diff --git a/apps/webapp/app/services/runsReplicationService.server.ts b/apps/webapp/app/services/runsReplicationService.server.ts
index 97ceb23ea8..8e32b2dbdd 100644
--- a/apps/webapp/app/services/runsReplicationService.server.ts
+++ b/apps/webapp/app/services/runsReplicationService.server.ts
@@ -462,13 +462,13 @@ export class RunsReplicationService {
 
       // Insert task runs and payloads with retry logic for connection errors
       const [taskRunError, taskRunResult] = await this.#insertWithRetry(
-        () => this.#insertTaskRunInserts(taskRunInserts),
+        (attempt) => this.#insertTaskRunInserts(taskRunInserts, attempt),
         "task run inserts",
         flushId
       );
 
       const [payloadError, payloadResult] = await this.#insertWithRetry(
-        () => this.#insertPayloadInserts(payloadInserts),
+        (attempt) => this.#insertPayloadInserts(payloadInserts, attempt),
         "payload inserts",
         flushId
       );
@@ -502,7 +502,7 @@ export class RunsReplicationService {
 
   // New method to handle inserts with retry logic for connection errors
   async #insertWithRetry<T>(
-    insertFn: () => Promise<T>,
+    insertFn: (attempt: number) => Promise<T>,
     operationName: string,
     flushId: string
   ): Promise<[Error | null, T | null]> {
@@ -510,16 +510,17 @@ export class RunsReplicationService {
 
     for (let attempt = 1; attempt <= this._insertMaxRetries; attempt++) {
       try {
-        const result = await insertFn();
+        const result = await insertFn(attempt);
         return [null, result];
       } catch (error) {
         lastError = error instanceof Error ? error : new Error(String(error));
 
         // Check if this is a retryable connection error
-        if (this.#isRetryableConnectionError(lastError) && attempt < this._insertMaxRetries) {
+        if (this.#isRetryableConnectionError(lastError)) {
           const delay = this.#calculateConnectionRetryDelay(attempt);
 
-          this.logger.warn(`Retrying ${operationName} due to connection error`, {
+          this.logger.warn(`Retrying RunReplication insert due to connection error`, {
+            operationName,
             flushId,
             attempt,
             maxRetries: this._insertMaxRetries,
@@ -567,7 +568,7 @@ export class RunsReplicationService {
     return delay + jitter;
   }
 
-  async #insertTaskRunInserts(taskRunInserts: TaskRunV2[]) {
+  async #insertTaskRunInserts(taskRunInserts: TaskRunV2[], attempt: number) {
     return await startSpan(this._tracer, "insertTaskRunsInserts", async (span) => {
       const [insertError, insertResult] = await this.options.clickhouse.taskRuns.insert(
         taskRunInserts,
@@ -581,18 +582,20 @@ export class RunsReplicationService {
       );
 
       if (insertError) {
-        this.logger.error("Error inserting task run inserts", {
+        this.logger.error("Error inserting task run inserts attempt", {
           error: insertError,
+          attempt,
         });
 
         recordSpanError(span, insertError);
+        throw insertError;
       }
 
       return insertResult;
     });
   }
 
-  async #insertPayloadInserts(payloadInserts: RawTaskRunPayloadV1[]) {
+  async #insertPayloadInserts(payloadInserts: RawTaskRunPayloadV1[], attempt: number) {
     return await startSpan(this._tracer, "insertPayloadInserts", async (span) => {
       const [insertError, insertResult] = await this.options.clickhouse.taskRuns.insertPayloads(
         payloadInserts,
@@ -606,11 +609,13 @@ export class RunsReplicationService {
       );
 
       if (insertError) {
-        this.logger.error("Error inserting payload inserts", {
+        this.logger.error("Error inserting payload inserts attempt", {
           error: insertError,
+          attempt,
         });
 
         recordSpanError(span, insertError);
+        throw insertError;
       }
 
       return insertResult;