If you notice “Send to > Compressed Folder” not working, it’s possible that file size is the cause and you should resort to third-party compression tools like WinZip, WinRAR, 7-zip, etc. Aside from that, you could perform a clean boot, boot into Safe Mode with networking and so on. Take a look at this article to be able to compress files as you see fit on your Windows computer.
A List Of Solutions
Use Third-Party Compression Tools
While the compression tool of Windows is adequate in most of the cases, there is a size restriction which complicates the compression process at times. Thus, regarding “Send to > Compressed Folder” not working, it’s a good idea to switch to third-party compression tools. Nowadays, a wide range of tools exist but in terms of utility, WinZip, WinRAR and 7-zip stand out from the rest. Launch your web browser, download and install a third-party compression tool then compress the files one more time.
Perform A Clean Boot
You suspect that a third-party app is disrupting the compression of files on your Windows PC? Then it won’t hurt to perform a clean boot. To perform a clean boot, you must go through the steps down below:
- Step 1: Press Windows key, type msconfig and press Enter.
- Step 2: In System Configuration, navigate to Services tab, click Hide all Microsoft services and pick Disable all.
- Step 3: Navigate to the Startup tab, hit Open Task Manager and disable everything in sight.
- Step 4: Close Task Manager, return to System Configuration and hit OK.
- Step 5: Restart your computer.
Note: If the Windows compression tool works as expected following clean boot, you could conclude that an app is at fault. That means you should get rid of recently installed apps. When the issue is out of the way, you could change back to normal startup.
- Step 1: Press Windows key, type msconfig and press Enter.
- Step 2: In System Configuration, pick Normal Startup and click OK.
- Step 3: Restart your computer.
Boot Into Safe Mode With Networking
Like clean boot, Safe Mode is able to help Windows users locate the cause behind all sorts of problems and fix them. About “Send to > Compressed Folder” not working, you should give Safe Mode With Networking a go.
- Step 1: Press Windows + I to open Settings.
- Step 2: Select Update & Security then choose Recovery.
- Step 3: Hit Restart now under Advanced startup.
- Step 4: When the screen comes back on, go to Troubleshoot > Advanced options > Startup Settings > Restart.
- Step 5: Press 5 (F5) to boot into Safe Mode with Networking.
Other Common Questions 
What must be done to compress files?
To zip (compress) a file, you must first locate the file to be compressed. Next, hold down (or right-click) the file, hover your mouse over Send to and hit Compressed (zipped) folder. Soon, at the same place, a new zipped folder with the same name would be created. Of course, you could always have the option of using third-party compression tools.
How do I fix a compressed folder error?
In the beginning, it’s a good idea to restart Windows Explorer (open Task Manager, right-click Windows Explorer and pick Restart). Aside from that, you could download and install Windows File and Folder troubleshooter then run it. Last but not least, if you cannot recall the last you updated Windows, you should check for updates. If an update is available, it’s strongly recommended that you update Windows at the earliest opportunity.
How come my .ZIP file is not opening?
Corruption, incomplete downloads as a result of unstable Internet connection, viruses and so on could mess up the opening of .ZIP files. Depending on the situation, you could recover files via specific recovery tools but the odds of success vary from case to case.
As PCWorld’s senior editor, Mark focuses on Microsoft news and chip technology, among other beats. He has formerly written for PCMag, BYTE, Slashdot, eWEEK, and ReadWrite.