Error: "Couldn’t communicate with a helper application" when trying to compress files

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Level 1

4 points

Error: "Couldn’t communicate with a helper application" when trying to compress files

Suddenly when I try to compress files I receive the message 'Couldn’t communicate with a helper application.' In a previous post, it was recommended to change the Read and Write setting in the Get Info box. I made those changes and it did not make a difference. I have also updated my computer and it has not fixed the issue. I am currently having to copy folders onto a flash drive and transfer them to a PC to then compile and send which is quite frustrating.

I am using Mac Ventura Version 13.3.1

MacBook Air 13″

Posted on May 1, 2023 9:42 PM

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Answer 1

HWTech

Level 9

67,220 points

May 2, 2023 2:16 PM in response to bjackson55

You should be updating the original post if the thread is not locked. Otherwise It would be helpful to include a link to the previous thread so we can see what has already been discussed to prevent repeating the same steps again. We are just other regular users such as yourself volunteering our own personal time to assist people on these forums.

In the mean time it may be useful to see your system configuration by running & posting an EtreCheck report here.

Sounds more like some sort of software issue, most likely with some third party software.

After running EtreCheck & posting the report, try booting into Safe Mode to see if you have the same problem.

Also, knowing where these files are located may be important.

Are these files being synced to a cloud syncing service such as iCloud, Google Drive, Drop Box, One Drive, etc.?

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Answer 2

bjackson55 Author

Level 1

4 points

May 2, 2023 5:12 PM in response to HWTech

My apologies, I did not respond to the original post because it was locked. I did not link it because I can no longer find the original post when I search for it, and the only response, which just said to change the Get Info from read only to read and write, did not help the user solve the issue. The person responding simply responded with the link here: If you can’t compress a file or folder on Mac - Apple Support

I have even tried creating a folder on my desktop and putting a blank txt file in it and trying to compress that, and get the same error. It is happening with ALL folders/files on my computer. I have tried on the desktop, in documents, etc with no luck.

My EtreCheck report is attached. Thank you so much for your help.

EtreCheck

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Answer 3

HWTech

Level 9

67,220 points

May 4, 2023 8:19 PM in response to bjackson55

Looks like both the Finder crashed once and DropBox crashed three times. Otherwise I don't see anything which would interfere with the normal operation of macOS although I'm not a macOS software expert.

Try running Disk Utility First Aid on the hidden Container. Within Disk Utility click "View" and select "Show All Devices" so that the hidden Container appears on the left pane of Disk Utility. Select the hidden Container which has your "Macintosh HD" & "Data" volumes and run First Aid. Even if First Aid says everything is "Ok" click "Show Details" and scroll back through the report to see if any unfixed errors are listed. If there are any unfixed errors listed, then try running First Aid while booted into Recovery Mode, otherwise you will need to erase the drive followed by reinstalling macOS & restoring from a backup.

Make sure the Drop Box software is completely up to date.

I'm wondering whether Drop Box is interfering somehow. I have heard from other contributors that many of the file syncing apps/services don't use the native macOS built-in features so the file syncing apps tend to work the system harder.

So is there any difference with being able to compress a folder while booted into Safe Mode?

Are there any special characters in the file or folders involved? If so, then those special characters could be causing a problem.

How large is the file or folder?

What type of files are you trying to compress?

Will these archives of compressed files be utilized only by you on macOS or will you be sharing them with others? With Windows users? Do you want these compressed files in .zip format, or would another type of compressed archive file be acceptable? I have had some issues creating .zip archives (not with the error you are receiving here though), and instead of wasting time on it I just used an alternate type of compressed archive format such as .tgz.

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Answer 4

bjackson55 Author

Level 1

4 points

May 22, 2023 6:55 PM in response to HWTech

Hello,

I did recently add a new dropbox account to my desktop. I had a personal account for years with no issues. Then recently added am "advanced" account from my university to my desktop. Soon after this is when I noticed new issues, like not being able to compress files and often getting an error message when I try to copy things into new folders. It's making it almost impossible to use my laptop at this point. The files are not large. It occurs for ALL files. Even if I create a folder with a blank txt file it will not compress or copy and paste to a new folder. I ran the First Aid on the hidden Container, that info is below in the additional text file. I tried compressing all of my folders (large and small, just containing a few txt files or excel files) in Safe Mode and received the same messages "Couldn’t communicate with a helper application." and "The Finder can’t complete the operation because some data in “” can’t be read or written. (Error code -36)".

I am a researcher so the majority of what I need to be able to copy and compress is data that needs to be sent to collaborators. I would prefer to compress the files in .zip format.

Dropbox and everything else are up to date. I will look into Recovery Mode, but it seems like I will need to backup my laptop first? I have not done this before and will look into it.

First Aid

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Error: "Couldn’t communicate with a helper application" when trying to compress files

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