Improve AI filtering error handling and visibility

- Add listAvailableModels() and validateModel() to openai.ts
- Improve testOpenAIConnection() to test configured model
- Add checkAIStatus endpoint to filtering router
- Add pre-execution AI config check in executeRules
- Improve error messages in AI filtering service (rate limit, quota, etc.)
- Add AI status warning banner on round detail page for filtering rounds

Now admins get clear errors when AI is misconfigured instead of silent flags.

Co-Authored-By: Claude Opus 4.5 <noreply@anthropic.com>

src/app/(admin)/admin/rounds/[id]/page.tsx

@@ -84,6 +84,10 @@ function RoundDetailContent({ roundId }: { roundId: string }) {
     { roundId },
     { enabled: isFilteringRound }
   )
+  const { data: aiStatus } = trpc.filtering.checkAIStatus.useQuery(
+    { roundId },
+    { enabled: isFilteringRound }
+  )
 
   const utils = trpc.useUtils()
   const updateStatus = trpc.round.updateStatus.useMutation({
@@ -485,6 +489,22 @@ function RoundDetailContent({ roundId }: { roundId: string }) {
             </div>
           </CardHeader>
           <CardContent className="space-y-4">
+            {/* AI Status Warning */}
+            {aiStatus?.hasAIRules && !aiStatus?.configured && (
+              <div className="flex items-center gap-3 p-4 rounded-lg bg-amber-500/10 border border-amber-500/20">
+                <AlertTriangle className="h-5 w-5 text-amber-600 flex-shrink-0" />
+                <div className="flex-1">
+                  <p className="font-medium text-amber-700">AI Configuration Required</p>
+                  <p className="text-sm text-amber-600">
+                    {aiStatus.error || 'AI screening rules require OpenAI to be configured.'}
+                  </p>
+                </div>
+                <Button variant="outline" size="sm" asChild>
+                  <Link href="/admin/settings">Configure AI</Link>
+                </Button>
+              </div>
+            )}
+
             {/* Stats */}
             {filteringStats && filteringStats.total > 0 ? (
               <div className="grid gap-4 sm:grid-cols-4">

src/lib/openai.ts

@@ -66,12 +66,12 @@ export async function isOpenAIConfigured(): Promise<boolean> {
 }
 
 /**
- * Test OpenAI connection
+ * List available models from OpenAI API
  */
-export async function testOpenAIConnection(): Promise<{
+export async function listAvailableModels(): Promise<{
   success: boolean
+  models?: string[]
   error?: string
-  model?: string
 }> {
   try {
     const client = await getOpenAI()
@@ -83,9 +83,90 @@ export async function testOpenAIConnection(): Promise<{
       }
     }
 
-    // Simple test request
+    const response = await client.models.list()
+    const chatModels = response.data
+      .filter((m) => m.id.includes('gpt') || m.id.includes('o1') || m.id.includes('o3') || m.id.includes('o4'))
+      .map((m) => m.id)
+      .sort()
+
+    return {
+      success: true,
+      models: chatModels,
+    }
+  } catch (error) {
+    return {
+      success: false,
+      error: error instanceof Error ? error.message : 'Unknown error',
+    }
+  }
+}
+
+/**
+ * Validate that a specific model is available
+ */
+export async function validateModel(modelId: string): Promise<{
+  valid: boolean
+  error?: string
+}> {
+  try {
+    const client = await getOpenAI()
+
+    if (!client) {
+      return {
+        valid: false,
+        error: 'OpenAI API key not configured',
+      }
+    }
+
+    // Try a minimal completion with the model
+    await client.chat.completions.create({
+      model: modelId,
+      messages: [{ role: 'user', content: 'test' }],
+      max_tokens: 1,
+    })
+
+    return { valid: true }
+  } catch (error) {
+    const message = error instanceof Error ? error.message : 'Unknown error'
+    // Check for specific model errors
+    if (message.includes('does not exist') || message.includes('model_not_found')) {
+      return {
+        valid: false,
+        error: `Model "${modelId}" is not available with your API key`,
+      }
+    }
+    return {
+      valid: false,
+      error: message,
+    }
+  }
+}
+
+/**
+ * Test OpenAI connection with the configured model
+ */
+export async function testOpenAIConnection(): Promise<{
+  success: boolean
+  error?: string
+  model?: string
+  modelTested?: string
+}> {
+  try {
+    const client = await getOpenAI()
+
+    if (!client) {
+      return {
+        success: false,
+        error: 'OpenAI API key not configured',
+      }
+    }
+
+    // Get the configured model
+    const configuredModel = await getConfiguredModel()
+
+    // Test with the configured model
     const response = await client.chat.completions.create({
-      model: 'gpt-4o-mini',
+      model: configuredModel,
       messages: [{ role: 'user', content: 'Hello' }],
       max_tokens: 5,
     })
@@ -93,11 +174,25 @@ export async function testOpenAIConnection(): Promise<{
     return {
       success: true,
       model: response.model,
+      modelTested: configuredModel,
     }
   } catch (error) {
+    const message = error instanceof Error ? error.message : 'Unknown error'
+    const configuredModel = await getConfiguredModel()
+
+    // Check for model-specific errors
+    if (message.includes('does not exist') || message.includes('model_not_found')) {
       return {
         success: false,
-      error: error instanceof Error ? error.message : 'Unknown error',
+        error: `Model "${configuredModel}" is not available. Check Settings → AI to select a valid model.`,
+        modelTested: configuredModel,
+      }
+    }
+
+    return {
+      success: false,
+      error: message,
+      modelTested: configuredModel,
     }
   }
 }

src/server/routers/filtering.ts

@@ -4,8 +4,48 @@ import { Prisma } from '@prisma/client'
 import { router, adminProcedure, protectedProcedure } from '../trpc'
 import { executeFilteringRules } from '../services/ai-filtering'
 import { logAudit } from '../utils/audit'
+import { isOpenAIConfigured, testOpenAIConnection } from '@/lib/openai'
 
 export const filteringRouter = router({
+  /**
+   * Check if AI is configured and ready for filtering
+   */
+  checkAIStatus: protectedProcedure
+    .input(z.object({ roundId: z.string() }))
+    .query(async ({ ctx, input }) => {
+      // Check if round has AI rules
+      const aiRules = await ctx.prisma.filteringRule.count({
+        where: {
+          roundId: input.roundId,
+          ruleType: 'AI_SCREENING',
+          isActive: true,
+        },
+      })
+
+      if (aiRules === 0) {
+        return { hasAIRules: false, configured: true, error: null }
+      }
+
+      // Check if OpenAI is configured
+      const configured = await isOpenAIConfigured()
+      if (!configured) {
+        return {
+          hasAIRules: true,
+          configured: false,
+          error: 'OpenAI API key not configured',
+        }
+      }
+
+      // Test the connection
+      const testResult = await testOpenAIConnection()
+      return {
+        hasAIRules: true,
+        configured: testResult.success,
+        error: testResult.error || null,
+        model: testResult.modelTested,
+      }
+    }),
+
   /**
    * Get filtering rules for a round
    */
@@ -146,6 +186,30 @@ export const filteringRouter = router({
         })
       }
 
+      // Check if any AI_SCREENING rules exist
+      const hasAIRules = rules.some((r) => r.ruleType === 'AI_SCREENING' && r.isActive)
+
+      if (hasAIRules) {
+        // Verify OpenAI is configured before proceeding
+        const aiConfigured = await isOpenAIConfigured()
+        if (!aiConfigured) {
+          throw new TRPCError({
+            code: 'PRECONDITION_FAILED',
+            message:
+              'AI screening rules require OpenAI to be configured. Go to Settings → AI to configure your API key.',
+          })
+        }
+
+        // Also verify the model works
+        const testResult = await testOpenAIConnection()
+        if (!testResult.success) {
+          throw new TRPCError({
+            code: 'PRECONDITION_FAILED',
+            message: `AI configuration error: ${testResult.error}. Go to Settings → AI to fix.`,
+          })
+        }
+      }
+
       // Get projects in this round
       const roundProjectEntries = await ctx.prisma.roundProject.findMany({
         where: { roundId: input.roundId },

src/server/services/ai-filtering.ts

@@ -383,13 +383,40 @@ Return your evaluation as JSON.`
       }
     }
   } catch (error) {
-    // OpenAI error — flag all for manual review
+    // OpenAI error — flag all for manual review with specific error info
     console.error('[AI Filtering] OpenAI API error:', error)
+
+    // Extract meaningful error message
+    let errorType = 'unknown_error'
+    let errorDetail = 'Unknown error occurred'
+
+    if (error instanceof Error) {
+      const message = error.message.toLowerCase()
+      if (message.includes('rate_limit') || message.includes('rate limit')) {
+        errorType = 'rate_limit'
+        errorDetail = 'OpenAI rate limit exceeded. Try again in a few minutes.'
+      } else if (message.includes('model') && (message.includes('not found') || message.includes('does not exist'))) {
+        errorType = 'model_not_found'
+        errorDetail = 'The configured AI model is not available. Check Settings → AI.'
+      } else if (message.includes('insufficient_quota') || message.includes('quota')) {
+        errorType = 'quota_exceeded'
+        errorDetail = 'OpenAI API quota exceeded. Check your billing settings.'
+      } else if (message.includes('invalid_api_key') || message.includes('unauthorized')) {
+        errorType = 'invalid_api_key'
+        errorDetail = 'Invalid OpenAI API key. Check Settings → AI.'
+      } else if (message.includes('context_length') || message.includes('token')) {
+        errorType = 'context_length'
+        errorDetail = 'Request too large. Try with fewer projects or shorter descriptions.'
+      } else {
+        errorDetail = error.message
+      }
+    }
+
     for (const p of projects) {
       results.set(p.id, {
         meetsCriteria: false,
         confidence: 0,
-        reasoning: `AI screening error — flagged for manual review`,
+        reasoning: `AI screening error (${errorType}): ${errorDetail}`,
         qualityScore: 5,
         spamRisk: false,
       })