diff --git a/src/app/(admin)/admin/projects/page.tsx b/src/app/(admin)/admin/projects/page.tsx
index 1baa4d8..da9ac08 100644
--- a/src/app/(admin)/admin/projects/page.tsx
+++ b/src/app/(admin)/admin/projects/page.tsx
@@ -252,9 +252,16 @@ export default function ProjectsPage() {
   // AI batch tagging mutation
   const batchTagProjects = trpc.tag.batchTagProjects.useMutation({
     onSuccess: (result) => {
-      toast.success(
-        `AI Tagging complete: ${result.processed} tagged, ${result.skipped} skipped, ${result.failed} failed`
-      )
+      if (result.errors && result.errors.length > 0) {
+        // Show first error if there are any
+        toast.error(`AI Tagging issue: ${result.errors[0]}`)
+      } else if (result.processed === 0 && result.skipped === 0 && result.failed === 0) {
+        toast.info('No projects to tag - all projects in this round already have tags')
+      } else {
+        toast.success(
+          `AI Tagging complete: ${result.processed} tagged, ${result.skipped} skipped, ${result.failed} failed`
+        )
+      }
       setAiTagDialogOpen(false)
       setSelectedRoundForTagging('')
       utils.project.list.invalidate()
diff --git a/src/server/services/ai-tagging.ts b/src/server/services/ai-tagging.ts
index 14f6940..63c08c0 100644
--- a/src/server/services/ai-tagging.ts
+++ b/src/server/services/ai-tagging.ts
@@ -101,15 +101,23 @@ async function getTaggingSettings(): Promise<{
   const settings = await prisma.systemSettings.findMany({
     where: {
       key: {
-        in: ['ai_tagging_enabled', 'ai_tagging_max_tags'],
+        in: ['ai_tagging_enabled', 'ai_tagging_max_tags', 'ai_enabled'],
       },
     },
   })
 
   const settingsMap = new Map(settings.map((s) => [s.key, s.value]))
 
+  // AI tagging is enabled if:
+  // 1. ai_tagging_enabled is explicitly 'true', OR
+  // 2. ai_tagging_enabled is not set but ai_enabled is 'true' (fall back to general AI setting)
+  const taggingEnabled = settingsMap.get('ai_tagging_enabled')
+  const aiEnabled = settingsMap.get('ai_enabled')
+
+  const enabled = taggingEnabled === 'true' || (taggingEnabled === undefined && aiEnabled === 'true')
+
   return {
-    enabled: settingsMap.get('ai_tagging_enabled') === 'true',
+    enabled,
     maxTags: parseInt(settingsMap.get('ai_tagging_max_tags') || String(DEFAULT_MAX_TAGS)),
   }
 }
@@ -409,34 +417,73 @@ export async function batchTagProjects(
   onProgress?: (processed: number, total: number) => void
 ): Promise<BatchTaggingResult> {
   const settings = await getTaggingSettings()
+  console.log('[AI Tagging] Settings:', settings)
+
   if (!settings.enabled) {
+    console.log('[AI Tagging] AI tagging is disabled in settings')
     return {
       processed: 0,
       failed: 0,
       skipped: 0,
-      errors: ['AI tagging is disabled'],
+      errors: ['AI tagging is disabled. Enable it in Settings > AI or set ai_enabled to true.'],
       results: [],
     }
   }
 
-  // Get untagged projects in round
-  const projects = await prisma.project.findMany({
-    where: {
-      roundId,
-      projectTags: { none: {} }, // Only projects with no tags
-    },
-    include: {
-      files: { select: { fileType: true } },
-      _count: { select: { teamMembers: true, files: true } },
-    },
-  })
-
-  if (projects.length === 0) {
+  // Check if OpenAI is configured
+  const openai = await getOpenAI()
+  if (!openai) {
+    console.log('[AI Tagging] OpenAI is not configured')
     return {
       processed: 0,
       failed: 0,
       skipped: 0,
-      errors: [],
+      errors: ['OpenAI API is not configured. Add your API key in Settings > AI.'],
+      results: [],
+    }
+  }
+
+  // Check if there are any available tags
+  const availableTags = await getAvailableTags()
+  console.log(`[AI Tagging] Found ${availableTags.length} available expertise tags`)
+  if (availableTags.length === 0) {
+    return {
+      processed: 0,
+      failed: 0,
+      skipped: 0,
+      errors: ['No expertise tags defined. Create tags in Settings > Tags first.'],
+      results: [],
+    }
+  }
+
+  // Get ALL projects in round to check their tag status
+  const allProjects = await prisma.project.findMany({
+    where: { roundId },
+    include: {
+      files: { select: { fileType: true } },
+      _count: { select: { teamMembers: true, files: true } },
+      projectTags: { select: { tagId: true } },
+    },
+  })
+
+  console.log(`[AI Tagging] Found ${allProjects.length} total projects in round`)
+
+  // Filter to only projects that truly have no tags (empty tags array AND no projectTags)
+  const untaggedProjects = allProjects.filter(p =>
+    (p.tags.length === 0) && (p.projectTags.length === 0)
+  )
+
+  const alreadyTaggedCount = allProjects.length - untaggedProjects.length
+  console.log(`[AI Tagging] ${untaggedProjects.length} untagged projects, ${alreadyTaggedCount} already have tags`)
+
+  if (untaggedProjects.length === 0) {
+    return {
+      processed: 0,
+      failed: 0,
+      skipped: alreadyTaggedCount,
+      errors: alreadyTaggedCount > 0
+        ? []
+        : ['No projects found in this round'],
       results: [],
     }
   }
@@ -446,8 +493,8 @@ export async function batchTagProjects(
   let failed = 0
   const errors: string[] = []
 
-  for (let i = 0; i < projects.length; i++) {
-    const project = projects[i]
+  for (let i = 0; i < untaggedProjects.length; i++) {
+    const project = untaggedProjects[i]
     try {
       const result = await tagProject(project.id, userId)
       results.push(result)
@@ -459,7 +506,7 @@ export async function batchTagProjects(
 
     // Report progress
     if (onProgress) {
-      onProgress(i + 1, projects.length)
+      onProgress(i + 1, untaggedProjects.length)
     }
   }