The lack of end-to-end encryption in Skype has long been a concern for security conscious business users. However, in August 2018 Microsoft announced the availability of Private Conversations, offering users the ability to protect chats, calls and file sharing with end-to-end encryption built on the Signal protocol.

So, does this fix what was a noticeable gap in Skype’s security armoury? And is it now a suitable tool for secure enterprise messaging?

Unfortunately for businesses invested in Skype, the answer is no. Here’s why:

No group chats or calls

With Skype, end-to-end encryption is restricted to one-to-one conversations only. There is no support for group chats or conference calling as you’d get with Wire; which (in addition to offering secure group chats), was the first open source, end-to-end encrypted collaboration platform to offer a secure video conferencing service.

For enterprise users who need to communicate securely with their team and clients, this is a major limitation; and one that puts any information that you disclose over a group chat or audio call at risk from eavesdropping.

Only one device at a time

Skype’s Private Conversation feature can only be accessed on one device at a time – with messages tied to the device that initiated the session. This can be problematic for users that need to switch devices during a conversation (from a PC to a smartphone, for example).

Switching to a different device requires the user to send a new invitation to the contact – effectively starting a new private Conversation. The user also loses the chat history, and any files shared during the session, as they move between devices.

With Wire, your account is kept in sync across up to eight devices. This makes it simple to seamlessly move between Wire on a browser (Windows and Mac), desktop app, smartphone, or tablet.

Not enabled by default

Skype’s Private Conversation feature is not the default option. Users must go through additional steps (see below), to start an end-to-end encrypted session. This increases the likelihood of users forgetting (or simply skipping), the feature altogether.

With Wire, end-to-end encryption is enabled by default. There are no configuration settings to manage, meaning every employee conversation is secure.

Invite (and wait) before you chat

Initiating a Skype Private Conversation isn’t a seamless (or immediate) experience. When a user wants to start a Private Conversation with an existing contact for the first time, an invitation is sent.

While this happens, the user is able to compose, but not send a message. Instead, they must wait for the invitation to be accepted. If the chat is urgent, this means the user must sit and wait patiently in the app for a response.

Because end-to-end encryption is enabled by default in Wire, there is no delay in initiating a new secure session with a contact.

Your contact must have the right version of Skype

Skype’s Private Conversation feature is only available on v.8 and above. If your contact hasn’t upgraded to the latest version, it won’t be possible to initiate a secure end-to-end encrypted conversation.

Unfortunately there is no way for users to know if a contact (such as a client) is using a compatible version of the app until a Private Conversation invitation fails.

With Wire, end-to-encryption is standard across all of our desktop, Android and Apple iOS mobile apps – and even our Guest Room feature. This means that even if your contact doesn’t have a Wire account, you are still guaranteed the level of security you need to protect your chats, file transfers, audio and video calls.

It’s taken Microsoft a long time to introduce end-to-end encryption to Skype, and bring the app in-line with the security offered by other consumer messaging apps (such as Whatsapp).

However, while it’s implementation of end-to-end encryption will likely meet the needs of most consumer Skype users, we don’t believe the same is true for business users.

Try Wire Pro

Wire is the most trusted, and secure end-to-end encrypted collaboration and chat platform available, and the perfect choice for businesses looking to protect their internal and external communications.

Analysis of Skype’s Private Conversation feature correct at time of publication (Nov 2018)