diff --git a/app/assets/javascripts/app/controllers/chat.coffee b/app/assets/javascripts/app/controllers/chat.coffee
index 0381eff35..f8e969e86 100644
--- a/app/assets/javascripts/app/controllers/chat.coffee
+++ b/app/assets/javascripts/app/controllers/chat.coffee
@@ -474,9 +474,10 @@ class ChatWindow extends App.Controller
       event.data.callback()
 
     @$('.js-customerChatInput').ce({
-      mode:      'richtext'
-      multiline: true
-      maxlength: 40000
+      mode:       'richtext'
+      multiline:  true
+      maxlength:  40000
+      imageWidth: 'relative'
     })
 
   disconnect: =>
diff --git a/app/assets/javascripts/app/lib/base/jquery.contenteditable.js b/app/assets/javascripts/app/lib/base/jquery.contenteditable.js
index cf32462c8..32b336806 100644
--- a/app/assets/javascripts/app/lib/base/jquery.contenteditable.js
+++ b/app/assets/javascripts/app/lib/base/jquery.contenteditable.js
@@ -6,6 +6,7 @@
 # maxlength:     123
 # multiline:     true / disable enter + strip on paste
 # placeholder:   'some placeholder'
+# imageWidth:    absolute (<img style="width: XXpx; height: XXXpx" src="">) || relative (<img style="width: 100%; max-width: XXpx;" src="">)
 */
 
   var pluginName = 'ce',
@@ -13,6 +14,7 @@
     debug:     false,
     mode:      'richtext',
     multiline: true,
+    imageWidth: 'absolute',
     allowKey:  {
       8: true, // backspace
       9: true, // tab
@@ -284,7 +286,12 @@
               }
               _this.log('image inserted')
               result = dataUrl
-              img = "<img style=\"width: " + width + "px; height: " + height + "px\" src=\"" + result + "\">"
+              if (_this.options.imageWidth == 'absolute') {
+                img = "<img style=\"width: " + width + "px; height: " + height + "px\" src=\"" + result + "\">"
+              }
+              else {
+                img = "<img style=\"width: 100%; max-width: " + width + "px;\" src=\"" + result + "\">"
+              }
               document.execCommand('insertHTML', false, img)
             }
 
@@ -399,7 +406,12 @@
             //console.log('dataUrl', dataUrl)
             _this.log('image inserted')
             result = dataUrl
-            img = $("<img style=\"width: " + width + "px; height: " + height + "px\" src=\"" + result + "\">")
+            if (_this.options.imageWidth == 'absolute') {
+              img = $("<img style=\"width: " + width + "px; height: " + height + "px\" src=\"" + result + "\">")
+            }
+            else {
+              img = $("<img style=\"width: 100%; max-width: " + width + "px;\" src=\"" + result + "\">")
+            }
             img = img.get(0)
 
             if (document.caretPositionFromPoint) {
diff --git a/db/migrate/20120101000010_create_ticket.rb b/db/migrate/20120101000010_create_ticket.rb
index e8c68dd0f..d9bb29bd5 100644
--- a/db/migrate/20120101000010_create_ticket.rb
+++ b/db/migrate/20120101000010_create_ticket.rb
@@ -434,7 +434,7 @@ class CreateTicket < ActiveRecord::Migration
 
     create_table :chat_messages do |t|
       t.integer :chat_session_id,                     null: false
-      t.string  :content,                limit: 5000, null: false
+      t.text    :content,    limit: 20.megabytes + 1, null: false
       t.integer :created_by_id,                       null: true
       t.timestamps limit: 3, null: false
     end
diff --git a/db/migrate/20170420000001_chat_increase_message_size.rb b/db/migrate/20170420000001_chat_increase_message_size.rb
new file mode 100644
index 000000000..6b14384cd
--- /dev/null
+++ b/db/migrate/20170420000001_chat_increase_message_size.rb
@@ -0,0 +1,10 @@
+class ChatIncreaseMessageSize < ActiveRecord::Migration
+  def up
+
+    # return if it's a new setup
+    return if !Setting.find_by(name: 'system_init_done')
+
+    change_column :chat_messages, :content, :text, limit: 20.megabytes + 1, null: false
+  end
+
+end
diff --git a/lib/sessions/event.rb b/lib/sessions/event.rb
index ed7ecb62e..3aa7f0b4b 100644
--- a/lib/sessions/event.rb
+++ b/lib/sessions/event.rb
@@ -7,13 +7,17 @@ class Sessions::Event
     begin
       backend = load_adapter(adapter)
     rescue => e
-      return { error: "No such event #{params[:event]}" }
+      return { event: 'error', data: { error: "No such event #{params[:event]}", payload: params[:payload] } }
     end
 
-    instance = backend.new(params)
-    result = instance.run
-    instance.destroy
-    result
+    begin
+      instance = backend.new(params)
+      result = instance.run
+      instance.destroy
+      result
+    rescue => e
+      return { event: 'error', data: { error: e.message, payload: params[:payload] } }
+    end
   end
 
 end