How to Zip a File on Mac (and Send It)

Zip One File

Apple says compressed files take up less disk space than uncompressed files, which is why zipping helps with backups and with sending things over the internet. See Apple's guide to zipping and unzipping on Mac. These steps are for a Mac. We did not cover an iPhone.

1. In a Finder window or on the desktop, find the file.
2. Control-click it.
3. Choose Compress from the shortcut menu.

Apple says that when you compress a single item, the compressed file has the name of the original item with the .zip extension.

Zip Several Files

Apple says that if you compress multiple items at once, the compressed file is called Archive.zip. Select the items first. Finder's usual way to pick several items is to hold Command and click each one. Then Control-click one of them and choose Compress.

We did not check the exact menu wording for several items on a Mac, and Apple's page does not give it. It names only the result, Archive.zip. Apple's page has no rename step either, so give the file a clearer name with Finder's usual rename before you send it.

Zip a Folder

A folder works the same way as a file: Control-click the folder, then choose Compress, as in Apple's guide. For sending a whole folder by email, see our guide to sending a folder by email.

The second way is Terminal. Apple's built-in manual for zip (type man zip in Terminal) gives this example for zipping a folder and everything inside it:

zip -r foo.zip foo

Here foo.zip is the new file and foo is the folder. The manual says -r means recurse into directories, which is what pulls in everything inside the folder. Nothing in the manual says which program Finder's Compress uses, so we do not claim the two give an identical file.

Unzip a File

Apple's instruction is to double-click the .zip file. The unzipped item appears in the same folder as the .zip file, and you can delete the .zip file afterward if you want to. See Apple's guide.

If the zip will not open, Apple says to make sure you have enough space on your Mac for the unzipped item. If someone else sent it, Apple says there might be a problem with the file, so ask them to zip it again and resend it.

If the person you send to is on Windows, Microsoft says to right-click the zipped folder, choose Extract All... and follow the instructions, or open it and drag a single file out. See Microsoft's guide to zipping and unzipping. Microsoft's page says nothing about zips made on a Mac, and we did not test one.

Password

Apple's Finder page lists no password step for a zip, so Compress cannot add one. There are two Mac routes, and each has limits.

Terminal. Apple's built-in manual for zip describes -e as encrypting the contents with a password that you type at a prompt and that is not shown on screen:

zip -e name.zip file

Do not use -P to put the password in the command. The manual marks it "THIS IS INSECURE!" because the password stays in the command line. The manual also says that where security is truly important, you should use strong encryption such as Pretty Good Privacy instead of the relatively weak standard encryption that zip utilities provide.

Two more limits apply once the zip leaves your Mac:

• Gmail does not allow password-protected archives with archived content. See Google's list of blocked attachments.
• Windows 11, version 24H2 supports compression and decompression of various formats but not operations on encrypted archive files, and Microsoft suggests apps such as 7-zip or WinRAR. See Microsoft's guide.

Encrypted disk image. Apple's other route is a file that only a Mac is meant to open. Its Disk Utility guide says confidential documents can go in an encrypted disk image:

1. Open Disk Utility and choose File > New Image > Blank Image.
2. Set a name, a size and a format. For a Mac on macOS 10.13 or later, Apple says to choose APFS or APFS (Case-sensitive).
3. Click the Encryption pop-up menu and choose an option.
4. Enter and re-enter a password.
5. Set Image Format to read/write and save.

Apple warns that if you forget this password, you will not be able to open the disk image or see any of the files. Apple's page does not say whether a Windows PC can open a disk image, and we could not confirm it.

Size

Does a zip come out smaller? Sometimes. Apple says compressed files take up less disk space, and gives no figure. Microsoft says some types of files, like JPEG images, are already highly compressed, so zipping several JPEG pictures leaves the total size about the same as the original collection. See Microsoft's guide. We did not measure any file ourselves.

Permissions

If Compress will not work, Apple says to check the permissions on the item. These are the steps from Apple's page on files you cannot compress:

1. Select the item, then choose File > Get Info.
2. Click next to Sharing & Permissions to expand the section.
3. Click the pop-up menu next to your user name to see the permissions settings.
4. If you are not logged in as an administrator, you may need to click to unlock it, then enter an administrator name and password, or use Touch ID or your Apple Watch.
5. Change the permissions to Read & Write or Read only.

If you cannot change them, Apple says to contact an administrator of your Mac or the owner of the file or folder.

Limits

A zip is one file, so it meets the same limits as any attachment.

• Email size. Gmail takes 25 MB on a personal account, per Google. iCloud Mail takes 20 MB, per Apple, and Mail Drop takes up to 5 GB with the file kept for 30 days, per Apple's Mail Drop page. We read these on 23 October 2026. Our guides to Mail Drop and the Outlook attachment limit hold the full tables.
• File types. Gmail does not allow some file types, including inside a zip, such as .exe or .js files, per Google.
• Passwords. A password-protected zip can be refused by Gmail or fail to open on Windows 11, as above.
• Folders. Apple's Mail Drop page lists an uncompressed folder as a reason a send may not use Mail Drop, so zip it first.

Send It

Zipping is half the job. For the sending half we already have guides, so we do not repeat their tables here:

• A zip that fits: attach it. Our guide to sending a folder by email covers Apple Mail, Gmail and Outlook.
• A zip up to 5 GB from Apple Mail: Mail Drop on Mac.
• A zip that Outlook refuses: the Outlook attachment limit.
• A person nearby: AirDrop not working on Mac covers the fixes and a backup link.

Past the limit, send a link instead. iCloud Drive, Google Drive, Dropbox and WeTransfer all do it, and Loop does it under your own name.

Loop

Loop is a Mac app that turns a file into your own branded link. It adds nothing to zipping itself: Finder makes the zip, and Loop does not make one, compress one or put a password inside one. For one zip sent once, attach it, or paste a link from storage you already have.

Loop helps when zips go out to clients again and again and you want them under your name. What is true when you share a zip:

• A zip you made is shared as a plain file. The reader sees the file name and its size with "No preview for this file type", and a Download button. They need no account and can use any browser.
• A zip with an index.html at its top, or inside its one top folder, is offered as a Website. That is how Finder zips a website folder. Loop treats it as a page to host. To send the zip itself, hold Option while you drop it, and choose Files instead of Website under Share As.
• Dropping several files makes a Download All button. Loop builds the zip for the reader, so you do not zip them first. That zip is stored, not compressed, so it is not smaller than the originals.
• The link Password does not encrypt the zip. It is a gate on the page, checked before the file is served. The zip itself is not password-protected.

You can add an expiry to a link, but it is optional and defaults to Never. Loop tells you when someone downloads, with a notification on your Mac, once for each visitor's browser for each link, while Loop is running. It sends no email or phone alert, and it runs on a Mac on your side only. We do not promise a maximum file size.

Cost

Zipping in Finder is free. Sending a link costs nothing on a free plan, and the paid options are below.

These are US dollars for one person, before tax, on the cheapest paid plan that does the job. Apple says Mail Drop attachments do not count against your iCloud storage, but the sender must be signed in to an Apple Account. iCloud+ 50 GB is $0.99 a month, billed monthly, which is $11.88 over a year, and Apple's page was published on 16 September 2026. Google One 100 GB is $19.99 a year, and Google gives 15 GB free, from an archived US copy of 19 October, and Google Drive links set to "Anyone with the link" work without signing in. Dropbox Plus is $9.99 a month billed yearly on an archived US copy of 2 November, which is $119.88 a year. WeTransfer Starter is $7 a month billed yearly, which is $84, from our 20 October note, because its pricing page would not load on 2 November. Its free plan allows 10 transfers or 3 GB in any 30-day period, as of its page updated 23 October 2026.

Loop's files are stored in your own Cloudflare account, free up to 10 GB. Past that, Cloudflare bills you. Cloudflare's pricing page, updated 30 October 2026, lists $0.015 per GB-month with no data-transfer charge for downloads, so 100 GB stored for a month is about $1.35 after the free 10 GB. Cloudflare may also ask for a card when you switch storage on.

Loop includes a 14-day free trial that starts on first run, and Loop asks for no payment to begin it. During the trial a small "Shared with Loop" badge shows on the pages your clients see, and it goes with a licence. Loop is $49 once for one person.