To attach multiple files, hold the Ctrl (PC) or ⌘ (Mac) key while selecting your files. Selecting multiple files at once is not possible using Internet Explorer.
You can send messages up to 25 megabytes (MB) in size. If you'd like to send attachments that are larger than this, you can insert from Google Drive instead.
You may not be able to send larger attachments to contacts who use other email services with smaller attachment limits. If your attachment is too large to be sent to your contacts, you can also insert using Google Drive to get larger files to them.
As a security measure to prevent potential viruses, Gmail doesn't allow you to send or receive executable files (such as files ending in .exe).
If your attachment exceeds 30 MB, it is recommended you use Google Drive to send it.
In the Google Drive window that comes up, select your file by clicking once on it.
You can toggle between Grid View and List View with the toolbar buttons.
A selection of items not in sequence - Click once on the first item and then hold the Ctrl (PC/Linux) or ⌘ (Mac) key and click on other items you'd like to select.
Then click the insert button to add them to your message.
**If you need to attach multiple items in different Google Drive nested folders, you will have to repeat steps 1-4 for each group of attachments.
If you'd like to remove a file you've attached to a message, click the x to the right of the file name at the bottom of the message.