diff --git a/apps/rowboat/app/scripts/rag-worker.ts b/apps/rowboat/app/scripts/rag-worker.ts
index 95f85fa2b..be2105837 100644
--- a/apps/rowboat/app/scripts/rag-worker.ts
+++ b/apps/rowboat/app/scripts/rag-worker.ts
@@ -61,6 +61,27 @@ async function retryable<T>(fn: () => Promise<T>, maxAttempts: number = 3): Prom
     }
 }
 
+// Fixed namespace for deriving deterministic Qdrant point IDs (RFC 4122 v5).
+const EMBEDDING_ID_NAMESPACE = 'a4d1f3e2-7b6c-5a4d-9e8f-1c2b3a4d5e6f';
+
+/**
+ * Derives a stable, deterministic point ID for an embedding from its document
+ * id and chunk index. Re-processing the same document chunk (e.g. when a job is
+ * retried after the Qdrant upsert succeeded but a later step failed) produces
+ * the same id, so the upsert overwrites the existing point instead of inserting
+ * a duplicate. Returns a valid UUID, as required by `EmbeddingRecord.id`.
+ */
+function embeddingPointId(docId: string, chunkIndex: number): string {
+    const namespace = Buffer.from(EMBEDDING_ID_NAMESPACE.replace(/-/g, ''), 'hex');
+    const name = Buffer.from(`${docId}-chunk-${chunkIndex}`, 'utf8');
+    const hash = crypto.createHash('sha1').update(namespace).update(name).digest();
+    const bytes = hash.subarray(0, 16);
+    bytes[6] = (bytes[6] & 0x0f) | 0x50; // version 5
+    bytes[8] = (bytes[8] & 0x3f) | 0x80; // RFC 4122 variant
+    const hex = bytes.toString('hex');
+    return `${hex.slice(0, 8)}-${hex.slice(8, 12)}-${hex.slice(12, 16)}-${hex.slice(16, 20)}-${hex.slice(20)}`;
+}
+
 async function runProcessFilePipeline(_logger: PrefixLogger, usageTracker: UsageTracker, job: z.infer<typeof DataSource>, doc: z.infer<typeof DataSourceDoc>) {
     if (doc.data.type !== 'file_local' && doc.data.type !== 'file_s3') {
         throw new Error("Invalid data source type");
@@ -153,7 +174,7 @@ async function runProcessFilePipeline(_logger: PrefixLogger, usageTracker: Usage
     // store embeddings in qdrant
     logger.log("Storing embeddings in Qdrant");
     const points: z.infer<typeof EmbeddingRecord>[] = embeddings.map((embedding, i) => ({
-        id: crypto.randomUUID(),
+        id: embeddingPointId(doc.id, i),
         vector: embedding,
         payload: {
             projectId: job.projectId,
@@ -222,7 +243,7 @@ async function runScrapePipeline(_logger: PrefixLogger, usageTracker: UsageTrack
     // store embeddings in qdrant
     logger.log("Storing embeddings in Qdrant");
     const points: z.infer<typeof EmbeddingRecord>[] = embeddings.map((embedding, i) => ({
-        id: crypto.randomUUID(),
+        id: embeddingPointId(doc.id, i),
         vector: embedding,
         payload: {
             projectId: job.projectId,
@@ -274,7 +295,7 @@ async function runProcessTextPipeline(_logger: PrefixLogger, usageTracker: Usage
     // store embeddings in qdrant
     logger.log("Storing embeddings in Qdrant");
     const points: z.infer<typeof EmbeddingRecord>[] = embeddings.map((embedding, i) => ({
-        id: crypto.randomUUID(),
+        id: embeddingPointId(doc.id, i),
         vector: embedding,
         payload: {
             projectId: job.projectId,