diff --git a/CHANGELOG.md b/CHANGELOG.md
index a95b2901..3b4d5528 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,8 @@ The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.1.0/),
 and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
 
 ## [Unreleased]
+### Fixed
+- Fixed the sleep timer freezing and the app closing when the timer was set again and then canceled ([#345])
 
 ## [1.8.1] - 2026-02-14
 ### Changed
@@ -124,6 +126,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 [#261]: https://github.com/FossifyOrg/Music-Player/issues/261
 [#269]: https://github.com/FossifyOrg/Music-Player/issues/269
 [#298]: https://github.com/FossifyOrg/Music-Player/issues/298
+[#345]: https://github.com/FossifyOrg/Music-Player/issues/345
 [#361]: https://github.com/FossifyOrg/Music-Player/issues/361
 
 [Unreleased]: https://github.com/FossifyOrg/Music-Player/compare/1.8.1...HEAD
diff --git a/app/src/main/kotlin/org/fossify/musicplayer/activities/MainActivity.kt b/app/src/main/kotlin/org/fossify/musicplayer/activities/MainActivity.kt
index 9865320b..13437365 100644
--- a/app/src/main/kotlin/org/fossify/musicplayer/activities/MainActivity.kt
+++ b/app/src/main/kotlin/org/fossify/musicplayer/activities/MainActivity.kt
@@ -481,14 +481,14 @@ class MainActivity : SimpleMusicActivity() {
     private fun startSleepTimer() {
         binding.sleepTimerHolder.fadeIn()
         withPlayer {
-            sendCommand(CustomCommands.TOGGLE_SLEEP_TIMER)
+            sendCommand(CustomCommands.START_SLEEP_TIMER)
         }
     }
 
     private fun stopSleepTimer() {
         binding.sleepTimerHolder.fadeOut()
         withPlayer {
-            sendCommand(CustomCommands.TOGGLE_SLEEP_TIMER)
+            sendCommand(CustomCommands.STOP_SLEEP_TIMER)
         }
     }
 
diff --git a/app/src/main/kotlin/org/fossify/musicplayer/playback/CustomCommands.kt b/app/src/main/kotlin/org/fossify/musicplayer/playback/CustomCommands.kt
index 2b01e934..63418094 100644
--- a/app/src/main/kotlin/org/fossify/musicplayer/playback/CustomCommands.kt
+++ b/app/src/main/kotlin/org/fossify/musicplayer/playback/CustomCommands.kt
@@ -12,7 +12,8 @@ import org.fossify.musicplayer.helpers.PATH
 enum class CustomCommands(val customAction: String) {
     CLOSE_PLAYER(customAction = PATH + "CLOSE_PLAYER"),
     RELOAD_CONTENT(customAction = PATH + "RELOAD_CONTENT"),
-    TOGGLE_SLEEP_TIMER(customAction = PATH + "TOGGLE_SLEEP_TIMER"),
+    START_SLEEP_TIMER(customAction = PATH + "START_SLEEP_TIMER"),
+    STOP_SLEEP_TIMER(customAction = PATH + "STOP_SLEEP_TIMER"),
     SET_NEXT_ITEM(customAction = PATH + "SET_NEXT_ITEM"),
     SET_SHUFFLE_ORDER(customAction = PATH + "SET_SHUFFLE_ORDER");
 
diff --git a/app/src/main/kotlin/org/fossify/musicplayer/playback/MediaSessionCallback.kt b/app/src/main/kotlin/org/fossify/musicplayer/playback/MediaSessionCallback.kt
index 82f589ba..8dc635c0 100644
--- a/app/src/main/kotlin/org/fossify/musicplayer/playback/MediaSessionCallback.kt
+++ b/app/src/main/kotlin/org/fossify/musicplayer/playback/MediaSessionCallback.kt
@@ -74,7 +74,8 @@ internal fun PlaybackService.getMediaSessionCallback() = object : MediaLibrarySe
         when (command) {
             CustomCommands.CLOSE_PLAYER -> stopService()
             CustomCommands.RELOAD_CONTENT -> reloadContent()
-            CustomCommands.TOGGLE_SLEEP_TIMER -> toggleSleepTimer()
+            CustomCommands.START_SLEEP_TIMER -> startSleepTimer()
+            CustomCommands.STOP_SLEEP_TIMER -> stopSleepTimer()
             CustomCommands.SET_SHUFFLE_ORDER -> setShuffleOrder(args)
             CustomCommands.SET_NEXT_ITEM -> setNextItem(args)
         }
diff --git a/app/src/main/kotlin/org/fossify/musicplayer/playback/SleepTimer.kt b/app/src/main/kotlin/org/fossify/musicplayer/playback/SleepTimer.kt
index c468dd51..cfbb1a71 100644
--- a/app/src/main/kotlin/org/fossify/musicplayer/playback/SleepTimer.kt
+++ b/app/src/main/kotlin/org/fossify/musicplayer/playback/SleepTimer.kt
@@ -5,17 +5,8 @@ import org.fossify.musicplayer.extensions.config
 import org.fossify.musicplayer.models.Events
 import org.greenrobot.eventbus.EventBus
 
-private var isActive = false
 private var sleepTimer: CountDownTimer? = null
 
-internal fun PlaybackService.toggleSleepTimer() {
-    if (isActive) {
-        stopSleepTimer()
-    } else {
-        startSleepTimer()
-    }
-}
-
 internal fun PlaybackService.startSleepTimer() {
     val millisInFuture = config.sleepInTS - System.currentTimeMillis() + 1000L
     sleepTimer?.cancel()
@@ -34,12 +25,10 @@ internal fun PlaybackService.startSleepTimer() {
     }
 
     sleepTimer?.start()
-    isActive = true
 }
 
 internal fun PlaybackService.stopSleepTimer() {
     sleepTimer?.cancel()
     sleepTimer = null
-    isActive = false
     config.sleepInTS = 0
 }