Honestly, switching from Windows to Mac—or even just using macOS for years without really digging into the shortcuts—can feel like trying to write with your non-dominant hand. You know what you want to do, but the fingers just don't cooperate. One of those "basic" things that's actually not basic at all is figuring out how to grab more than one file at a time. It sounds simple. It should be simple. But then you’re clicking around, your previous selections are disappearing, and you're ready to toss your MacBook Pro out the window.
Selecting multiple files on a Mac is essentially the gateway to being a power user. Whether you’re trying to dump 200 vacation photos into a folder or clearing out a messy desktop, you’ve got to master the "clutch" keys. We are talking about Command and Shift. They do different things, and if you mix them up, you’ll just end up frustrated.
The Click-and-Drag: The "Lasso" Method
If your files are all sitting together in a nice little group, the easiest way is the classic drag. You click on a blank spot in the folder—not on a file, or you'll just move that one file—and pull your cursor across the items you want. A little grey box appears. Anything that box touches gets selected.
This is great for Icon View, but it’s a bit finicky in List View. If you try to drag in a list, you have to be careful to start your click in the white space to the side of the file names. If you click the name itself, macOS thinks you’re trying to move that specific file.
How Do I Select Multiple Files on a Mac When They Aren't Together?
This is the big one. Usually, you don't want every single thing in a folder. You want that PDF from Tuesday, the JPEG from last month, and that one spreadsheet. This is where the Command (⌘) key becomes your best friend.
- Click your first file.
- Hold down the Command key.
- Keep holding it while you click every other file you want.
- If you accidentally click one you don't want, just click it again (while still holding Command) to deselect it.
It’s basically a toggle. This works across every view in Finder—Icons, List, Columns, and Gallery. You've probably seen people call this "non-contiguous selection." That’s just a fancy way of saying "files that aren't touching each other."
The Shift Key: For When You’re Dealing with a Huge Range
If you have a list of 500 files and you need the first 200, don't use Command. You'll get carpal tunnel. Instead, use the Shift key.
- Click the first file in the range.
- Hold down Shift.
- Click the last file in the range.
- Boom. Everything in between is now highlighted.
Wait, a quick warning: This works like a charm in List View and Column View. However, if you are in Icon View, the Shift key often acts exactly like the Command key. It won't necessarily grab a "range" because, in Icon view, "between" doesn't really mean anything to the computer. If you need a range, switch to List View (Command + 2), do your selection, and switch back.
The "Select All" Nuclear Option
Sometimes you just want everything. Maybe you're emptying a "Downloads" folder that’s become a digital graveyard.
The shortcut is Command + A.
It’s the universal "All" command. You can even use this in combination with the other tricks. Hit Command + A to grab everything, then hold Command and click the three files you actually want to keep to deselect them. It’s often faster to select everything and "un-select" the exceptions than to click 50 individual items.
Selecting Files Without a Mouse (The Keyboard-Only Way)
If you're on a MacBook and hate the trackpad, or your mouse battery just died, you aren't stuck. You can select files using just the arrows.
First, make sure you're in the right window. Use the arrow keys to move the highlight to your first file. Then, hold Shift and use the Up or Down arrows. The selection will expand as you move. This is super precise and honestly feels a bit more "pro" once you get the hang of it.
Why Can't I Select My Files? (Troubleshooting)
Occasionally, macOS acts up. If you're holding Command and clicking but nothing is happening, check a few things:
📖 Related: How can I delete a video from Facebook and actually make it disappear
- Permissions: If you're in a system folder, sometimes selection is restricted.
- Desktop Stacks: If you use "Stacks" on your desktop, you can't select individual files inside a stack until you click the stack to expand it.
- The "Empty Space" Problem: As mentioned before, if you're trying to drag-select, you must start in the empty space. If your folder is packed tight with no white space, try enlarging the window or switching to List View where there's more "dead air" on the right side.
Master the Sidebar and Status Bar
While you're at it, do yourself a favor and turn on the Status Bar. Go to the menu bar, hit View, and then Show Status Bar.
Why? Because when you select multiple files, the bottom of the window will suddenly tell you exactly how many you’ve grabbed and how much space they take up. No more guessing if you've highlighted 10 files or 11.
Putting it All Together
Selection is just the first step. Once you have those files highlighted, you can:
- Right-click (or Control-click) to "New Folder with Selection." This is a massive time-saver.
- Press Command + Delete to trash them all at once.
- Press Spacebar to enter Quick Look, which lets you scroll through your selection with the arrow keys to verify you got the right ones.
Actionable Next Steps:
Open your Downloads folder right now. It's probably a mess. Try the Shift-click method to grab a big chunk of old installers. Then, use Command-click to cherry-pick a few files you want to save. Drag them into a new folder. Once you do it three times, the muscle memory kicks in, and you'll never have to look this up again.