resonator1six
Level 1 (0 points)

Q: Unable to send images using iMessage

I have used iMessage to send images for years, I could just drag and drop photos into the message body and send. Now all I get are error messages that the message could not be sent. I have checked all my preferences, rebooted, done all the basic things one would expect that might cause an error to happen but nothing works.

 

I can send images using any of my other iDevices without a hitch, the problem only occurs on my iMac.

Does anyone have a solution?

 

There are a lot of posts and YT videos about this problem while using iPhones and iPad but I cannot find anything regarding the iMac.

 

I would really appreciate any advice to figure this out. I'm up to date on all my software, running the latest on everything.

iMac, iOS 9.0.1, updated to 10.10.5

Posted on Jan 9, 2016 5:57 PM

by Linc Davis,Solvedanswer
Linc Davis Linc Davis
Level 10 (208,037 points)
Applications
A:

Please remove "Little Snitch" completely. It serves no real purpose anyway except to interfere with normal operation, but if you test after removing it and find no change, you can reinstall it.

Any third-party software that doesn't install from the App Store or by drag-and-drop into the Applications folder, and uninstall by drag-and-drop to the Trash, is a system modification.

Whenever you remove system modifications, they must be removed completely, and the only way to do that is to use the uninstallation tool, if any, provided by the developers, or to follow their instructions. If the software has been incompletely removed, you may have to re-download or even reinstall it in order to finish the job.

I never install system modifications myself, and except as stated in this comment, I don't know how to uninstall them. You'll have to do your own research to find that information.

Here are some general guidelines to get you started. Suppose you want to remove something called “BrickMyMac” (a hypothetical example.) First, consult the product's Help menu, if there is one, for instructions. Finding none there, look on the developer's website, say www.brickmymac.com. (That may not be the actual name of the site; if necessary, search the Web for the product name.) If you don’t find anything on the website or in your search, contact the developer. While you're waiting for a response, download BrickMyMac.dmg and open it. There may be an application in there such as “Uninstall BrickMyMac.” If not, open “BrickMyMac.pkg” and look for an Uninstall button. The uninstaller might also be accessed by clicking the Customize button, if there is one.

Back up all data before making any changes.

You will generally have to restart the computer in order to complete an uninstallation. Until you do that, there may be no effect, or unpredictable effects.

If you can’t remove software in any other way, you’ll have to erase and install OS X. Never install any third-party software unless you're sure you know how to uninstall it; otherwise you may create problems that are very hard to solve.

Trying to remove complex system modifications by hunting for files by name often will not work and may make the problem worse. The same goes for "utilities" such as "AppCleaner" and the like that purport to remove software.

Posted on Jan 16, 2016 10:35 PM

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resonator1six

Q: Unable to send images using iMessage

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  • by resonator1six,

    resonator1six resonator1six Jan 15, 2016 7:29 PM in response to Linc Davis
    Level 1 (0 points)
    Jan 15, 2016 7:29 PM in response to Linc Davis

    The certificates all look good, I deleted about 6 expired ones and followed your instructions as directed.

     

    Tried to send a text with picture and it fails to work.

  • by Linc Davis,

    Linc Davis Linc Davis Jan 15, 2016 8:35 PM in response to resonator1six
    Level 10 (208,037 points)
    Applications
    Jan 15, 2016 8:35 PM in response to resonator1six

    Please take these steps to resynchronize the iCloud keychain. Your keychain on iCloud and your other Apple devices won't be affected. Take Step 2 only if Step 1 doesn't solve the problem.

    Step 1

    Back up all data.

    Open the iCloud preference pane and uncheck the Keychain box. You'll be prompted to delete the local iCloud keychain. Confirm—the data will remain on the servers. Then re-check the box. Follow one of the procedures described in this support article to set up iCloud Keychain on an additional device. Test.

    Step 2

    If you still have problems, uncheck the Keychain box again and continue.

    Triple-click the line below on this page to select it, then copy the text to the Clipboard by pressing the key combination  command-C: 

    ~/Library/Keychains

    In the Finder, select

              Go ▹ Go to Folder...

    from the menu bar and paste into the box that opens by pressing command-V. You may not see what you pasted because a line break is included. Press return.

    A folder named "Keychains" should open. Inside it is a subfolder with a long name similar to (but not the same as) this:

               421DE5CA-D745-3AC1-91B0-CE5FC0ABA128

    The above is only an example; yours will have a different name of the same general form. Drag the subfolder (not the Keychains folder) to the Trash and empty.

    Restart the computer and re-enable iCloud Keychain.

  • by resonator1six,

    resonator1six resonator1six Jan 16, 2016 1:30 PM in response to Linc Davis
    Level 1 (0 points)
    Jan 16, 2016 1:30 PM in response to Linc Davis

    Well, yet again I have followed your instructions, found the folder you spoke of, deleted it, restarted, logged back into keychain....and still does not work.

     

    I'm amazed that this problem in not seemingly impossible to track down, but that nobody else on this support forum has not had the same problem.

     

    If you have another exercise for me to perform I'm up for it, because we've gone this far.

  • by Linc Davis,Solvedanswer

    Linc Davis Linc Davis Jan 16, 2016 10:35 PM in response to resonator1six
    Level 10 (208,037 points)
    Applications
    Jan 16, 2016 10:35 PM in response to resonator1six

    Please remove "Little Snitch" completely. It serves no real purpose anyway except to interfere with normal operation, but if you test after removing it and find no change, you can reinstall it.

    Any third-party software that doesn't install from the App Store or by drag-and-drop into the Applications folder, and uninstall by drag-and-drop to the Trash, is a system modification.

    Whenever you remove system modifications, they must be removed completely, and the only way to do that is to use the uninstallation tool, if any, provided by the developers, or to follow their instructions. If the software has been incompletely removed, you may have to re-download or even reinstall it in order to finish the job.

    I never install system modifications myself, and except as stated in this comment, I don't know how to uninstall them. You'll have to do your own research to find that information.

    Here are some general guidelines to get you started. Suppose you want to remove something called “BrickMyMac” (a hypothetical example.) First, consult the product's Help menu, if there is one, for instructions. Finding none there, look on the developer's website, say www.brickmymac.com. (That may not be the actual name of the site; if necessary, search the Web for the product name.) If you don’t find anything on the website or in your search, contact the developer. While you're waiting for a response, download BrickMyMac.dmg and open it. There may be an application in there such as “Uninstall BrickMyMac.” If not, open “BrickMyMac.pkg” and look for an Uninstall button. The uninstaller might also be accessed by clicking the Customize button, if there is one.

    Back up all data before making any changes.

    You will generally have to restart the computer in order to complete an uninstallation. Until you do that, there may be no effect, or unpredictable effects.

    If you can’t remove software in any other way, you’ll have to erase and install OS X. Never install any third-party software unless you're sure you know how to uninstall it; otherwise you may create problems that are very hard to solve.

    Trying to remove complex system modifications by hunting for files by name often will not work and may make the problem worse. The same goes for "utilities" such as "AppCleaner" and the like that purport to remove software.

  • by resonator1six,

    resonator1six resonator1six Jan 16, 2016 9:42 PM in response to Linc Davis
    Level 1 (0 points)
    Jan 16, 2016 9:42 PM in response to Linc Davis

    Removed Little Snitch and voila! Problem solved.

     

    I have used Little Snitch and send messages with images before though, but I may have denied access to one app that interfered with iMessage.

     

    Thanks for staying with me LInc and figuring this out. I can now see why you're at level 10.

     

    Kudos!

  • by resonator1six,

    resonator1six resonator1six Jan 16, 2016 10:35 PM in response to Linc Davis
    Level 1 (0 points)
    Jan 16, 2016 10:35 PM in response to Linc Davis

    Just for the record, after uninstalling Little Snitch I went back in reinstalled it, a fresh version. Then when launching iMessage and trying to send a JPEG Little Snitch asked me for approval and I approved it "forever", as it gives you multiple options.

     

    I sent a test image and it went through this time without a hitch. At some point Little Snitch had some conflicting approvals or denials, take your pick and was screwing up my ability to use the iMessage app.

     

    So I just wanted to let you anyone who might run into a similar problem using Little Snitch to just uninstall the app, reinstall it and start fresh and you should be good to go. I personally like the app Little Snitch as it gives me just an added layer of protection and allows me control my internet traffic.

     

    That's it.

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