diff --git a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.test.ts b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.test.ts
index a4873c1f26..5656d40ec1 100644
--- a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.test.ts
+++ b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.test.ts
@@ -31,6 +31,7 @@ import {
   ToolCallEvent,
   AgentStartEvent,
   AgentFinishEvent,
+  WebFetchFallbackAttemptEvent,
 } from '../types.js';
 import { AgentTerminateMode } from '../../agents/types.js';
 import { GIT_COMMIT_INFO, CLI_VERSION } from '../../generated/git-commit.js';
@@ -945,4 +946,21 @@ describe('ClearcutLogger', () => {
       );
     });
   });
+
+  describe('logWebFetchFallbackAttemptEvent', () => {
+    it('logs an event with the proper name and reason', () => {
+      const { logger } = setup();
+      const event = new WebFetchFallbackAttemptEvent('private_ip');
+
+      logger?.logWebFetchFallbackAttemptEvent(event);
+
+      const events = getEvents(logger!);
+      expect(events.length).toBe(1);
+      expect(events[0]).toHaveEventName(EventNames.WEB_FETCH_FALLBACK_ATTEMPT);
+      expect(events[0]).toHaveMetadataValue([
+        EventMetadataKey.GEMINI_CLI_WEB_FETCH_FALLBACK_REASON,
+        'private_ip',
+      ]);
+    });
+  });
 });
diff --git a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
index 5fe283648d..6d69b06c55 100644
--- a/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
+++ b/packages/core/src/telemetry/clearcut-logger/clearcut-logger.ts
@@ -35,6 +35,7 @@ import type {
   SmartEditCorrectionEvent,
   AgentStartEvent,
   AgentFinishEvent,
+  WebFetchFallbackAttemptEvent,
 } from '../types.js';
 import { EventMetadataKey } from './event-metadata-key.js';
 import type { Config } from '../../config/config.js';
@@ -83,6 +84,7 @@ export enum EventNames {
   SMART_EDIT_CORRECTION = 'smart_edit_correction',
   AGENT_START = 'agent_start',
   AGENT_FINISH = 'agent_finish',
+  WEB_FETCH_FALLBACK_ATTEMPT = 'web_fetch_fallback_attempt',
 }
 
 export interface LogResponse {
@@ -1111,6 +1113,20 @@ export class ClearcutLogger {
     this.flushIfNeeded();
   }
 
+  logWebFetchFallbackAttemptEvent(event: WebFetchFallbackAttemptEvent): void {
+    const data: EventValue[] = [
+      {
+        gemini_cli_key: EventMetadataKey.GEMINI_CLI_WEB_FETCH_FALLBACK_REASON,
+        value: event.reason,
+      },
+    ];
+
+    this.enqueueLogEvent(
+      this.createLogEvent(EventNames.WEB_FETCH_FALLBACK_ATTEMPT, data),
+    );
+    this.flushIfNeeded();
+  }
+
   /**
    * Adds default fields to data, and returns a new data array.  This fields
    * should exist on all log events.
diff --git a/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts b/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
index 2e0da3a0c2..2e242cb424 100644
--- a/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
+++ b/packages/core/src/telemetry/clearcut-logger/event-metadata-key.ts
@@ -7,6 +7,7 @@
 // Defines valid event metadata keys for Clearcut logging.
 export enum EventMetadataKey {
   // Deleted enums: 24
+  // Next ID: 117
 
   GEMINI_CLI_KEY_UNKNOWN = 0,
 
@@ -98,6 +99,9 @@ export enum EventMetadataKey {
   // Logs a smart edit correction event.
   GEMINI_CLI_SMART_EDIT_CORRECTION = 110,
 
+  // Logs the reason for web fetch fallback.
+  GEMINI_CLI_WEB_FETCH_FALLBACK_REASON = 116,
+
   // ==========================================================================
   // GenAI API Request Event Keys
   // ===========================================================================
diff --git a/packages/core/src/telemetry/constants.ts b/packages/core/src/telemetry/constants.ts
index 083ecdb677..f93871e5d7 100644
--- a/packages/core/src/telemetry/constants.ts
+++ b/packages/core/src/telemetry/constants.ts
@@ -35,6 +35,8 @@ export const EVENT_MODEL_SLASH_COMMAND = 'gemini_cli.slash_command.model';
 export const EVENT_SMART_EDIT_STRATEGY = 'gemini_cli.smart_edit.strategy';
 export const EVENT_MODEL_ROUTING = 'gemini_cli.model_routing';
 export const EVENT_SMART_EDIT_CORRECTION = 'gemini_cli.smart_edit.correction';
+export const EVENT_WEB_FETCH_FALLBACK_ATTEMPT =
+  'gemini_cli.web_fetch_fallback_attempt';
 
 // Agent Events
 export const EVENT_AGENT_START = 'gemini_cli.agent.start';
diff --git a/packages/core/src/telemetry/index.ts b/packages/core/src/telemetry/index.ts
index fa1718f675..04bf3587d8 100644
--- a/packages/core/src/telemetry/index.ts
+++ b/packages/core/src/telemetry/index.ts
@@ -44,6 +44,7 @@ export {
   logExtensionEnable,
   logExtensionInstallEvent,
   logExtensionUninstall,
+  logWebFetchFallbackAttempt,
 } from './loggers.js';
 export type { SlashCommandEvent, ChatCompressionEvent } from './types.js';
 export {
@@ -59,6 +60,7 @@ export {
   ConversationFinishedEvent,
   KittySequenceOverflowEvent,
   ToolOutputTruncatedEvent,
+  WebFetchFallbackAttemptEvent,
 } from './types.js';
 export { makeSlashCommandEvent, makeChatCompressionEvent } from './types.js';
 export type { TelemetryEvent } from './types.js';
diff --git a/packages/core/src/telemetry/loggers.test.ts b/packages/core/src/telemetry/loggers.test.ts
index 127c6d7e3c..9f956ac490 100644
--- a/packages/core/src/telemetry/loggers.test.ts
+++ b/packages/core/src/telemetry/loggers.test.ts
@@ -40,6 +40,7 @@ import {
   EVENT_TOOL_OUTPUT_TRUNCATED,
   EVENT_AGENT_START,
   EVENT_AGENT_FINISH,
+  EVENT_WEB_FETCH_FALLBACK_ATTEMPT,
 } from './constants.js';
 import {
   logApiRequest,
@@ -60,6 +61,7 @@ import {
   logExtensionUninstall,
   logAgentStart,
   logAgentFinish,
+  logWebFetchFallbackAttempt,
 } from './loggers.js';
 import { ToolCallDecision } from './tool-call-decision.js';
 import {
@@ -81,6 +83,7 @@ import {
   ExtensionUninstallEvent,
   AgentStartEvent,
   AgentFinishEvent,
+  WebFetchFallbackAttemptEvent,
 } from './types.js';
 import * as metrics from './metrics.js';
 import {
@@ -1494,4 +1497,36 @@ describe('loggers', () => {
       );
     });
   });
+
+  describe('logWebFetchFallbackAttempt', () => {
+    const mockConfig = {
+      getSessionId: () => 'test-session-id',
+      getUsageStatisticsEnabled: () => true,
+    } as unknown as Config;
+
+    beforeEach(() => {
+      vi.spyOn(ClearcutLogger.prototype, 'logWebFetchFallbackAttemptEvent');
+    });
+
+    it('should log web fetch fallback attempt event', () => {
+      const event = new WebFetchFallbackAttemptEvent('private_ip');
+
+      logWebFetchFallbackAttempt(mockConfig, event);
+
+      expect(
+        ClearcutLogger.prototype.logWebFetchFallbackAttemptEvent,
+      ).toHaveBeenCalledWith(event);
+
+      expect(mockLogger.emit).toHaveBeenCalledWith({
+        body: 'Web fetch fallback attempt. Reason: private_ip',
+        attributes: {
+          'session.id': 'test-session-id',
+          'user.email': 'test-user@example.com',
+          'event.name': EVENT_WEB_FETCH_FALLBACK_ATTEMPT,
+          'event.timestamp': '2025-01-01T00:00:00.000Z',
+          reason: 'private_ip',
+        },
+      });
+    });
+  });
 });
diff --git a/packages/core/src/telemetry/loggers.ts b/packages/core/src/telemetry/loggers.ts
index 3dce516619..0ba68cf266 100644
--- a/packages/core/src/telemetry/loggers.ts
+++ b/packages/core/src/telemetry/loggers.ts
@@ -39,6 +39,7 @@ import {
   EVENT_SMART_EDIT_CORRECTION,
   EVENT_AGENT_START,
   EVENT_AGENT_FINISH,
+  EVENT_WEB_FETCH_FALLBACK_ATTEMPT,
 } from './constants.js';
 import type {
   ApiErrorEvent,
@@ -73,6 +74,7 @@ import type {
   SmartEditCorrectionEvent,
   AgentStartEvent,
   AgentFinishEvent,
+  WebFetchFallbackAttemptEvent,
 } from './types.js';
 import {
   recordApiErrorMetrics,
@@ -863,7 +865,7 @@ export function logSmartEditCorrectionEvent(
 
   const logger = logs.getLogger(SERVICE_NAME);
   const logRecord: LogRecord = {
-    body: `Smart Edit Tool Correction: ${event.correction}`,
+    body: `Smart Edit Correction`,
     attributes,
   };
   logger.emit(logRecord);
@@ -906,3 +908,24 @@ export function logAgentFinish(config: Config, event: AgentFinishEvent): void {
 
   recordAgentRunMetrics(config, event);
 }
+
+export function logWebFetchFallbackAttempt(
+  config: Config,
+  event: WebFetchFallbackAttemptEvent,
+): void {
+  ClearcutLogger.getInstance(config)?.logWebFetchFallbackAttemptEvent(event);
+  if (!isTelemetrySdkInitialized()) return;
+
+  const attributes: LogAttributes = {
+    ...getCommonAttributes(config),
+    ...event,
+    'event.name': EVENT_WEB_FETCH_FALLBACK_ATTEMPT,
+  };
+
+  const logger = logs.getLogger(SERVICE_NAME);
+  const logRecord: LogRecord = {
+    body: `Web fetch fallback attempt. Reason: ${event.reason}`,
+    attributes,
+  };
+  logger.emit(logRecord);
+}
diff --git a/packages/core/src/telemetry/types.ts b/packages/core/src/telemetry/types.ts
index bb6c705d0a..ba8a1924ab 100644
--- a/packages/core/src/telemetry/types.ts
+++ b/packages/core/src/telemetry/types.ts
@@ -690,7 +690,8 @@ export type TelemetryEvent =
   | ToolOutputTruncatedEvent
   | ModelSlashCommandEvent
   | AgentStartEvent
-  | AgentFinishEvent;
+  | AgentFinishEvent
+  | WebFetchFallbackAttemptEvent;
 
 export class ExtensionDisableEvent implements BaseTelemetryEvent {
   'event.name': 'extension_disable';
@@ -769,3 +770,15 @@ export class AgentFinishEvent implements BaseTelemetryEvent {
     this.terminate_reason = terminate_reason;
   }
 }
+
+export class WebFetchFallbackAttemptEvent implements BaseTelemetryEvent {
+  'event.name': 'web_fetch_fallback_attempt';
+  'event.timestamp': string;
+  reason: 'private_ip' | 'primary_failed';
+
+  constructor(reason: 'private_ip' | 'primary_failed') {
+    this['event.name'] = 'web_fetch_fallback_attempt';
+    this['event.timestamp'] = new Date().toISOString();
+    this.reason = reason;
+  }
+}
diff --git a/packages/core/src/tools/web-fetch.test.ts b/packages/core/src/tools/web-fetch.test.ts
index 585f662c0f..b79ae5b928 100644
--- a/packages/core/src/tools/web-fetch.test.ts
+++ b/packages/core/src/tools/web-fetch.test.ts
@@ -11,12 +11,21 @@ import { ApprovalMode } from '../config/config.js';
 import { ToolConfirmationOutcome } from './tools.js';
 import { ToolErrorType } from './tool-error.js';
 import * as fetchUtils from '../utils/fetch.js';
+import {
+  logWebFetchFallbackAttempt,
+  WebFetchFallbackAttemptEvent,
+} from '../telemetry/index.js';
 
 const mockGenerateContent = vi.fn();
 const mockGetGeminiClient = vi.fn(() => ({
   generateContent: mockGenerateContent,
 }));
 
+vi.mock('../telemetry/index.js', () => ({
+  logWebFetchFallbackAttempt: vi.fn(),
+  WebFetchFallbackAttemptEvent: vi.fn(),
+}));
+
 vi.mock('../utils/fetch.js', async (importOriginal) => {
   const actual = await importOriginal<typeof fetchUtils>();
   return {
@@ -70,6 +79,59 @@ describe('WebFetchTool', () => {
       const result = await invocation.execute(new AbortController().signal);
       expect(result.error?.type).toBe(ToolErrorType.WEB_FETCH_PROCESSING_ERROR);
     });
+
+    it('should log telemetry when falling back due to private IP', async () => {
+      vi.spyOn(fetchUtils, 'isPrivateIp').mockReturnValue(true);
+      // Mock fetchWithTimeout to succeed so fallback proceeds
+      vi.spyOn(fetchUtils, 'fetchWithTimeout').mockResolvedValue({
+        ok: true,
+        text: () => Promise.resolve('some content'),
+      } as Response);
+      mockGenerateContent.mockResolvedValue({
+        candidates: [{ content: { parts: [{ text: 'fallback response' }] } }],
+      });
+
+      const tool = new WebFetchTool(mockConfig);
+      const params = { prompt: 'fetch https://private.ip' };
+      const invocation = tool.build(params);
+      await invocation.execute(new AbortController().signal);
+
+      expect(logWebFetchFallbackAttempt).toHaveBeenCalledWith(
+        mockConfig,
+        expect.any(WebFetchFallbackAttemptEvent),
+      );
+      expect(WebFetchFallbackAttemptEvent).toHaveBeenCalledWith('private_ip');
+    });
+
+    it('should log telemetry when falling back due to primary fetch failure', async () => {
+      vi.spyOn(fetchUtils, 'isPrivateIp').mockReturnValue(false);
+      // Mock primary fetch to return empty response, triggering fallback
+      mockGenerateContent.mockResolvedValueOnce({
+        candidates: [],
+      });
+      // Mock fetchWithTimeout to succeed so fallback proceeds
+      vi.spyOn(fetchUtils, 'fetchWithTimeout').mockResolvedValue({
+        ok: true,
+        text: () => Promise.resolve('some content'),
+      } as Response);
+      // Mock fallback LLM call
+      mockGenerateContent.mockResolvedValueOnce({
+        candidates: [{ content: { parts: [{ text: 'fallback response' }] } }],
+      });
+
+      const tool = new WebFetchTool(mockConfig);
+      const params = { prompt: 'fetch https://public.ip' };
+      const invocation = tool.build(params);
+      await invocation.execute(new AbortController().signal);
+
+      expect(logWebFetchFallbackAttempt).toHaveBeenCalledWith(
+        mockConfig,
+        expect.any(WebFetchFallbackAttemptEvent),
+      );
+      expect(WebFetchFallbackAttemptEvent).toHaveBeenCalledWith(
+        'primary_failed',
+      );
+    });
   });
 
   describe('shouldConfirmExecute', () => {
diff --git a/packages/core/src/tools/web-fetch.ts b/packages/core/src/tools/web-fetch.ts
index 5e1e9bf531..95baab28c3 100644
--- a/packages/core/src/tools/web-fetch.ts
+++ b/packages/core/src/tools/web-fetch.ts
@@ -23,6 +23,10 @@ import { getResponseText } from '../utils/partUtils.js';
 import { fetchWithTimeout, isPrivateIp } from '../utils/fetch.js';
 import { convert } from 'html-to-text';
 import { ProxyAgent, setGlobalDispatcher } from 'undici';
+import {
+  logWebFetchFallbackAttempt,
+  WebFetchFallbackAttemptEvent,
+} from '../telemetry/index.js';
 
 const URL_FETCH_TIMEOUT_MS = 10000;
 const MAX_CONTENT_LENGTH = 100000;
@@ -184,6 +188,10 @@ ${textContent}
     const isPrivate = isPrivateIp(url);
 
     if (isPrivate) {
+      logWebFetchFallbackAttempt(
+        this.config,
+        new WebFetchFallbackAttemptEvent('private_ip'),
+      );
       return this.executeFallback(signal);
     }
 
@@ -243,6 +251,10 @@ ${textContent}
       }
 
       if (processingError) {
+        logWebFetchFallbackAttempt(
+          this.config,
+          new WebFetchFallbackAttemptEvent('primary_failed'),
+        );
         return this.executeFallback(signal);
       }