feat: raindrop optional observability through env vars

extensions/cli/package.json

@@ -44,11 +44,15 @@
   },
   "homepage": "https://continue.dev",
   "dependencies": {
+    "@ai-sdk/anthropic": "^2.0.54",
+    "@ai-sdk/openai": "^2.0.80",
     "@sentry/profiling-node": "^9.43.0",
+    "ai": "^5.0.109",
     "fdir": "^6.4.2",
     "find-up": "^8.0.0",
     "fzf": "^0.5.2",
-    "js-yaml": "^4.1.1"
+    "js-yaml": "^4.1.1",
+    "raindrop-ai": "^0.0.69"
   },
   "devDependencies": {
     "@continuedev/config-yaml": "file:../../packages/config-yaml",
@@ -59,10 +63,13 @@
     "@opentelemetry/api": "^1.9.0",
     "@opentelemetry/exporter-metrics-otlp-grpc": "^0.203.0",
     "@opentelemetry/exporter-metrics-otlp-http": "^0.203.0",
+    "@opentelemetry/exporter-trace-otlp-proto": "^0.203.0",
     "@opentelemetry/instrumentation-fs": "^0.23.0",
     "@opentelemetry/instrumentation-http": "^0.203.0",
     "@opentelemetry/resources": "^2.0.1",
     "@opentelemetry/sdk-node": "^0.203.0",
+    "@opentelemetry/sdk-trace-base": "^2.0.1",
+    "@opentelemetry/sdk-trace-node": "^2.0.1",
     "@opentelemetry/semantic-conventions": "^1.36.0",
     "@semantic-release/changelog": "^6.0.3",
     "@semantic-release/git": "^10.0.1",

extensions/cli/src/commands/chat.ts

@@ -1,3 +1,4 @@
+/* eslint-disable max-lines */
 import { ModelConfig } from "@continuedev/config-yaml";
 import { BaseLlmApi } from "@continuedev/openai-adapters";
 import chalk from "chalk";
@@ -14,6 +15,7 @@ import { initializeServices, services } from "../services/index.js";
 import { serviceContainer } from "../services/ServiceContainer.js";
 import {
   AgentFileServiceState,
+  AuthServiceState,
   ModelServiceState,
   SERVICE_NAMES,
 } from "../services/types.js";
@@ -24,6 +26,10 @@ import {
 } from "../session.js";
 import { streamChatResponse } from "../stream/streamChatResponse.js";
 import { posthogService } from "../telemetry/posthogService.js";
+import {
+  raindropService,
+  setupRaindropMetadataFromParams,
+} from "../telemetry/raindropService.js";
 import { telemetryService } from "../telemetry/telemetryService.js";
 import { startTUIChat } from "../ui/index.js";
 import { gracefulExit } from "../util/exit.js";
@@ -221,6 +227,45 @@ function processAndOutputResponse(
   }
 }
 
+// Helper function to set up Raindrop metadata for headless mode
+async function setupRaindropMetadata(): Promise<void> {
+  const authState = await serviceContainer.get<AuthServiceState>(
+    SERVICE_NAMES.AUTH,
+  );
+  const chatHistoryState = await serviceContainer.get(
+    SERVICE_NAMES.CHAT_HISTORY,
+  );
+
+  setupRaindropMetadataFromParams(
+    authState.authConfig?.userId || "anonymous",
+    (chatHistoryState as any).sessionId,
+    "cn-headless",
+  );
+}
+
+// Helper function to validate prompt in headless mode
+function validateHeadlessPrompt(
+  userInput: string | undefined,
+  options: ChatOptions,
+): void {
+  if (!userInput || !userInput.trim()) {
+    // If resuming or forking, allow empty prompt - just exit successfully after showing history
+    if (options.resume || options.fork) {
+      // For resume/fork with no new input, we've already loaded the history
+      // Just exit successfully (the history was already loaded into chatHistory)
+      gracefulExit(0);
+      return;
+    }
+
+    throw new Error(
+      'Headless mode requires a prompt. Use: cn -p "your prompt"\n' +
+        'Or pipe input: echo "prompt" | cn -p\n' +
+        "Or use agent files: cn -p --agent my-org/my-agent\n" +
+        "Note: Agent files must contain a prompt field.",
+    );
+  }
+}
+
 // Helper function to handle auto-compaction for headless mode
 async function handleAutoCompaction(
   chatHistory: ChatHistoryItem[],
@@ -453,6 +498,9 @@ async function runHeadlessMode(
     toolPermissionOverrides: permissionOverrides,
   });
 
+  // Set Raindrop metadata if enabled
+  await setupRaindropMetadata();
+
   // Get required services from the service container
   const modelState = await serviceContainer.get<ModelServiceState>(
     SERVICE_NAMES.MODEL,
@@ -492,26 +540,8 @@ async function runHeadlessMode(
     initialPrompt,
   );
 
-  // Critical validation: Ensure we have actual prompt text in headless mode
-  // This prevents the CLI from hanging in TTY-less environments when question() is called
-  // We check AFTER processing all prompts (including agent files) to ensure we have real content
-  // EXCEPTION: Allow empty prompts when resuming/forking since they may just want to view history
-  if (!initialUserInput || !initialUserInput.trim()) {
-    // If resuming or forking, allow empty prompt - just exit successfully after showing history
-    if (options.resume || options.fork) {
-      // For resume/fork with no new input, we've already loaded the history above
-      // Just exit successfully (the history was already loaded into chatHistory)
-      await gracefulExit(0);
-      return;
-    }
-
-    throw new Error(
-      'Headless mode requires a prompt. Use: cn -p "your prompt"\n' +
-        'Or pipe input: echo "prompt" | cn -p\n' +
-        "Or use agent files: cn -p --agent my-org/my-agent\n" +
-        "Note: Agent files must contain a prompt field.",
-    );
-  }
+  // Validate prompt in headless mode
+  validateHeadlessPrompt(initialUserInput, options);
 
   let isFirstMessage = true;
   while (true) {
@@ -585,6 +615,22 @@ export async function chat(prompt?: string, options: ChatOptions = {}) {
         toolPermissionOverrides: permissionOverrides,
       });
 
+      // Set Raindrop metadata if enabled
+      if (raindropService.isEnabled()) {
+        const authState = await serviceContainer.get<AuthServiceState>(
+          SERVICE_NAMES.AUTH,
+        );
+        const chatHistoryState = await serviceContainer.get(
+          SERVICE_NAMES.CHAT_HISTORY,
+        );
+
+        raindropService.setMetadata({
+          userId: authState.authConfig?.userId || "anonymous",
+          convoId: (chatHistoryState as any).sessionId,
+          eventName: "cn-chat",
+        });
+      }
+
       const agentFileState = await serviceContainer.get<AgentFileServiceState>(
         SERVICE_NAMES.AGENT_FILE,
       );

extensions/cli/src/commands/serve.ts

@@ -1,9 +1,15 @@
+/* eslint-disable max-lines */
 import chalk from "chalk";
 import type { ChatHistoryItem } from "core/index.js";
 import express, { Request, Response } from "express";
+import { v4 as uuidv4 } from "uuid";
 
 import { ToolPermissionServiceState } from "src/services/ToolPermissionService.js";
 import { posthogService } from "src/telemetry/posthogService.js";
+import {
+  raindropService,
+  setupRaindropMetadataFromParams,
+} from "src/telemetry/raindropService.js";
 import { prependPrompt } from "src/util/promptProcessor.js";
 
 import { getAccessToken, getAssistantSlug } from "../auth/workos.js";
@@ -71,6 +77,19 @@ export function shouldQueueInitialPrompt(
   return !hasConversation;
 }
 
+/**
+ * Get the actual prompt from parameter or stdin.
+ * Checks stdin for piped input if no prompt parameter provided.
+ */
+function getActualPrompt(prompt?: string): string | undefined {
+  if (prompt) {
+    return prompt;
+  }
+  // Try to read from stdin (for piped input like: cat file | cn serve)
+  const stdinInput = readStdinSync();
+  return stdinInput || undefined;
+}
+
 // eslint-disable-next-line max-statements
 export async function serve(prompt?: string, options: ServeOptions = {}) {
   await posthogService.capture("sessionStart", {});
@@ -79,14 +98,7 @@ export async function serve(prompt?: string, options: ServeOptions = {}) {
   setAgentId(options.id);
 
   // Check if prompt should come from stdin instead of parameter
-  let actualPrompt = prompt;
-  if (!prompt) {
-    // Try to read from stdin (for piped input like: cat file | cn serve)
-    const stdinInput = readStdinSync();
-    if (stdinInput) {
-      actualPrompt = stdinInput;
-    }
-  }
+  const actualPrompt = getActualPrompt(prompt);
 
   const timeoutSeconds = parseInt(options.timeout || "300", 10);
   const timeoutMs = timeoutSeconds * 1000;
@@ -103,6 +115,16 @@ export async function serve(prompt?: string, options: ServeOptions = {}) {
     headless: true, // Skip onboarding in serve mode
   });
 
+  // Set Raindrop metadata if enabled
+  if (raindropService.isEnabled()) {
+    const authState = await getService<AuthServiceState>(SERVICE_NAMES.AUTH);
+    setupRaindropMetadataFromParams(
+      authState.authConfig?.userId || "anonymous",
+      uuidv4(), // Generate unique ID for serve session
+      "cn-serve",
+    );
+  }
+
   // Get initialized services from the service container
   const [configState, modelState, permissionsState, agentFileState] =
     await Promise.all([

extensions/cli/src/services/index.ts

@@ -1,5 +1,6 @@
 import { loadAuthConfig } from "../auth/workos.js";
 import { initializeWithOnboarding } from "../onboarding.js";
+import { raindropService } from "../telemetry/raindropService.js";
 import { setBetaUploadArtifactToolEnabled } from "../tools/toolsConfig.js";
 import { logger } from "../util/logger.js";
 
@@ -58,6 +59,9 @@ export async function initializeServices(initOptions: ServiceInitOptions = {}) {
 
   const commandOptions = initOptions.options || {};
 
+  // Initialize Raindrop observability early (opt-in via RAINDROP_API_KEY)
+  await raindropService.initialize();
+
   // Configure beta tools based on command options
   if (commandOptions.betaUploadArtifactTool) {
     setBetaUploadArtifactToolEnabled(true);