diff --git a/lib/debug/breakpoint.rb b/lib/debug/breakpoint.rb
index 37102ab72..802d230b3 100644
--- a/lib/debug/breakpoint.rb
+++ b/lib/debug/breakpoint.rb
@@ -263,22 +263,29 @@ class CatchBreakpoint < Breakpoint
     attr_reader :last_exc
     include SkipPathHelper
 
-    def initialize pat, cond: nil, command: nil
+    def initialize pat, cond: nil, command: nil, path: nil
       @pat = pat.freeze
       @key = [:catch, @pat].freeze
       @last_exc = nil
 
       @cond = cond
       @command = command
+      @path = path
 
       super()
     end
 
     def setup
       @tp = TracePoint.new(:raise){|tp|
-        next if skip_path?(tp.path)
         exc = tp.raised_exception
         next if SystemExit === exc
+
+        if @path
+          next if !tp.path.match?(@path)
+        elsif skip_path?(tp.path)
+          next
+        end
+
         next if !safe_eval(tp.binding, @cond) if @cond
         should_suspend = false
 
@@ -303,9 +310,10 @@ def description
   end
 
   class CheckBreakpoint < Breakpoint
-    def initialize expr
+    def initialize expr, path
       @expr = expr.freeze
       @key = [:check, @expr].freeze
+      @path = path
 
       super()
     end
@@ -315,6 +323,7 @@ def setup
         next if tp.path.start_with? __dir__
         next if tp.path.start_with? '<internal:'
         next if ThreadClient.current.management?
+        next if @path && !tp.path.match?(@path)
 
         if safe_eval tp.binding, @expr
           suspend
@@ -328,7 +337,7 @@ def to_s
   end
 
   class WatchIVarBreakpoint < Breakpoint
-    def initialize ivar, object, current, cond: nil, command: nil
+    def initialize ivar, object, current, cond: nil, command: nil, path: nil
       @ivar = ivar.to_sym
       @object = object
       @key = [:watch, object.object_id, @ivar].freeze
@@ -337,6 +346,7 @@ def initialize ivar, object, current, cond: nil, command: nil
 
       @cond = cond
       @command = command
+      @path = path
       super()
     end
 
@@ -362,6 +372,7 @@ def setup
       @tp = TracePoint.new(:line, :return, :b_return){|tp|
         next if tp.path.start_with? __dir__
         next if tp.path.start_with? '<internal:'
+        next if @path && !tp.path.match?(@path)
 
         watch_eval
       }
@@ -381,7 +392,7 @@ def to_s
   class MethodBreakpoint < Breakpoint
     attr_reader :sig_method_name, :method
 
-    def initialize b, klass_name, op, method_name, cond: nil, command: nil
+    def initialize b, klass_name, op, method_name, cond: nil, command: nil, path: nil
       @sig_klass_name = klass_name
       @sig_op = op
       @sig_method_name = method_name
@@ -393,6 +404,7 @@ def initialize b, klass_name, op, method_name, cond: nil, command: nil
       @cond = cond
       @cond_class = nil
       @command = command
+      @path = path
       @key = "#{klass_name}#{op}#{method_name}".freeze
 
       super(false)
@@ -402,7 +414,10 @@ def setup
       @tp = TracePoint.new(:call){|tp|
         next if !safe_eval(tp.binding, @cond) if @cond
         next if @cond_class && !tp.self.kind_of?(@cond_class)
-        next if @override_method ? (caller_locations(2, 1).first.to_s.start_with?(__dir__)) : tp.path.start_with?(__dir__)
+
+        caller_location = caller_locations(2, 1).first.to_s
+        next if @path && !caller_location.match?(@path)
+        next if caller_location.start_with?(__dir__)
 
         suspend
       }
diff --git a/lib/debug/session.rb b/lib/debug/session.rb
index 6a85ad069..2d29f42ec 100644
--- a/lib/debug/session.rb
+++ b/lib/debug/session.rb
@@ -1251,7 +1251,7 @@ def delete_bp arg = nil
       end
     end
 
-    BREAK_KEYWORDS = %w(if: do: pre:).freeze
+    BREAK_KEYWORDS = %w(if: do: pre: path:).freeze
 
     def parse_break arg
       mode = :sig
@@ -1271,6 +1271,7 @@ def repl_add_breakpoint arg
       expr = parse_break arg.strip
       cond = expr[:if]
       cmd = ['break', expr[:pre], expr[:do]] if expr[:pre] || expr[:do]
+      path = Regexp.compile(expr[:path]) if expr[:path]
 
       case expr[:sig]
       when /\A(\d+)\z/
@@ -1278,10 +1279,10 @@ def repl_add_breakpoint arg
       when /\A(.+)[:\s+](\d+)\z/
         add_line_breakpoint $1, $2.to_i, cond: cond, command: cmd
       when /\A(.+)([\.\#])(.+)\z/
-        @tc << [:breakpoint, :method, $1, $2, $3, cond, cmd]
+        @tc << [:breakpoint, :method, $1, $2, $3, cond, cmd, path]
         return :noretry
       when nil
-        add_check_breakpoint cond
+        add_check_breakpoint cond, path
       else
         @ui.puts "Unknown breakpoint format: #{arg}"
         @ui.puts
@@ -1293,8 +1294,9 @@ def repl_add_catch_breakpoint arg
       expr = parse_break arg.strip
       cond = expr[:if]
       cmd = ['catch', expr[:pre], expr[:do]] if expr[:pre] || expr[:do]
+      path = Regexp.compile(expr[:path]) if expr[:path]
 
-      bp = CatchBreakpoint.new(expr[:sig], cond: cond, command: cmd)
+      bp = CatchBreakpoint.new(expr[:sig], cond: cond, command: cmd, path: path)
       add_bp bp
     end
 
@@ -1302,8 +1304,9 @@ def repl_add_watch_breakpoint arg
       expr = parse_break arg.strip
       cond = expr[:if]
       cmd = ['watch', expr[:pre], expr[:do]] if expr[:pre] || expr[:do]
+      path = Regexp.compile(expr[:path]) if expr[:path]
 
-      @tc << [:breakpoint, :watch, expr[:sig], cond, cmd]
+      @tc << [:breakpoint, :watch, expr[:sig], cond, cmd, path]
     end
 
     def add_catch_breakpoint pat
@@ -1311,8 +1314,8 @@ def add_catch_breakpoint pat
       add_bp bp
     end
 
-    def add_check_breakpoint expr
-      bp = CheckBreakpoint.new(expr)
+    def add_check_breakpoint expr, path
+      bp = CheckBreakpoint.new(expr, path)
       add_bp bp
     end
 
diff --git a/lib/debug/thread_client.rb b/lib/debug/thread_client.rb
index 5161f6409..f7d913487 100644
--- a/lib/debug/thread_client.rb
+++ b/lib/debug/thread_client.rb
@@ -635,8 +635,8 @@ def class_method_map(classes)
     def make_breakpoint args
       case args.first
       when :method
-        klass_name, op, method_name, cond, cmd = args[1..]
-        bp = MethodBreakpoint.new(current_frame.binding, klass_name, op, method_name, cond: cond, command: cmd)
+        klass_name, op, method_name, cond, cmd, path = args[1..]
+        bp = MethodBreakpoint.new(current_frame.binding, klass_name, op, method_name, cond: cond, command: cmd, path: path)
         begin
           bp.enable
         rescue Exception => e
@@ -646,8 +646,8 @@ def make_breakpoint args
 
         bp
       when :watch
-        ivar, object, result, cond, command = args[1..]
-        WatchIVarBreakpoint.new(ivar, object, result, cond: cond, command: command)
+        ivar, object, result, cond, command, path = args[1..]
+        WatchIVarBreakpoint.new(ivar, object, result, cond: cond, command: command, path: path)
       else
         raise "unknown breakpoint: #{args}"
       end
@@ -890,7 +890,7 @@ def wait_next_action_
             bp = make_breakpoint args
             event! :result, :method_breakpoint, bp
           when :watch
-            ivar, cond, command = args[1..]
+            ivar, cond, command, path = args[1..]
             result = frame_eval(ivar)
 
             if @success_last_eval
@@ -900,7 +900,7 @@ def wait_next_action_
                 else
                   current_frame.self
                 end
-              bp = make_breakpoint [:watch, ivar, object, result, cond, command]
+              bp = make_breakpoint [:watch, ivar, object, result, cond, command, path]
               event! :result, :watch_breakpoint, bp
             else
               event! :result, nil
diff --git a/test/debug/break_test.rb b/test/debug/break_test.rb
index 42945a589..1fcd5bbc3 100644
--- a/test/debug/break_test.rb
+++ b/test/debug/break_test.rb
@@ -203,6 +203,37 @@ def test_debugger_doesnt_stop_when_other_instance_calls_the_inherited_method
         type "c"
       end
     end
+
+    class PathOptionTest < TestCase
+      def extra_file
+        <<~RUBY
+        Foo.new.bar
+        RUBY
+      end
+
+      def program(extra_file_path)
+        <<~RUBY
+         1| class Foo
+         2|   def bar; end
+         3| end
+         4|
+         5| Foo.new.bar
+         6|
+         7| load "#{extra_file_path}"
+        RUBY
+      end
+
+      def test_break_only_stops_when_path_matches
+        with_extra_tempfile do |extra_file|
+          debug_code(program(extra_file.path)) do
+            type "break Foo#bar path: #{extra_file.path}"
+            type 'c'
+            assert_line_text(/#{extra_file.path}/)
+            type 'c'
+          end
+        end
+      end
+    end
   end
 
   class BreakAtCMethodsTest < TestCase
@@ -275,6 +306,32 @@ def test_break_C_method_with_singleton_method
         type 'c'
       end
     end
+
+    class PathOptionTest < TestCase
+      def extra_file
+        <<~RUBY
+        1.abs
+        RUBY
+      end
+
+      def program(extra_file_path)
+        <<~RUBY
+        1| load "#{extra_file_path}"
+        2| 1.abs
+        RUBY
+      end
+
+      def test_break_only_stops_when_path_matches
+        with_extra_tempfile do |extra_file|
+          debug_code(program(extra_file.path)) do
+            type "break Integer#abs path: #{extra_file.path}"
+            type 'c'
+            assert_line_text(/#{extra_file.path}/)
+            type 'c'
+          end
+        end
+      end
+    end
   end
 
   class BreakAtCMethod2Test < TestCase
@@ -477,27 +534,6 @@ def test_conditional_breakpoint_stops_for_repeated_iterations
       end
     end
 
-    def test_conditional_breakpoint_stops_if_condition_is_true
-      debug_code program do
-        type 'break if: n == 1'
-        assert_line_text(/#0  BP - Check  n == 1/)
-        type 'continue'
-        assert_line_num 8
-        type 'quit'
-        type 'y'
-      end
-    end
-
-    def test_conditional_breakpoint_shows_error
-      debug_code(program) do
-        type 'break if: xyzzy'
-        type 'b 23'
-        type 'c'
-        assert_debuggee_line_text(/EVAL ERROR/)
-        type 'c'
-      end
-    end
-
     def test_conditional_breakpoint_stops_at_specified_location_if_condition_is_true
       debug_code(program) do
         type 'break 16 if: d == 1'
@@ -543,4 +579,69 @@ def test_break_with_space_between_file_and_line_stops_at_correct_place
       end
     end
   end
+
+  class ConditionalBreakTest < TestCase
+    def program
+      <<~RUBY
+     1| a = 1
+     2| a += 1
+     3| a += 2
+     4| a += 3
+     5|
+     6| binding.b
+      RUBY
+    end
+
+
+    def test_conditional_breakpoint_stops_if_condition_is_true
+      debug_code program do
+        type 'break if: a == 4'
+        assert_line_text(/#0  BP - Check  a == 4/)
+        type 'c'
+        assert_line_num 4
+        type 'c'
+        type 'c'
+      end
+    end
+
+    def test_conditional_breakpoint_shows_error
+      debug_code(program) do
+        type 'break if: xyzzy'
+        type 'c'
+        assert_debuggee_line_text(/EVAL ERROR/)
+        type 'c'
+      end
+    end
+
+    class PathOptionTest < TestCase
+      def extra_file
+        <<~RUBY
+        a = 100
+        b = 1
+        _ = 0
+        RUBY
+      end
+
+      def program(extra_file_path)
+        <<~RUBY
+       1| a = 200
+       2| b = 1
+       3| _ = 0
+       4| load "#{extra_file_path}"
+        RUBY
+      end
+
+      def test_conditional_breakpoint_only_stops_when_path_matches
+        with_extra_tempfile do |extra_file|
+          debug_code(program(extra_file.path)) do
+            type "break if: b == 1 path: #{extra_file.path}"
+            type 'c'
+            type 'a + b'
+            assert_line_text(/101/)
+            type 'c'
+          end
+        end
+      end
+    end
+  end
 end
diff --git a/test/debug/catch_test.rb b/test/debug/catch_test.rb
index a01ffd548..18293b7f2 100644
--- a/test/debug/catch_test.rb
+++ b/test/debug/catch_test.rb
@@ -148,4 +148,57 @@ def test_catch_with_namespace_stops_at_exception
       end
     end
   end
+
+  class PathOptionTest < TestCase
+    def extra_file
+      <<~RUBY
+        def bar
+          raise "bar"
+        rescue
+        end
+      RUBY
+    end
+
+    def program(extra_file_path)
+      <<~RUBY
+     1| load "#{extra_file_path}"
+     2|
+     3| def foo
+     4|   raise "foo"
+     5| rescue
+     6| end
+     7|
+     8| foo
+     9| bar
+      RUBY
+    end
+
+    def test_catch_only_stops_when_path_matches
+      with_extra_tempfile do |extra_file|
+        debug_code(program(extra_file.path)) do
+          type "catch RuntimeError path: #{extra_file.path}"
+          type 'c'
+          assert_line_text(/bar/)
+          type 'c'
+        end
+      end
+    end
+
+    def test_the_path_option_supersede_skip_path_config
+      with_extra_tempfile do |extra_file|
+        debug_code(program(extra_file.path)) do
+          type "config set skip_path #{extra_file.path}"
+          type 'c'
+        end
+
+        debug_code(program(extra_file.path)) do
+          type "config set skip_path #{extra_file.path}"
+          type "catch RuntimeError path: #{extra_file.path}"
+          type 'c'
+          assert_line_text(/bar/)
+          type 'c'
+        end
+      end
+    end
+  end
 end
diff --git a/test/debug/watch_test.rb b/test/debug/watch_test.rb
index 940b1117c..e4b4bf892 100644
--- a/test/debug/watch_test.rb
+++ b/test/debug/watch_test.rb
@@ -103,5 +103,43 @@ def test_condition_is_evaluated_in_the_watched_object
         end
       end
     end
+
+    class PathOptionTest < TestCase
+      def extra_file
+        <<~RUBY
+        STUDENT.age = 25
+        _ = 1 # for the debugger to stop
+        RUBY
+      end
+
+      def program(extra_file_path)
+        <<~RUBY
+         1| class Student
+         2|   attr_accessor :age
+         3|
+         4|   def initialize
+         5|     binding.b(do: "watch @age path: #{extra_file_path}")
+         6|   end
+         7| end
+         8|
+         9| STUDENT = Student.new
+        10|
+        11| load "#{extra_file_path}"
+        12|
+        13| STUDENT.age = 30
+        14| _ = 1
+        RUBY
+      end
+
+      def test_watch_only_stops_when_path_matches
+        with_extra_tempfile do |extra_file|
+          debug_code(program(extra_file.path)) do
+            type 'c'
+            assert_line_text(/@age =  -> 25/)
+            type 'c'
+          end
+        end
+      end
+    end
   end
 end
diff --git a/test/support/test_case.rb b/test/support/test_case.rb
index a8740eb95..7baee0504 100644
--- a/test/support/test_case.rb
+++ b/test/support/test_case.rb
@@ -2,6 +2,7 @@
 
 require 'test/unit'
 require 'tempfile'
+require 'securerandom'
 
 require_relative 'utils'
 require_relative 'assertions'
@@ -23,5 +24,15 @@ def remove_temp_file
       File.unlink(@temp_file) if @temp_file
       @temp_file = nil
     end
+
+    def with_extra_tempfile
+      t = Tempfile.create([SecureRandom.hex(5), '.rb']).tap do |f|
+        f.write(extra_file)
+        f.close
+      end
+      yield t
+    ensure
+      File.unlink t if t
+    end
   end
 end