diff --git a/README.md b/README.md
index b1a8559..267d7d3 100644
--- a/README.md
+++ b/README.md
@@ -19,7 +19,7 @@ Maven
 <dependency>
   <groupId>gg.flyte</groupId>
   <artifactId>twilight</artifactId>
-  <version>1.0.25</version>
+  <version>1.0.26</version>
 </dependency>
 ```
 
@@ -29,14 +29,14 @@ maven {
     url "https://repo.flyte.gg/releases"
 }
 
-implementation "gg.flyte:twilight:1.0.25"
+implementation "gg.flyte:twilight:1.0.26"
 ```
 
 Gradle (Kotlin DSL)
 ```kotlin
 maven("https://repo.flyte.gg/releases")
 
-implementation("gg.flyte:twilight:1.0.25")
+implementation("gg.flyte:twilight:1.0.26")
 ```
 
 Certain features of Twilight require configuration, which can be done via the Twilight class. To setup a Twilight class instance, you can use the `twilight` method as shown below:
diff --git a/build.gradle.kts b/build.gradle.kts
index 51b46cd..f4d895e 100644
--- a/build.gradle.kts
+++ b/build.gradle.kts
@@ -5,7 +5,7 @@ plugins {
 }
 
 group = "gg.flyte"
-version = "1.0.25"
+version = "1.0.26"
 
 repositories {
     mavenCentral()
diff --git a/src/main/kotlin/gg/flyte/twilight/event/Event.kt b/src/main/kotlin/gg/flyte/twilight/event/Event.kt
index 317aa3b..051fa46 100644
--- a/src/main/kotlin/gg/flyte/twilight/event/Event.kt
+++ b/src/main/kotlin/gg/flyte/twilight/event/Event.kt
@@ -1,10 +1,12 @@
 package gg.flyte.twilight.event
 
 import gg.flyte.twilight.Twilight
+import gg.flyte.twilight.event.custom.admin.listener.OpEventListener
 import gg.flyte.twilight.event.custom.interact.listener.InteractEventListener
 import gg.flyte.twilight.extension.applyForEach
 import gg.flyte.twilight.inventory.GUIListener
 import org.bukkit.event.*
+import org.bukkit.scheduler.BukkitTask
 import java.time.Instant
 
 /**
@@ -47,8 +49,12 @@ open class CustomTwilightListener {
      * The list of events registered to this custom Twilight Event
      */
     val events = mutableListOf<TwilightListener>()
+    val runnables = mutableListOf<BukkitTask>()
 
-    fun unregister() = events.applyForEach { unregister() }
+    fun unregister() {
+        events.applyForEach { unregister() }
+        runnables.applyForEach { cancel() }
+    }
 }
 
 /**
@@ -113,6 +119,7 @@ open class TwilightEvent(async: Boolean = false) : Event(async), Cancellable {
  */
 val customEvents = listOf<CustomTwilightListener>(
     GUIListener,
-    InteractEventListener
+    InteractEventListener,
+    OpEventListener
 )
 
diff --git a/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerDeopEvent.kt b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerDeopEvent.kt
new file mode 100644
index 0000000..1f5eb2d
--- /dev/null
+++ b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerDeopEvent.kt
@@ -0,0 +1,32 @@
+package gg.flyte.twilight.event.custom.admin
+
+import gg.flyte.twilight.event.TwilightEvent
+import org.bukkit.Bukkit
+import org.bukkit.OfflinePlayer
+import org.bukkit.block.Block
+import org.bukkit.block.BlockFace
+import org.bukkit.entity.Player
+import org.bukkit.event.block.Action
+import org.bukkit.inventory.ItemStack
+import org.bukkit.util.Vector
+import java.util.*
+
+/**
+ * Represents an event that occurs when a player is de-op'd (de-promoted from operator status).
+ * This event contains information about the affected player's UUID and name.
+ */
+class PlayerDeopEvent(
+    val uuid: UUID,  // The UUID of the player being de-op'd.
+    val name: String  // The name of the player being de-op'd.
+) : TwilightEvent() {
+    /**
+     * Represents the offline player associated with this event.
+     */
+    val offlinePlayer: OfflinePlayer = Bukkit.getOfflinePlayer(uuid)
+
+    /**
+     * Represents the online player associated with this event, if available.
+     * This property will be null if the player is not currently online.
+     */
+    val player: Player? = if (offlinePlayer.isOnline) offlinePlayer.player else null
+}
\ No newline at end of file
diff --git a/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerOpChangeEvent.kt b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerOpChangeEvent.kt
new file mode 100644
index 0000000..3cb4b7c
--- /dev/null
+++ b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerOpChangeEvent.kt
@@ -0,0 +1,32 @@
+package gg.flyte.twilight.event.custom.admin
+
+import gg.flyte.twilight.event.TwilightEvent
+import org.bukkit.Bukkit
+import org.bukkit.OfflinePlayer
+import org.bukkit.block.Block
+import org.bukkit.block.BlockFace
+import org.bukkit.entity.Player
+import org.bukkit.event.block.Action
+import org.bukkit.inventory.ItemStack
+import org.bukkit.util.Vector
+import java.util.*
+
+/**
+ * Represents an event that occurs when a player's operator status changes.
+ * This event contains information about the affected player's UUID and name.
+ */
+class PlayerOpChangeEvent(
+    val uuid: UUID,  // The UUID of the player whose operator status changed.
+    val name: String  // The name of the player whose operator status changed.
+) : TwilightEvent() {
+    /**
+     * Represents the offline player associated with this event.
+     */
+    val offlinePlayer: OfflinePlayer = Bukkit.getOfflinePlayer(uuid)
+
+    /**
+     * Represents the online player associated with this event, if available.
+     * This property will be null if the player is not currently online.
+     */
+    val player: Player? = if (offlinePlayer.isOnline) offlinePlayer.player else null
+}
diff --git a/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerOpEvent.kt b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerOpEvent.kt
new file mode 100644
index 0000000..3354a17
--- /dev/null
+++ b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/PlayerOpEvent.kt
@@ -0,0 +1,32 @@
+package gg.flyte.twilight.event.custom.admin
+
+import gg.flyte.twilight.event.TwilightEvent
+import org.bukkit.Bukkit
+import org.bukkit.OfflinePlayer
+import org.bukkit.block.Block
+import org.bukkit.block.BlockFace
+import org.bukkit.entity.Player
+import org.bukkit.event.block.Action
+import org.bukkit.inventory.ItemStack
+import org.bukkit.util.Vector
+import java.util.*
+
+/**
+ * Represents an event that occurs when a player is op'd (promoted to operator status).
+ * This event contains information about the affected player's UUID and name.
+ */
+class PlayerOpEvent(
+    val uuid: UUID,  // The UUID of the player being op'd.
+    val name: String  // The name of the player being op'd.
+) : TwilightEvent() {
+    /**
+     * Represents the offline player associated with this event.
+     */
+    val offlinePlayer: OfflinePlayer = Bukkit.getOfflinePlayer(uuid)
+
+    /**
+     * Represents the online player associated with this event, if available.
+     * This property will be null if the player is not currently online.
+     */
+    val player: Player? = if (offlinePlayer.isOnline) offlinePlayer.player else null
+}
diff --git a/src/main/kotlin/gg/flyte/twilight/event/custom/admin/listener/OpEventListener.kt b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/listener/OpEventListener.kt
new file mode 100644
index 0000000..57f621d
--- /dev/null
+++ b/src/main/kotlin/gg/flyte/twilight/event/custom/admin/listener/OpEventListener.kt
@@ -0,0 +1,58 @@
+package gg.flyte.twilight.event.custom.admin.listener
+
+import gg.flyte.twilight.Twilight
+import gg.flyte.twilight.event.CustomTwilightListener
+import gg.flyte.twilight.event.custom.admin.PlayerDeopEvent
+import gg.flyte.twilight.event.custom.admin.PlayerOpChangeEvent
+import gg.flyte.twilight.event.custom.admin.PlayerOpEvent
+import gg.flyte.twilight.extension.applyForEach
+import gg.flyte.twilight.gson.GSON
+import gg.flyte.twilight.scheduler.repeat
+import java.io.File
+import java.util.*
+
+object OpEventListener : CustomTwilightListener() {
+    private val opsFile = File("${Twilight.plugin.dataFolder}/../../ops.json")
+    private var opsData = mutableSetOf<OpData>()
+    private var opsLastChanged: Long? = null
+
+    init {
+        if (opsFile.exists()) {
+            opsLastChanged = opsFile.lastModified()
+            opsData += getOpsData()
+        }
+
+        runnables += repeat(async = true) {
+            if (!opsFile.exists()) return@repeat cancel()
+            if (!hasOpsChanged()) return@repeat
+
+            val newOpsData = getOpsData()
+
+            // Removed ops
+            opsData.subtract(newOpsData).toSet().applyForEach {
+                opsData -= this
+                Twilight.plugin.server.pluginManager.callEvent(PlayerDeopEvent(uuid, name))
+                Twilight.plugin.server.pluginManager.callEvent(PlayerOpChangeEvent(uuid, name))
+            }
+
+            // Added ops
+            newOpsData.subtract(opsData).toSet().applyForEach {
+                opsData += this
+                Twilight.plugin.server.pluginManager.callEvent(PlayerOpEvent(uuid, name))
+                Twilight.plugin.server.pluginManager.callEvent(PlayerOpChangeEvent(uuid, name))
+            }
+        }
+    }
+
+    data class OpData(
+        val uuid: UUID,
+        val name: String,
+        val level: Int,
+        val bypassPlayerLimit: Boolean
+    )
+
+    private fun getOpsData(): Set<OpData> = GSON.fromJson(opsFile.reader(), Array<OpData>::class.java).toSet()
+
+    private fun hasOpsChanged(): Boolean = (opsLastChanged ?: 0) < opsFile.lastModified()
+
+}