diff --git a/lib/hooks.ts b/lib/hooks.ts
index 72fda69..f24d52c 100644
--- a/lib/hooks.ts
+++ b/lib/hooks.ts
@@ -48,6 +48,11 @@ export function createEventHandler(
             return
         }
 
+        if (event.type === "session.compacted") {
+            logger.info("Session compaction detected - updating state")
+            state.lastCompaction = Date.now()
+        }
+
         if (event.type === "session.status" && event.properties.status.type === "idle") {
             if (!config.strategies.onIdle.enabled) {
                 return
diff --git a/lib/messages/prune.ts b/lib/messages/prune.ts
index 2ecb2bc..918056e 100644
--- a/lib/messages/prune.ts
+++ b/lib/messages/prune.ts
@@ -3,7 +3,7 @@ import type { Logger } from "../logger"
 import type { PluginConfig } from "../config"
 import { loadPrompt } from "../prompt"
 import { extractParameterKey, buildToolIdList } from "./utils"
-import { getLastUserMessage } from "../shared-utils"
+import { getLastUserMessage, isMessageCompacted } from "../shared-utils"
 import { UserMessage } from "@opencode-ai/sdk"
 
 const PRUNED_TOOL_INPUT_REPLACEMENT = '[Input removed to save context]'
@@ -17,7 +17,7 @@ const buildPrunableToolsList = (
     messages: WithParts[],
 ): string => {
     const lines: string[] = []
-    const toolIdList: string[] = buildToolIdList(messages)
+    const toolIdList: string[] = buildToolIdList(state, messages, logger)
 
     state.toolParameters.forEach((toolParameterEntry, toolCallId) => {
         if (state.prune.toolIds.includes(toolCallId)) {
@@ -26,9 +26,6 @@ const buildPrunableToolsList = (
         if (config.strategies.pruneTool.protectedTools.includes(toolParameterEntry.tool)) {
             return
         }
-        if (toolParameterEntry.compacted) {
-            return
-        }
         const numericId = toolIdList.indexOf(toolCallId)
         const paramKey = extractParameterKey(toolParameterEntry.tool, toolParameterEntry.parameters)
         const description = paramKey ? `${toolParameterEntry.tool}, ${paramKey}` : toolParameterEntry.tool
@@ -111,6 +108,10 @@ const pruneToolOutputs = (
     messages: WithParts[]
 ): void => {
     for (const msg of messages) {
+        if (isMessageCompacted(state, msg)) {
+            continue
+        }
+
         for (const part of msg.parts) {
             if (part.type !== 'tool') {
                 continue
diff --git a/lib/messages/utils.ts b/lib/messages/utils.ts
index 1ae2c7d..48f453c 100644
--- a/lib/messages/utils.ts
+++ b/lib/messages/utils.ts
@@ -1,4 +1,6 @@
-import type { WithParts } from "../state"
+import { Logger } from "../logger"
+import { isMessageCompacted } from "../shared-utils"
+import type { SessionState, WithParts } from "../state"
 
 /**
  * Extracts a human-readable key from tool metadata for display purposes.
@@ -71,9 +73,16 @@ export const extractParameterKey = (tool: string, parameters: any): string => {
     return paramStr.substring(0, 50)
 }
 
-export function buildToolIdList(messages: WithParts[]): string[] {
+export function buildToolIdList(
+    state: SessionState,
+    messages: WithParts[],
+    logger: Logger
+): string[] {
     const toolIds: string[] = []
     for (const msg of messages) {
+        if (isMessageCompacted(state, msg)) {
+            continue
+        }
         if (msg.parts) {
             for (const part of msg.parts) {
                 if (part.type === 'tool' && part.callID && part.tool) {
diff --git a/lib/shared-utils.ts b/lib/shared-utils.ts
index cdcfb5b..9cb60a1 100644
--- a/lib/shared-utils.ts
+++ b/lib/shared-utils.ts
@@ -1,4 +1,12 @@
-import { WithParts } from "./state"
+import { Logger } from "./logger"
+import { SessionState, WithParts } from "./state"
+
+export const isMessageCompacted = (
+    state: SessionState,
+    msg: WithParts
+): boolean => {
+    return msg.info.time.created < state.lastCompaction
+}
 
 export const getLastUserMessage = (
     messages: WithParts[]
@@ -11,3 +19,13 @@ export const getLastUserMessage = (
     }
     return null
 }
+
+export const checkForCompaction = (
+    state: SessionState,
+    messages: WithParts[],
+    logger: Logger
+): void => {
+    for (const msg of messages) {
+
+    }
+}
diff --git a/lib/state/persistence.ts b/lib/state/persistence.ts
index 21f0092..89d6772 100644
--- a/lib/state/persistence.ts
+++ b/lib/state/persistence.ts
@@ -16,6 +16,7 @@ export interface PersistedSessionState {
     prune: Prune
     stats: SessionStats;
     lastUpdated: string;
+    lastCompacted: number
 }
 
 const STORAGE_DIR = join(
@@ -55,6 +56,7 @@ export async function saveSessionState(
             prune: sessionState.prune,
             stats: sessionState.stats,
             lastUpdated: new Date().toISOString(),
+            lastCompacted: sessionState.lastCompaction
         };
 
         const filePath = getSessionFilePath(sessionState.sessionId);
@@ -99,8 +101,7 @@ export async function loadSessionState(
         }
 
         logger.info("Loaded session state from disk", {
-            sessionId: sessionId,
-            totalTokensSaved: state.stats.totalPruneTokens
+            sessionId: sessionId
         });
 
         return state;
diff --git a/lib/state/state.ts b/lib/state/state.ts
index 19dc854..035f81b 100644
--- a/lib/state/state.ts
+++ b/lib/state/state.ts
@@ -41,7 +41,8 @@ export function createSessionState(): SessionState {
         },
         toolParameters: new Map<string, ToolParameterEntry>(),
         nudgeCounter: 0,
-        lastToolPrune: false
+        lastToolPrune: false,
+        lastCompaction: 0
     }
 }
 
@@ -58,6 +59,7 @@ export function resetSessionState(state: SessionState): void {
     state.toolParameters.clear()
     state.nudgeCounter = 0
     state.lastToolPrune = false
+    state.lastCompaction = 0
 }
 
 export async function ensureSessionInitialized(
@@ -95,4 +97,5 @@ export async function ensureSessionInitialized(
         pruneTokenCounter: persisted.stats?.pruneTokenCounter || 0,
         totalPruneTokens: persisted.stats?.totalPruneTokens || 0,
     }
+    state.lastCompaction = persisted.lastCompacted || 0
 }
diff --git a/lib/state/tool-cache.ts b/lib/state/tool-cache.ts
index a6140c7..ee2e2dc 100644
--- a/lib/state/tool-cache.ts
+++ b/lib/state/tool-cache.ts
@@ -1,6 +1,7 @@
 import type { SessionState, ToolStatus, WithParts } from "./index"
 import type { Logger } from "../logger"
 import { PluginConfig } from "../config"
+import { isMessageCompacted } from "../shared-utils"
 
 const MAX_TOOL_CACHE_SIZE = 1000
 
@@ -19,10 +20,17 @@ export async function syncToolCache(
         state.nudgeCounter = 0
 
         for (const msg of messages) {
+            if (isMessageCompacted(state, msg)) {
+                continue
+            }
+
             for (const part of msg.parts) {
                 if (part.type !== "tool" || !part.callID) {
                     continue
                 }
+                if (state.toolParameters.has(part.callID)) {
+                    continue
+                }
 
                 if (part.tool === "prune") {
                     state.nudgeCounter = 0
@@ -31,10 +39,6 @@ export async function syncToolCache(
                 }
                 state.lastToolPrune = part.tool === "prune"
 
-                if (state.toolParameters.has(part.callID)) {
-                    continue
-                }
-
                 state.toolParameters.set(
                     part.callID,
                     {
@@ -42,14 +46,12 @@ export async function syncToolCache(
                         parameters: part.state?.input ?? {},
                         status: part.state.status as ToolStatus | undefined,
                         error: part.state.status === "error" ? part.state.error : undefined,
-                        compacted: part.state.status === "completed" && !!part.state.time.compacted,
                     }
                 )
+                logger.info("Cached tool id: " + part.callID)
             }
         }
-
-        // logger.info(`nudgeCounter=${state.nudgeCounter}, lastToolPrune=${state.lastToolPrune}`)
-
+        logger.info("Synced cache - size: " + state.toolParameters.size)
         trimToolParametersCache(state)
     } catch (error) {
         logger.warn("Failed to sync tool parameters from OpenCode", {
diff --git a/lib/state/types.ts b/lib/state/types.ts
index e1b92a7..678bf29 100644
--- a/lib/state/types.ts
+++ b/lib/state/types.ts
@@ -12,7 +12,6 @@ export interface ToolParameterEntry {
     parameters: any
     status?: ToolStatus
     error?: string
-    compacted?: boolean
 }
 
 export interface SessionStats {
@@ -32,4 +31,5 @@ export interface SessionState {
     toolParameters: Map<string, ToolParameterEntry>
     nudgeCounter: number
     lastToolPrune: boolean
+    lastCompaction: number
 }
diff --git a/lib/strategies/deduplication.ts b/lib/strategies/deduplication.ts
index eaa9798..21c4be6 100644
--- a/lib/strategies/deduplication.ts
+++ b/lib/strategies/deduplication.ts
@@ -20,7 +20,7 @@ export const deduplicate = (
     }
 
     // Build list of all tool call IDs from messages (chronological order)
-    const allToolIds = buildToolIdList(messages)
+    const allToolIds = buildToolIdList(state, messages, logger)
     if (allToolIds.length === 0) {
         return
     }
@@ -68,7 +68,7 @@ export const deduplicate = (
         }
     }
 
-    state.stats.totalPruneTokens += calculateTokensSaved(messages, newPruneIds)
+    state.stats.totalPruneTokens += calculateTokensSaved(state, messages, newPruneIds)
 
     if (newPruneIds.length > 0) {
         state.prune.toolIds.push(...newPruneIds)
diff --git a/lib/strategies/on-idle.ts b/lib/strategies/on-idle.ts
index 50dbb2f..f0870c2 100644
--- a/lib/strategies/on-idle.ts
+++ b/lib/strategies/on-idle.ts
@@ -7,6 +7,7 @@ import { selectModel, ModelInfo } from "../model-selector"
 import { saveSessionState } from "../state/persistence"
 import { sendUnifiedNotification } from "../ui/notification"
 import { calculateTokensSaved, getCurrentParams } from "./utils"
+import { isMessageCompacted } from "../shared-utils"
 
 export interface OnIdleResult {
     prunedCount: number
@@ -18,6 +19,7 @@ export interface OnIdleResult {
  * Parse messages to extract tool information.
  */
 function parseMessages(
+    state: SessionState,
     messages: WithParts[],
     toolParametersCache: Map<string, ToolParameterEntry>
 ): {
@@ -28,6 +30,9 @@ function parseMessages(
     const toolMetadata = new Map<string, ToolParameterEntry>()
 
     for (const msg of messages) {
+        if (isMessageCompacted(state, msg)) {
+            continue
+        }
         if (msg.parts) {
             for (const part of msg.parts) {
                 if (part.type === "tool" && part.callID) {
@@ -224,7 +229,7 @@ export async function runOnIdle(
         }
 
         const currentParams = getCurrentParams(messages, logger)
-        const { toolCallIds, toolMetadata } = parseMessages(messages, state.toolParameters)
+        const { toolCallIds, toolMetadata } = parseMessages(state, messages, state.toolParameters)
 
         const alreadyPrunedIds = state.prune.toolIds
         const unprunedToolCallIds = toolCallIds.filter(id => !alreadyPrunedIds.includes(id))
@@ -273,7 +278,7 @@ export async function runOnIdle(
         const allPrunedIds = [...new Set([...alreadyPrunedIds, ...newlyPrunedIds])]
         state.prune.toolIds = allPrunedIds
 
-        state.stats.pruneTokenCounter += calculateTokensSaved(messages, newlyPrunedIds)
+        state.stats.pruneTokenCounter += calculateTokensSaved(state, messages, newlyPrunedIds)
 
         // Build tool metadata map for notification
         const prunedToolMetadata = new Map<string, ToolParameterEntry>()
diff --git a/lib/strategies/prune-tool.ts b/lib/strategies/prune-tool.ts
index a83694f..e361325 100644
--- a/lib/strategies/prune-tool.ts
+++ b/lib/strategies/prune-tool.ts
@@ -41,6 +41,9 @@ export function createPruneTool(
             const { client, state, logger, config, workingDirectory } = ctx
             const sessionId = toolCtx.sessionID
 
+            logger.info("Prune tool invoked")
+            logger.info(JSON.stringify(args))
+
             if (!args.ids || args.ids.length === 0) {
                 logger.debug("Prune tool called but args.ids is empty or undefined: " + JSON.stringify(args))
                 return "No IDs provided. Check the <prunable-tools> list for available IDs to prune."
@@ -72,7 +75,7 @@ export function createPruneTool(
             const messages: WithParts[] = messagesResponse.data || messagesResponse
 
             const currentParams = getCurrentParams(messages, logger)
-            const toolIdList: string[] = buildToolIdList(messages)
+            const toolIdList: string[] = buildToolIdList(state, messages, logger)
 
             // Validate that all numeric IDs are within bounds
             if (numericToolIds.some(id => id < 0 || id >= toolIdList.length)) {
@@ -102,7 +105,7 @@ export function createPruneTool(
                 }
             }
 
-            state.stats.pruneTokenCounter += calculateTokensSaved(messages, pruneToolIds)
+            state.stats.pruneTokenCounter += calculateTokensSaved(state, messages, pruneToolIds)
 
             await sendUnifiedNotification(
                 client,
diff --git a/lib/strategies/utils.ts b/lib/strategies/utils.ts
index 126e5e1..3c6a1b1 100644
--- a/lib/strategies/utils.ts
+++ b/lib/strategies/utils.ts
@@ -1,8 +1,8 @@
-import { WithParts } from "../state"
+import { SessionState, WithParts } from "../state"
 import { UserMessage } from "@opencode-ai/sdk"
 import { Logger } from "../logger"
 import { encode } from 'gpt-tokenizer'
-import { getLastUserMessage } from "../shared-utils"
+import { getLastUserMessage, isMessageCompacted } from "../shared-utils"
 
 export function getCurrentParams(
     messages: WithParts[],
@@ -40,12 +40,16 @@ function estimateTokensBatch(texts: string[]): number[] {
  * TODO: Make it count message content that are not tool outputs. Currently it ONLY covers tool outputs and errors
  */
 export const calculateTokensSaved = (
+    state: SessionState,
     messages: WithParts[],
     pruneToolIds: string[]
 ): number => {
     try {
         const contents: string[] = []
         for (const msg of messages) {
+            if (isMessageCompacted(state, msg)) {
+                continue
+            }
             for (const part of msg.parts) {
                 if (part.type !== 'tool' || !pruneToolIds.includes(part.callID)) {
                     continue