diff --git a/src/cli/print.ts b/src/cli/print.ts
index 7a9ca405c..9873c7a21 100644
--- a/src/cli/print.ts
+++ b/src/cli/print.ts
@@ -377,9 +377,6 @@ const cronJitterConfigModule =
   require('../utils/cronJitterConfig.js') as typeof import('../utils/cronJitterConfig.js')
 const cronGate =
   require('@claude-code-best/builtin-tools/tools/ScheduleCronTool/prompt.js') as typeof import('@claude-code-best/builtin-tools/tools/ScheduleCronTool/prompt.js')
-const extractMemoriesModule = feature('EXTRACT_MEMORIES')
-  ? (require('../services/extractMemories/extractMemories.js') as typeof import('../services/extractMemories/extractMemories.js'))
-  : null
 /* eslint-enable @typescript-eslint/no-require-imports */
 
 const SHUTDOWN_TEAM_PROMPT = `<system-reminder>
@@ -985,7 +982,14 @@ export async function runHeadless(
   // the forked agent mid-flight. Gated by isExtractModeActive so the
   // tengu_slate_thimble flag controls non-interactive extraction end-to-end.
   if (feature('EXTRACT_MEMORIES') && isExtractModeActive()) {
-    await extractMemoriesModule!.drainPendingExtraction()
+    try {
+      const { drainPendingExtraction } = await import(
+        '../services/extractMemories/extractMemories.js'
+      )
+      await drainPendingExtraction()
+    } catch {
+      // Module load failure — non-critical at shutdown
+    }
   }
 
   gracefulShutdownSync(
diff --git a/src/query/stopHooks.ts b/src/query/stopHooks.ts
index a3b354c9a..f63f1ee0d 100644
--- a/src/query/stopHooks.ts
+++ b/src/query/stopHooks.ts
@@ -39,9 +39,6 @@ import { getTaskListId, listTasks } from '../utils/tasks.js'
 import { getAgentName, getTeamName, isTeammate } from '../utils/teammate.js'
 
 /* eslint-disable @typescript-eslint/no-require-imports */
-const extractMemoriesModule = feature('EXTRACT_MEMORIES')
-  ? (require('../services/extractMemories/extractMemories.js') as typeof import('../services/extractMemories/extractMemories.js'))
-  : null
 const jobClassifierModule = feature('TEMPLATES')
   ? (require('../jobs/classifier.js') as typeof import('../jobs/classifier.js'))
   : null
@@ -154,12 +151,16 @@ export async function* handleStopHooks(
       // Fire-and-forget in both interactive and non-interactive. For -p/SDK,
       // print.ts drains the in-flight promise after flushing the response
       // but before gracefulShutdownSync (see drainPendingExtraction).
-      void extractMemoriesModule!.executeExtractMemories(
-        stopHookContext,
-        toolUseContext.appendSystemMessage as
-          | ((msg: import('../types/message.js').SystemMessage) => void)
-          | undefined,
-      )
+      void import('../services/extractMemories/extractMemories.js')
+        .then(({ executeExtractMemories }) =>
+          executeExtractMemories(
+            stopHookContext,
+            toolUseContext.appendSystemMessage as
+              | ((msg: import('../types/message.js').SystemMessage) => void)
+              | undefined,
+          ),
+        )
+        .catch(() => {})
     }
     if (!toolUseContext.agentId && !poorMode) {
       void executeAutoDream(stopHookContext, toolUseContext.appendSystemMessage)
diff --git a/src/utils/backgroundHousekeeping.ts b/src/utils/backgroundHousekeeping.ts
index fa5672132..6312dd62b 100644
--- a/src/utils/backgroundHousekeeping.ts
+++ b/src/utils/backgroundHousekeeping.ts
@@ -4,9 +4,6 @@ import { initMagicDocs } from '../services/MagicDocs/magicDocs.js'
 import { initSkillImprovement } from './hooks/skillImprovement.js'
 
 /* eslint-disable @typescript-eslint/no-require-imports */
-const extractMemoriesModule = feature('EXTRACT_MEMORIES')
-  ? (require('../services/extractMemories/extractMemories.js') as typeof import('../services/extractMemories/extractMemories.js'))
-  : null
 const registerProtocolModule = feature('LODESTONE')
   ? (require('./deepLink/registerProtocol.js') as typeof import('./deepLink/registerProtocol.js'))
   : null
@@ -32,7 +29,13 @@ export function startBackgroundHousekeeping(): void {
   void initMagicDocs()
   void initSkillImprovement()
   if (feature('EXTRACT_MEMORIES')) {
-    extractMemoriesModule!.initExtractMemories()
+    void import('../services/extractMemories/extractMemories.js')
+      .then(({ initExtractMemories }) => {
+        initExtractMemories()
+      })
+      .catch(() => {
+        // Module load failure — non-critical, memory extraction just won't run
+      })
   }
   initAutoDream()
   void autoUpdateMarketplacesAndPluginsInBackground()