diff --git a/src/cli/App.tsx b/src/cli/App.tsx
index 9f157c3..d3218fe 100644
--- a/src/cli/App.tsx
+++ b/src/cli/App.tsx
@@ -11888,6 +11888,7 @@ ${SYSTEM_REMINDER_CLOSE}
                 model: currentModelId ?? undefined,
                 // Account info
                 billing_tier: billingTier ?? undefined,
+                server_version: telemetry.getServerVersion() ?? undefined,
                 // Recent chunk log for diagnostics
                 recent_chunks: chunkLog.getEntries(),
                 // Debug log tail for diagnostics
diff --git a/src/telemetry/index.ts b/src/telemetry/index.ts
index 4d2863b..e49562d 100644
--- a/src/telemetry/index.ts
+++ b/src/telemetry/index.ts
@@ -1,3 +1,4 @@
+import { getServerUrl } from "../agent/client";
 import { getLettaCodeHeaders } from "../agent/http-headers";
 import { settingsManager } from "../settings-manager";
 import { debugLogFile } from "../utils/debug";
@@ -72,6 +73,7 @@ class TelemetryManager {
   private toolCallCount = 0;
   private sessionEndTracked = false;
   private flushInterval: NodeJS.Timeout | null = null;
+  private serverVersion: string | null = null;
   private readonly FLUSH_INTERVAL_MS = 5 * 60 * 1000; // 5 minutes
   private readonly MAX_BATCH_SIZE = 100;
   private sessionStatsGetter?: () => {
@@ -125,6 +127,9 @@ class TelemetryManager {
 
     this.trackSessionStart();
 
+    // Fetch server version for diagnostics (best-effort, non-blocking)
+    this.fetchServerVersion().catch(() => {});
+
     // Set up periodic flushing
     this.flushInterval = setInterval(() => {
       this.flush().catch((err) => {
@@ -209,6 +214,34 @@ class TelemetryManager {
     this.currentAgentId = agentId;
   }
 
+  /**
+   * Fetch and cache server version from /v1/health (fire-and-forget, best-effort)
+   */
+  async fetchServerVersion(): Promise<void> {
+    try {
+      const baseURL = getServerUrl();
+      const settings = await settingsManager.getSettingsWithSecureTokens();
+      const apiKey =
+        process.env.LETTA_API_KEY || settings.env?.LETTA_API_KEY || "";
+      const res = await fetch(`${baseURL}/v1/health`, {
+        headers: { Authorization: `Bearer ${apiKey}` },
+        signal: AbortSignal.timeout(3000),
+      });
+      if (res.ok) {
+        const data = (await res.json()) as { version?: string };
+        if (data.version) {
+          this.serverVersion = data.version;
+        }
+      }
+    } catch {
+      // Best-effort — don't let this affect startup
+    }
+  }
+
+  getServerVersion(): string | null {
+    return this.serverVersion;
+  }
+
   /**
    * Set a getter function for session stats (called from App.tsx)
    * This allows safety net handlers to access stats even if not explicitly passed
@@ -438,6 +471,7 @@ class TelemetryManager {
           },
           body: JSON.stringify({
             service: "letta-code",
+            server_version: this.serverVersion || undefined,
             events: eventsToSend,
           }),
         },