Smart Messaging


Smart Messaging is modern, and designed around cell phones. Always on, almost always with a data connection. Instant Messaging is mostly used to mean messaging services from the 90s and based on computers that are connected, where you login and logout. Think ICQ, MSN and AOL Messenger. Before that we had email and message boards.

My goal: I want simple, useful communication between me and my friends. The power should be in my hands as to who can contact me. I should have privacy and security balanced with easy of use and usefulness. I want to strike what appears to me to be the right balance.

People who don’t care at all about security and privacy may find my choices too limiting. Those who want 100% end-to-end encryption will find my choices dangerous.

My Ideal Smart Messenger Experience

What I need from a smart messenger: A centrally stored conversation platform to talk to all my contacts. This includes people who don’t have smart devices.

  • Multi-device, multi-platform clients: Android, iOS, web at the least. Blackberry, still? Maybe. Desktop clients are a nice-to-have, but some way to send messages from a computer.
  • Centrally stored message history, with search. It should work on all devices, unlike Wire.
  • Ability to add people by phone number, username or email to preserve privacy. (Should not require exposed phone number or email.)
  • Encrypted on-the-wire communication

Hangouts is the only service to meet these needs.

Nice to haves:
  • Push to speak voice messaging.
  • Video messaging.
  • End-to-end encryption.
  • Group chats with different coloured chat bubbles.

Multi Device Models

To be able to send and receive messages to and from multiple devices, there are several ways to do this.

  • Centrally stored cloud sync: Google Hangouts, Facebook Messenger and Telegram. All messages are stored in the cloud, and when you login to a new devices you have access to all older messages.
  • Mobile first/primary device: WhatsApp, Allo, Signal, Line, Wire. All messages are sent to your primary device. This means your entire message history including photos and videos take up space on your devices, going back years or decades. 3 ways of managing message histories:
    • Message mirroring: WhatsApp. You can ‘login’ to a second device (usually only a computer) which your mobile devices sends a copy (mirrors) of all messages received, sometimes including history. Message mirroring only works when your mobile device has a consistent data connection.
    • Some (WhatsApp, Allo) have an automated backup feature. When activated, it will auto backup your messages history to iCloud or Google Drive. (Security risk?) This allows your history to be transferred to a new primary devices.
    • Others have a datafile backup feature, including Line.
  • Mobile first multi device: Wire. All messages are sent to all logged in devices. There is no message history. If your devices is off or logged off (or not connected?) it does not receive those messages. (Unless all devices are logged off. Then it’s the first to login.)

Thinking about the upcoming Allo Web and if it will be more like Google Hangouts or WhatsApp, a hybrid solution occurred to me. It could use WhatsApp style message mirroring of old messages, and a Wire model of duplicating new messages. This way all new messages will come to the web app even if your phone is having connection issues. But you could go back through your chat history from when your computer was off.


Allo is a new messaging service from Google that is consumer focused.


  • All messages are encrypted on the wire, and end-to-end encryption is an option.
  • A good experience with themes, full-width images, and shout/whisper messages.
  • The Google Assistant is both fun and useful when invited in to chats.
  • (Coming soon.) Computer interface via web/extension


  • Group chat: no leader, no manager. Totally egalitarian, which means you cannot remove people.
  • Not multi-device.
  • Only on Android and iOS.
  • Chats are stored centrally, technically, but not accessible to the user.


This is one of the hardest thumbs down to give. Initially, I really liked everything about Telegram. I liked the experience of it. I like how enthusiastic the development team is. They keep adding more features and have it running on nearly everything.

But I don’t trust Telegram. To give them the benefit of the doubt, I believe they are aloof and don’t have the technical background to understand their security mistakes. They are unwilling to broker disagreement. As a result, they come off as arrogant and unwilling to admit when they are wrong.


  • It’s a chatter-friend experience. Fun and packed with features.
  • All messages are saved on the server, which means it is a true multi-device solution.
  • All messages are encrypted in transit. (But not real encryption.)
  • It allows for end-to-end encryption. (But not real encryption.)
  • Voices messages. I love voice messages. Though a few years ago one contact had trouble getting it to work.
  • It is well made and has content good updates.


  • Not real encryption: It’s encryption is custom made and unproven. It’s probably better than no encryption. It was designed by mathematicians, not security experts. I cannot trust this.
  • People found that Telegram saves your messages in clear text on the phone, meaning hackers could get at it (jailbroken/rooted). Their response was this shouldn’t matter in an ideal world, but that’s not good enough for me. It’s not a response I can trust.

What is overblown: People against Telegram because they think all messages need to be end-to-end encrypted.


In some area, especial Asia, Line is pretty popular. It has some good features:


  • Groups: It has a lot of good group management features. Groups can have files, documents, and you can share in a bulletin board like display with likes.
  • Add contact: You can add people by username, QR code or face-to-face by shaking phones. This is good for privacy because you do not have to give out your cell phone number.
  • Lite version with less features but takes less storage, less memory and runs faster.


  • Messages are not stored centrally, and delete when you log out.
  • Not multi-device. You cannot have a tablet and phone logged in.