A guide to sending anonymous emails with attachments

When sending anonymous emails with attachments, you must go the extra mile to protect your privacy. Discover the most effective way to ensure confidentiality.
Encrypted attachment icons.
From sharing sensitive files to providing employee feedback without revealing your identity, there are many reasons for sending anonymous emails with attachments. The problem is that disguising yourself via email can be challenging. Your address is tied to plenty of PII (personally identifiable information) beyond your name, like your IP address, ISP, and even location.Luckily, there is a way to ensure full anonymity and confidentiality, and this guide will show you how to send private emails that can’t be tied back to you. Before we dive into the details, we must debunk some myths regarding the typical methods users resort to when trying to stay anonymous on the web.
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How to send an anonymous email in Outlook or other Big Tech services

If you use one of the popular email services like Gmail, Yahoo, or Outlook, you’ll have trouble staying anonymous. Users typically attempt to conceal their private information by taking the following steps:
  1. Creating a burner email
  2. Using a VPN (Virtual Private Network)
  3. Encrypting their email
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How much confidentiality does a burner email offer?

The most obvious way to send anonymous emails is by creating a disposable account. While this might be a good option for hiding a user’s name, it’s still far from providing complete privacy.This is because a burner email is still tied to the sender’s IP address. The recipient won’t have much trouble finding it, which might reveal other information, like the location the message was sent from. Even if the user deletes the account after sending the email, the records of it will still be available.That’s why users often opt for another security layer to mask their private information, such as a VPN.

Using a VPN to hide an IP address

A VPN encrypts a user’s connection and gives them an alternative IP address. Combined with a disposable account, it seems like a good way to enjoy some privacy. When a user connects to a VPN, their online traffic can’t be monitored by third parties or the ISP (Internet Service Provider). The new IP address can come from anywhere in the world, so the user’s location is masked as well.While this sounds like a solid way to stay anonymous, it still leaves some vulnerabilities. The ISP might not see the websites or services used, but they can see the amount of transferred data. If the attachments a user sends are large and there’s an unusually high data transfer, this could raise some red flags.Besides, the ISP can see the new IP address provided by the VPN service alongside connection timestamps. If a user shares extremely sensitive files or knowledge and the situation escalates to a full-on investigation, the recipient could connect the dots and trace the email back to them.It’s also not easy to find a trustworthy VPN, as many options promise complete privacy but fail to deliver it. VPNs are common targets of attacks, many of which have ended up revealing plenty of sensitive information.Even when choosing a reliable service, there’s always a possibility of a breach, which might lead to email interception. A VPN lowers the chances of an email falling into the wrong hands, but it doesn’t eliminate them. The most reliable method of securing your email correspondence is via encryption.

How email encryption helps you stay anonymous

The first two steps you saw offer surface-level confidentiality, which might be enough if your anonymous emails don’t contain anything that would compel the recipient to dig deeper. If you need complete peace of mind, you should use an email service that provides encryption.This way, the email’s contents will be scrambled and inaccessible to anyone besides the person with the decryption key—in theory. The problem with encryption is that most providers don’t offer sufficient security. They typically use one of two common encryption types:
  • Encryption in transitProtects your emails while they’re traveling between endpoints
  • Encryption at rest—Safeguards emails stored on the provider’s servers
Neither option can give you full anonymity, especially when you consider that most providers store emails and user data on their servers. Even if your correspondence is safe from third parties, your service provider can still access it, which means an email can be tied back to you.To take full ownership of your emails and data, you need an email service provider offering end-to-end encryption (E2EE).

E2EE—the safest way to send confidential emails

End-to-end encryption protects your emails and attachments from the moment they leave your device. It lets you create and store the encryption key, which means your service provider doesn’t have it on their servers. Since the provider can’t access the decryption key, they can’t decipher your messages.E2EE fixes the biggest issues of other encryption types, as shown in this comparison:
Encryption typeEncryption in transitEncryption at restE2EE
Protection levelSecures data moving through the networkProtects data sitting on the serversSafeguards all static and moving data between endpoints
Key creation and ownershipEmail service providerEmail service/Cloud providerEnd user
VulnerabilitiesMidpoint—The recipient’s provider decrypts the message before sending it to them, so a third party can intercept the plain-text copyServers—In case of a breach, a third party can steal decryption keys from the provider’s server and decipher users’ emailsEndpoint only—As long as the key doesn’t leave the user’s device, emails can’t be decrypted even if they’re intercepted
E2EE can vary greatly in implementation. Big Tech providers typically offer S/MIME encryption, which is decent but requires buying the certificate separately and going through a complex setup.The right E2EE email service should let you stay safe online regardless of your tech skills. Skiff Mail makes privacy available to everyone without unnecessary costs or complicated processes.

How Skiff Mail helps you send anonymous emails

Skiff Mail offers robust end-to-end encryption paired with cutting-edge security and privacy standards. Your anonymity begins the moment you sign up, as you don’t need to leave any personal details to get started.Once you do, you can enjoy full confidentiality and be certain nobody can access your emails or data. Skiff doesn’t create or store decryption keys, so it can’t see your correspondence. The email leaves your device encrypted, and only the recipient with the decryption key can decipher your messages.Your login credentials are also safe as the platform supports zero-knowledge authentication using the Secure Remote Password algorithm.Skiff offers various features that heighten your security and create an enjoyable user experience:
  1. Unlimited email search
  2. Beautifully-designed user interface (UI)
  3. Crypto wallet integrations
  4. Additional privacy-first platforms

Search for important conversations without restrictions

The email search function is much different in encrypted email services than in typical Big Tech solutions. E2EE options don’t store any unencrypted data on their servers, so browsing must happen locally. Offering a thorough and precise search feature in an E2EE environment isn’t easy, so most providers reserve this option for paying customers.Skiff doesn’t place useful features behind a paywall, so all users can enjoy lightning-fast, unlimited email and text search. You can have all important information at your fingertips.

Stay productive with an intuitive user interface

Robust security features usually come at the cost of the user interface. Skiff made sure there’s no trade-off between the two, so all of the platform’s many features are laid out intuitively.Whether you’re using Skiff on a browser, iPhone, Android, or Mac, you can stay focused and get work done without distracting bloatware. There are also no annoying ads, as Skiff doesn’t collect or sell user data.Skiff is open source, so developers and designers can freely review the codebase. Visit Skiff’s GitHub and read the whitepaper for more information on the company’s encryption method.

Step into a decentralized world with crypto integrations

The rise of blockchain took the online world by storm, and Skiff is on top of all the latest trends. The platform integrates with major crypto wallets to let you stay anonymous:

Explore Skiff’s secure productivity suite

Besides Skiff Mail, you can use three platforms to stay organized and share files without privacy concerns:
  • Skiff Pages—Create, edit, and share docs in an end-to-end encrypted environment
  • Skiff Drive—Store your sensitive files securely and take advantage of the optional decentralized storage with InterPlanetary File System (IPFS) integration
  • Skiff Calendar—Schedule private events safely and customize the calendar by choosing the features you need

Get started with Skiff and enjoy complete anonymity

You can start using Skiff Mail and safeguard your online correspondence in three quick steps:
  1. Visit the signup page
  2. Choose your account name and set a strong password
  3. Send private emails with Skiff Mail and explore other privacy-first products
If you don’t want to start fresh when creating a new account, take advantage of Skiff’s one-click migration. You can transfer all your emails and data from another provider in no time to shield them with the platform’s high-end security measures. Skiff doesn’t store unencrypted copies, so all your threads and files will be safe from the moment you migrate.All the features you saw are available with Skiff’s free plan. You get everything you need to stay anonymous, including four Skiff.com aliases to conceal your identity. If you want more features like custom domains, you can upgrade to one of the paid plans:
EssentialFrom $3/month
ProFrom $8/month
BusinessFrom $12/month

Don’t forget to secure your devices

When sending an anonymous email, your provider isn’t the only aspect to consider. You must also protect your device from attacks to ensure it doesn’t get corrupted by malware.While using a reliable VPN when connected to a home or public network is an option, remember that it doesn’t offer absolute protection. Follow the right security practices to stay safe:
  • Set strong passwords
  • Enable two-factor authentication (you can use Skiff’s Authenticator app)
  • Don’t send sensitive emails from shared devices or accounts
  • Use antivirus software with email scanning
These practices don’t involve any extensive or complicated work, and they’re effective enough to prevent most attack types and ensure your private data doesn’t leak.You can also take additional steps to secure your email attachments. You can password-protect them using the editing platform’s native features if there are any. If not, numerous online tools can lock your files, but make sure to go with an option that won’t store copies on their servers.

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