diff --git a/backend/onyx/background/celery/tasks/monitoring/tasks.py b/backend/onyx/background/celery/tasks/monitoring/tasks.py
index 6f09ca15f..20782ae7f 100644
--- a/backend/onyx/background/celery/tasks/monitoring/tasks.py
+++ b/backend/onyx/background/celery/tasks/monitoring/tasks.py
@@ -68,20 +68,22 @@ class Metric(BaseModel):
         task_logger.info(json.dumps(data))
 
     def emit(self, tenant_id: str | None) -> None:
-        # Convert value to appropriate type
-        float_value = (
-            float(self.value) if isinstance(self.value, (int, float)) else None
-        )
-        int_value = int(self.value) if isinstance(self.value, int) else None
-        string_value = str(self.value) if isinstance(self.value, str) else None
-        bool_value = bool(self.value) if isinstance(self.value, bool) else None
-
-        if (
-            float_value is None
-            and int_value is None
-            and string_value is None
-            and bool_value is None
-        ):
+        # Convert value to appropriate type based on the input value
+        bool_value = None
+        float_value = None
+        int_value = None
+        string_value = None
+        # NOTE: have to do bool first, since `isinstance(True, int)` is true
+        # e.g. bool is a subclass of int
+        if isinstance(self.value, bool):
+            bool_value = self.value
+        elif isinstance(self.value, int):
+            int_value = self.value
+        elif isinstance(self.value, float):
+            float_value = self.value
+        elif isinstance(self.value, str):
+            string_value = self.value
+        else:
             task_logger.error(
                 f"Invalid metric value type: {type(self.value)} "
                 f"({self.value}) for metric {self.name}."
@@ -183,35 +185,41 @@ def _build_connector_start_latency_metric(
     )
 
 
-def _build_run_success_metric(
-    cc_pair: ConnectorCredentialPair, recent_attempt: IndexAttempt, redis_std: Redis
-) -> Metric | None:
-    metric_key = _CONNECTOR_INDEX_ATTEMPT_RUN_SUCCESS_KEY_FMT.format(
-        cc_pair_id=cc_pair.id,
-        index_attempt_id=recent_attempt.id,
-    )
-
-    if _has_metric_been_emitted(redis_std, metric_key):
-        task_logger.info(
-            f"Skipping metric for connector {cc_pair.connector.id} "
-            f"index attempt {recent_attempt.id} because it has already been "
-            "emitted"
-        )
-        return None
-
-    if recent_attempt.status in [
-        IndexingStatus.SUCCESS,
-        IndexingStatus.FAILED,
-        IndexingStatus.CANCELED,
-    ]:
-        return Metric(
-            key=metric_key,
-            name="connector_run_succeeded",
-            value=recent_attempt.status == IndexingStatus.SUCCESS,
-            tags={"source": str(cc_pair.connector.source)},
+def _build_run_success_metrics(
+    cc_pair: ConnectorCredentialPair,
+    recent_attempts: list[IndexAttempt],
+    redis_std: Redis,
+) -> list[Metric]:
+    metrics = []
+    for attempt in recent_attempts:
+        metric_key = _CONNECTOR_INDEX_ATTEMPT_RUN_SUCCESS_KEY_FMT.format(
+            cc_pair_id=cc_pair.id,
+            index_attempt_id=attempt.id,
         )
 
-    return None
+        if _has_metric_been_emitted(redis_std, metric_key):
+            task_logger.info(
+                f"Skipping metric for connector {cc_pair.connector.id} "
+                f"index attempt {attempt.id} because it has already been "
+                "emitted"
+            )
+            continue
+
+        if attempt.status in [
+            IndexingStatus.SUCCESS,
+            IndexingStatus.FAILED,
+            IndexingStatus.CANCELED,
+        ]:
+            metrics.append(
+                Metric(
+                    key=metric_key,
+                    name="connector_run_succeeded",
+                    value=attempt.status == IndexingStatus.SUCCESS,
+                    tags={"source": str(cc_pair.connector.source)},
+                )
+            )
+
+    return metrics
 
 
 def _collect_connector_metrics(db_session: Session, redis_std: Redis) -> list[Metric]:
@@ -224,7 +232,7 @@ def _collect_connector_metrics(db_session: Session, redis_std: Redis) -> list[Me
 
     metrics = []
     for cc_pair in cc_pairs:
-        # Get most recent attempt in the last hour
+        # Get all attempts in the last hour
         recent_attempts = (
             db_session.query(IndexAttempt)
             .filter(
@@ -232,31 +240,29 @@ def _collect_connector_metrics(db_session: Session, redis_std: Redis) -> list[Me
                 IndexAttempt.time_created >= one_hour_ago,
             )
             .order_by(IndexAttempt.time_created.desc())
-            .limit(2)
             .all()
         )
-        recent_attempt = recent_attempts[0] if recent_attempts else None
+        most_recent_attempt = recent_attempts[0] if recent_attempts else None
         second_most_recent_attempt = (
             recent_attempts[1] if len(recent_attempts) > 1 else None
         )
 
         # if no metric to emit, skip
-        if not recent_attempt:
+        if most_recent_attempt is None:
             continue
 
         # Connector start latency
         start_latency_metric = _build_connector_start_latency_metric(
-            cc_pair, recent_attempt, second_most_recent_attempt, redis_std
+            cc_pair, most_recent_attempt, second_most_recent_attempt, redis_std
         )
         if start_latency_metric:
             metrics.append(start_latency_metric)
 
         # Connector run success/failure
-        run_success_metric = _build_run_success_metric(
-            cc_pair, recent_attempt, redis_std
+        run_success_metrics = _build_run_success_metrics(
+            cc_pair, recent_attempts, redis_std
         )
-        if run_success_metric:
-            metrics.append(run_success_metric)
+        metrics.extend(run_success_metrics)
 
     return metrics