diff --git a/checkie.gemspec b/checkie.gemspec
index 97109dd..e7a91ff 100644
--- a/checkie.gemspec
+++ b/checkie.gemspec
@@ -1,8 +1,8 @@
 Gem::Specification.new do |s|
   s.name = %q{checkie}
-  s.version = "0.0.1"
+  s.version = "0.0.3"
   s.authors = %q{Alignable}
-  s.date = %q{2018-05-23}
+  s.date = %q{2026-02-04}
   s.summary = %q{Hi, It's Checkie! Looks like you're trying to write some code}
   s.files = [
     "lib/checkie.rb"
@@ -11,9 +11,10 @@ Gem::Specification.new do |s|
   s.license       = 'MIT'
 
   s.add_runtime_dependency 'dotenv'
-  s.add_runtime_dependency "octokit", "~>4.22.0"
+  s.add_runtime_dependency "octokit"
   s.add_runtime_dependency "git_diff_parser"
   s.add_runtime_dependency "activesupport"
+  s.add_runtime_dependency "anthropic"
 
   # to write specs for rules.rb
   s.add_runtime_dependency "rspec"
diff --git a/lib/checkie.rb b/lib/checkie.rb
index e34539a..743b436 100644
--- a/lib/checkie.rb
+++ b/lib/checkie.rb
@@ -19,11 +19,19 @@ def matching(file_pattern, &block)
   Checkie::Parser.instance.add_matching_file(file_pattern,&block)
 end
 
+def matching_ai(file_pattern, rules:, exclude: nil, &block)
+  Checkie::Parser.instance.add_matching_file(file_pattern, ai: true, rules: rules, exclude: exclude, &block)
+end
+
 
 def file_rule(name,description,references:[])
   Checkie::Parser.instance.add_file_rule(name, description, references: references)
 end
 
+def file_rule_ai(name, description, **opts)
+  Checkie::Parser.instance.add_file_rule(name, description, **opts.merge({ai: true}))
+end
+
 def run(url, action)
   Checkie::Runner.new.run(url, action)
 end
diff --git a/lib/checkie/matcher.rb b/lib/checkie/matcher.rb
index a7a3609..8ec28a2 100644
--- a/lib/checkie/matcher.rb
+++ b/lib/checkie/matcher.rb
@@ -16,6 +16,49 @@ def check(rule,references = nil )
     @rules[rule.to_s] += references if references
   end
 
+  def match_ai
+    ruleset_to_files = {exploration: {}, standard: {}}
+    @pr.each do |file|
+      std_rules, exp_rules = gather_rules_ai(file[:filename])
+      next if std_rules.empty? && exp_rules.empty?
+
+      changeset = {name: file[:filename], patch: file[:patch]}
+      unless exp_rules.empty?
+        subset_key = :exploration
+        ruleset_to_files[subset_key][exp_rules] ||= []
+        ruleset_to_files[subset_key][exp_rules] << changeset
+      end
+      unless std_rules.empty?
+        subset_key = :standard
+        ruleset_to_files[subset_key][std_rules] ||= []
+        ruleset_to_files[subset_key][std_rules] << changeset
+      end
+    end
+
+    {
+      exploration: ruleset_to_files[:exploration].map { |k, v| [k.join("\n"), v] },
+      standard: ruleset_to_files[:standard].map { |k, v| [k.join("\n"), v] }
+    }
+  end
+
+  def gather_rules_ai(path)
+    applicable = Set[]
+    exploration = Set[]
+    parser.matches_ai.each do |rule|
+      next unless File.fnmatch(rule[:pattern], path, File::FNM_EXTGLOB)
+      next if rule[:exclude] && rule[:exclude].any? { |p| File.fnmatch(p, path, File::FNM_EXTGLOB) }
+
+      rule[:rules].compact.each do |r|
+        if r[:exploration]
+          exploration.add(r[:description])
+        else
+          applicable.add(r[:description])
+        end
+      end
+    end
+    [applicable, exploration]
+  end
+
   def match
     all_files = Checkie::FileMatchSet.new(self)
 
diff --git a/lib/checkie/parser.rb b/lib/checkie/parser.rb
index 5d64162..ad23c4e 100644
--- a/lib/checkie/parser.rb
+++ b/lib/checkie/parser.rb
@@ -2,7 +2,7 @@
 class Checkie::Parser
   include Singleton
 
-  attr_reader :matches, :rules
+  attr_reader :matches, :rules, :matches_ai, :rules_ai
 
   def initialize
     reinitialize
@@ -10,23 +10,44 @@ def initialize
 
   def reinitialize
     @rules = {}
+    @rules_ai = {}
     @matches = []
+    @matches_ai = []
   end
 
-  def add_matching_file(glob_pattern, matching_proc=nil, &block)
+  def add_matching_file(glob_pattern, matching_proc=nil, **opts, &block)
     matching_proc ||= block
-    @matches << { pattern: glob_pattern, 
-                  matching_proc: matching_proc 
-                }
+    obj = { pattern: glob_pattern, 
+            matching_proc: matching_proc 
+          }
+    if opts[:ai]
+      obj[:rules] = opts[:rules].map do |r|
+        @rules_ai[r.to_s]
+      end
+      if opts[:exclude]
+         obj[:exclude] = Array(opts[:exclude])
+      end
+      @matches_ai << obj
+    else
+      @matches << obj
+    end
   end
 
-  def add_file_rule(name, description, references: [])
-    raise "Duplicate rule #{name}" if @rules[name.to_s].present?
-    @rules[name.to_s] = {
-                name: name.to_s,
-                description: description,
-                references: references
-              }
+  def add_file_rule(name, description, **opts)
+    raise "Duplicate rule #{name}" if @rules_ai[name.to_s].present? || @rules_ai[name.to_s].present?
+    if opts[:ai]
+      @rules_ai[name.to_s] = {
+        name: name.to_s,
+        description: description,
+        exploration: opts[:exploration],
+      }
+    else
+      @rules[name.to_s] = {
+                  name: name.to_s,
+                  description: description,
+                  references: opts[:references]
+                }
+    end
   end
 
 end
diff --git a/lib/checkie/poster.rb b/lib/checkie/poster.rb
index 59ed564..305c32c 100644
--- a/lib/checkie/poster.rb
+++ b/lib/checkie/poster.rb
@@ -10,6 +10,28 @@ def initialize(details, dry_run: true)
     @dry_run = dry_run
   end
 
+  def post_ai_annotations!(rules)
+    if rules.length > 0
+      annotations = annotations_ai(rules)
+      sha = @details[:head][:sha]
+      
+      annotations.each do |a|
+        if @dry_run
+          pp a
+        else
+          repo_id = @details[:base][:repo][:id]
+          sha = @details[:head][:sha]
+          check_run_id = client.check_runs_for_ref(repo_id, sha, check_name: "checkie")&.check_runs&.first&.id
+          annotations.each_slice(GITHUB_ANNOTATION_BATCH) do |a|
+            client.update_check_run(repo_id, check_run_id, output: { annotations: a, title: "CheckieAI", summary: "#{annotations.length} annotations"})
+          end
+        end
+      rescue Octokit::UnprocessableEntity
+        pp "Bad request sent! Probably a line number issue: #{a[:path]}:#{a[:start_line]}"
+      end
+    end
+  end
+
   # Post file rules as annotations
   def post_annotations!(rules)
     if rules.length > 0
@@ -32,6 +54,27 @@ def post_annotations!(rules)
 
   private
 
+  def annotations_ai(rules)
+    arr = []
+    rules.each do |r|
+      r = r[:violations]
+      next if r.empty?
+      r.each do |annotation|
+        # Because Claude can be stupid.
+        next if annotation[:suggestion].downcase.include?("no violation")
+        arr << {
+          path: annotation[:file],
+          start_line: annotation[:line_number],
+          end_line: annotation[:line_number],
+          title: annotation[:rule],
+          message: "#{annotation[:issue]}\n#{annotation[:suggestion]}",
+          annotation_level: "warning"
+        }
+      end
+    end
+    return arr
+  end
+
   def annotations(rules)
     arr = []
 
diff --git a/lib/checkie/runner.rb b/lib/checkie/runner.rb
index c2feb7f..d744b7e 100644
--- a/lib/checkie/runner.rb
+++ b/lib/checkie/runner.rb
@@ -1,3 +1,5 @@
+require "open3"
+require "anthropic"
 class Checkie::Runner
   # Action is the pull request action type
   def run(url, action)
@@ -8,9 +10,148 @@ def run(url, action)
       data = fetcher.fetch_files
 
       matcher = Checkie::Matcher.new(data)
-      rules = matcher.match
+      rules = matcher.match_ai
+      ai_rules = call_claude(rules[:exploration]) + call_claude_api(rules[:standard])
+      reg_rules = matcher.match
+      poster.post_ai_annotations!(ai_rules)
+      poster.post_annotations!(reg_rules)
+    end
+  end
+
+  def call_claude(rule_mapping)
+    # assumes that non-exploratory rules have been filtered out
+    rule_mapping.map do |mapping|
+      # mappping == [rule strings joined by \n, arr of patch diffs]
+      prompt = create_prompt(mapping[0], mapping[1])
+
+      repo_dir = File.expand_path("../../", Dir.pwd)
+      res = Open3.capture3("claude", "--model", "haiku", "--dangerously-skip-permissions", "-p", prompt, chdir: repo_dir)
+      puts res[0]
+      prefix = res[0].index("```json")
+      postfix = res[0].index("```", prefix + 7)
+      unless prefix && postfix
+        puts "Bad response from Claude!!", res[0]
+        next
+      end
+      parsed = res[0][prefix+7...postfix]
+      JSON.parse(parsed)
+    end
+  end
+
+  def call_claude_api(rule_mapping)
+    # Assumes that exploratory rules have been filtered out
+    client = Anthropic::Client.new(api_key: ENV["ANTHROPIC_API_KEY"])
+
+    rule_mapping.map do |mapping|
+      # mapping == [rule strings joined by \n, arr of patch diffs]
+      prompt = create_prompt(mapping[0], mapping[1])
+
+      begin
+        response = client.messages.create(
+          model: "claude-haiku-4-5-20251001",
+          max_tokens: 4096,
+          messages: [
+            {
+              role: "user",
+              content: prompt
+            }
+          ],
+          tools: [
+            {
+              name: "report_violations",
+              description: "Report code style violations found in the PR diff",
+              input_schema: structured_schema
+            }
+          ],
+          tool_choice: {
+            type: "tool",
+            name: "report_violations"
+          }
+        )
+
+        # Extract the tool use result
+        tool_use = response.content&.find { |block| block.type == :tool_use }
+        if tool_use && tool_use.input
+          tool_use.input
+        else
+          puts "No tool use found in response"
+          { "violations" => [] }
+        end
+      rescue => e
+        puts "Error calling Claude API: #{e.message}"
+        { "violations" => [] }
+      end
+    end
+  end
 
-      poster.post_annotations!(rules)
+  def structured_schema
+    {
+      type: "object",
+      properties: {
+        violations: {
+          type: "array",
+          items: {
+            type: "object",
+            properties: {
+              file: { type: "string", description: "Path to the file" },
+              rule: { type: "string", description: "Name of the rule violated" },
+              line_number: { type: "integer", description: "Line number in the diff (must be a + or - line)" },
+              issue: { type: "string", description: "Description of what's wrong" },
+              suggestion: { type: "string", description: "How to fix the issue" }
+            },
+            required: ["file", "rule", "line_number", "issue", "suggestion"]
+          }
+        }
+      },
+      required: ["violations"]
+    }
+  end
+
+  def create_prompt(rules, diffs)
+    formatted =  diffs.map do |d|
+      <<-PATCH
+        File: #{d[:name]}
+        #{d[:patch]}
+      PATCH
     end
+    <<-PROMPT
+    You are an AI code reviewer, going through PRs and identifying any changes that 
+    don't follow the teams established best practices.
+
+    Code style rules:
+    #{rules}
+
+    Git PR diff to evaluate:
+    #{formatted}
+
+    IMPORTANT: The diff above only shows files matching the rules being checked. Before flagging
+    any missing files (like spec files), you MUST use the Read tool or Glob tool to verify the file
+    does not exist in the repository. Do not assume a file is missing just because it's not in the
+    diff above - it may have been added elsewhere in the PR.
+    One block / line of code may violate multiple rules. Include any and all violations.
+
+    Instructions:
+    1. For each changed file, check if modified lines ONLY WITHIN THE DIFF violate any rules. 
+      1.1 DO NOT make your own assumptions about how to interpret the rules
+      1.2 DO NOT make up your own rules, such as grammar violations
+      1.3 DO NOT RESPOND WITH VIOLATIONS ON UNCHANGED CODE
+    2. You may read all related files for context
+
+    Ensure all parts of your response are succinct and to the point. DO NOT ramble.
+    Return valid JSON only:
+    {
+      "violations": [
+        {
+          "file": "path/to/file.rb",
+          "rule": "rule name",
+          "line_number": 10,
+          "issue": "what's wrong",
+          "suggestion": "how to fix"
+        }
+      ]
+    }
+
+    Return empty violations array if no issues found: {"violations": []}
+    PROMPT
   end
 end
diff --git a/spec/checkie/matcher_spec.rb b/spec/checkie/matcher_spec.rb
index 1b273b7..bd83792 100644
--- a/spec/checkie/matcher_spec.rb
+++ b/spec/checkie/matcher_spec.rb
@@ -32,7 +32,7 @@
       expect(matcher.match).to eq({"readme"=>[["README.md", {additions: 45, deletions: 0, :url=>"https://github.com/Alignable/checkie/blob/dd52731e1f894f53e5972e57255405961ca4ab38/README.md"}]] })
 
     end
-    
+
     it 'supports extglob' do
       instance.add_matching_file("{README,abc}*") do |changes,files|
         files.added do
@@ -43,4 +43,119 @@
     end
   end
 
+  describe "#match_ai" do
+    it "returns empty rulesets without any AI rules" do
+      expect(matcher.match_ai).to eq({exploration: [], standard: []})
+    end
+
+    it "returns standard rules when AI rules are added" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_matching_file("README*", ai: true, rules: [:readme_check])
+
+      result = matcher.match_ai
+      expect(result[:standard].length).to eq(1)
+      expect(result[:standard][0][0]).to eq("You edited readme")
+      expect(result[:standard][0][1].length).to eq(1)
+      expect(result[:standard][0][1][0][:name]).to eq("README.md")
+      expect(result[:exploration]).to eq([])
+    end
+
+    it "returns exploration rules when marked as exploration" do
+      instance.add_file_rule(:readme_explore, "Consider readme impact", ai: true, exploration: true)
+      instance.add_matching_file("README*", ai: true, rules: [:readme_explore])
+
+      result = matcher.match_ai
+      expect(result[:exploration].length).to eq(1)
+      expect(result[:exploration][0][0]).to eq("Consider readme impact")
+      expect(result[:exploration][0][1].length).to eq(1)
+      expect(result[:exploration][0][1][0][:name]).to eq("README.md")
+      expect(result[:standard]).to eq([])
+    end
+
+    it "separates standard and exploration rules" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_file_rule(:readme_explore, "Consider readme impact", ai: true, exploration: true)
+      instance.add_matching_file("README*", ai: true, rules: [:readme_check, :readme_explore])
+
+      result = matcher.match_ai
+      expect(result[:standard].length).to eq(1)
+      expect(result[:exploration].length).to eq(1)
+      expect(result[:standard][0][0]).to eq("You edited readme")
+      expect(result[:exploration][0][0]).to eq("Consider readme impact")
+    end
+
+    it "supports exclude patterns" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_matching_file("*", ai: true, rules: [:readme_check], exclude: "README*")
+
+      result = matcher.match_ai
+      expect(result[:standard]).to eq([])
+      expect(result[:exploration]).to eq([])
+    end
+
+    it "supports array of exclude patterns" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_matching_file("*", ai: true, rules: [:readme_check], exclude: ["README*", "LICENSE*"])
+
+      result = matcher.match_ai
+      expect(result[:standard]).to eq([])
+      expect(result[:exploration]).to eq([])
+    end
+  end
+
+  describe "#gather_rules_ai" do
+    it "returns empty sets for non-matching paths" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_matching_file("README*", ai: true, rules: [:readme_check])
+
+      standard, exploration = matcher.gather_rules_ai("other_file.txt")
+      expect(standard.to_a).to eq([])
+      expect(exploration.to_a).to eq([])
+    end
+
+    it "returns standard rules for matching paths" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_matching_file("README*", ai: true, rules: [:readme_check])
+
+      standard, exploration = matcher.gather_rules_ai("README.md")
+      expect(standard.to_a).to eq(["You edited readme"])
+      expect(exploration.to_a).to eq([])
+    end
+
+    it "returns exploration rules for matching paths" do
+      instance.add_file_rule(:readme_explore, "Consider readme impact", ai: true, exploration: true)
+      instance.add_matching_file("README*", ai: true, rules: [:readme_explore])
+
+      standard, exploration = matcher.gather_rules_ai("README.md")
+      expect(standard.to_a).to eq([])
+      expect(exploration.to_a).to eq(["Consider readme impact"])
+    end
+
+    it "excludes paths matching exclude pattern" do
+      instance.add_file_rule(:readme_check, "You edited readme", ai: true)
+      instance.add_matching_file("*", ai: true, rules: [:readme_check], exclude: ["README*"])
+
+      standard, exploration = matcher.gather_rules_ai("README.md")
+      expect(standard.to_a).to eq([])
+      expect(exploration.to_a).to eq([])
+    end
+
+    it "excludes paths matching any pattern in exclude array" do
+      instance.add_file_rule(:doc_check, "You edited documentation", ai: true)
+      instance.add_matching_file("*", ai: true, rules: [:doc_check], exclude: ["README*", "LICENSE*"])
+
+      standard_readme, exploration_readme = matcher.gather_rules_ai("README.md")
+      expect(standard_readme.to_a).to eq([])
+      expect(exploration_readme.to_a).to eq([])
+
+      standard_license, exploration_license = matcher.gather_rules_ai("LICENSE.txt")
+      expect(standard_license.to_a).to eq([])
+      expect(exploration_license.to_a).to eq([])
+
+      standard_other, exploration_other = matcher.gather_rules_ai("other_file.rb")
+      expect(standard_other.to_a).to eq(["You edited documentation"])
+      expect(exploration_other.to_a).to eq([])
+    end
+  end
+
 end
diff --git a/spec/checkie/parser_spec.rb b/spec/checkie/parser_spec.rb
index 2afc9f1..b33171e 100644
--- a/spec/checkie/parser_spec.rb
+++ b/spec/checkie/parser_spec.rb
@@ -16,6 +16,13 @@
 
       expect(instance.rules["something"]).to be_present
     end
+    
+    it "adds an ai rule to the ai list" do
+      expect do
+        instance.add_file_rule(:something, "Because", ai: true)
+      end.to change { instance.rules_ai.length }.by(1)
+      expect(instance.rules_ai["something"]).to be_present
+    end
   end
 
   describe "add_matching_file" do