diff --git a/.ruby-version b/.ruby-version
index 8c50098..be94e6f 100644
--- a/.ruby-version
+++ b/.ruby-version
@@ -1 +1 @@
-3.1
+3.2.2
diff --git a/Changelog.md b/Changelog.md
index 225e39a..7e36df5 100644
--- a/Changelog.md
+++ b/Changelog.md
@@ -16,6 +16,10 @@ _latest update: Mon 17 Apr 2023, 18:07:04, CEST_
   It makes sense to integrate cvss gem within the project.
 * Fixed issue #260. Removed old codesake-dawn named rake tasks. dawn is not
   intended to be run via rake anymore.
+* Issue #268. As part of the Hackweek (https://t.ly/epoSZ), dawn must be able
+  to parse a Sinatra application to spot vulnerabilities. As Sinatra code can
+  be also self contained in a single file, this must be allowed as a valid
+  target.
 
 
 ## Version 2.2.0 (2023-04-17)
diff --git a/dawnscanner.gemspec b/dawnscanner.gemspec
index c8ae121..2745931 100644
--- a/dawnscanner.gemspec
+++ b/dawnscanner.gemspec
@@ -31,6 +31,8 @@ Gem::Specification.new do |gem|
   # For CLI we will use thor
   gem.add_dependency 'thor'
 
+  gem.add_dependency 'parser'
+
   # gem.add_dependency 'sqlite3'
   # gem.add_dependency 'datamapper'
   # gem.add_dependency 'dm-sqlite-adapter'
diff --git a/lib/dawn/core.rb b/lib/dawn/core.rb
index 05dc424..4a4ba47 100644
--- a/lib/dawn/core.rb
+++ b/lib/dawn/core.rb
@@ -1,4 +1,5 @@
 require "yaml"
+require 'parser/current'
 
 module Dawn
   class Core
@@ -79,8 +80,34 @@ def self.guess_mvc(gemfile_lock)
 
     end
 
+    ##
+    # detect_mvc_from_file is a method to check if a ruby script is a self
+    # contained web application, most likely if it is a Sinatra web application
+    # or a simple script.
+    #
+    # TODO: this method has a known bug. It relies only on the presence of a
+    # "require 'sinatra'" statement to detect a sinatra app. In case of a
+    # malformed ruby script, requiring sinatra gem but not defining a real
+    # sinatra app, dawnscanner will be fooled.
+    #
+    # @param target [String] the target filename
+    # @return [Object] a Dawn::Sinatra instance or nil in case of error
+    def self.detect_mvc_from_file(target)
+      code = File.read(target)
+      parsed_code = Parser::CurrentRuby.parse(code)
+      ast = Dawn::Processor::Require.new
+      ast.process_all(parsed_code)
+
+      return Dawn::Sinatra.new(target) if ast.is_sinatra
+
+      return nil
+    end
+
     def self.detect_mvc(target)
 
+      # Issue#268
+      return detect_mvc_from_file(target) if (File.file?(target) and File.extname(target) == ".rb")
+
       raise ArgumentError.new("you must set target directory") if target.nil?
 
       my_dir = Dir.pwd
diff --git a/lib/dawn/processor/require.rb b/lib/dawn/processor/require.rb
new file mode 100644
index 0000000..804efca
--- /dev/null
+++ b/lib/dawn/processor/require.rb
@@ -0,0 +1,20 @@
+module Dawn
+  module Processor
+    class Require < AST::Processor
+      attr_reader :is_sinatra
+
+      def initialize()
+        @is_sinatra = false
+        super()
+      end
+
+      def on_send(node)
+        if (node.children[1].to_s == "require")
+          if node.children[2].children[0].to_s == "sinatra"
+            @is_sinatra = true
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/lib/dawnscanner.rb b/lib/dawnscanner.rb
index 27c7b02..b5b1d20 100644
--- a/lib/dawnscanner.rb
+++ b/lib/dawnscanner.rb
@@ -9,7 +9,8 @@
 
 require "dawn/cli/dawn_cli"
 
-# KB 
+require "dawn/processor/require"
+# KB
 require "dawn/knowledge_base"
 
 # General purpose utilities
diff --git a/spec/lib/dawn/issue_268_spec.rb b/spec/lib/dawn/issue_268_spec.rb
new file mode 100644
index 0000000..1f10aa1
--- /dev/null
+++ b/spec/lib/dawn/issue_268_spec.rb
@@ -0,0 +1,14 @@
+require "spec_helper"
+
+describe "A single ruby file with a Sinatra application " do
+  before (:all) do
+    @engine = Dawn::Core.detect_mvc("./spec/support/sinatra_hello_app.rb")
+  end
+  it "is a good target too" do
+    expect(@engine).not_to be_nil
+  end
+
+  it "is recognized as a Sinatra app" do
+    expect(@engine).to be_a Dawn::Sinatra
+  end
+end