3 files changed, 76 insertions, 61 deletions

diff --git a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
index d36a16b5..fd5a9ab2 100644
--- a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
+++ b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
@@ -22,12 +22,13 @@ import {
 } from '../types.js';
 import { EventMetadataKey } from './event-metadata-key.js';
 import { Config } from '../../config/config.js';
-import { getInstallationId } from '../../utils/user_id.js';
+import { safeJsonStringify } from '../../utils/safeJsonStringify.js';
 import {
   getCachedGoogleAccount,
   getLifetimeGoogleAccounts,
 } from '../../utils/user_account.js';
-import { safeJsonStringify } from '../../utils/safeJsonStringify.js';
+import { HttpError, retryWithBackoff } from '../../utils/retry.js';
+import { getInstallationId } from '../../utils/user_id.js';
 
 const start_session_event_name = 'start_session';
 const new_prompt_event_name = 'new_prompt';
@@ -113,66 +114,81 @@ export class ClearcutLogger {
     });
   }
 
-  flushToClearcut(): Promise<LogResponse> {
+  async flushToClearcut(): Promise<LogResponse> {
     if (this.config?.getDebugMode()) {
       console.log('Flushing log events to Clearcut.');
     }
     const eventsToSend = [...this.events];
-    this.events.length = 0;
+    if (eventsToSend.length === 0) {
+      return {};
+    }
 
-    return new Promise<Buffer>((resolve, reject) => {
-      const request = [
-        {
-          log_source_name: 'CONCORD',
-          request_time_ms: Date.now(),
-          log_event: eventsToSend,
-        },
-      ];
-      const body = safeJsonStringify(request);
-      const options = {
-        hostname: 'play.googleapis.com',
-        path: '/log',
-        method: 'POST',
-        headers: { 'Content-Length': Buffer.byteLength(body) },
-      };
-      const bufs: Buffer[] = [];
-      const req = https.request(
-        {
-          ...options,
-          agent: this.getProxyAgent(),
-        },
-        (res) => {
-          res.on('data', (buf) => bufs.push(buf));
-          res.on('end', () => {
-            resolve(Buffer.concat(bufs));
-          });
-        },
-      );
-      req.on('error', (e) => {
-        if (this.config?.getDebugMode()) {
-          console.log('Clearcut POST request error: ', e);
-        }
-        // Add the events back to the front of the queue to be retried.
-        this.events.unshift(...eventsToSend);
-        reject(e);
+    const flushFn = () =>
+      new Promise<Buffer>((resolve, reject) => {
+        const request = [
+          {
+            log_source_name: 'CONCORD',
+            request_time_ms: Date.now(),
+            log_event: eventsToSend,
+          },
+        ];
+        const body = safeJsonStringify(request);
+        const options = {
+          hostname: 'play.googleapis.com',
+          path: '/log',
+          method: 'POST',
+          headers: { 'Content-Length': Buffer.byteLength(body) },
+        };
+        const bufs: Buffer[] = [];
+        const req = https.request(
+          {
+            ...options,
+            agent: this.getProxyAgent(),
+          },
+          (res) => {
+            if (
+              res.statusCode &&
+              (res.statusCode < 200 || res.statusCode >= 300)
+            ) {
+              const err: HttpError = new Error(
+                `Request failed with status ${res.statusCode}`,
+              );
+              err.status = res.statusCode;
+              res.resume();
+              return reject(err);
+            }
+            res.on('data', (buf) => bufs.push(buf));
+            res.on('end', () => resolve(Buffer.concat(bufs)));
+          },
+        );
+        req.on('error', reject);
+        req.end(body);
       });
-      req.end(body);
-    })
-      .then((buf: Buffer) => {
-        try {
-          this.last_flush_time = Date.now();
-          return this.decodeLogResponse(buf) || {};
-        } catch (error: unknown) {
-          console.error('Error flushing log events:', error);
-          return {};
-        }
-      })
-      .catch((error: unknown) => {
-        // Handle all errors to prevent unhandled promise rejections
-        console.error('Error flushing log events:', error);
-        // Return empty response to maintain the Promise<LogResponse> contract
-        return {};
+
+    try {
+      const responseBuffer = await retryWithBackoff(flushFn, {
+        maxAttempts: 3,
+        initialDelayMs: 200,
+        shouldRetry: (err: unknown) => {
+          if (!(err instanceof Error)) return false;
+          const status = (err as HttpError).status as number | undefined;
+          // If status is not available, it's likely a network error
+          if (status === undefined) return true;
+
+          // Retry on 429 (Too many Requests) and 5xx server errors.
+          return status === 429 || (status >= 500 && status < 600);
+        },
       });
+
+      this.events.splice(0, eventsToSend.length);
+      this.last_flush_time = Date.now();
+      return this.decodeLogResponse(responseBuffer) || {};
+    } catch (error) {
+      if (this.config?.getDebugMode()) {
+        console.error('Clearcut flush failed after multiple retries.', error);
+      }
+      return {};
+    }
   }
 
   // Visible for testing. Decodes protobuf-encoded response from Clearcut server.
diff --git a/packages/core/src/utils/retry.test.ts b/packages/core/src/utils/retry.test.ts
index f84d2004..196e7341 100644
--- a/packages/core/src/utils/retry.test.ts
+++ b/packages/core/src/utils/retry.test.ts
@@ -6,14 +6,9 @@
 
 /* eslint-disable @typescript-eslint/no-explicit-any */
 import { describe, it, expect, vi, beforeEach, afterEach } from 'vitest';
-import { retryWithBackoff } from './retry.js';
+import { retryWithBackoff, HttpError } from './retry.js';
 import { setSimulate429 } from './testUtils.js';
 
-// Define an interface for the error with a status property
-interface HttpError extends Error {
-  status?: number;
-}
-
 // Helper to create a mock function that fails a certain number of times
 const createFailingFunction = (
   failures: number,
diff --git a/packages/core/src/utils/retry.ts b/packages/core/src/utils/retry.ts
index b29bf7df..81300882 100644
--- a/packages/core/src/utils/retry.ts
+++ b/packages/core/src/utils/retry.ts
@@ -10,6 +10,10 @@ import {
   isGenericQuotaExceededError,
 } from './quotaErrorDetection.js';
 
+export interface HttpError extends Error {
+  status?: number;
+}
+
 export interface RetryOptions {
   maxAttempts: number;
   initialDelayMs: number;