When trying to compress a folder, I am getting a 'Couldn't communicate with a helper application.' message. Why is this?

Where are these files located? Within your home user folder, or on an external drive, or network share? Are these items being synced to the cloud?

How large is the folder? File types within the folder?

It would also help to confirm the exact model Mac and the version of macOS used. You can get this information by clicking the Apple menu and selecting "About This Mac".

I've encountered issues where some types of files may prevent the compression algorithm from working for whatever reason. I usually end up trying to use another app to compress the folder or I use another compression algorithm.

Try booting into Safe Mode to see if you can compress that folder. If this works, then it is likely you have some third party software installed which is interfering. @Luis Sequeira1 did ask to have an EtreCheck report posted as well since many times third party software can interfere with the normal operation of macOS.

TheArtworker wrote:

I was busy compressing and transferring files during a back up of my iMac (running Mac OS Monterey 12.4) when all of a sudden I got a 'Couldn't communicate with a helper application.' dialogue warning. I have been trying to get my files compressed in some way all afternoon to no avail. I have also now reloaded Mac OS Monterey, but I am STILL getting the message!

? not so clear trying to compress, trying un compress, trying to move locations...(?)

Create a new folder and transfer the content?

Command i opens the info pane, do you have permissions, ignore permissions option. r/w privledges?

Change default application?

Control key >Open with options?

Try a different compression software besides the built in Archive Utility— if there is an issue

/System/Library/CoreServices/Applications/Archive Utility.app

Zip and unzip files and folders on Mac - Apple Support

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Keka

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The Unarchiver

iZip Unarchiver

Remo Zip

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Did you try restarting your mac? Often a transient issue can be cleared by restarting.

If the issue persists after restarting, Please run Etrecheck and post its full report here. Use the "additional text" button and paste the report into the text box.

It happens whenever I try to compress something that's on my desktop (or in a folder on my desktop). However, I can compress fine if I open Finder and compress the same folder from within Finder instead of the icon on the desktop. It happens no matter what file types in the folder or size of the folder. My Mac info is MacBook Pro (13-inch, 2020), running Monterey

Before I figured out I could compress the folder from a Finder window, I used the command line "zip" tool, but that's a lot less convenient.

I'll try booting to Safe Mode and see if it still happens there.

I just had this problem too when trying to compress a folder. I rebooted my mac, but it didn't help.

Do you have "Documents and Desktop in iCloud"?

I booted in safe mode a couple of days ago, and it didn't change anything. I still got the error when trying to compress a folder on my desktop.

My Documents & Desktop are in iCloud.

I just tried again, and everything seems fine now ... I love intermittent problems ... ugh.