From 84c6a579b261542df42437cc73fcf804f55ad4ea Mon Sep 17 00:00:00 2001
From: Ajax Davis <thomasalwyndavis@gmail.com>
Date: Thu, 4 Dec 2025 16:51:27 +1000
Subject: [PATCH] feat: add automatic health check updates on Railway tool
 failures
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Add real-time health status updates when tools fail to load or execute:

- Add @tpmjs/db dependency to playground package
- Create reportToolFailure() function to update health status on errors
- Trigger health check updates for:
  1. Import failures (Railway load-and-describe errors)
  2. Execution failures (Railway execute-tool errors)
- Updates are non-blocking and run in background
- Each tool failure now logs:
  - 🏥 Triggering health check for {package}/{export}
  - ✅ Health status updated for {package}/{export}

This complements the proactive health checking (daily cron + manual recheck)
with reactive health updates from actual tool usage errors.

Handles multiple errors in batch loading - each error triggers its own
health check update independently and asynchronously.

🤖 Generated with [Claude Code](https://claude.com/claude-code)

Co-Authored-By: Claude <noreply@anthropic.com>
---
 apps/playground/package.json                  |  1 +
 .../playground/src/lib/dynamic-tool-loader.ts | 76 +++++++++++++++++++
 2 files changed, 77 insertions(+)

diff --git a/apps/playground/package.json b/apps/playground/package.json
index 88ba084..30a269a 100644
--- a/apps/playground/package.json
+++ b/apps/playground/package.json
@@ -13,6 +13,7 @@
   "dependencies": {
     "@ai-sdk/openai": "3.0.0-beta.74",
     "@ai-sdk/react": "3.0.0-beta.131",
+    "@tpmjs/db": "workspace:*",
     "@tpmjs/env": "workspace:*",
     "@tpmjs/hello": "workspace:*",
     "@tpmjs/search-registry": "workspace:*",
diff --git a/apps/playground/src/lib/dynamic-tool-loader.ts b/apps/playground/src/lib/dynamic-tool-loader.ts
index 51379cf..6f966b8 100644
--- a/apps/playground/src/lib/dynamic-tool-loader.ts
+++ b/apps/playground/src/lib/dynamic-tool-loader.ts
@@ -1,6 +1,8 @@
+import { prisma } from '@tpmjs/db';
 import { jsonSchema, tool } from 'ai';
 
 // Cache for tool wrappers (process-level)
+// biome-ignore lint/suspicious/noExplicitAny: Tool types from AI SDK are complex
 const moduleCache = new Map<string, any>();
 
 // Cache for per-conversation active tools
@@ -36,6 +38,51 @@ function getConversationEnv(conversationId: string): Record<string, string> {
   return conversationEnv.get(conversationId) || {};
 }
 
+/**
+ * Report tool failure and trigger async health check
+ * Non-blocking - logs error and triggers health check in background
+ */
+async function reportToolFailure(
+  packageName: string,
+  exportName: string,
+  error: string,
+  phase: 'import' | 'execution'
+): Promise<void> {
+  try {
+    // Find the tool in the database
+    const tool = await prisma.tool.findFirst({
+      where: {
+        exportName,
+        package: {
+          npmPackageName: packageName,
+        },
+      },
+      select: { id: true },
+    });
+
+    if (!tool) {
+      console.warn(`⚠️  Tool not found in database for health check: ${packageName}/${exportName}`);
+      return;
+    }
+
+    console.log(`🏥 Triggering health check for ${packageName}/${exportName} (${tool.id})`);
+
+    // Update health status immediately (optimistic)
+    await prisma.tool.update({
+      where: { id: tool.id },
+      data: {
+        [phase === 'import' ? 'importHealth' : 'executionHealth']: 'BROKEN',
+        healthCheckError: error,
+        lastHealthCheck: new Date(),
+      },
+    });
+
+    console.log(`✅ Health status updated for ${packageName}/${exportName}`);
+  } catch (err) {
+    console.error('❌ Failed to report tool failure:', err);
+  }
+}
+
 /**
  * Dynamically load a tool via Railway service
  * Railway service runs with --experimental-network-imports and can import from esm.sh
@@ -77,6 +124,17 @@ export async function loadToolDynamically(
     if (!response.ok) {
       const errorText = await response.text();
       console.error(`❌ Railway service error (${response.status}): ${errorText}`);
+
+      // Trigger health check update in background (non-blocking)
+      reportToolFailure(
+        packageName,
+        exportName,
+        `Railway service error (${response.status}): ${errorText}`,
+        'import'
+      ).catch((err) =>
+        console.error(`Failed to report tool failure for ${packageName}/${exportName}:`, err)
+      );
+
       return null;
     }
 
@@ -84,6 +142,13 @@ export async function loadToolDynamically(
 
     if (!data.success) {
       console.error(`❌ Failed to load tool: ${data.error}`);
+
+      // Trigger health check update in background (non-blocking)
+      reportToolFailure(packageName, exportName, data.error || 'Unknown error', 'import').catch(
+        (err) =>
+          console.error(`Failed to report tool failure for ${packageName}/${exportName}:`, err)
+      );
+
       return null;
     }
 
@@ -125,6 +190,17 @@ export async function loadToolDynamically(
 
         if (!result.success) {
           console.error(`❌ Tool execution failed: ${result.error}`);
+
+          // Trigger health check update in background (non-blocking)
+          reportToolFailure(
+            packageName,
+            exportName,
+            result.error || 'Tool execution failed',
+            'execution'
+          ).catch((err) =>
+            console.error(`Failed to report tool failure for ${packageName}/${exportName}:`, err)
+          );
+
           throw new Error(result.error || 'Tool execution failed');
         }