diff --git a/src/store.ts b/src/store.ts
index f17404d..ac3cf16 100644
--- a/src/store.ts
+++ b/src/store.ts
@@ -1337,6 +1337,12 @@ export async function generateEmbeddings(
     const batches = buildEmbeddingBatches(docsToEmbed, maxDocsPerBatch, maxBatchBytes);
 
     for (const batchMeta of batches) {
+      // Abort early if session has been invalidated
+      if (!session.isValid) {
+        console.warn(`⚠ Session expired — skipping remaining document batches`);
+        break;
+      }
+
       const batchDocs = getEmbeddingDocsForBatch(db, batchMeta);
       const batchChunks: ChunkItem[] = [];
       const batchBytes = batchMeta.reduce((sum, doc) => sum + Math.max(0, doc.bytes), 0);
@@ -1345,7 +1351,7 @@ export async function generateEmbeddings(
         if (!doc.body.trim()) continue;
 
         const title = extractTitle(doc.body, doc.path);
-        const chunks = await chunkDocumentByTokens(doc.body);
+        const chunks = await chunkDocumentByTokens(doc.body, undefined, undefined, undefined, session.signal);
 
         for (let seq = 0; seq < chunks.length; seq++) {
           batchChunks.push({
@@ -1383,6 +1389,23 @@ export async function generateEmbeddings(
       let batchChunkBytesProcessed = 0;
 
       for (let batchStart = 0; batchStart < batchChunks.length; batchStart += BATCH_SIZE) {
+        // Abort early if session has been invalidated (e.g. max duration exceeded)
+        if (!session.isValid) {
+          const remaining = batchChunks.length - batchStart;
+          errors += remaining;
+          console.warn(`⚠ Session expired — skipping ${remaining} remaining chunks`);
+          break;
+        }
+
+        // Abort early if error rate is too high (>80% of processed chunks failed)
+        const processed = chunksEmbedded + errors;
+        if (processed >= BATCH_SIZE && errors > processed * 0.8) {
+          const remaining = batchChunks.length - batchStart;
+          errors += remaining;
+          console.warn(`⚠ Error rate too high (${errors}/${processed}) — aborting embedding`);
+          break;
+        }
+
         const batchEnd = Math.min(batchStart + BATCH_SIZE, batchChunks.length);
         const chunkBatch = batchChunks.slice(batchStart, batchEnd);
         const texts = chunkBatch.map(chunk => formatDocForEmbedding(chunk.text, chunk.title));
@@ -1402,20 +1425,26 @@ export async function generateEmbeddings(
           }
         } catch {
           // Batch failed — try individual embeddings as fallback
-          for (const chunk of chunkBatch) {
-            try {
-              const text = formatDocForEmbedding(chunk.text, chunk.title);
-              const result = await session.embed(text);
-              if (result) {
-                insertEmbedding(db, chunk.hash, chunk.seq, chunk.pos, new Float32Array(result.embedding), model, now);
-                chunksEmbedded++;
-              } else {
+          // But skip if session is already invalid (avoids N doomed retries)
+          if (!session.isValid) {
+            errors += chunkBatch.length;
+            batchChunkBytesProcessed += chunkBatch.reduce((sum, c) => sum + c.bytes, 0);
+          } else {
+            for (const chunk of chunkBatch) {
+              try {
+                const text = formatDocForEmbedding(chunk.text, chunk.title);
+                const result = await session.embed(text);
+                if (result) {
+                  insertEmbedding(db, chunk.hash, chunk.seq, chunk.pos, new Float32Array(result.embedding), model, now);
+                  chunksEmbedded++;
+                } else {
+                  errors++;
+                }
+              } catch {
                 errors++;
               }
-            } catch {
-              errors++;
+              batchChunkBytesProcessed += chunk.bytes;
             }
-            batchChunkBytesProcessed += chunk.bytes;
           }
         }
 
@@ -2092,7 +2121,8 @@ export async function chunkDocumentByTokens(
   content: string,
   maxTokens: number = CHUNK_SIZE_TOKENS,
   overlapTokens: number = CHUNK_OVERLAP_TOKENS,
-  windowTokens: number = CHUNK_WINDOW_TOKENS
+  windowTokens: number = CHUNK_WINDOW_TOKENS,
+  signal?: AbortSignal
 ): Promise<{ text: string; pos: number; tokens: number }[]> {
   const llm = getDefaultLlamaCpp();
 
@@ -2110,6 +2140,9 @@ export async function chunkDocumentByTokens(
   const results: { text: string; pos: number; tokens: number }[] = [];
 
   for (const chunk of charChunks) {
+    // Respect abort signal to avoid runaway tokenization
+    if (signal?.aborted) break;
+
     const tokens = await llm.tokenize(chunk.text);
 
     if (tokens.length <= maxTokens) {
@@ -2123,6 +2156,7 @@ export async function chunkDocumentByTokens(
       const subChunks = chunkDocument(chunk.text, safeMaxChars, Math.floor(overlapChars * actualCharsPerToken / 2), Math.floor(windowChars * actualCharsPerToken / 2));
 
       for (const subChunk of subChunks) {
+        if (signal?.aborted) break;
         const subTokens = await llm.tokenize(subChunk.text);
         results.push({
           text: subChunk.text,