diff --git a/lib/pry/config.rb b/lib/pry/config.rb
index 999722ae..64e3467c 100644
--- a/lib/pry/config.rb
+++ b/lib/pry/config.rb
@@ -49,10 +49,11 @@ class Pry
     # @param [Pry::Hooks] v Only accept `Pry::Hooks` now!
     def hooks=(v)
       if v.is_a?(Hash)
-        raise ObsoleteError, "Hash is now obsolete! Use a Pry::Hooks object instead! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+        warn "Hash-based hooks are now deprecated! Use a `Pry::Hooks` object instead! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+        @hooks = Pry::Hooks.from_hash(v)
+      else
+        @hooks = v
       end
-
-      @hooks = v
     end
 
     # Get/Set the stack of input objects that a Pry instance switches
diff --git a/lib/pry/hooks.rb b/lib/pry/hooks.rb
index 2b846b61..2c9ce925 100644
--- a/lib/pry/hooks.rb
+++ b/lib/pry/hooks.rb
@@ -1,6 +1,31 @@
 class Pry
+
+  # Implements a hooks system for Pry. A hook is a callable that is
+  # associated with an event. A number of events are currently
+  # provided by Pry, these include: `:when_started`, `:before_session`, `:after_session`.
+  # A hook must have a name, and is connected with an event by the
+  # `Pry::Hooks#add_hook` method.
+  # @example Adding a hook for the `:before_session` event.
+  #   Pry.config.hooks.add_hook(:before_session, :say_hi) do
+  #     puts "hello"
+  #   end
   class Hooks
 
+    # Converts a hash to a `Pry::Hooks` instance. All hooks defined
+    # this way are anonymous. This functionality is primarily to
+    # provide backwards-compatibility with the old hash-based hook
+    # system in Pry versions < 0.9.8
+    # @param [Hash] hash The hash to convert to `Pry::Hooks`.
+    # @return [Pry::Hooks] The resulting `Pry::Hooks` instance.
+    def self.from_hash(hash)
+      instance = new
+      hash.each do |k, v|
+        instance.add_hook(k, nil, v)
+      end
+
+      instance
+    end
+
     def initialize
       @hooks = {}
     end
@@ -26,14 +51,18 @@ class Pry
 
     # FIXME:
     # This is a hack to alert people of the new API.
-    def [](*)
-      raise ObsoleteError, "`Pry.hooks[]` is no longer supported. Please use the new Pry::Hooks API! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+    def [](event_name)
+      warn "`Pry.hooks[]` is deprecated! Please use the new `Pry::Hooks` API! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+
+      get_hook(event_name, nil)
     end
 
     # FIXME:
     # This is a hack to alert people of the new API.
-    def []=(*)
-      raise ObsoleteError, "`Pry.hooks[]=` is no longer supported. Please use the new Pry::Hooks API! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+    def []=(event_name, callable)
+      warn "`Pry.hooks[]=` is deprecated! Please use the new `Pry::Hooks` API! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+
+      add_hook(event_name, nil, callable)
     end
 
     # Destructively merge the contents of two `Pry:Hooks` instances.
@@ -85,15 +114,23 @@ class Pry
     def add_hook(event_name, hook_name, callable=nil, &block)
       @hooks[event_name] ||= []
 
-      # do not allow duplicates
-      raise ArgumentError, "Hook with name '#{hook_name}' already defined!" if hook_exists?(event_name, hook_name)
+      # do not allow duplicates, but allow multiple `nil` hooks
+      # (anonymous hooks)
+      if hook_exists?(event_name, hook_name) && !hook_name.nil?
+        raise ArgumentError, "Hook with name '#{hook_name}' already defined!"
+      end
+
+      if !block && !callable
+        raise ArgumentError, "Must provide a block or callable."
+      end
+
+      # ensure we only have one anonymous hook
+      @hooks[event_name].delete_if { |h, k| h.nil? } if hook_name.nil?
 
       if block
         @hooks[event_name] << [hook_name, block]
       elsif callable
         @hooks[event_name] << [hook_name, callable]
-      else
-        raise ArgumentError, "Must provide a block or callable."
       end
 
       self
@@ -194,6 +231,15 @@ class Pry
 
     alias_method :clear, :delete_hooks
 
+    # Remove all events and hooks, clearing out the Pry::Hooks
+    # instance completely.
+    # @example
+    #   my_hooks = Pry::Hooks.new.add_hook(:before_session, :say_hi) { puts "hi!" }
+    #   my_hooks.clear_all
+    def clear_all
+      @hooks = {}
+    end
+
     # @param [Symbol] event_name Name of the event.
     # @param [Symbol] hook_name Name of the hook.
     # @return [Boolean] Whether the hook by the name `hook_name`
diff --git a/lib/pry/pry_instance.rb b/lib/pry/pry_instance.rb
index 92c04774..700fff27 100644
--- a/lib/pry/pry_instance.rb
+++ b/lib/pry/pry_instance.rb
@@ -33,10 +33,11 @@ class Pry
   # @param [Pry::Hooks] v Only accept `Pry::Hooks` now!
   def hooks=(v)
     if v.is_a?(Hash)
-      raise ObsoleteError, "Error: Hash is now obsolete! Use a Pry::Hooks object instead! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+      warn "Hash-based hooks are now deprecated! Use a `Pry::Hooks` object instead! http://rubydoc.info/github/pry/pry/master/Pry/Hooks"
+      @hooks = Pry::Hooks.from_hash(v)
+    else
+      @hooks = v
     end
-
-    @hooks = v
   end
 
   # Create a new `Pry` object.
diff --git a/test/test_hooks.rb b/test/test_hooks.rb
index 1fc1436c..a86098cc 100644
--- a/test/test_hooks.rb
+++ b/test/test_hooks.rb
@@ -152,7 +152,7 @@ describe Pry::Hooks do
       hooks_dup.get_hook(:test_hook, :testing).should == @hooks.get_hook(:test_hook, :testing)
     end
 
-     it 'adding a new event to dupped instance should not affect original' do
+    it 'adding a new event to dupped instance should not affect original' do
       @hooks.add_hook(:test_hook, :testing) { :none_such }
       hooks_dup = @hooks.dup
 
@@ -161,7 +161,7 @@ describe Pry::Hooks do
       hooks_dup.get_hook(:other_test_hook, :testing).should.not == @hooks.get_hook(:other_test_hook, :testing)
     end
 
-     it 'adding a new hook to dupped instance should not affect original' do
+    it 'adding a new hook to dupped instance should not affect original' do
       @hooks.add_hook(:test_hook, :testing) { :none_such }
       hooks_dup = @hooks.dup
 
@@ -417,50 +417,74 @@ describe Pry::Hooks do
     end
   end
 
-  describe "obsolete API" do
-    describe "Pry.config.hooks" do
-      it 'should raise a Pry::ObsoleteError when assigning a hash' do
-        begin
-          Pry.config.hooks = {}
-        rescue => ex
-        end
+  describe "anonymous hooks" do
+    it 'should allow adding of hook without a name' do
+      @hooks.add_hook(:test_hook, nil) {}
+      @hooks.hook_count(:test_hook).should == 1
+    end
 
-        ex.is_a?(Pry::ObsoleteError).should == true
+    it 'should only allow one anonymous hook to exist' do
+      @hooks.add_hook(:test_hook, nil) {  }
+      @hooks.add_hook(:test_hook, nil) {  }
+      @hooks.hook_count(:test_hook).should == 1
+    end
+
+    it 'should execute most recently added anonymous hook' do
+      x = nil
+      y = nil
+      @hooks.add_hook(:test_hook, nil) { y = 1 }
+      @hooks.add_hook(:test_hook, nil) { x = 2 }
+      @hooks.exec_hook(:test_hook)
+      y.should == nil
+      x.should == 2
+    end
+  end
+
+  describe "deprecated hash-based API" do
+    after do
+      Pry.config.hooks.clear_all if Pry.config.hooks
+    end
+
+    describe "Pry.config.hooks" do
+      it 'should allow a hash-assignment' do
+        Pry.config.hooks = { :before_session => proc { :hello } }
+        Pry.config.hooks.get_hook(:before_session, nil).call.should == :hello
       end
 
       describe "Pry.config.hooks[]" do
-        it 'should raise a Pry::ObsoleteError when accessing it in a hash style, Pry.config.hooks[]' do
-          begin
-            Pry.config.hooks[:before_session]
-          rescue => ex
-          end
-
-          ex.is_a?(Pry::ObsoleteError).should == true
+        it 'should return the only anonymous hook' do
+          Pry.config.hooks = { :before_session => proc { :hello } }
+          Pry.config.hooks[:before_session].call.should == :hello
         end
 
-        it 'should raise a Pry::ObsoleteError when accessing it in a hash style, Pry.config.hooks[]=' do
-          begin
-            Pry.config.hooks[:before_session]
-          rescue => ex
-          end
-
-          ex.is_a?(Pry::ObsoleteError).should == true
+        it 'should add an anonymous hook when using Pry.config.hooks[]=' do
+          Pry.config.hooks[:before_session] = proc { :bing }
+          Pry.config.hooks.hook_count(:before_session).should == 1
         end
 
+        it 'should add overwrite previous anonymous hooks with new one when calling Pry.config.hooks[]= multiple times' do
+          x = nil
+          Pry.config.hooks[:before_session] = proc { x = 1 }
+          Pry.config.hooks[:before_session] = proc { x = 2 }
+
+          Pry.config.hooks.exec_hook(:before_session)
+          Pry.config.hooks.hook_count(:before_session).should == 1
+          x.should == 2
+        end
       end
-
     end
 
     describe "Pry.start" do
-      it 'should raise a Pry::ObsoleteError when passing in a :hooks option with a hash' do
-        begin
-          Pry.start binding, :hooks => { :before_session => proc { puts 'yo' } }
-        rescue => ex
+      it 'should accept a hash for :hooks parameter' do
+
+        redirect_pry_io(InputTester.new("exit-all"), out=StringIO.new) do
+          Pry.start binding, :hooks => { :before_session => proc { |output, _, _| output.puts 'hello friend' } }
         end
 
-        ex.is_a?(Pry::ObsoleteError).should == true
+        out.string.should =~ /hello friend/
       end
 
     end
   end
+
 end