images from the web. It’s a practical way of exchanging information.

Since the release of OS X 10.10 Yosemite, however, this function has not worked reliably when sending screenshots via AIM accounts (it seems to work with iMessages). When you sent a screenshot before Yosemite, you’d see the progress of the screenshot in Messages’ File Transfers window. But in Yosemite, the File Transfers window shows the screenshot as Sent, even before it is fully transferred. So if the screenshot doesn’t get sent, you won’t know it until you ask the person you sent it to. (This only applies to screenshots that you paste; screenshots that you have saved as files, and that you drag to the Messages window, send reliably.)

And screenshots fail often. With one friend, we have to ask each other every time we send screenshots to make sure they’re sent, because there’s no feedback. When this happens, you have to force quit a background process to get it to work again. Quitting Messages alone won’t work.

To do this, open Activity Monitor, which is in your /Applications/Utilities folder. Click in the search field, and type “imagent.” Click on that process to select it, then click the x button at the top-left of the window, and then click Force Quit.

Activity monitor

This quits the imagent background process, and also quits Messages. When you relaunch Messages, screenshots should work again.

Rob Griffiths has explains how to write an AppleScript that can simplify this procedure. Just run the script and it will kill the imagent process.

8 thoughts on “Fix a Problem Sending Screenshots in OS X’s Messages

  1. Thanks for this information, Kirk. Your article raises a number of related questions for me. In your experience, if sending a screenshot fails on the first attempt, and you kill the process as you described, do your chances increase for the second attempt? I’m guessing that the problem you describe uses the key combination , followed by with the cursor in the Messages window. Or are you using another approach? Have you observed any difference in behavior between and ?

    How about other graphics that you paste into Messages? If I were to try and copy and paste a JPEG or PNG from some other source into Messages, would I see the same (mis)behavior? I’m still running Mavericks, because of various bugs reported in Yosemite, reported by you and others.

    • The web page stripped out my text detailing the key combinations. In my text above, I had “Command-Control-Shift-3” and “Command-Control-Shift-4” without quotation marks and in angle brackets, a common convention for indicating key combinations. Apparently, this site doesn’t like that.

      • Sorry about the characters getting stripped.

        I find that, in most cases, killing the process gets it to work again; for a while. But I’m going to update the post with a link to an AppleScript that you can use that will make this easier to do.

        I don’t paste files, but I drag them, and they seem to work every time. But I would suspect that pasting a file that you’ve copied in the Finder will have the same effect as pasting a screenshot you’ve captured to the clipboard.

  2. Thanks for this information, Kirk. Your article raises a number of related questions for me. In your experience, if sending a screenshot fails on the first attempt, and you kill the process as you described, do your chances increase for the second attempt? I’m guessing that the problem you describe uses the key combination , followed by with the cursor in the Messages window. Or are you using another approach? Have you observed any difference in behavior between and ?

    How about other graphics that you paste into Messages? If I were to try and copy and paste a JPEG or PNG from some other source into Messages, would I see the same (mis)behavior? I’m still running Mavericks, because of various bugs reported in Yosemite, reported by you and others.

    • The web page stripped out my text detailing the key combinations. In my text above, I had “Command-Control-Shift-3” and “Command-Control-Shift-4” without quotation marks and in angle brackets, a common convention for indicating key combinations. Apparently, this site doesn’t like that.

      • Sorry about the characters getting stripped.

        I find that, in most cases, killing the process gets it to work again; for a while. But I’m going to update the post with a link to an AppleScript that you can use that will make this easier to do.

        I don’t paste files, but I drag them, and they seem to work every time. But I would suspect that pasting a file that you’ve copied in the Finder will have the same effect as pasting a screenshot you’ve captured to the clipboard.

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