to commonly asked questions.

iCloud Drive

Moving Documents from iCloud to Dropbox

Just making sure this is OK.  When I move some documents to DropBox I often get this warning.  I pay for Dropbox annually so I guess it’s separate from I cloud.  I pay $10 per month for additional I cloud storage (mainly for photos). 


Totally fine to move standard documents from iCloud to Dropbox. You don’t really want them to live in both places as that will get confusing with what version is the most recent. So the warning you see is one cloud service saying “hey, it’s leaving our hands. Hope you realize we won’t have it anymore”. Totally fine.

Keep in mind, MOVING a document is different than COPYING a document. Copying a document to a new location (therefore creating a new copy of the file) requires you to hold down Option before dragging. You’ll see the green plus sign which means you are making a new copy of the same document but the original one will stay where it was as well. Only do this if you have a specific reason to have more than one of the same document.

Don't run a business with iCloud desktop syncing.

Why is it taking so long to pull an attachment into mail from my desktop? I have iCloud desktop syncing turned on.

Back to iCloud desktop and performance in regard to attachments. Personally, my take is that I would not run a business relying on iCloud desktop syncing. It’s the equivalent of relying on the dewy decimal system to pull a book off the library shelf everything you want to work on your research paper then returning it immediately back to the bookshelf. Better to just have a copy of the book you need on hand at all times.

So options to consider:

1. Turn off iCloud desktop and document syncing and give up the ability to have desktops across computers looking the same. Items would live only locally and performance would improve.

2. Leave iCloud desktop syncing on but rely more on local folders for important work requiring quick access to documents. (Sort of defeats the point I know.)

3. Turn to dropbox. As I mentioned, iCloud is not something I would use to run a business but dropbox is. It’s quick, reliable, stable.

Items on my desktop are greyed out.

I know this should be obvious to me There are three videos on my desktop I’d like upload to Vimeo. They are “greyed out” when I try to designate the file in the app. See T. Laird on desktop and screenshot from Vimeo.

This is likely being caused by the fact that you may have desktop syncing turned on via iCloud. Check here:

Then check here to see if desktop and documents syncing is turned on:

If it is checked then you could either try turning off iCloud Drive desktop/documents syncing then upload your resource or you could also try moving the item to a non syncing folder like the movies folder in your user folder. Those would then be force to download in their entirety and you should be able to upload them to Vimeo from there.

Why aren't my desktop and documents folders syncing across my computers?

Lately, I’ve noticed that nothing is synching between the two computers. If I file something in my Documents on the desktop, it doesn’t appear in the files on the laptop. Is there a quick fix to this?

Sounds like iCloud Drive's desktop/Documents folder syncing is not active on one or more of your devices. To check that this feature is turned on go to System preferences/AppleID/iCloud on each of the machines. Here's a brief overview:

If the option below is not checked for you, check it. However, there are consequences. Your Desktop and Documents folder will move from their traditional location inside the user's folder to the iCloud Drive folder.

You can now find your Desktop and Documents folder in the iCloud Drive area in the finder window on the left column as seen below.

This will merge the contents of both computers. You may see your desktop items disappear temporarily. This frightens people but nothing is actually gone. Just moved to a new folder dedicated to syncing to the cloud.

Note: You can also see the contents of these folders via your phone or iPad using the app called "Files". It's already on your devices. Apple devices ship with it pre-installed.

If you have any questions or run into issues, I'm happy to assist. As you can see above, I don't personally use iCloud Drive syncing as it turns the desktop folder into a cloud based location which means everything you place there syncs. While this is great for most people, I use the desktop area as a heavy workspace and can't afford the performance loss that syncing causes. In other words, editing a video, audio file, or similar that lives on an iCloud desktop is slower compared to a non syncing folder.

Message about iClloud archiving

Two things: is this library suppose to be saving into the iCloud?
So I bought more  iCloud space and then got this message.



Buying more storage was the correct move. It's common for our generation to have over 200 gigs of content therefore pushing us up to the next tier plan (2TB). Younger people have less pictures and are fine with the lower amount of storage.

The second item is also fine. Apple did not implement the documents/desktop iCloud syncing as seamlessly as I would hope so you'll see these confusing messages from time to time about "iCloud Drive archive". Nothing really to worry about.

Should I use iCloud drive?

I downloaded the new operating system BigSur. Asking if i want to download all of my files in iCloud. Assuming the answer is No? Says will use 990.2MB.

Personally I prefer not to sync my documents and desktop folder to iCloud Drive which is what you’re talking about here. The plus is that your documents and desktop items are then backed up to the cloud. That’s great. The negatives are that you it tasks your computer more than it should which means less processor power for other things. Second negative, you have to make sure you have enough space in the cloud. Apple is hoping you buy more. Third negative, it means that the Desktop and Documents folder are basically useless for major tasks like editing video or audio files with professional level programs. Those files would have to find new homes. Not applicable to your use but I like to be thorough in my answers so I thought I’d mention it.

Also, keep in mind there are competitors to iCloud Drive syncing like Google Drive, Microsoft's One Drive, and Dropbox. Dropbox being my first choice.

Restoring iCloud documents from the cloud.

I don’t know why, but all my folders and things that were on my desktop before our session, are not there. Please tell me how to restore them. You may recall we switched AppleIDs on my computer.

Sounds like Mike was probably syncing your desktop and documents items to his cloud space. Should be an easy fix. I’m happy to assist but if you’d like to try on your own here’s what you can do:

Go to and log into HIS iCloud account (based on Select iCloud Drive from the menu.

Locate the items you want back. You can hold down the option key while clicking to select more than one file at the same time. Note, you cannot select folders using this method.
Then hit the download icon at the top. Those files will now be in your downloads folder and you can move them where ever you’d like from there.

Where did my documents go from these folders?

It is really weird that so much of the documents are missing from this level of folder…any ideas about what I did wrong? If this happened when I cleaned up the desktop why are the parent folders still in place but all the contents gone?

I am perplexed...

1. The screenshot you took is a little too small for me to make out some of the details. However,

2. It looks like you are looking at an iCloud Drive folder. I have seen this behavior before. Check to see if you have an iCloud Drive “Archive” folder in your home folder and if you do, check to see if the documents you are looking for are in the Archive. This can happen when iCloud Drive is disabled then re-enabled.

3. Cleaning the desktop would not effect folders that live in other places. Even if you had aliases pointing elsewhere and tossed out the originals, you would still see the abandoned alias file. So that’s not what happened. I’m guessing this is related to iCloud.

4. Check at to see if you can locate those documents via a web browser.

5. Do you have a time machine backup that we could use to recover these files. I LOVE time machine and it usually saves the day.

Where did my iCloud documents go?

I tried to open the files I keep in the I Cloud drive on my desktop yesterday (I keep all of my Excel documents, word documents, and many pictures in the file) and the drive was empty. I opened the I Cloud screen and checked the I Cloud Drive box (picture 1) and for the past day and 1/2 the screen in the second picture has been showing.

The I Cloud Drive worked fine before you came on Friday so I think something must have happened while you were here. Perhaps a setting was changed????

Can you help me with this over the phone ASAP? I use the files in the I Cloud Drive daily.

My photo albums starting moving to my I Pad and I phone yesterday. It took 3 days which was surprising to me, but so happy that seems to be working. I need to move some professional photos from a folder in the I Cloud Drive (which I can’t find) to an album in Photos.


Ahh, I recall. Remember we logged out of your husband's account to log into yours. this was nessasary in order to allow your pictures a chance to sync. However, in doing so, we removed the documents from your computer that were living in his iCloud account. The documents and other files are not gone. They're still in his iCloud storage area. You just don't have access to them within your user. A few ways to solve this:

Choice 1: relog into his account and drag the files you want into a different folder then log back into your own. (this is a bit painful.)

Choice 2: Log into his iCloud account using and download the files you want via the web browser. You can then store them anywhere you'd like.

Make sense? I can help with the large moving but if you just need a few files for now, for your work, you can use choice 2 in the mean time.

iCloud Drive desktop documents sync

Apple has been chasing the success and functionality of Dropbox for some time and their latest iteration, iCloud drive, is not an equal either. I do not recommend using desktop and documents sync. Like Filevault, they are trying to get you to implement it by default but it turns things into a big mess. For 20 years your desktop and documents folder have resided in the Home directory. Now Apple makes those folders invisible and places aliases into the iCloud directory. This means if you don't see that coming, you'll most likely be very confused as to where everything went.

I get a lot of complaints "where did all my stuff go?" This also causes your desktop to continuously sync with the cloud which means you pay a price in performance. If you are working locally on a project that lives temporarily on your desktop, as many of us do, now the computer is split between syncing to the cloud and you working on the file. Imagine trying to cut video that lives in the dropbox folder. Not a good way of doing things.

Apple will continue to improve iCloud functionality and it will most likely surpass dropbox at some point, but for now, stay away from it.
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