diff --git a/lib/smart_todo/cli.rb b/lib/smart_todo/cli.rb
index 0d73923..b04bffb 100644
--- a/lib/smart_todo/cli.rb
+++ b/lib/smart_todo/cli.rb
@@ -106,12 +106,40 @@ def process_todos(todos)
         end
 
         @errors.concat(todo.errors)
-        dispatches << [event_message, todo] if event_met
+
+        next unless event_met
+
+        event_message = append_context_if_applicable(event_message, todo, event_met, events)
+
+        dispatches << [event_message, todo]
       end
 
       dispatches
     end
 
+    private
+
+    # @param event_message [String] the original event message
+    # @param todo [Todo] the todo object that may contain context
+    # @param event [Event] the event that was met
+    # @param events [Events] the events instance for fetching issue context
+    # @return [String] the event message, potentially with context appended
+    def append_context_if_applicable(event_message, todo, event, events)
+      return event_message unless should_apply_context?(todo, event)
+
+      org, repo, issue_number = todo.context.arguments
+      context_message = events.issue_context(org, repo, issue_number)
+
+      context_message ? "#{event_message}\n\n#{context_message}" : event_message
+    end
+
+    # @param todo [Todo] the todo object to check for context
+    # @param event [Event] the event to check
+    # @return [Boolean] true if context should be applied, false otherwise
+    def should_apply_context?(todo, event)
+      !!todo.context
+    end
+
     def process_dispatches(dispatches)
       queue = Queue.new
       dispatches.each { |dispatch| queue << dispatch }
diff --git a/lib/smart_todo/events.rb b/lib/smart_todo/events.rb
index fb21fb5..1ee1d4e 100644
--- a/lib/smart_todo/events.rb
+++ b/lib/smart_todo/events.rb
@@ -157,6 +157,32 @@ def pull_request_close(organization, repo, pr_number)
       end
     end
 
+    # Retrieve context information for an issue
+    # This is used when a TODO has a context: issue() attribute
+    #
+    # @param organization [String] the GitHub organization name
+    # @param repo [String] the GitHub repo name
+    # @param issue_number [String, Integer]
+    # @return [String, nil]
+    def issue_context(organization, repo, issue_number)
+      headers = github_headers(organization, repo)
+      response = github_client.get("/repos/#{organization}/#{repo}/issues/#{issue_number}", headers)
+
+      if response.code_type < Net::HTTPClientError
+        nil
+      else
+        issue = JSON.parse(response.body)
+        state = issue["state"]
+        title = issue["title"]
+        assignee = issue["assignee"] ? "@#{issue["assignee"]["login"]}" : "unassigned"
+
+        "📌 Context: Issue ##{issue_number} - \"#{title}\" [#{state}] (#{assignee}) - " \
+          "https://github.com/#{organization}/#{repo}/issues/#{issue_number}"
+      end
+    rescue Net::HTTPError, JSON::ParserError
+      nil
+    end
+
     # Check if the installed ruby version meets requirements.
     #
     # @param requirements [Array<String>] a list of version specifiers
diff --git a/lib/smart_todo/todo.rb b/lib/smart_todo/todo.rb
index 51bdcb2..1bc0c26 100644
--- a/lib/smart_todo/todo.rb
+++ b/lib/smart_todo/todo.rb
@@ -4,6 +4,7 @@ module SmartTodo
   class Todo
     attr_reader :filepath, :comment, :indent
     attr_reader :events, :assignees, :errors
+    attr_accessor :context
 
     def initialize(source, filepath = "-e")
       @filepath = filepath
@@ -12,6 +13,7 @@ def initialize(source, filepath = "-e")
 
       @events = []
       @assignees = []
+      @context = nil
       @errors = []
 
       parse(source[(indent + 1)..])
@@ -66,6 +68,28 @@ def visit_keyword_hash_node(node)
             end
           when :to
             metadata.assignees << visit(element.value)
+          when :context
+            value = visit(element.value)
+
+            unless value.is_a?(String)
+              metadata.errors << "Incorrect `:context` format: expected string value"
+              next
+            end
+
+            unless value =~ %r{^([^/]+)/([^#]+)#(\d+)$}
+              metadata.errors << "Incorrect `:context` format: expected \"org/repo#issue_number\""
+              next
+            end
+
+            org = ::Regexp.last_match(1)
+            repo = ::Regexp.last_match(2)
+            issue_number = ::Regexp.last_match(3)
+
+            if org.empty? || repo.empty?
+              metadata.errors << "Incorrect `:context` format: org and repo cannot be empty"
+            else
+              metadata.context = CallNode.new(:issue, [org, repo, issue_number], element.value.location)
+            end
           end
         end
       end
diff --git a/test/smart_todo/cli_test.rb b/test/smart_todo/cli_test.rb
index 92eddee..c7a6216 100644
--- a/test/smart_todo/cli_test.rb
+++ b/test/smart_todo/cli_test.rb
@@ -150,5 +150,41 @@ def hello
         end
       end
     end
+
+    def test_should_apply_context_returns_false_without_context
+      cli = CLI.new
+      todo = Todo.new("# TODO(on: date('2015-03-01'), to: 'john@example.com')")
+      event = Todo::CallNode.new(:date, ["2015-03-01"], nil)
+
+      refute(cli.send(:should_apply_context?, todo, event))
+    end
+
+    def test_should_apply_context_returns_true_for_issue_close_event_with_context
+      cli = CLI.new
+      todo = Todo.new(
+        "# TODO(on: issue_close('org', 'repo', '123'), to: 'john@example.com', context: \"org/repo#456\")",
+      )
+      event = Todo::CallNode.new(:issue_close, ["org", "repo", "123"], nil)
+
+      assert(cli.send(:should_apply_context?, todo, event))
+    end
+
+    def test_should_apply_context_returns_true_for_pull_request_close_event_with_context
+      cli = CLI.new
+      todo = Todo.new(
+        "# TODO(on: pull_request_close('org', 'repo', '123'), to: 'john@example.com', context: \"org/repo#456\")",
+      )
+      event = Todo::CallNode.new(:pull_request_close, ["org", "repo", "123"], nil)
+
+      assert(cli.send(:should_apply_context?, todo, event))
+    end
+
+    def test_should_apply_context_returns_true_for_regular_event_with_context
+      cli = CLI.new
+      todo = Todo.new("# TODO(on: date('2015-03-01'), to: 'john@example.com', context: \"org/repo#456\")")
+      event = Todo::CallNode.new(:date, ["2015-03-01"], nil)
+
+      assert(cli.send(:should_apply_context?, todo, event))
+    end
   end
 end
diff --git a/test/smart_todo/events/issue_context_test.rb b/test/smart_todo/events/issue_context_test.rb
new file mode 100644
index 0000000..70f3c29
--- /dev/null
+++ b/test/smart_todo/events/issue_context_test.rb
@@ -0,0 +1,147 @@
+# frozen_string_literal: true
+
+require "test_helper"
+
+module SmartTodo
+  class Events
+    class IssueContextTest < Minitest::Test
+      def test_when_issue_exists_and_is_open
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "open",
+            title: "Add support for caching",
+            number: 123,
+            assignee: { login: "johndoe" },
+          })
+
+        expected = "📌 Context: Issue #123 - \"Add support for caching\" [open] (@johndoe) - " \
+          "https://github.com/rails/rails/issues/123"
+
+        assert_equal(expected, issue_context("rails", "rails", "123"))
+      end
+
+      def test_when_issue_exists_and_is_closed
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "closed",
+            title: "Fix memory leak",
+            number: 456,
+            assignee: { login: "janedoe" },
+          })
+
+        expected = "📌 Context: Issue #456 - \"Fix memory leak\" [closed] (@janedoe) - " \
+          "https://github.com/shopify/smart_todo/issues/456"
+
+        assert_equal(expected, issue_context("shopify", "smart_todo", "456"))
+      end
+
+      def test_when_issue_has_no_assignee
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "open",
+            title: "Improve documentation",
+            number: 789,
+            assignee: nil,
+          })
+
+        expected = "📌 Context: Issue #789 - \"Improve documentation\" [open] (unassigned) - " \
+          "https://github.com/org/repo/issues/789"
+
+        assert_equal(expected, issue_context("org", "repo", "789"))
+      end
+
+      def test_when_issue_does_not_exist
+        stub_request(:get, /api.github.com/)
+          .to_return(status: 404)
+
+        assert_nil(issue_context("rails", "rails", "999"))
+      end
+
+      def test_when_token_env_is_not_present
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "open",
+            title: "Test issue",
+            number: 1,
+            assignee: nil,
+          })
+
+        result = issue_context("rails", "rails", "1")
+        assert(result.include?("📌 Context: Issue #1"))
+
+        assert_requested(:get, /api.github.com/) do |request|
+          assert(!request.headers.key?("Authorization"))
+        end
+      end
+
+      def test_when_token_env_is_present
+        ENV[GITHUB_TOKEN] = "abc123"
+
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "open",
+            title: "Test issue",
+            number: 2,
+            assignee: nil,
+          })
+
+        result = issue_context("rails", "rails", "2")
+        assert(result.include?("📌 Context: Issue #2"))
+
+        assert_requested(:get, /api.github.com/) do |request|
+          assert_equal("token abc123", request.headers["Authorization"])
+        end
+      ensure
+        ENV.delete(GITHUB_TOKEN)
+      end
+
+      def test_when_organization_specific_token_is_present
+        ENV["#{GITHUB_TOKEN}__RAILS"] = "rails_token"
+
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "open",
+            title: "Test issue",
+            number: 3,
+            assignee: nil,
+          })
+
+        result = issue_context("rails", "rails", "3")
+        assert(result.include?("📌 Context: Issue #3"))
+
+        assert_requested(:get, /api.github.com/) do |request|
+          assert_equal("token rails_token", request.headers["Authorization"])
+        end
+      ensure
+        ENV.delete("#{GITHUB_TOKEN}__RAILS")
+      end
+
+      def test_when_repo_specific_token_is_present
+        ENV["#{GITHUB_TOKEN}__RAILS__RAILS"] = "rails_rails_token"
+
+        stub_request(:get, /api.github.com/)
+          .to_return_json(body: {
+            state: "open",
+            title: "Test issue",
+            number: 4,
+            assignee: nil,
+          })
+
+        result = issue_context("rails", "rails", "4")
+        assert(result.include?("📌 Context: Issue #4"))
+
+        assert_requested(:get, /api.github.com/) do |request|
+          assert_equal("token rails_rails_token", request.headers["Authorization"])
+        end
+      ensure
+        ENV.delete("#{GITHUB_TOKEN}__RAILS__RAILS")
+      end
+
+      private
+
+      def issue_context(*args)
+        Events.new.issue_context(*args)
+      end
+    end
+  end
+end
diff --git a/test/smart_todo/integration_test.rb b/test/smart_todo/integration_test.rb
index 0667a52..c780f08 100644
--- a/test/smart_todo/integration_test.rb
+++ b/test/smart_todo/integration_test.rb
@@ -104,6 +104,115 @@ def hello
       )
     end
 
+    def test_includes_context_when_date_is_met_with_issue_context
+      ruby_code = <<~EOM
+        # TODO(on: date('2015-03-01'), to: 'john@example.com', context: "shopify/smart_todo#123")
+        #   Implement the caching strategy discussed in the issue
+        def hello
+        end
+      EOM
+
+      stub_request(:get, /api.github.com/)
+        .to_return(body: JSON.dump(
+          state: "open",
+          title: "Add caching support",
+          number: 123,
+          assignee: { login: "developer" },
+        ))
+
+      generate_ruby_file(ruby_code) do |file|
+        run_cli(file)
+      end
+
+      assert_slack_message_sent(
+        "Hello :wave:,",
+        "We are past the *2015-03-01* due date",
+        "📌 Context: Issue #123",
+        "Add caching support",
+        "Implement the caching strategy discussed in the issue",
+      )
+    end
+
+    def test_includes_context_when_gem_release_is_met_with_issue_context
+      ruby_code = <<~EOM
+        # TODO(on: gem_release('rails', '> 5.1'), to: 'john@example.com', context: "rails/rails#456")
+        #   Upgrade to new Rails version as per issue
+        def hello
+        end
+      EOM
+
+      stub_request(:get, /rubygems.org/)
+        .to_return(body: JSON.dump([{ number: "5.1.1" }]))
+
+      stub_request(:get, /api.github.com/)
+        .to_return(body: JSON.dump(
+          state: "closed",
+          title: "Rails upgrade needed",
+          number: 456,
+          assignee: nil,
+        ))
+
+      generate_ruby_file(ruby_code) do |file|
+        run_cli(file)
+      end
+
+      assert_slack_message_sent(
+        "Hello :wave:,",
+        "The gem *rails* was released to version *5.1.1*",
+        "📌 Context: Issue #456",
+        "Rails upgrade needed",
+        "Upgrade to new Rails version as per issue",
+      )
+    end
+
+    def test_context_does_not_affect_todos_without_events_triggered
+      ruby_code = <<~EOM
+        # TODO(on: date('2099-12-31'), to: 'john@example.com', context: "shopify/smart_todo#789")
+        #   This TODO is not ready yet
+        def hello
+        end
+      EOM
+
+      generate_ruby_file(ruby_code) do |file|
+        stub_slack_request
+        CLI.new.run([file.path, "--slack_token", "123", "--fallback_channel", '#general"', "--dispatcher", "slack"])
+      end
+
+      assert_not_requested(:post, /chat.postMessage/)
+      assert_not_requested(:get, /api.github.com/)
+    end
+
+    def test_context_included_with_issue_close_event
+      ruby_code = <<~EOM
+        # TODO(on: issue_close('shopify', 'smart_todo', '100'), to: 'john@example.com', context: "shopify/smart_todo#999")
+        #   This context should be included
+        def hello
+        end
+      EOM
+
+      stub_request(:get, %r{api.github.com.*issues/100})
+        .to_return(body: JSON.dump(state: "closed"))
+
+      stub_request(:get, %r{api.github.com.*issues/999})
+        .to_return(body: JSON.dump(
+          title: "Context Issue",
+          state: "open",
+          assignee: { login: "developer" },
+        ))
+
+      generate_ruby_file(ruby_code) do |file|
+        run_cli(file)
+      end
+
+      assert_slack_message_sent(
+        "Hello :wave:,",
+        "The issue https://github.com/shopify/smart_todo/issues/100 is now closed",
+        "This context should be included",
+        "Context:",
+        "Context Issue",
+      )
+    end
+
     private
 
     def assert_slack_message_sent(*messages)
diff --git a/test/smart_todo/smart_todo_cop_test.rb b/test/smart_todo/smart_todo_cop_test.rb
index c87b963..3a334e0 100644
--- a/test/smart_todo/smart_todo_cop_test.rb
+++ b/test/smart_todo/smart_todo_cop_test.rb
@@ -487,6 +487,67 @@ def hello
       RUBY
     end
 
+    def test_does_not_add_offense_when_todo_has_valid_context_with_issue
+      expect_no_offense(<<~RUBY)
+        # TODO(on: date('2019-08-04'), to: 'john@example.com', context: "shopify/smart_todo#123")
+        def hello
+        end
+      RUBY
+    end
+
+    def test_does_not_add_offense_when_todo_has_context_with_different_events
+      expect_no_offense(<<~RUBY)
+        # TODO(on: gem_release('rails', '> 6.0'), to: 'john@example.com', context: "rails/rails#456")
+        def hello
+        end
+
+        # TODO(on: gem_bump('rails', '> 7.0'), to: 'john@example.com', context: "rails/rails#789")
+        def hello
+        end
+
+        # TODO(on: ruby_version('> 3.0'), to: 'john@example.com', context: "ruby/ruby#123")
+        def hello
+        end
+      RUBY
+    end
+
+    def test_add_offense_when_todo_has_context_with_wrong_number_of_arguments
+      expect_offense(<<~RUBY)
+        # TODO(on: date('2019-08-04'), to: 'john@example.com', context: "shopify/smart_todo")
+        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ SmartTodo/SmartTodoCop: Invalid TODO format: Incorrect `:context` format: expected "org/repo#issue_number". For more info please look at https://github.com/Shopify/smart_todo/wiki/Syntax
+        def hello
+        end
+      RUBY
+    end
+
+    def test_add_offense_when_todo_has_context_with_non_string_arguments
+      expect_offense(<<~RUBY)
+        # TODO(on: date('2019-08-04'), to: 'john@example.com', context: 123)
+        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ SmartTodo/SmartTodoCop: Invalid TODO format: Incorrect `:context` format: expected string value. For more info please look at https://github.com/Shopify/smart_todo/wiki/Syntax
+        def hello
+        end
+      RUBY
+    end
+
+    def test_add_offense_when_todo_has_context_with_invalid_function
+      expect_offense(<<~RUBY)
+        # TODO(on: date('2019-08-04'), to: 'john@example.com', context: "shopify-smart_todo-123")
+        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ SmartTodo/SmartTodoCop: Invalid TODO format: Incorrect `:context` format: expected "org/repo#issue_number". For more info please look at https://github.com/Shopify/smart_todo/wiki/Syntax
+        def hello
+        end
+      RUBY
+    end
+
+    def test_context_does_not_require_assignee_when_event_does
+      # Even though context is present, the TODO still requires an assignee for the event
+      expect_offense(<<~RUBY)
+        # TODO(on: date('2019-08-04'), context: "shopify/smart_todo#123")
+        ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^ #{expected_message}
+        def hello
+        end
+      RUBY
+    end
+
     private
 
     def expected_message