diff --git a/dev/sentry.cr b/dev/sentry.cr
new file mode 100644
index 00000000..86d3261c
--- /dev/null
+++ b/dev/sentry.cr
@@ -0,0 +1,109 @@
+module Sentry
+  FILE_TIMESTAMPS = {} of String => String # {file => timestamp}
+
+  class ProcessRunner
+    getter app_process : (Nil | Process) = nil
+    property process_name : String
+    property should_build = true
+    property files = [] of String
+
+    def initialize(
+                   @process_name : String,
+                   @build_command : String,
+                   @run_command : String,
+                   @build_args : Array(String) = [] of String,
+                   @run_args : Array(String) = [] of String,
+                   files = [] of String,
+                   should_build = true)
+      @files = files
+      @should_build = should_build
+      @should_kill = false
+      @app_built = false
+    end
+
+    private def build_app_process
+      puts "🤖  compiling #{process_name}..."
+      build_args = @build_args
+      if build_args.size > 0
+        Process.run(@build_command, build_args, shell: true, output: Process::Redirect::Inherit, error: Process::Redirect::Inherit)
+      else
+        Process.run(@build_command, shell: true, output: Process::Redirect::Inherit, error: Process::Redirect::Inherit)
+      end
+    end
+
+    private def create_app_process
+      app_process = @app_process
+      if app_process.is_a? Process
+        unless app_process.terminated?
+          puts "🤖  killing #{process_name}..."
+          app_process.kill
+        end
+      end
+
+      puts "🤖  starting #{process_name}..."
+      run_args = @run_args
+      if run_args.size > 0
+        @app_process = Process.new(@run_command, run_args, output: Process::Redirect::Inherit, error: Process::Redirect::Inherit)
+      else
+        @app_process = Process.new(@run_command, output: Process::Redirect::Inherit, error: Process::Redirect::Inherit)
+      end
+    end
+
+    private def get_timestamp(file : String)
+      File.stat(file).mtime.to_s("%Y%m%d%H%M%S")
+    end
+
+    # Compiles and starts the application
+    #
+    def start_app
+      return create_app_process unless @should_build
+      build_result = build_app_process()
+      if build_result && build_result.success?
+        @app_built = true
+        create_app_process()
+      elsif !@app_built # if build fails on first time compiling, then exit
+        puts "🤖  Compile time errors detected. SentryBot shutting down..."
+        exit 1
+      end
+    end
+
+    # Scans all of the `@files`
+    #
+    def scan_files
+      file_changed = false
+      app_process = @app_process
+      files = @files
+      Dir.glob(files) do |file|
+        timestamp = get_timestamp(file)
+        if FILE_TIMESTAMPS[file]? && FILE_TIMESTAMPS[file] != timestamp
+          FILE_TIMESTAMPS[file] = timestamp
+          file_changed = true
+          puts "🤖  #{file}"
+        elsif FILE_TIMESTAMPS[file]?.nil?
+          puts "🤖  watching file: #{file}"
+          FILE_TIMESTAMPS[file] = timestamp
+          file_changed = true if (app_process && !app_process.terminated?)
+        end
+      end
+
+      start_app() if (file_changed || app_process.nil?)
+    end
+
+    def run
+      puts "🤖  Your SentryBot is vigilant. beep-boop..."
+
+      loop do
+        if @should_kill
+          puts "🤖  Powering down your SentryBot..."
+          break
+        end
+        scan_files
+        sleep 1
+      end
+    end
+
+    def kill
+      @should_kill = true
+    end
+  end
+end
diff --git a/dev/sentry_cli.cr b/dev/sentry_cli.cr
new file mode 100644
index 00000000..6e3f4530
--- /dev/null
+++ b/dev/sentry_cli.cr
@@ -0,0 +1,99 @@
+require "option_parser"
+require "yaml"
+require "./sentry"
+
+process_name = nil
+
+begin
+  shard_yml = YAML.parse File.read("shard.yml")
+  name = shard_yml["name"]?
+  process_name = name.as_s if name
+rescue e
+end
+
+build_args = [] of String
+build_command = "crystal build ./src/#{process_name}.cr"
+run_args = [] of String
+run_command = "./#{process_name}"
+files = ["./src/**/*.cr", "./src/**/*.ecr"]
+files_cleared = false
+show_help = false
+should_build = true
+
+OptionParser.parse! do |parser|
+  parser.banner = "Usage: ./sentry [options]"
+  parser.on(
+    "-n NAME",
+    "--name=NAME",
+    "Sets the name of the app process (current name: #{process_name})") { |name| process_name = name }
+  parser.on(
+    "-b COMMAND",
+    "--build=COMMAND",
+    "Overrides the default build command") { |command| build_command = command }
+  parser.on(
+    "--build-args=ARGS",
+    "Specifies arguments for the build command") do |args|
+    args_arr = args.strip.split(" ")
+    build_args = args_arr if args_arr.size > 0
+  end
+  parser.on(
+    "--no-build",
+    "Skips the build step") { should_build = false }
+  parser.on(
+    "-r COMMAND",
+    "--run=COMMAND",
+    "Overrides the default run command") { |command| run_command = command }
+  parser.on(
+    "--run-args=ARGS",
+    "Specifies arguments for the run command") do |args|
+    args_arr = args.strip.split(" ")
+    run_args = args_arr if args_arr.size > 0
+  end
+  parser.on(
+    "-w FILE",
+    "--watch=FILE",
+    "Overrides default files and appends to list of watched files") do |file|
+    unless files_cleared
+      files.clear
+      files_cleared = true
+    end
+    files << file
+  end
+  parser.on(
+    "-i",
+    "--info",
+    "Shows the values for build/run commands, build/run args, and watched files") do
+    puts "
+      name:       #{process_name}
+      build:      #{build_command}
+      build args: #{build_args}
+      run:        #{run_command}
+      run args:   #{run_args}
+      files:      #{files}
+    "
+  end
+  parser.on(
+    "-h",
+    "--help",
+    "Show this help") do
+    puts parser
+    exit 0
+  end
+end
+
+if process_name
+  process_runner = Sentry::ProcessRunner.new(
+    process_name: process_name.as(String),
+    build_command: build_command,
+    run_command: run_command,
+    build_args: build_args,
+    run_args: run_args,
+    should_build: should_build,
+    files: files
+  )
+
+  process_runner.run
+else
+  puts "🤖  Sentry error: 'name' not given and not found in shard.yml"
+  exit 1
+end
diff --git a/sentry b/sentry
new file mode 100755
index 00000000..aeb90127
Binary files /dev/null and b/sentry differ