diff --git a/lib/mongoid/criteria.rb b/lib/mongoid/criteria.rb
index 43b8339d8b..f607df5933 100644
--- a/lib/mongoid/criteria.rb
+++ b/lib/mongoid/criteria.rb
@@ -1,5 +1,6 @@
 # encoding: utf-8
 require "mongoid/criteria/findable"
+require "mongoid/criteria/includable"
 require "mongoid/criteria/inspectable"
 require "mongoid/criteria/marshalable"
 require "mongoid/criteria/modifiable"
@@ -19,6 +20,7 @@ class Criteria
     include Origin::Queryable
     include Findable
     include Inspectable
+    include Includable
     include Marshalable
     include Modifiable
     include Scopable
@@ -194,62 +196,6 @@ def initialize(klass)
       klass ? super(klass.aliased_fields, klass.fields) : super({}, {})
     end
 
-    # Eager loads all the provided relations. Will load all the documents
-    # into the identity map whose ids match based on the extra query for the
-    # ids.
-    #
-    # @note This will work for embedded relations that reference another
-    #   collection via belongs_to as well.
-    #
-    # @note Eager loading brings all the documents into memory, so there is a
-    #   sweet spot on the performance gains. Internal benchmarks show that
-    #   eager loading becomes slower around 100k documents, but this will
-    #   naturally depend on the specific application.
-    #
-    # @example Eager load the provided relations.
-    #   Person.includes(:posts, :game)
-    #
-    # @param [ Array<Symbol> ] relations The names of the relations to eager
-    #   load.
-    #
-    # @return [ Criteria ] The cloned criteria.
-    #
-    # @since 2.2.0
-    def includes(*relations)
-      relations.flatten.each do |name|
-        metadata = klass.reflect_on_association(name)
-        raise Errors::InvalidIncludes.new(klass, relations) unless metadata
-        inclusions.push(metadata) unless inclusions.include?(metadata)
-      end
-      clone
-    end
-
-    # Get a list of criteria that are to be executed for eager loading.
-    #
-    # @example Get the eager loading inclusions.
-    #   Person.includes(:game).inclusions
-    #
-    # @return [ Array<Metadata> ] The inclusions.
-    #
-    # @since 2.2.0
-    def inclusions
-      @inclusions ||= []
-    end
-
-    # Set the inclusions for the criteria.
-    #
-    # @example Set the inclusions.
-    #   criteria.inclusions = [ meta ]
-    #
-    # @param [ Array<Metadata> ] The inclusions.
-    #
-    # @return [ Array<Metadata> ] The new inclusions.
-    #
-    # @since 3.0.0
-    def inclusions=(value)
-      @inclusions = value
-    end
-
     # Merges another object with this +Criteria+ and returns a new criteria.
     # The other object may be a +Criteria+ or a +Hash+. This is used to
     # combine multiple scopes together, where a chained scope situation
diff --git a/lib/mongoid/criteria/includable.rb b/lib/mongoid/criteria/includable.rb
new file mode 100644
index 0000000000..08edbfdbb1
--- /dev/null
+++ b/lib/mongoid/criteria/includable.rb
@@ -0,0 +1,142 @@
+# encoding: utf-8
+module Mongoid
+  class Criteria
+
+    # Module providing functionality for parsing (nested) inclusion definitions.
+    module Includable
+
+      # Eager loads all the provided relations. Will load all the documents
+      # into the identity map whose ids match based on the extra query for the
+      # ids.
+      #
+      # @note This will work for embedded relations that reference another
+      #   collection via belongs_to as well.
+      #
+      # @note Eager loading brings all the documents into memory, so there is a
+      #   sweet spot on the performance gains. Internal benchmarks show that
+      #   eager loading becomes slower around 100k documents, but this will
+      #   naturally depend on the specific application.
+      #
+      # @example Eager load the provided relations.
+      #   Person.includes(:posts, :game)
+      #
+      # @param [ Array<Symbol>, Array<Hash> ] relations The names of the relations to eager
+      #   load.
+      #
+      # @return [ Criteria ] The cloned criteria.
+      #
+      # @since 2.2.0
+      def includes(*relations)
+        relations.flatten.each do |relation|
+          if relation.is_a?(Hash)
+            extract_nested_inclusion(klass, relation)
+          else
+            add_inclusion(klass, relation)
+          end
+        end
+        clone
+      end
+
+      # Get a list of criteria that are to be executed for eager loading.
+      #
+      # @example Get the eager loading inclusions.
+      #   Person.includes(:game).inclusions
+      #
+      # @return [ Array<Metadata> ] The inclusions.
+      #
+      # @since 2.2.0
+      def inclusions
+        @inclusions ||= []
+      end
+
+      # Set the inclusions for the criteria.
+      #
+      # @example Set the inclusions.
+      #   criteria.inclusions = [ meta ]
+      #
+      # @param [ Array<Metadata> ] The inclusions.
+      #
+      # @return [ Array<Metadata> ] The new inclusions.
+      #
+      # @since 3.0.0
+      def inclusions=(value)
+        @inclusions = value
+      end
+
+      private
+
+      # Add an inclusion definition to the list of inclusions for the criteria.
+      #
+      # @example Add an inclusion.
+      #   criteria.add_inclusion(Person, :posts)
+      #
+      # @param [ Class, String, Symbol ] _klass The class or string/symbol of the class name.
+      # @param [ Symbol ] relation The relation.
+      #
+      # @raise [ Errors::InvalidIncludes ] If no relation is found.
+      #
+      # @since 5.1.0
+      def add_inclusion(_klass, relation)
+        metadata = get_inclusion_metadata(_klass, relation)
+        raise Errors::InvalidIncludes.new(_klass, [ relation ]) unless metadata
+        inclusions.push(metadata) unless inclusions.include?(metadata)
+      end
+
+      # Extract inclusion definitions from a list.
+      #
+      # @example Extract the inclusions from a list.
+      #   criteria.extract_relations_list(:posts, [{ :alerts => :items }])
+      #
+      # @param [ Symbol ] association The name of the association.
+      # @param [ Array ] relations A list of associations.
+      #
+      # @since 5.1.0
+      def extract_relations_list(association, relations)
+        relations.each do |relation|
+          if relation.is_a?(Hash)
+            extract_nested_inclusion(association, relation)
+          else
+            add_inclusion(association, relation)
+          end
+        end
+      end
+
+      # Extract nested inclusion.
+      #
+      # @example Extract the inclusions from a nested definition.
+      #   criteria.extract_nested_inclusion(User, { :posts => [:alerts] })
+      #
+      # @param [ Class, Symbol ] _klass The class for which the inclusion should be added.
+      # @param [ Hash ] relation The nested inclusion.
+      #
+      # @since 5.1.0
+      def extract_nested_inclusion(_klass, relation)
+        relation.each do |association, _inclusion|
+          add_inclusion(_klass, association)
+          if _inclusion.is_a?(Array)
+            extract_relations_list(association, _inclusion)
+          else
+            add_inclusion(association, _inclusion)
+          end
+        end
+      end
+
+      # Get the metadata for an inclusion.
+      #
+      # @example Get the metadata for an inclusion definition.
+      #   criteria.get_inclusion_metadata(User, :posts)
+      #
+      # @param [ Class, Symbol, String ] _klass The class for determining the association metadata
+      # @param [ Symbol  ] association The name of the association.
+      #
+      # @since 5.1.0
+      def get_inclusion_metadata(_klass, association)
+        if _klass.is_a?(Class)
+          _klass.reflect_on_association(association)
+        else
+          _klass.to_s.classify.constantize.reflect_on_association(association)
+        end
+      end
+    end
+  end
+end
diff --git a/lib/mongoid/relations/eager.rb b/lib/mongoid/relations/eager.rb
index 779a2fb01e..a7952b2b58 100644
--- a/lib/mongoid/relations/eager.rb
+++ b/lib/mongoid/relations/eager.rb
@@ -34,11 +34,18 @@ def eager_load(docs)
       end
 
       def preload(relations, docs)
-
-        relations.group_by do |metadata|
-          metadata.relation
-        end.each do |relation, associations|
-          relation.eager_load_klass.new(associations, docs).run
+        grouped_relations = relations.group_by do |metadata|
+          metadata.inverse_class_name
+        end
+        grouped_relations.keys.each do |_klass|
+          grouped_relations[_klass] = grouped_relations[_klass].group_by do |metadata|
+            metadata.relation
+          end
+        end
+        grouped_relations.each do |_klass, associations|
+          docs = associations.collect do |_relation, association|
+            _relation.eager_load_klass.new(association, docs).run
+          end.flatten
         end
       end
     end
diff --git a/lib/mongoid/relations/eager/base.rb b/lib/mongoid/relations/eager/base.rb
index 8d9da20003..0a19601eff 100644
--- a/lib/mongoid/relations/eager/base.rb
+++ b/lib/mongoid/relations/eager/base.rb
@@ -45,10 +45,12 @@ def shift_metadata
         #
         # @since 4.0.0
         def run
+          @loaded = []
           while shift_metadata
             preload
+            @loaded << @docs.collect { |d| d.send(@metadata.name) }
           end
-          @docs
+          @loaded.flatten
         end
 
         # Preload the current relation.
diff --git a/spec/app/models/alert.rb b/spec/app/models/alert.rb
index 48ed2eb402..76976c615a 100644
--- a/spec/app/models/alert.rb
+++ b/spec/app/models/alert.rb
@@ -2,4 +2,6 @@ class Alert
   include Mongoid::Document
   field :message, type: String
   belongs_to :account
+  has_many :items
+  belongs_to :post
 end
diff --git a/spec/app/models/post.rb b/spec/app/models/post.rb
index 4a8b41cb06..13bf317f2f 100644
--- a/spec/app/models/post.rb
+++ b/spec/app/models/post.rb
@@ -14,6 +14,7 @@ class Post
   has_and_belongs_to_many :tags, before_add: :before_add_tag, after_add: :after_add_tag, before_remove: :before_remove_tag, after_remove: :after_remove_tag
   has_many :videos, validate: false
   has_many :roles, validate: false
+  has_many :alerts
 
   belongs_to :posteable, polymorphic: true
   accepts_nested_attributes_for :posteable, autosave: true
diff --git a/spec/mongoid/criteria_spec.rb b/spec/mongoid/criteria_spec.rb
index 19fc523dde..ccfc41c97a 100644
--- a/spec/mongoid/criteria_spec.rb
+++ b/spec/mongoid/criteria_spec.rb
@@ -1147,12 +1147,72 @@
       end
     end
 
-    context "when providing a hash" do
+    context "when providing a list of associations" do
 
-      it "raises an error" do
-        expect {
-          Person.includes(preferences: :members)
-        }.to raise_error(Mongoid::Errors::InvalidIncludes)
+      let!(:user) do
+        User.create(posts: [ post1 ], descriptions: [ description1 ])
+      end
+
+      let!(:post1) do
+        Post.create
+      end
+
+      let!(:description1) do
+        Description.create(details: 1)
+      end
+
+      let(:result) do
+        User.includes(:posts, :descriptions).first
+      end
+
+      it "executes the query" do
+        expect(result).to eq(user)
+      end
+
+      it "includes the related objects" do
+        expect(result.posts).to eq([ post1 ])
+        expect(result.descriptions).to eq([ description1 ])
+      end
+    end
+
+    context "when providing a nested association" do
+
+      let!(:user) do
+        User.create
+      end
+
+      before do
+        p = Post.create(alerts: [ Alert.create ])
+        user.posts = [ p ]
+        user.save
+      end
+
+      let(:result) do
+        User.includes(:posts => [:alerts]).first
+      end
+
+      it "executes the query" do
+        expect(result).to eq(user)
+      end
+
+      it "includes the related objects" do
+        expect(result.posts.size).to eq(1)
+        expect(result.posts.first.alerts.size).to eq(1)
+      end
+    end
+
+    context "when providing a deeply nested association" do
+
+      let!(:user) do
+        User.create
+      end
+
+      let(:results) do
+        User.includes(:posts => [{ :alerts => :items }]).to_a
+      end
+
+      it "executes the query" do
+        expect(results.first).to eq(user)
       end
     end