How to Email Multiple Files in a ZIP File

01
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Make a ZIP File for Easier Management and Reduced File Sizes

If you want to send multiple documents or images via email, sending a compressed ZIP file can keep all of the files together so your recipient can store them easier. By compressing them into a ZIP file, you might even reduce the overall file size and bypass email size limits.

The following steps show exactly how to create a ZIP file in Windows using the built-in compression utility. Once you make the ZIP file, you can attach it to an email like you would any file, or store it elsewhere for backup purposes.

Note: Adding files to a ZIP file does not move the files into the ZIP file nor does it delete anything. What happens when you make a ZIP file is that the contents you choose to include are copied to a ZIP file and the originals are left untouched.

02
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Locate the Files You Want Compressed, and Then Make the ZIP File

Select "File | New | Compressed (zipped) Folder" from the menu
Select "File | New | Compressed (zipped) Folder" from the menu. Heinz Tschabitscher

Using Windows Explorer, open the files you want to include in the ZIP file. You can do this for your internal hard drives like the C drive, flash drives, external hard drives, your Desktop items, documents, images, etc. 

Whether it's one or more files or folders that you want in the ZIP file is irrelevant. Highlight whatever you will compress and then right-click one of the highlighted items. Click the Send to menu from the context menu that shows, and then choose Compressed (zipped) folder.

Tip: If later, after you finish making and renaming the ZIP file, you want to add more files to it, just drag and drop them right onto the ZIP file. They'll be copied into the ZIP archive automatically.

03
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Name the New ZIP File

Type the name you want the attachment to carry
Type the name you want the attachment to carry. Heinz Tschabitscher

Type the name you want the attachment to carry. Make it something descriptive so that the recipient can understand what's inside.

For example, if the ZIP file holds a bunch of vacation images, name it something like "Vacation Pics 2002" and not something obscure like "the files you wanted," "photos" or "my files," and especially not something unrelated like "videos."

04
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Attach the ZIP File as an Email Attachment

Drag-and-drop the zip file onto the message
Drag-and-drop the zip file onto the message. Heinz Tschabitscher

Every email client is a little different when it comes to composing messages and including attachments. No matter the client, you have to get to the point in the program where you can add files as attachments; you should choose the new ZIP file you created.

For example, in Microsoft Outlook, this is how you'd email the ZIP file:

  1. Click New Email from the Home tab of Outlook or skip down to the next step if you're already composing a message or you want to send the ZIP file as a reply or forward.
  2. In the Message tab of the email, click Attach File (it's in the Include section). If you'd rather, you can drag the ZIP file directly onto the message from Windows Explorer and skip the rest of these steps.
  3. Choose the Browse This PC... option to look for the ZIP file.
  4. Click on it once you find it, and choose Open to attach it to the email.

Note: If the ZIP file is too large to send over email, you'll be told that it's "bigger than the server allows." You can remedy this by uploading the file to a cloud storage service like OneDrive or pCloud, and then sharing the link.