How to Send Anonymous Email Attachments

The world of sending and receiving anonymous emails is absolutely shady. Maybe you want to play an April Fool’s prank, send out an anonymous love letter or – in the very worst of cases which no one could possibly condone – you might want to send out a virus. Regardless of how insidious your intent might be, it’s really not that hard to be anonymous on the Internet or to send anonymous mail to somebody, though it’s not always advisable.

Tip

Use email aliases to send anonymous emails from any persona you wish.

To send and receive anonymous email might actually be a good thing for your company, especially if you’re trying to create the image of a larger operation when you really only have one or two employees with a number of roles. Hey, we’ve all been in that startup whose HR person is also the office manager. It happens, but in this case, that person might want to send email anonymously as “HR” and “Office Management” rather than using their names.

Sending anonymous mail to somebody this way is extremely easy using email aliases, which can all be filtered through the same email address. If you have multiple roles, you’ll never need to check multiple email accounts again.

If you’re a Gmail user, it’s a little bit easier to send anonymous mail to somebody. Remember: nobody really likes anonymous email attachments, but nonetheless, sometimes we want to watch the world burn. If you’re a Gmail user, this is called an “alias.” This covers up your real email address and saves you from having to use your actual name when you reach out to people or send an anonymous email attachment.

You can opt to have multiple aliases filtered to a single email address or just one alias that goes right to your main account. Here’s how to set up an alias in a couple of steps:

1. Go to your company Gmail (or speak to the owner of the account).
2. Click the nine-square grid icon and find the “Admin” button.
3. Navigate to “Users” and click on the account you want the alias for.
4. Click “Account” and under “Aliases” add your alias. Save your changes.

You’ll also need to do an additional step in order to send emails from this alias. You’ll have to register it with your account. To do so:

1. Login to your main Gmail account and navigate to settings.
2. Click “Accounts.”
3. Where it says “send mail as,” click “add another email address you own” and enter your alias. Click “next step.”
4. Remember to check “reply from the same address the message was sent” to avoid any slip-ups that might reveal your identity.
   
   

Always test out your alias before you send an anonymous email to somebody because odds are you don’t want them to know who you are and slip-ups are very easy. There are also similar steps you can take in other services like Apple Mail, where aliases are added via the “preferences section” or in Microsoft Outlook.

Signing up for a free account through a service like Gmail or Yahoo is the simplest way to send and receive anonymous emails. Simply go to those websites and create your desired username and identity. Be warned: you can track an IP address on Gmail or Yahoo accounts, so you might not want to send something too terrible to another person if you’re using a free email server. It’s difficult to remain truly anonymous if you know the right workarounds.

It’s impossible to condone using an anonymous email service to send anonymous mail to somebody, but nonetheless, you might be desperate. Services like this include sendanonymousemail.net and 5ymail.com, but we warned that a lot of these services are shady. They log your IP address and are riddled with viruses. Use with caution, or better yet, don’t send an anonymous email at all.