@@ -24,18 +24,6 @@ program_desc 'The Coderly Toolbelt'
 
 version Code::VERSION
 
-desc 'Authorize with GitHub'
-command :authorize, :login do |c|
-  c.flag 'username', desc: 'GitHub username'
-  c.flag 'password', desc: 'GitHub password'
-  c.action do |global_options, options, args|
-    username = options[:username]
-    password = options[:password]
-
-    Code::GitHubAPI.new.authorize(username: username, password: password)
-  end
-end
-
 desc 'Describe some switch here'
 switch [:s,:switch]
 
@@ -52,6 +40,9 @@ desc 'Upload your feature branch to GitHub'
 command :publish, :pr do |c|
   c.switch [:master], desc: 'Make the pull request based off the master branch'
   c.action do |global_options, options, args|
+
+    $gitHubAPI.ensure_authorized
+
     message = args.join(' ')
 
     base_branch = nil
@@ -76,13 +67,15 @@ end
 desc "Marks the current branch's pr as awaiting review"
 command :ready do |c|
   c.action do |global_options, options, args|
+    $gitHubAPI.ensure_authorized
     Code::Branch.current.mark_prs_as_awaiting_review
   end
 end
 
 desc "Quickly create a pull request from your changes on development."
 command :hotfix, :fix do |c|
   c.action do |global_options, options, args|
+    $gitHubAPI.ensure_authorized
     hotfix_name = args.join('-')
     $git.hotfix hotfix_name
   end
@@ -146,6 +139,7 @@ end
 
 pre do |global, command, options, args|
   $git = Code::Git.new
+  $gitHubAPI = Code::GitHubAPI.new
   true
 end
 
 
@@ -1,28 +1,32 @@
 require "octokit"
 require "code/repository"
+require "securerandom"
 
 module Code
 
   class GitHubAPI
 
-    NoAuthTokenError = Class.new(StandardError)
-
-    AUTHORIZATION_NOTE = "Code gem authorization token"
+    def authorization_note
+      "CoderlyCode-" + SecureRandom.uuid
+    end
 
     def initialize(repository: Repository.current)
       @repository = repository
     end
 
+    def ensure_authorized
+      if not authorized?
+        username = prompt 'GitHub username'
+        password = prompt 'GitHub password'
+
+        authorize(username: username, password: password)
+      end
+    end
+
     def authorize(username:, password:)
       client = self.octokit_client_instance_from_basic_auth(username: username, password: password)
 
-      authorization = client.authorizations.detect { |auth| auth[:note] == AUTHORIZATION_NOTE }
-
-      if authorization
-        token = authorization[:token]
-      else
-        token = client.create_authorization(scopes: ["repo"], note: AUTHORIZATION_NOTE)[:token]
-      end
+      token = client.create_authorization(scopes: ["repo"], note: authorization_note)[:token]
 
       puts "Successfully authorized with token #{token}"
       self.authorization_token = token
@@ -45,6 +49,10 @@ def label_pr(pull_request, label)
       add_label_to_pr(pull_request.number, label)
     end
 
+    def authorized?
+      !authorization_token.empty?
+    end
+
     private
 
     def current_organization
@@ -65,12 +73,17 @@ def add_label_to_pr(number, label)
 
     def authorization_token
       token = System.result('git config --get oauth.token')
-      raise NoAuthTokenError, "Couldn't retrieve an authorization token. Make sure you authorize through 'code authorize --username {username} --password {password}' first" if System.command_failed?
       token
     end
 
     def authorization_token=(token)
       System.result("git config --global oauth.token #{token}")
     end
+
+    def prompt(prompt_text)
+      print prompt_text + ':'
+      input = gets
+      input.strip
+    end
   end
 end
@@ -0,0 +1,36 @@
+require 'code/github_api'
+
+module Code
+  describe GitHubAPI do
+    let(:api) { GitHubAPI.new }
+
+    describe '#ensure_authorized' do
+
+      context 'when system is authorized' do
+        before do
+          allow(api).to receive(:authorized?).and_return(true)
+        end
+
+        it 'should not call #authorize' do
+          expect(api).not_to receive(:authorize)
+          expect(api).not_to receive(:prompt)
+
+          api.ensure_authorized
+        end
+      end
+
+      context 'when system is not authorized' do
+        before do
+          allow(api).to receive(:authorized?).and_return(false)
+        end
+
+        it 'should call #authorize' do
+          expect(api).to receive(:authorize)
+          expect(api).to receive(:prompt).twice
+
+          api.ensure_authorized
+        end
+      end
+    end
+  end
+end