diff --git a/CHANGELOG.md b/CHANGELOG.md
index c3a175277..1eb58a405 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,9 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/),
 
 ## [UNRELEASED]
 
+### Added
+- Added `rollback` ability to undo on matching status
+
 ## [1.9.1] - 2025-10-22
 
 ### Added
diff --git a/docs/basics/setup.md b/docs/basics/setup.md
index 273e0abc8..070e071f5 100644
--- a/docs/basics/setup.md
+++ b/docs/basics/setup.md
@@ -24,6 +24,22 @@ end
 IncompleteTask.execute #=> raises CMDx::UndefinedMethodError
 ```
 
+## Rollback
+
+Undo any operations linked to the given status, helping to restore a pristine state.
+
+```ruby
+class ValidateDocument < CMDx::Task
+  def work
+    # Your logic here...
+  end
+
+  def rollback
+    # Your undo logic...
+  end
+end
+```
+
 ## Inheritance
 
 Share configuration across tasks using inheritance:
@@ -65,3 +81,4 @@ Tasks follow a predictable execution pattern:
 | **Execution** | `executing` | `success`/`failed`/`skipped` | `work` method runs |
 | **Completion** | `executed` | `success`/`failed`/`skipped` | Result finalized |
 | **Freezing** | `executed` | `success`/`failed`/`skipped` | Task becomes immutable |
+| **Rollback** | `executed` | `failed`/`skipped` | Work undone |
diff --git a/docs/getting_started.md b/docs/getting_started.md
index aa695c197..0706956a3 100644
--- a/docs/getting_started.md
+++ b/docs/getting_started.md
@@ -78,6 +78,16 @@ CMDx.configure do |config|
 end
 ```
 
+### Rollpoints
+
+Control when a `rollback` of task execution is called.
+
+```ruby
+CMDx.configure do |config|
+  config.task_rollpoints = ["failed"] # String or Array[String]
+end
+```
+
 ### Backtraces
 
 Enable detailed backtraces for non-fault exceptions to improve debugging. Optionally clean up stack traces to remove framework noise.
@@ -245,6 +255,7 @@ class GenerateInvoice < CMDx::Task
   settings(
     # Global configuration overrides
     task_breakpoints: ["failed"],                # Breakpoint override
+    task_rollpoints: ["failed", "skipped"],      # Rollpoint override
     workflow_breakpoints: [],                    # Breakpoint override
     backtrace: true,                             # Toggle backtrace
     backtrace_cleaner: ->(bt) { bt[0..5] },      # Backtrace cleaner
@@ -252,6 +263,7 @@ class GenerateInvoice < CMDx::Task
 
     # Task configuration settings
     breakpoints: ["failed"],                     # Contextual pointer for :task_breakpoints and :workflow_breakpoints
+    rollpoints: ["failed", "skipped"],           # Contextual pointer for :task_rollpoints
     log_level: :info,                            # Log level override
     log_formatter: CMDx::LogFormatters::Json.new # Log formatter override
     tags: ["billing", "financial"],              # Logging tags
diff --git a/lib/cmdx/configuration.rb b/lib/cmdx/configuration.rb
index bcaf6ce42..af04ec813 100644
--- a/lib/cmdx/configuration.rb
+++ b/lib/cmdx/configuration.rb
@@ -9,6 +9,9 @@ class Configuration
     # @rbs DEFAULT_BREAKPOINTS: Array[String]
     DEFAULT_BREAKPOINTS = %w[failed].freeze
 
+    # @rbs DEFAULT_ROLLPOINTS: Array[String]
+    DEFAULT_ROLLPOINTS = %w[failed].freeze
+
     # Returns the middleware registry for task execution.
     #
     # @return [MiddlewareRegistry] The middleware registry
@@ -59,6 +62,16 @@ class Configuration
     # @rbs @task_breakpoints: Array[String]
     attr_accessor :task_breakpoints
 
+    # Returns the statuses that trigger a task execution rollback.
+    #
+    # @return [Array<String>] Array of status names that trigger rollback
+    #
+    # @example
+    #   config.task_rollpoints = ["failed", "skipped"]
+    #
+    # @rbs @task_rollpoints: Array[String]
+    attr_accessor :task_rollpoints
+
     # Returns the breakpoint statuses for workflow execution interruption.
     #
     # @return [Array<String>] Array of status names that trigger breakpoints
@@ -130,6 +143,7 @@ def initialize
       @validators = ValidatorRegistry.new
 
       @task_breakpoints = DEFAULT_BREAKPOINTS
+      @task_rollpoints = DEFAULT_ROLLPOINTS
       @workflow_breakpoints = DEFAULT_BREAKPOINTS
 
       @backtrace = false
@@ -161,6 +175,7 @@ def to_h
         coercions: @coercions,
         validators: @validators,
         task_breakpoints: @task_breakpoints,
+        task_rollpoints: @task_rollpoints,
         workflow_breakpoints: @workflow_breakpoints,
         backtrace: @backtrace,
         backtrace_cleaner: @backtrace_cleaner,
diff --git a/lib/cmdx/executor.rb b/lib/cmdx/executor.rb
index bf90aaee4..ebdea7b06 100644
--- a/lib/cmdx/executor.rb
+++ b/lib/cmdx/executor.rb
@@ -118,15 +118,12 @@ def execute!
     #
     # @return [Boolean] Whether execution should halt
     #
-    # @example
-    #   halt_execution?(fault_exception)
-    #
     # @rbs (Exception exception) -> bool
     def halt_execution?(exception)
-      breakpoints = task.class.settings[:breakpoints] || task.class.settings[:task_breakpoints]
-      breakpoints = Array(breakpoints).map(&:to_s).uniq
+      statuses = task.class.settings[:breakpoints] || task.class.settings[:task_breakpoints]
+      statuses = Array(statuses).map(&:to_s).uniq
 
-      breakpoints.include?(exception.result.status)
+      statuses.include?(exception.result.status)
     end
 
     # Determines if execution should be retried based on retry configuration.
@@ -135,9 +132,6 @@ def halt_execution?(exception)
     #
     # @return [Boolean] Whether execution should be retried
     #
-    # @example
-    #   retry_execution?(standard_error)
-    #
     # @rbs (Exception exception) -> bool
     def retry_execution?(exception)
       available_retries = (task.class.settings[:retries] || 0).to_i
@@ -169,9 +163,6 @@ def retry_execution?(exception)
     #
     # @raise [Exception] The provided exception
     #
-    # @example
-    #   raise_exception(standard_error)
-    #
     # @rbs (Exception exception) -> void
     def raise_exception(exception)
       Chain.clear
@@ -244,7 +235,7 @@ def post_execution!
       invoke_callbacks(:on_bad) if task.result.bad?
     end
 
-    # Finalizes execution by freezing the task and logging results.
+    # Finalizes execution by freezing the task, logging results, and rolling back work.
     #
     # @rbs () -> Result
     def finalize_execution!
@@ -253,6 +244,8 @@ def finalize_execution!
 
       freeze_execution!
       clear_chain!
+
+      rollback_execution!
     end
 
     # Logs the execution result at the configured log level.
@@ -309,5 +302,18 @@ def clear_chain!
       Chain.clear
     end
 
+    # Rolls back the work of a task.
+    #
+    # @rbs () -> void
+    def rollback_execution!
+      return unless task.respond_to?(:rollback)
+
+      statuses = task.class.settings[:rollpoints] || task.class.settings[:task_rollpoints]
+      statuses = Array(statuses).map(&:to_s).uniq
+      return unless statuses.include?(task.result.status)
+
+      task.rollback
+    end
+
   end
 end
diff --git a/spec/cmdx/executor_spec.rb b/spec/cmdx/executor_spec.rb
index 70d128a29..fe3185f38 100644
--- a/spec/cmdx/executor_spec.rb
+++ b/spec/cmdx/executor_spec.rb
@@ -562,4 +562,131 @@
       end
     end
   end
+
+  describe "#rollback_execution!" do
+    context "when task does not respond to rollback" do
+      before do
+        allow(task).to receive(:respond_to?).with(:rollback).and_return(false)
+        allow(task.result).to receive(:status).and_return("failed")
+      end
+
+      it "does not call rollback" do
+        expect(task).not_to receive(:rollback)
+
+        worker.send(:rollback_execution!)
+      end
+    end
+
+    context "when task responds to rollback" do
+      before do
+        allow(task).to receive(:respond_to?).with(:rollback).and_return(true)
+        allow(task).to receive(:rollback)
+      end
+
+      context "when rollpoints setting exists" do
+        before do
+          allow(task.class).to receive(:settings).and_return({ rollpoints: %w[failed skipped] })
+        end
+
+        context "when result status is in rollpoints" do
+          before do
+            allow(task.result).to receive(:status).and_return("failed")
+          end
+
+          it "calls rollback" do
+            expect(task).to receive(:rollback)
+
+            worker.send(:rollback_execution!)
+          end
+        end
+
+        context "when result status is not in rollpoints" do
+          before do
+            allow(task.result).to receive(:status).and_return("success")
+          end
+
+          it "does not call rollback" do
+            expect(task).not_to receive(:rollback)
+
+            worker.send(:rollback_execution!)
+          end
+        end
+      end
+
+      context "when task_rollpoints setting exists" do
+        before do
+          allow(task.class).to receive(:settings).and_return({ task_rollpoints: [:failed] })
+        end
+
+        it "converts symbols to strings and calls rollback" do
+          allow(task.result).to receive(:status).and_return("failed")
+
+          expect(task).to receive(:rollback)
+
+          worker.send(:rollback_execution!)
+        end
+      end
+
+      context "when no rollpoints are configured" do
+        before do
+          allow(task.class).to receive(:settings).and_return({})
+          allow(task.result).to receive(:status).and_return("failed")
+        end
+
+        it "does not call rollback" do
+          expect(task).not_to receive(:rollback)
+
+          worker.send(:rollback_execution!)
+        end
+      end
+
+      context "when rollpoints is nil" do
+        before do
+          allow(task.class).to receive(:settings).and_return({ rollpoints: nil })
+          allow(task.result).to receive(:status).and_return("failed")
+        end
+
+        it "does not call rollback" do
+          expect(task).not_to receive(:rollback)
+
+          worker.send(:rollback_execution!)
+        end
+      end
+
+      context "with duplicate rollpoints" do
+        before do
+          allow(task.class).to receive(:settings).and_return({ rollpoints: ["failed", "failed", :failed] })
+          allow(task.result).to receive(:status).and_return("failed")
+        end
+
+        it "removes duplicates after string conversion and calls rollback" do
+          expect(task).to receive(:rollback).once
+
+          worker.send(:rollback_execution!)
+        end
+      end
+
+      context "with multiple statuses in rollpoints" do
+        before do
+          allow(task.class).to receive(:settings).and_return({ rollpoints: %w[failed skipped] })
+        end
+
+        it "calls rollback when status is failed" do
+          allow(task.result).to receive(:status).and_return("failed")
+
+          expect(task).to receive(:rollback)
+
+          worker.send(:rollback_execution!)
+        end
+
+        it "calls rollback when status is skipped" do
+          allow(task.result).to receive(:status).and_return("skipped")
+
+          expect(task).to receive(:rollback)
+
+          worker.send(:rollback_execution!)
+        end
+      end
+    end
+  end
 end