diff --git a/core/src/commonMain/kotlin/com/xebia/functional/xef/llm/assistants/CachedTool.kt b/core/src/commonMain/kotlin/com/xebia/functional/xef/llm/assistants/CachedTool.kt
index 61cfdee57..e7402af5a 100644
--- a/core/src/commonMain/kotlin/com/xebia/functional/xef/llm/assistants/CachedTool.kt
+++ b/core/src/commonMain/kotlin/com/xebia/functional/xef/llm/assistants/CachedTool.kt
@@ -5,6 +5,29 @@ import arrow.fx.coroutines.timeInMillis
 import kotlin.time.Duration
 import kotlin.time.Duration.Companion.days
 
+sealed interface CachedToolEvent {
+  /** Fired when a new entry is added to the cache. */
+  data class Created<K, V>(
+    val key: CachedToolKey<K>,
+    val value: CachedToolValue<V>,
+    val mapSize: Int
+  ) : CachedToolEvent
+
+  /** Fired when an entry is found in the cache, but its value has been updated. */
+  data class Updated<K, V>(
+    val key: CachedToolKey<K>,
+    val oldValue: CachedToolValue<V>,
+    val newValue: CachedToolValue<V>
+  ) : CachedToolEvent
+
+  /** Fired when an expired event has been removed from the cache. */
+  data class Evicted<K, V>(val key: CachedToolKey<K>, val value: CachedToolValue<V>) :
+    CachedToolEvent
+
+  /** Fired when all expired entries have been removed from the cache. */
+  data class ExpiredPurged(val mapSize: Int, val removedEntries: Int) : CachedToolEvent
+}
+
 data class CachedToolKey<K>(val value: K, val seed: String)
 
 data class CachedToolValue<V>(val value: V, val accessTimestamp: Long, val writeTimestamp: Long) {
@@ -73,6 +96,9 @@ abstract class CachedTool<Input, Output>(
    */
   abstract suspend fun onCacheMissed(input: Input): Output
 
+  /** Invoked on [CachedToolEvent] firing, after every cache mutation. */
+  open fun onCacheEvent(event: CachedToolEvent) = Unit
+
   /**
    * Criteria to check if the cache should be used for the given [input]. By default, it returns
    * true, meaning always use the cache if available.
@@ -108,7 +134,7 @@ abstract class CachedTool<Input, Output>(
   suspend fun getValidCacheSnapshot(): Map<Input, Output> {
     val validEntries =
       cache.modify { cachedToolInfo ->
-        val validEntries = cachedToolInfo.filterExpired().filter { (key, _) -> key.seed == seed }
+        val validEntries = cachedToolInfo.purgeExpired().filter { (key, _) -> key.seed == seed }
         Pair(cachedToolInfo, validEntries)
       }
     return validEntries.map { it.key.value to it.value.value }.toMap()
@@ -120,12 +146,22 @@ abstract class CachedTool<Input, Output>(
         if (output.isExpired()) {
           val updatedCache =
             when (config.cacheEvictionPolicy) {
-              CachedToolConfig.CacheEvictionPolicy.SINGLE -> cachedToolInfo.apply { remove(input) }
-              CachedToolConfig.CacheEvictionPolicy.ALL -> cachedToolInfo.filterExpired()
+              CachedToolConfig.CacheEvictionPolicy.SINGLE ->
+                cachedToolInfo.apply {
+                  remove(input)?.also { removedOutput ->
+                    onCacheEvent(CachedToolEvent.Evicted(input, removedOutput))
+                  }
+                }
+              CachedToolConfig.CacheEvictionPolicy.ALL ->
+                cachedToolInfo.purgeExpired(sendCacheEvents = true).also { purged ->
+                  val removedEntries = cachedToolInfo.size - purged.size
+                  onCacheEvent(CachedToolEvent.ExpiredPurged(cachedToolInfo.size, removedEntries))
+                }
             }
           Pair(updatedCache, null)
         } else {
           val updatedOutput = output.withAccessTimestamp()
+          onCacheEvent(CachedToolEvent.Updated(input, output, updatedOutput))
           Pair(cachedToolInfo, updatedOutput.value)
         }
       } ?: Pair(cachedToolInfo, null)
@@ -134,15 +170,24 @@ abstract class CachedTool<Input, Output>(
         val response = block()
         if (shouldCacheOutput(input.value, response)) {
           cache.update { cachedToolInfo ->
-            cachedToolInfo[input] = CachedToolValue.withActualResponse(response)
+            val output = CachedToolValue.withActualResponse(response)
+            cachedToolInfo[input] = output
+            onCacheEvent(CachedToolEvent.Created(input, output, cachedToolInfo.size))
             cachedToolInfo
           }
         }
         response
       }
 
-  private fun MutableMap<CachedToolKey<Input>, CachedToolValue<Output>>.filterExpired() =
-    this.filter { (_, value) -> !value.isExpired() }.toMutableMap()
+  private fun MutableMap<CachedToolKey<Input>, CachedToolValue<Output>>.purgeExpired(
+    sendCacheEvents: Boolean = false
+  ) =
+    this.filterNot { (key, value) ->
+        val expired = value.isExpired()
+        if (sendCacheEvents && expired) onCacheEvent(CachedToolEvent.Evicted(key, value))
+        expired
+      }
+      .toMutableMap()
 
   private fun CachedToolValue<Output>.isExpired(): Boolean =
     when (config.cacheExpirationPolicy) {