Dear Lifehacker, I want to be able to right-click a file in Windows explorer, hit "Send to Gmail", and automatically attach the file to a new email. Is this possible? Sincerely, Gmailer
You can integrate Gmail or even Yahoo email directly into Windows using the previously mentioned Affixa application, which registers itself as the default email application on your computer and handles file uploading to Gmail.
Once installed, add in your Gmail account and check the box for "Launch Gmail after creating a draft message". If you don't select this, each file will be located in your Gmail Drafts folder, and you could manually forward the messages from there.
Now you should be able to use Send To -> Mail Recipient from the context menu to attach files.
As long as you are logged into Gmail in your default browser, you should be taken to a new message ready to send. If you'd rather not have all the Windows file metadata pre-populated in the email, you can change that option in the Affixa preferences.
If you would rather pull your attachments back out of Gmail, you can use our guide to download them all at once.
Love and Geekery, Lifehacker