My Mac Won't Download Files

How to fix iPod won’t download music when syncing with iTunes? This guide will help you out with a quick & effective method.

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“I have an old 32G iPod classic that has worked for more than 10 years. Recently I uploaded some CDs I purchased to iTunes, verified they were in iTunes and tried to download to my iPod. However, it said it was ‘syncing’ but took only a second or two and nothing changed on my iPod. Looking further I see that this computer and my iPad are the only two ‘authorized’ devices. I’ve never ‘un-authorized’ my iPod that I’m aware of. How should I do to download music on to my iPod? Thank You in advance!”

— From Apple Support Community

The above question is one of the most common iPods won’t connect with iTunes issues, and the causes of this question are various: such as iTunes isn’t the latest version, USB cable is not available, manual misoperation and more. In this quick guide, we will offer a simple & effective way to solve this problem, and also list some useful tips and tricks related to iPod won’t recognize iTunes you may encounter in daily life.

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Part 1. How to Fix iPod Won’t Download Music While Syncing with iTunes

If syncing now works but no songs is moving over to your iPod classic/nano/shuffle, you may try the following tips:

  1. Open iTunes, under the “Summary” tab, check if “Manually manage music and videos” is enabled or not, if it is then trying toggling it off and on again, and then manually drag a song over to the iPod classic nano/shuffle/touch to force manual syncing.
  2. Look under the “Music”, “Movies”, “Apps”, “TV Shows” or respective tabs and be sure that “Sync Music “, “Sync Movies ” etc. is checked and enabled.
  3. Try checking and unchecking those boxes, then hit the “Sync” button again.

If these still don’t work, you may need an iTunes alternative like AnyFix that can help you fix 130+ system issues for iPhone/iPad/iPod touch/AppleTV in few clicks. Continue to take a look at the following content to find the best answer for you.

Part 2. How to Fix iPod Won’t Download Music While Syncing with AnyFix

Acting as one of the top iTunes alternatives, AnyFix can flawlessly fix iPod won’t download music while syncing with few clicks. All you need is to download AnyFix and install it on your computer, and then follow the detailed steps below to fix your trouble without hassles.

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Step 1. Launch AnyFix on your computer, click “System Repair” to go ahead.

Fix iPod Won’t Download Music While Syncing with AnyFix-1

Step 2. Select “iPod touch Problems”>click “Start Now” to fix the issue immediately.

Fix iPod Won’t Download Music While Syncing with AnyFix-2

In addition, you can also just try AnyTrans to transfer music to iPod without syncing. Follow part 3 to get a quick way to get what you want as easy as 1-2-3.

Part 3. How to Download Music to iPod from iTunes without Syncing

AnyTrans is a nice option to download music from iTunes to iPod without syncing. With it, you can transfer music, photos, playlists, audiobooks, podcasts, and more from computer/iTunes to iPod without any data loss.

Step 1. Download AnyTrans on your computer and launch it > Connect your iPod with the computer > AnyTrans will detect your device automatically for a while.

Step 2. Choose iTunes Library on the main interface. Here you will see all your iTunes music.

Step 3. Select several or all songs you want download > Click Send to Device icon to download music to your iPod.


Add Music to iPhone from iTunes Library in AnyTrans

Part 4. Other Useful Tips to Fix iPod Won’t Sync with iTunes

  1. Check USB and Wi-Fi connection and reconnect your iPod to the computer.
  2. Re-Authorize iTunes & the Computer.
  3. Try a Different USB Port & USB Cable.
  4. Turn off iCloud Music Library (iTunes Match) on iPod and iTunes.
  5. Update iOS and iTunes to the latest version.
  6. Uncheck “Read Only” and change permissions of the files you want to sync by right-clicking the files > Properties > Uncheck “Read Only”.
  7. Restart your iPod, iTunes, and computer.

The Bottom Line

That’s all about how to fix iPod won’t download music while syncing with iTunes, and hope this guide brings you more convenience on solving your troubles. Moreover, AnyFix is an all-in-one iOS system recovery tool that also helps you solve over 330+ iPhone/iPad/iPod touch/AppleTV/iTunes issues in few clicks. Let’s give it a try!

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Aug 28, 2020 • Filed to: Solve Mac Problems • Proven solutions

'Agh! Why I can’t delete a file?' is a common frustration with most Mac users. Usually, you find yourself having no clue on what to do next. Well, this article will guide you to your next and final step.

There are various reasons to delete a file. However, whatever reason you might have, your Mac might not agree with you.

Since the creation of on-screen technologies, terms such as 'delete', 'erase', and 'format' has been the go-to options in situations where somebody wanted to get rid of a file or application. Also, to safeguard a system in terms of freeing up space or easy removal of malware, the delete key has been beneficial.

However, in recent versions of operating systems, we have been unable in some cases to delete files from our computers. You have probably faced warnings such as ‘folder in use, cannot delete.’

So, how to delete files that won’t delete in Mac?

Well, we shall explain why you can’t delete a file and also the solutions in the sections below:

Part 1. Why I Can’t Delete File on Mac?

You have often wondered why you can’t delete an app on Mac. The presence of a Trash bin on Mac has always made it easy to sort out what you don’t need. However, this is not true.

There are underlying obstacles that can hinder you from clearing your system of specific files. At times these hindrances save us from deleting sensitive data, probably those required by the system to run.

However, the obstacles can, at times, go overboard. It is when you are unable to get rid of the average local files that you know are not useful to you and the system.

So why would the system or anything else keep you from doing so?

Well, some of the reasons include:

  • Your Mac system locks the file: Mac locks sensitive system files that are a must for its operations. When deleted, their absence can cause your Mac OS to ‘break.’ It might not even be able to boot up.
  • The file or folder is in use and can’t be deleted: Mostly happens when a file, e.g., a word document is opened and is in use. It prevents the disruption of your ongoing work. You might have wanted to delete the data accidentally.
  • An app has locked the file: When an application is developed such that its files cannot be tampered with, e.g., to prevent them from being edited or copied, they might be locked. It is thus a security measure for the program with regards to copyright restrictions.
  • The file is not available: Sometimes files are visible but cannot be accessed for one reason or the other. These could be music, documents, or a folder. Usually, they are ‘ghost files.’ You can’t delete such files because they are not there in the first place. It could be a thumbnail left behind.
  • Presence of a Finder bug: A bug, in this case, is a glitch of some sort that prevents the system or an app from carrying out its normal operations.

Part 2. Can't Delete Files? Go to the Finder

Usually, the most natural solution to cannot delete files is by dragging them to the Trash. In case you'd want the data back, command + Z would automatically undo your action. To empty Trash, you can access Finder by either double-clicking the Trash icon on your dock or go to the top left section on your Mac and select 'Finder.'

From the Finder menu, you can click on Empty Trash. Also, from the Trash icon at your dock, you can right-click and select Empty Trash.

But that doesn’t always work. An error “file can’t be deleted” may pop-up to alert you of this. In such a scenario, you can do the following:

Solution 1. Relaunch Finder

  1. Simultaneously press Command + Shift + Escape.
  2. On the menu that pops up select Relaunch

Make sure that the Finder loading is complete before you can start deleting.

Solution 2. Force quit Finder

There are several ways to force quit Finder. From the Apple logo at the top right.

  1. Click the Apple logo.
  2. From the menu, click on 'Force Quit Finder'.

It is the general way of doing it.

Solution 3. Secure Empty Trash

If you are familiar with the Terminal, you can use the ‘killall’ command to force quit Finder. After the successful deletion of a file, you may not be able to empty Trash as the file can’t be deleted from the Trash.

  1. Go to Finder on the top left.
  2. If Empty Trash didn’t work for you, select secure Empty Trash under it.

You can also press command and right-click the Trash icon to secure empty Trash.

Part 3. Cannot Delete Files? Fixes Without Finder

Where the Finder method of deleting apps has not worked out for you, try the following:

Where the item is a folder, delete each file manually to isolate the single erroneous file. If all files get deleted such that the folder is empty, try Trashing it.

Why Won't My Mac Download Pdf Files

Change permissions to empty the Trash. This method makes use of the Terminal using the command ‘chflags’.

  1. Go to Finder on the top left.
  2. If Empty Trash didn’t work for you, select secure Empty Trash under it.
  3. Change the folder to that of the Trash. Type “cd ~/.Trash” without the quotes.
  4. Change permissions by using “chflags -R nouchg ” without the quotes.

The command line can also be used to forcibly empty the Trash using the command ‘sudo rm -rf’. Beware, this command erases everything in the Trash without warning.


  1. Open the Terminal as described above. Also, you can use the spotlight to search for Terminal
  2. In the Terminal, change to the Trash folder as described above.
  3. Type “ls “to get a list of files in the Trash.
  4. Remove the specific stubborn file by typing “rm file.png,“ where the data is the item of your choice.

Using the sudo command erases everything in the Trash. Thus, you should only use it if you know what you are doing. You can also do a workaround.

  1. Create a file or folder with the same name as the file that can’t be deleted but in a separate location.
  2. Move this newly created file to the same location as the stubborn one and allow it to replace.
  3. The previous one automatically disappears. Now you can quickly delete the new one.
  4. Create a folder into which you then move the items you want to delete. The newly created folder will hopefully have permissions different from the previous one.
  5. Lastly, try to log in using an admin account. It will give you more power over your content.

If you accidentally deleted important files, just jump to Part 5 for the solutions or directly download Recoverit Data Recovery. It will help you recover all deleted files.

Part 4. Can't Delete File Because File Is in Use on Mac

When MacOS thinks the file you are trying to delete is in use by another process, emptying the Trash will not work. Therefore, the first thing to do is to quit all other programs to ensure no other application could use any of the files on your Mac.

To force quit apps on the dock:

My Mac Won't Download Files

  1. While pressing option on your keyboard, right-click on the app.
  2. On the menu that appears, click on force quit.

With this method, you’ll have to quit all apps one by one.

Using the Apple menu:

  1. Click on the logo on the top left.
  2. On the drop-down menu, select Force Quit.
  3. On the next menu of available apps, select the app, you would want to quit and click on the Force Quit button.

After force quitting all apps, now try deleting the file or folder.

If force quitting all programs doesn’t work for you, you can try restarting your Mac or even shutting it down then power it on.

Part 5. How to Retrieve Deleted Files on Mac

In the process of trying to delete one file, you can end up deleting several of them, and in extreme cases, you might get frustrated and accidentally format your drive.

However, that is not the end of the road. Wondershare offers you Recoverit Data Recovery Mac version 8.0. Recoverit data recovery software is a suitable comprehensive way to cater for recovery options irrespective of how data was lost.

The software has access to various storage devices including a corrupted Mac Hard drive, USB drive, iPod, SD card, etc. featuring compatibility with FAT 16/32, NTFS, and HFS+ file systems.

  • A more organized main menu page: The main menu now displays drives that are both internal and external, including lost partitions.
  • Enhanced precision: You can now choose the specific location on which to run a scan.
  • Enhanced retrieval of files: Recoverit can now retrieve raw files from internal drives and other external devices that even the computer cannot recognize.
  • Better preview of images: When scanning for images, recoverit data recovery software offers a sneak preview of images, videos, and documents in a larger window to enhance the experience.
  • Allows for recovery of data from Drone camera and GoPro
  • It’s able to recover files from more than ten drives.

So, how do you use Recoverit to recover lost files?

Step 1. Select a location where files are deleted

Launch the software and select the drive from where the data files are lost. If you don’t know which drive to search, tap on the “I can’t find my partition” option and hit the Start button.

Step 2. Scan the selected location

Typically, the software will run an all-around scan and search for the lost and deleted files on the entire drive.

Step 3. Preview and recover deleted Mac files

When the scan completes, the files will be listed on the screen. The software will sort out the files according to format to make the search easier. You can select multiple files at a time and have a preview at them.

My Mac Won't Download Files Free

You also have the option of doing a deep scan of the files at the bottom.

Part 6. Tips Against 'Can't Delete Files on Mac'

Some of the issues that you face with deleting files on your Mac and end up believing that they can’t be deleted is false. “Why so?” You ask.

  • 1. Settle your mind

First things, first, you needed to relax. Frustrations often lead to irrational behavior. When you feel like it’s becoming impossible and you have done everything don’t start throwing tantrums. Realize that some files can’t be deleted for a reason or you probably are yet to find out.

Why Won't My Mac Download Zip Files

  • 2. Research online on various methods

To find out what kind of files you should or shouldn’t get rid of, check on sites and articles such as this one. You can look at various methods of troubleshooting for an easy time.

  • 3. Use past experiences
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As a Mac user, you must have heard of similar cases from friends. Ask yourself what they did differently and try to follow their footsteps.

  • 4. Seek assistance

When memory fails you, and you can’t remember what to do, call the right people. Reach out to online experts who can assist.

  • 5. Be cautious

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Finally, with all that you do, be cautious. While struggling to delete a file, you can quickly end up getting rid of something as important as a system file. Double-check on stubborn files when clearing your Hard drive.


Clearing your system is as vital as deleting files and emptying the Trash on your Mac since, with everyday use, your device accumulates unnecessary files. So, when a file error such as 'file in use, cannot be deleted' pops up, be careful. Also, you should double-check the kind of files you install, especially third-party apps.

However, when you or anybody else is stuck on how to delete files that won’t be deleted, direct them to check out this article. I am sure you have significantly benefited from it so, help others too.

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