diff --git a/executor.go b/executor.go
index 279c416..f1c948c 100644
--- a/executor.go
+++ b/executor.go
@@ -549,8 +549,8 @@ func (e *Executor) runTaskOnHost(ctx context.Context, host string, hosts []strin
 		return coreerr.E("Executor.runTaskOnHost", sprintf("get client for %s", executionHost), err)
 	}
 
-	// Handle loops
-	if task.Loop != nil {
+	// Handle loops, including legacy with_file syntax.
+	if task.Loop != nil || task.WithFile != nil {
 		return e.runLoop(ctx, host, client, task, play)
 	}
 
@@ -704,7 +704,18 @@ func shouldRetryTask(task *Task, host string, e *Executor, result *TaskResult) b
 
 // runLoop handles task loops.
 func (e *Executor) runLoop(ctx context.Context, host string, client sshExecutorClient, task *Task, play *Play) error {
-	items := e.resolveLoop(task.Loop, host)
+	var (
+		items []any
+		err   error
+	)
+	if task.WithFile != nil {
+		items, err = e.resolveWithFileLoop(task.WithFile, host, task)
+	} else {
+		items = e.resolveLoop(task.Loop, host)
+	}
+	if err != nil {
+		return err
+	}
 
 	loopVar := "item"
 	if task.LoopControl != nil && task.LoopControl.LoopVar != "" {
@@ -817,6 +828,61 @@ func (e *Executor) runLoop(ctx context.Context, host string, client sshExecutorC
 	return nil
 }
 
+// resolveWithFileLoop resolves legacy with_file loop items into file contents.
+func (e *Executor) resolveWithFileLoop(loop any, host string, task *Task) ([]any, error) {
+	var paths []string
+
+	switch v := loop.(type) {
+	case []any:
+		paths = make([]string, 0, len(v))
+		for _, item := range v {
+			s := sprintf("%v", item)
+			if s = e.templateString(s, host, task); s != "" {
+				paths = append(paths, s)
+			}
+		}
+	case []string:
+		paths = make([]string, 0, len(v))
+		for _, item := range v {
+			if s := e.templateString(item, host, task); s != "" {
+				paths = append(paths, s)
+			}
+		}
+	case string:
+		if s := e.templateString(v, host, task); s != "" {
+			paths = []string{s}
+		}
+	default:
+		return nil, nil
+	}
+
+	items := make([]any, 0, len(paths))
+	for _, filePath := range paths {
+		content, err := e.readLoopFile(filePath)
+		if err != nil {
+			return nil, err
+		}
+		items = append(items, content)
+	}
+
+	return items, nil
+}
+
+func (e *Executor) readLoopFile(filePath string) (string, error) {
+	candidates := []string{filePath}
+	if e.parser != nil && e.parser.basePath != "" {
+		candidates = append([]string{joinPath(e.parser.basePath, filePath)}, candidates...)
+	}
+
+	for _, candidate := range candidates {
+		if data, err := coreio.Local.Read(candidate); err == nil {
+			return data, nil
+		}
+	}
+
+	return "", coreerr.E("Executor.readLoopFile", "read file "+filePath, nil)
+}
+
 // isCheckModeSafeTask reports whether a task can run without changing state
 // during check mode.
 func isCheckModeSafeTask(task *Task) bool {
diff --git a/executor_test.go b/executor_test.go
index 3f45b8e..95f0e54 100644
--- a/executor_test.go
+++ b/executor_test.go
@@ -231,6 +231,40 @@ func TestExecutor_RunTaskOnHost_Good_DelegateToUsesDelegatedClient(t *testing.T)
 	assert.Equal(t, 1, mock.commandCount())
 }
 
+func TestExecutor_RunTaskOnHosts_Good_WithFileUsesFileContents(t *testing.T) {
+	dir := t.TempDir()
+	require.NoError(t, writeTestFile(joinPath(dir, "fragments", "hello.txt"), []byte("hello from file"), 0644))
+
+	e := NewExecutor(dir)
+	mock := NewMockSSHClient()
+	e.SetInventoryDirect(&Inventory{
+		All: &InventoryGroup{
+			Hosts: map[string]*Host{
+				"host1": {},
+			},
+		},
+	})
+	e.clients["host1"] = mock
+
+	task := &Task{
+		Name:     "Read file loop",
+		Module:   "debug",
+		Args:     map[string]any{"msg": "{{ item }}"},
+		Register: "debug_result",
+		WithFile: []any{
+			"fragments/hello.txt",
+		},
+	}
+
+	err := e.runTaskOnHosts(context.Background(), []string{"host1"}, task, &Play{})
+	require.NoError(t, err)
+
+	require.NotNil(t, e.results["host1"])
+	require.NotNil(t, e.results["host1"]["debug_result"])
+	require.Len(t, e.results["host1"]["debug_result"].Results, 1)
+	assert.Equal(t, "hello from file", e.results["host1"]["debug_result"].Results[0].Msg)
+}
+
 func TestExecutor_ExecuteModule_Good_ShortFormCommunityAlias(t *testing.T) {
 	e := NewExecutor("/tmp")
 	mock := NewMockSSHClient()
diff --git a/parser.go b/parser.go
index de2a546..064b01c 100644
--- a/parser.go
+++ b/parser.go
@@ -388,6 +388,11 @@ func (t *Task) UnmarshalYAML(node *yaml.Node) error {
 		}
 	}
 
+	// Preserve with_file so the executor can resolve file contents at runtime.
+	if files, ok := m["with_file"]; ok && t.WithFile == nil {
+		t.WithFile = files
+	}
+
 	return nil
 }
 
diff --git a/types.go b/types.go
index fc9cba0..8300a05 100644
--- a/types.go
+++ b/types.go
@@ -114,6 +114,7 @@ type Task struct {
 	// Include/import directives
 	IncludeTasks string `yaml:"include_tasks,omitempty"`
 	ImportTasks  string `yaml:"import_tasks,omitempty"`
+	WithFile     any    `yaml:"with_file,omitempty"`
 	IncludeRole  *struct {
 		Name      string         `yaml:"name"`
 		TasksFrom string         `yaml:"tasks_from,omitempty"`
diff --git a/types_test.go b/types_test.go
index dabba99..5f2e920 100644
--- a/types_test.go
+++ b/types_test.go
@@ -204,6 +204,25 @@ with_dict:
 	assert.Equal(t, "two", second["value"])
 }
 
+func TestTypes_Task_UnmarshalYAML_Good_WithFile(t *testing.T) {
+	input := `
+name: Read files
+debug:
+  msg: "{{ item }}"
+with_file:
+  - templates/a.txt
+  - templates/b.txt
+`
+	var task Task
+	err := yaml.Unmarshal([]byte(input), &task)
+
+	require.NoError(t, err)
+	require.NotNil(t, task.WithFile)
+	files, ok := task.WithFile.([]any)
+	require.True(t, ok)
+	assert.Equal(t, []any{"templates/a.txt", "templates/b.txt"}, files)
+}
+
 func TestTypes_Task_UnmarshalYAML_Good_WithNotify(t *testing.T) {
 	input := `
 name: Install package