diff --git a/src/auto-reply/reply/commands-compact.ts b/src/auto-reply/reply/commands-compact.ts
index 2ef77fb77e2..fece4e2a63c 100644
--- a/src/auto-reply/reply/commands-compact.ts
+++ b/src/auto-reply/reply/commands-compact.ts
@@ -72,29 +72,32 @@ export const handleCompactCommand: CommandHandler = async (params) => {
 
   const thinkLevel = params.resolvedThinkLevel ?? (await params.resolveDefaultThinkingLevel());
 
-  const learnResult = await runLearnForSession({
-    sessionId,
-    sessionKey: params.sessionKey,
-    messageChannel: params.command.channel,
-    groupId: params.sessionEntry.groupId,
-    groupChannel: params.sessionEntry.groupChannel,
-    groupSpace: params.sessionEntry.space,
-    spawnedBy: params.sessionEntry.spawnedBy,
-    sessionFile: params.sessionEntry.sessionFile,
-    workspaceDir: params.workspaceDir,
-    agentDir: params.agentDir,
-    config: params.cfg,
-    skillsSnapshot: params.sessionEntry.skillsSnapshot,
-    provider: params.provider,
-    model: params.model,
-    thinkLevel,
-    customFocus: "What insights and lessons should be remembered before context compaction?",
-    senderIsOwner: params.command.senderIsOwner,
-    ownerNumbers: params.command.ownerList.length > 0 ? params.command.ownerList : undefined,
-  });
-  if (learnResult.ok) {
+  const learnResult = params.sessionEntry.sessionFile
+    ? await runLearnForSession({
+        sessionId,
+        sessionKey: params.sessionKey,
+        messageChannel: params.command.channel,
+        groupId: params.sessionEntry.groupId,
+        groupChannel: params.sessionEntry.groupChannel,
+        groupSpace: params.sessionEntry.space,
+        spawnedBy: params.sessionEntry.spawnedBy,
+        sessionFile: params.sessionEntry.sessionFile,
+        workspaceDir: params.workspaceDir,
+        agentDir: params.agentDir,
+        config: params.cfg,
+        skillsSnapshot: params.sessionEntry.skillsSnapshot,
+        provider: params.provider,
+        model: params.model,
+        thinkLevel,
+        customFocus: "What insights and lessons should be remembered before context compaction?",
+        senderIsOwner: params.command.senderIsOwner,
+        ownerNumbers: params.command.ownerList.length > 0 ? params.command.ownerList : undefined,
+      })
+    : null;
+
+  if (learnResult?.ok) {
     logVerbose(`Pre-compaction learning completed for session ${params.sessionKey}`);
-  } else {
+  } else if (learnResult) {
     logVerbose(
       `Pre-compaction learning failed for session ${params.sessionKey}: ${learnResult.message ?? "unknown error"}`,
     );
diff --git a/src/auto-reply/reply/commands-core.ts b/src/auto-reply/reply/commands-core.ts
index f76604ed5e4..abbeacf3fab 100644
--- a/src/auto-reply/reply/commands-core.ts
+++ b/src/auto-reply/reply/commands-core.ts
@@ -235,7 +235,7 @@ export async function handleCommands(params: HandleCommandsParams): Promise<Comm
     }
 
     // Trigger learning before reset/new commands (after ACP target resolution)
-    if (targetSessionEntry?.sessionId) {
+    if (targetSessionEntry?.sessionId && targetSessionEntry.sessionFile) {
       const learnResult = await runLearnForSession({
         sessionId: targetSessionEntry.sessionId,
         sessionKey: targetSessionKey,
diff --git a/src/auto-reply/reply/commands-learn.ts b/src/auto-reply/reply/commands-learn.ts
index 628796be56b..3c4ce50b632 100644
--- a/src/auto-reply/reply/commands-learn.ts
+++ b/src/auto-reply/reply/commands-learn.ts
@@ -1,8 +1,10 @@
 import fs from "node:fs/promises";
 import path from "node:path";
 import { runEmbeddedPiAgent } from "../../agents/pi-embedded.js";
+import type { SkillSnapshot } from "../../agents/skills.js";
 import type { OpenClawConfig } from "../../config/config.js";
 import { logVerbose } from "../../globals.js";
+import type { ThinkLevel } from "./directives.js";
 
 const LEARN_SYSTEM_PROMPT = [
   "Learning turn.",
@@ -68,10 +70,10 @@ export async function runLearnForSession(params: {
   workspaceDir: string;
   agentDir?: string;
   config: OpenClawConfig;
-  skillsSnapshot?: Record<string, unknown>;
+  skillsSnapshot?: SkillSnapshot;
   provider: string;
   model: string;
-  thinkLevel?: string;
+  thinkLevel?: ThinkLevel;
   customFocus?: string;
   senderIsOwner: boolean;
   ownerNumbers?: string[];
@@ -85,6 +87,7 @@ export async function runLearnForSession(params: {
 
   try {
     await runEmbeddedPiAgent({
+      runId: crypto.randomUUID(),
       sessionId: params.sessionId,
       sessionKey: params.sessionKey,
       sessionFile: resolvedSessionFile,
@@ -150,6 +153,13 @@ export const handleLearnCommand = async (
     params.ctx.CommandBody ?? params.ctx.RawBody ?? params.ctx.Body,
   );
 
+  if (!params.sessionEntry.sessionFile) {
+    return {
+      shouldContinue: false,
+      reply: { text: "Learning unavailable (missing session file)." },
+    };
+  }
+
   const result = await runLearnForSession({
     sessionId,
     sessionKey: params.sessionKey,
@@ -158,14 +168,7 @@ export const handleLearnCommand = async (
     groupChannel: params.sessionEntry.groupChannel,
     groupSpace: params.sessionEntry.space,
     spawnedBy: params.sessionEntry.spawnedBy,
-    sessionFile: resolveSessionFilePath(
-      sessionId,
-      params.sessionEntry,
-      resolveSessionFilePathOptions({
-        agentId: params.agentId,
-        storePath: params.storePath,
-      }),
-    ),
+    sessionFile: params.sessionEntry.sessionFile,
     workspaceDir: params.workspaceDir,
     agentDir: params.agentDir,
     config: params.cfg,