File compression / Zip error: Couldn’t communicate with a helper application

Hi Hizir49,

Thanks for coming to Apple Support Communities for help today.

First, verify that you are performing the zip steps correctly that are found here: Zip and unzip files and folders on Mac

"On your Mac, do any of the following:

• Compress a file or folder: Control-click it or tap it using two fingers, then choose Compress from the shortcut menu.

If you compress a single item, the compressed file has the name of the original item with the .zip extension. If you compress multiple items at once, the compressed file is called Archive.zip.

• Unzip (expand) a compressed item: Double-click the .zip file.

The unzipped item appears in the same folder as the .zip file. If you want to, you can delete the .zip file.

Note: If you can’t open the .zip file, make sure you have enough space on your Mac for the unzipped item. If you received the .zip file from someone else, there might be a problem with the file. Ask them to zip the file again and resend it."

If the issue continues, see if it happens in safe mode to further isolate the issue. This will prevent third-party apps from loading and clear cache as well that could be causing issues with your compression.

Here's How to use safe mode on your Mac.

"Determine whether you're using a Mac with Apple silicon, then follow the appropriate steps:

Apple silicon

1. Shut down your Mac.
2. Turn on your Mac and continue to press and hold the power button until you see the startup options window.
3. Select your startup disk, then press and hold the Shift key while clicking “Continue in Safe Mode.”
4. Log in to your Mac. You might be asked to log in again.

Intel processor

1. Turn on or restart your Mac, then immediately press and hold the Shift key as your Mac starts up.
2. Release the key when you see the login window, then log in to your Mac. 
3. You might be asked to log in again. On either the first or second login window, you should see ”Safe Boot” in the upper-right corner of the window."

Let us know what happens.

Have a fantastic day!

Hi Hizir49,

The article How to use safe mode on your Mac includes subsequent steps depending on the results of the test in safe mode:

"If the issue continues in safe mode

If the issue continues while in safe mode, or your Mac restarts several times and then shuts down while starting up in safe mode, you should reinstall macOS and make sure that your Apple software and third-party apps are up to date."

If that does not help, use Apple Support to investigate further with the assistance of AppleCare Support.

Regards.

I find that Zipping does not always work depending on file/folder names sometimes in the path. In my own personal experience you are much better off creating a .dmg archive using Disk Utility or using the command line utility "tar" to create a .tgz or .bz2 archive file. There may be GUI based utilities that which may allow you to do that.