diff --git a/packages/coding-agent/src/core/gateway/memory.ts b/packages/coding-agent/src/core/gateway/memory.ts
index 709ce4f..e66b479 100644
--- a/packages/coding-agent/src/core/gateway/memory.ts
+++ b/packages/coding-agent/src/core/gateway/memory.ts
@@ -479,6 +479,15 @@ function getRepoName(settings: MemoryMdSettings): string {
   return match?.[1] ?? "memory-md";
 }
 
+async function getGitHead(cwd: string): Promise<string | null> {
+  const result = await runGit(cwd, "rev-parse", "HEAD");
+  if (!result.success) {
+    return null;
+  }
+  const head = result.stdout.trim();
+  return head.length > 0 ? head : null;
+}
+
 async function getRepositoryDirtyState(
   localPath: string,
   projectPath?: string,
@@ -541,6 +550,7 @@ async function syncRepository(
         message: `Directory exists but is not a git repo: ${localPath}`,
       };
     }
+    const previousHead = await getGitHead(localPath);
     const pullResult = await runGit(localPath, "pull", "--rebase", "--autostash");
     if (!pullResult.success) {
       return {
@@ -549,14 +559,20 @@ async function syncRepository(
           pullResult.stderr.trim() || "Pull failed. Check repository state.",
       };
     }
+    const currentHead = await getGitHead(localPath);
     const updated =
-      pullResult.stdout.includes("Updating") ||
-      pullResult.stdout.includes("Fast-forward");
+      previousHead !== null &&
+      currentHead !== null &&
+      previousHead !== currentHead;
+    const message =
+      previousHead === null || currentHead === null
+        ? `Synchronized ${getRepoName(settings)}`
+        : updated
+          ? `Pulled latest changes from ${getRepoName(settings)}`
+          : `${getRepoName(settings)} is already up to date`;
     return {
       success: true,
-      message: updated
-        ? `Pulled latest changes from ${getRepoName(settings)}`
-        : `${getRepoName(settings)} is already up to date`,
+      message,
       updated,
     };
   }
@@ -861,17 +877,16 @@ export async function syncProjectMemory(
     };
   }
 
-  if (!repositoryReady) {
-    const cloned = await syncRepository(settings);
-    if (!cloned.success) {
-      return {
-        success: false,
-        message: cloned.message,
-        configured,
-        initialized,
-        dirty: null,
-      };
-    }
+  const syncResult = await syncRepository(settings);
+  if (!syncResult.success) {
+    return {
+      success: false,
+      message: syncResult.message,
+      configured,
+      initialized,
+      dirty: null,
+      updated: syncResult.updated,
+    };
   }
 
   const statusResult = await runGit(
@@ -941,5 +956,6 @@ export async function syncProjectMemory(
     initialized,
     dirty: await getRepositoryDirtyState(localPath, projectPath),
     committed: hasChanges,
+    updated: syncResult.updated,
   };
 }
diff --git a/packages/pi-memory-md/memory-md.ts b/packages/pi-memory-md/memory-md.ts
index ec54077..178388a 100644
--- a/packages/pi-memory-md/memory-md.ts
+++ b/packages/pi-memory-md/memory-md.ts
@@ -147,6 +147,18 @@ function getRepoName(settings: MemoryMdSettings): string {
   return match ? match[1] : "memory-md";
 }
 
+async function getGitHead(
+  pi: ExtensionAPI,
+  cwd: string,
+): Promise<string | null> {
+  const result = await gitExec(pi, cwd, "rev-parse", "HEAD");
+  if (!result.success) {
+    return null;
+  }
+  const head = result.stdout.trim();
+  return head.length > 0 ? head : null;
+}
+
 function loadScopedSettings(settingsPath: string): MemoryMdSettings {
   if (!fs.existsSync(settingsPath)) {
     return {};
@@ -286,6 +298,7 @@ export async function syncRepository(
       };
     }
 
+    const previousHead = await getGitHead(pi, localPath);
     const pullResult = await gitExec(
       pi,
       localPath,
@@ -301,15 +314,21 @@ export async function syncRepository(
     }
 
     isRepoInitialized.value = true;
+    const currentHead = await getGitHead(pi, localPath);
     const updated =
-      pullResult.stdout.includes("Updating") ||
-      pullResult.stdout.includes("Fast-forward");
+      previousHead !== null &&
+      currentHead !== null &&
+      previousHead !== currentHead;
     const repoName = getRepoName(settings);
+    const message =
+      previousHead === null || currentHead === null
+        ? `Synchronized [${repoName}]`
+        : updated
+          ? `Pulled latest changes from [${repoName}]`
+          : `[${repoName}] is already latest`;
     return {
       success: true,
-      message: updated
-        ? `Pulled latest changes from [${repoName}]`
-        : `[${repoName}] is already latest`,
+      message,
       updated,
     };
   }
@@ -477,6 +496,68 @@ export function createDefaultFiles(memoryDir: string): void {
   }
 }
 
+export function formatMemoryDirectoryTree(
+  memoryDir: string,
+  maxDepth = 3,
+  maxLines = 40,
+): string {
+  if (!fs.existsSync(memoryDir)) {
+    return "Unable to generate directory tree.";
+  }
+
+  const lines = [`${path.basename(memoryDir) || memoryDir}/`];
+  let truncated = false;
+
+  function visit(dir: string, depth: number, prefix: string): void {
+    if (depth >= maxDepth || lines.length >= maxLines) {
+      truncated = true;
+      return;
+    }
+
+    let entries: fs.Dirent[];
+    try {
+      entries = fs
+        .readdirSync(dir, { withFileTypes: true })
+        .filter((entry) => entry.name !== "node_modules")
+        .sort((left, right) => {
+          if (left.isDirectory() !== right.isDirectory()) {
+            return left.isDirectory() ? -1 : 1;
+          }
+          return left.name.localeCompare(right.name);
+        });
+    } catch {
+      truncated = true;
+      return;
+    }
+
+    for (const [index, entry] of entries.entries()) {
+      if (lines.length >= maxLines) {
+        truncated = true;
+        return;
+      }
+
+      const isLast = index === entries.length - 1;
+      const marker = isLast ? "\\-- " : "|-- ";
+      const childPrefix = `${prefix}${isLast ? "    " : "|   "}`;
+      lines.push(
+        `${prefix}${marker}${entry.name}${entry.isDirectory() ? "/" : ""}`,
+      );
+
+      if (entry.isDirectory()) {
+        visit(path.join(dir, entry.name), depth + 1, childPrefix);
+      }
+    }
+  }
+
+  visit(memoryDir, 0, "");
+
+  if (truncated) {
+    lines.push("... (tree truncated)");
+  }
+
+  return lines.join("\n");
+}
+
 function buildMemoryContext(
   settings: MemoryMdSettings,
   ctx: ExtensionContext,
@@ -779,25 +860,7 @@ export default function memoryMdExtension(pi: ExtensionAPI) {
         return;
       }
 
-      const { execSync } = await import("node:child_process");
-      let treeOutput = "";
-
-      try {
-        treeOutput = execSync(`tree -L 3 -I "node_modules" "${memoryDir}"`, {
-          encoding: "utf-8",
-        });
-      } catch {
-        try {
-          treeOutput = execSync(
-            `find "${memoryDir}" -type d -not -path "*/node_modules/*"`,
-            { encoding: "utf-8" },
-          );
-        } catch {
-          treeOutput = "Unable to generate directory tree.";
-        }
-      }
-
-      ctx.ui.notify(treeOutput.trim(), "info");
+      ctx.ui.notify(formatMemoryDirectoryTree(memoryDir).trim(), "info");
     },
   });
 }
diff --git a/packages/pi-memory-md/tools.ts b/packages/pi-memory-md/tools.ts
index 58feb2c..fd479f0 100644
--- a/packages/pi-memory-md/tools.ts
+++ b/packages/pi-memory-md/tools.ts
@@ -8,6 +8,7 @@ import type { MemoryFrontmatter, MemoryMdSettings } from "./memory-md.js";
 import {
   createDefaultFiles,
   ensureDirectoryStructure,
+  formatMemoryDirectoryTree,
   getCurrentDate,
   getMemoryDir,
   getProjectRepoPath,
@@ -184,6 +185,14 @@ export function registerMemorySync(
           };
         }
 
+        const syncResult = await syncRepository(pi, settings, isRepoInitialized);
+        if (!syncResult.success) {
+          return {
+            content: [{ type: "text", text: syncResult.message }],
+            details: { success: false, configured: true },
+          };
+        }
+
         const statusResult = await gitExec(
           pi,
           localPath,
@@ -793,26 +802,7 @@ export function registerMemoryCheck(
         };
       }
 
-      const { execSync } = await import("node:child_process");
-      let treeOutput = "";
-
-      try {
-        treeOutput = execSync(`tree -L 3 -I "node_modules" "${memoryDir}"`, {
-          encoding: "utf-8",
-        });
-      } catch {
-        try {
-          treeOutput = execSync(
-            `find "${memoryDir}" -type d -not -path "*/node_modules/*" | head -20`,
-            {
-              encoding: "utf-8",
-            },
-          );
-        } catch {
-          treeOutput =
-            "Unable to generate directory tree. Please check permissions.";
-        }
-      }
+      const treeOutput = formatMemoryDirectoryTree(memoryDir);
 
       const files = listMemoryFiles(memoryDir);
       const relPaths = files.map((f) => path.relative(memoryDir, f));