diff --git a/CHANGELOG.md b/CHANGELOG.md
index d1e00dcd..212f6329 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,7 @@ All notable changes to the Keyboard Macro Bata extension will be documented in t
   - Added Visual Studio Keymap support. (See [Keymap Wrappers](keymap-wrapper/README.md)) [#24](https://github.com/tshino/vscode-kb-macro/pull/24)
   - Added emacs-style prefix-arguments support through the keymap wrapper for Awesome Emacs Keymap. (See [Keymap Wrappers](keymap-wrapper/README.md)) [#25](https://github.com/tshino/vscode-kb-macro/pull/25)
   - Added new `kb-macro.abortPlayback` command. [#26](https://github.com/tshino/vscode-kb-macro/pull/26)
+  - Added new `kb-macro.playing` 'when'-clause context, which evaluates true when the macro playback is ongoing. [#27](https://github.com/tshino/vscode-kb-macro/pull/27)
 - Update
   - (Internal) Added colors to warnings and errors on the console output of generator scripts.
 
diff --git a/src/extension.js b/src/extension.js
index 6daa0ac1..e297a84d 100644
--- a/src/extension.js
+++ b/src/extension.js
@@ -67,6 +67,17 @@ function activate(context) {
             }
         }
     );
+    addEventListener(
+        keyboardMacro.onChangePlaybackState,
+        function({ playing, reason }) {
+            const contextName = ContextPrefix + 'playing';
+            vscode.commands.executeCommand('setContext', contextName, playing);
+
+            if (playing === false && reason === keyboardMacro.PlaybackStateReason.Abort) {
+                vscode.window.setStatusBarMessage('Playback aborted!', 3000);
+            }
+        }
+    );
     addEventListener(
         helperContext.onChangeContext,
         function({ name, value }) {
diff --git a/src/keyboard_macro.js b/src/keyboard_macro.js
index 413849e2..7719716c 100644
--- a/src/keyboard_macro.js
+++ b/src/keyboard_macro.js
@@ -8,8 +8,14 @@ const KeyboardMacro = function({ awaitController }) {
         Cancel: 1,
         Finish: 2
     };
+    const PlaybackStateReason = {
+        Start: 0,
+        Abort: 1,
+        Finish: 2
+    };
 
     let onChangeRecordingStateCallback = null;
+    let onChangePlaybackStateCallback = null;
     let onBeginWrappedCommandCallback = null;
     let onEndWrappedCommandCallback = null;
     let recording = false;
@@ -56,11 +62,21 @@ const KeyboardMacro = function({ awaitController }) {
     const onChangeRecordingState = function(callback) {
         onChangeRecordingStateCallback = callback;
     };
-    const notifyNewState = function(reason) {
+    const changeRecordingState = function(newState, reason) {
+        recording = newState;
         if (onChangeRecordingStateCallback) {
             onChangeRecordingStateCallback({ recording, reason });
         }
     };
+    const onChangePlaybackState = function(callback) {
+        onChangePlaybackStateCallback = callback;
+    };
+    const changePlaybackState = function(newState, reason) {
+        playing = newState;
+        if (onChangePlaybackStateCallback) {
+            onChangePlaybackStateCallback({ playing, reason });
+        }
+    };
     const onBeginWrappedCommand = function(callback) {
         onBeginWrappedCommandCallback = callback;
     };
@@ -75,22 +91,19 @@ const KeyboardMacro = function({ awaitController }) {
     const startRecording = makeGuardedCommandSync(function() {
         if (!recording) {
             sequence.clear();
-            recording = true;
-            notifyNewState(RecordingStateReason.Start);
+            changeRecordingState(true, RecordingStateReason.Start);
         }
     });
     const cancelRecording = makeGuardedCommandSync(function() {
         if (recording) {
             sequence.clear();
-            recording = false;
-            notifyNewState(RecordingStateReason.Cancel);
+            changeRecordingState(false, RecordingStateReason.Cancel);
         }
     });
     const finishRecording = makeGuardedCommandSync(function() {
         if (recording) {
             sequence.optimize();
-            recording = false;
-            notifyNewState(RecordingStateReason.Finish);
+            changeRecordingState(false, RecordingStateReason.Finish);
         }
     });
 
@@ -128,7 +141,7 @@ const KeyboardMacro = function({ awaitController }) {
 
     const playback = makeGuardedCommand(async function(args) {
         if (!recording) {
-            playing = true;
+            changePlaybackState(true, PlaybackStateReason.Start);
             shouldAbortPlayback = false;
             args = (args && typeof(args) === 'object') ? args : {};
             const repeat = typeof(args.repeat) === 'number' ? args.repeat : 1;
@@ -144,8 +157,12 @@ const KeyboardMacro = function({ awaitController }) {
             }
         }
     }, function teardown() {
-        playing = false;
-        shouldAbortPlayback = false;
+        if (shouldAbortPlayback) {
+            changePlaybackState(false, PlaybackStateReason.Abort);
+            shouldAbortPlayback = false;
+        } else {
+            changePlaybackState(false, PlaybackStateReason.Finish);
+        }
     });
 
     const abortPlayback = async function() {
@@ -191,7 +208,9 @@ const KeyboardMacro = function({ awaitController }) {
 
     return {
         RecordingStateReason,
+        PlaybackStateReason,
         onChangeRecordingState,
+        onChangePlaybackState,
         onBeginWrappedCommand,
         onEndWrappedCommand,
         registerInternalCommand,
diff --git a/test/suite/keyboard_macro.test.js b/test/suite/keyboard_macro.test.js
index e21a004e..53c9dfd9 100644
--- a/test/suite/keyboard_macro.test.js
+++ b/test/suite/keyboard_macro.test.js
@@ -36,6 +36,36 @@ describe('KeybaordMacro', () => {
             ]);
         });
     });
+    describe('onChangePlaybackState', () => {
+        beforeEach(async () => {
+            keyboardMacro.cancelRecording();
+        });
+        it('should set callback function', async () => {
+            const logs = [];
+            keyboardMacro.onChangePlaybackState((event) => {
+                logs.push(event);
+            });
+            keyboardMacro.registerInternalCommand('internal:delay', async () => {
+                await TestUtil.sleep(100);
+            });
+
+            keyboardMacro.startRecording();
+            keyboardMacro.push({ command: 'internal:delay' });
+            keyboardMacro.finishRecording();
+
+            await keyboardMacro.playback();
+            const promise = keyboardMacro.playback();
+            keyboardMacro.abortPlayback();
+            await promise;
+
+            assert.deepStrictEqual(logs, [
+                { playing: true, reason: keyboardMacro.PlaybackStateReason.Start },
+                { playing: false, reason: keyboardMacro.PlaybackStateReason.Finish },
+                { playing: true, reason: keyboardMacro.PlaybackStateReason.Start },
+                { playing: false, reason: keyboardMacro.PlaybackStateReason.Abort }
+            ]);
+        });
+    });
     describe('onBeginWrappedCommand, onEndWrappedCommand', () => {
         const logs = [];
         beforeEach(async () => {