diff --git a/surfsense_backend/app/etl_pipeline/etl_pipeline_service.py b/surfsense_backend/app/etl_pipeline/etl_pipeline_service.py
index 4cdd387b0..496c6d0c3 100644
--- a/surfsense_backend/app/etl_pipeline/etl_pipeline_service.py
+++ b/surfsense_backend/app/etl_pipeline/etl_pipeline_service.py
@@ -30,6 +30,7 @@ class EtlPipelineService:
         category = classify_file(request.filename)
         start = time.perf_counter()
         status = "success"
+        error_category: str | None = None
         result: EtlResult | None = None
         with ot.etl_extract_span(
             content_type=category.value,
@@ -75,8 +76,9 @@ class EtlPipelineService:
 
                 result = await self._extract_document(request)
                 return result
-            except Exception:
+            except Exception as exc:
                 status = "error"
+                error_category = ot_metrics.categorize_exception(exc)
                 raise
             finally:
                 with contextlib.suppress(Exception):
@@ -94,6 +96,7 @@ class EtlPipelineService:
                         etl_service=result.etl_service if result else None,
                         content_type=result.content_type if result else category.value,
                         status=status,
+                        error_category=error_category,
                     )
 
     async def _extract_image(self, request: EtlRequest) -> EtlResult:
@@ -134,11 +137,27 @@ class EtlPipelineService:
                         request.filename,
                         exc_info=True,
                     )
+                ot.add_event(
+                    "etl.fallback",
+                    {
+                        "fallback.from": "vision_llm",
+                        "fallback.to": "document_parser",
+                        "fallback.reason": ot_metrics.categorize_exception(exc),
+                    },
+                )
         else:
             logging.info(
                 "No vision LLM provided, falling back to document parser for %s",
                 request.filename,
             )
+            ot.add_event(
+                "etl.fallback",
+                {
+                    "fallback.from": "vision_llm",
+                    "fallback.to": "document_parser",
+                    "fallback.reason": "not_configured",
+                },
+            )
 
         try:
             with ot.etl_ocr_span(
@@ -246,6 +265,13 @@ class EtlPipelineService:
                 # Common case: the configured ETL service can't OCR
                 # this image format (or no service is configured at
                 # all). Don't spam warnings -- just no OCR for it.
+                ot.add_event(
+                    "etl.ocr.skipped",
+                    {
+                        "skip.reason": "unsupported_format",
+                        "error.category": ot_metrics.categorize_exception(exc),
+                    },
+                )
                 logging.debug("Skipping per-image OCR for %s: %s", image_name, exc)
                 return ""
             return ocr_result.markdown_content
@@ -264,9 +290,17 @@ class EtlPipelineService:
                 sp.set_attribute("image.skipped.too_large", result.skipped_too_large)
                 sp.set_attribute("image.skipped.duplicate", result.skipped_duplicate)
                 sp.set_attribute("etl.status", "success")
-        except Exception:
+        except Exception as exc:
             # Picture description is additive; never let it fail an
             # otherwise-successful document extraction.
+            ot.add_event(
+                "etl.degraded",
+                {
+                    "degraded.reason": "picture_describe_failed",
+                    "degraded.action": "return_parser_output",
+                    "error.category": ot_metrics.categorize_exception(exc),
+                },
+            )
             logging.warning(
                 "Picture description failed for %s, returning parser output unchanged",
                 request.filename,
@@ -319,7 +353,15 @@ class EtlPipelineService:
                 return await parse_with_azure_doc_intelligence(
                     request.file_path, processing_mode=mode_value
                 )
-            except Exception:
+            except Exception as exc:
+                ot.add_event(
+                    "etl.fallback",
+                    {
+                        "fallback.from": "azure_di",
+                        "fallback.to": "llamacloud",
+                        "fallback.reason": ot_metrics.categorize_exception(exc),
+                    },
+                )
                 logging.warning(
                     "Azure Document Intelligence failed for %s, "
                     "falling back to LlamaCloud",
diff --git a/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py b/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
index 2aa92bd9b..282bd6034 100644
--- a/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
+++ b/surfsense_backend/app/indexing_pipeline/indexing_pipeline_service.py
@@ -2,6 +2,7 @@ import asyncio
 import contextlib
 import hashlib
 import logging
+import sys
 import time
 from collections.abc import Awaitable, Callable
 from dataclasses import dataclass, field
@@ -445,6 +446,7 @@ class IndexingPipelineService:
             await self._enqueue_ai_sort_if_enabled(document)
 
         except RETRYABLE_LLM_ERRORS as e:
+            ot.record_error(persist_span, e)
             log_retryable_llm_error(ctx, e)
             outcome_status = "requeued"
             await rollback_and_persist_failure(
@@ -452,24 +454,28 @@ class IndexingPipelineService:
             )
 
         except PERMANENT_LLM_ERRORS as e:
+            ot.record_error(persist_span, e)
             log_permanent_llm_error(ctx, e)
             await rollback_and_persist_failure(
                 self.session, document, llm_permanent_message(e)
             )
 
         except RecursionError as e:
+            ot.record_error(persist_span, e)
             log_chunking_overflow(ctx, e)
             await rollback_and_persist_failure(
                 self.session, document, PipelineMessages.CHUNKING_OVERFLOW
             )
 
         except EMBEDDING_ERRORS as e:
+            ot.record_error(persist_span, e)
             log_embedding_error(ctx, e)
             await rollback_and_persist_failure(
                 self.session, document, embedding_message(e)
             )
 
         except Exception as e:
+            ot.record_error(persist_span, e)
             log_unexpected_error(ctx, e)
             await rollback_and_persist_failure(
                 self.session, document, safe_exception_message(e)
@@ -488,7 +494,7 @@ class IndexingPipelineService:
             document_type=document_type,
             status=outcome_status,
         )
-        persist_span_cm.__exit__(None, None, None)
+        persist_span_cm.__exit__(*sys.exc_info())
         return document
 
     async def _enqueue_ai_sort_if_enabled(self, document: Document) -> None: