diff --git a/home/doris-schoolhouse/app/routes/api_assignments.py b/home/doris-schoolhouse/app/routes/api_assignments.py
index 60a137b..e99800a 100644
--- a/home/doris-schoolhouse/app/routes/api_assignments.py
+++ b/home/doris-schoolhouse/app/routes/api_assignments.py
@@ -1,6 +1,7 @@
 import hashlib
 from pathlib import Path
 from typing import Any
+from urllib.parse import quote_plus
 
 from fastapi import APIRouter, File, Form, HTTPException, Request, UploadFile
 from fastapi.responses import RedirectResponse
@@ -40,33 +41,49 @@ def _confirm_submission_to_paperless(current: dict) -> dict:
         if value:
             fields[optional_key] = value
     artifact_kind = handoff.get("artifact_kind") or "document"
-    if artifact_kind == "source_bundle":
-        paperless_response = paperless.upload_source_bundle_receipt(current)
-        enrichment = paperless.enrich_direct_submission(current, paperless_response)
+    response: dict[str, Any]
+    body_obj: dict[str, Any]
+    ok = False
+    error_detail = None
+    try:
+        if artifact_kind == "source_bundle":
+            paperless_response = paperless.upload_source_bundle_receipt(current)
+            enrichment = paperless.enrich_direct_submission(current, paperless_response)
+            response = {
+                "ok": True,
+                "status_code": 200,
+                "body": paperless_response,
+                "mode": "direct-paperless",
+                "enrichment": enrichment,
+            }
+            task_id = paperless_response.get("task_id") or paperless_response.get("id")
+            body_obj = {
+                "paperless_document_id": enrichment.get("document_id"),
+                "paperless_title": enrichment.get("title") or paperless.build_submission_title(current),
+                "paperless_task_id": task_id,
+                "paperless_metadata": enrichment.get("metadata_payload"),
+            }
+            ok = True
+        else:
+            if handoff.get("artifact_kind"):
+                fields["artifact_kind"] = str(handoff["artifact_kind"])
+            if handoff.get("file_count"):
+                fields["file_count"] = str(handoff["file_count"])
+            response = webhooks.post_multipart(handoff["target_url"], fields, "document", file_path)
+            body = response.get("body", {}) if isinstance(response, dict) else {}
+            body_obj = body[0] if isinstance(body, list) and body and isinstance(body[0], dict) else (body if isinstance(body, dict) else {})
+            ok = bool(response.get("ok", False)) if isinstance(response, dict) else False
+        if not ok:
+            error_detail = str(response.get("error") or response.get("body") or "Paperless confirmation failed.")
+    except Exception as exc:
+        error_detail = f"{type(exc).__name__}: {exc}"
         response = {
-            "ok": True,
-            "status_code": 200,
-            "body": paperless_response,
-            "mode": "direct-paperless",
-            "enrichment": enrichment,
+            "ok": False,
+            "status_code": 500,
+            "mode": "direct-paperless" if artifact_kind == "source_bundle" else "webhook",
+            "error": error_detail,
         }
-        task_id = paperless_response.get("task_id") or paperless_response.get("id")
-        body_obj = {
-            "paperless_document_id": enrichment.get("document_id"),
-            "paperless_title": enrichment.get("title") or paperless.build_submission_title(current),
-            "paperless_task_id": task_id,
-            "paperless_metadata": enrichment.get("metadata_payload"),
-        }
-        ok = True
-    else:
-        if handoff.get("artifact_kind"):
-            fields["artifact_kind"] = str(handoff["artifact_kind"])
-        if handoff.get("file_count"):
-            fields["file_count"] = str(handoff["file_count"])
-        response = webhooks.post_multipart(handoff["target_url"], fields, "document", file_path)
-        body = response.get("body", {}) if isinstance(response, dict) else {}
-        body_obj = body[0] if isinstance(body, list) and body and isinstance(body[0], dict) else (body if isinstance(body, dict) else {})
-        ok = bool(response.get("ok", False)) if isinstance(response, dict) else False
+        body_obj = {}
     updates = {
         "status": "paperless-queued" if ok else "paperless-error",
         "confirmed_at": store.now(),
@@ -76,6 +93,7 @@ def _confirm_submission_to_paperless(current: dict) -> dict:
         "paperless_task_id": body_obj.get("paperless_task_id"),
     }
     updated = repo.update_submission(str(current.get("id")), updates) or current
+    updated["paperless_error_detail"] = error_detail
     grade_note = None
     if ok and updated.get("assignment_id"):
         grade_note = paperless.append_grade_note_if_available(str(updated.get("assignment_id")))
@@ -87,6 +105,7 @@ def _confirm_submission_to_paperless(current: dict) -> dict:
         "webhook": [response],
         "grade_note": grade_note,
         "file_count": handoff.get("file_count") or 1,
+        "error_detail": error_detail,
     }
 
 
@@ -220,7 +239,10 @@ async def intake_assignment(
         "backend": repo.backend,
     }
     if "text/html" in accept:
-        redirect_url = "/assignments/upload?submitted=" + str(created["id"]) + "&file_count=" + str(bundle["file_count"]) + "&artifact_kind=" + str(created.get("artifact_kind", "document")) + "&paperless_status=" + str(created.get("status", "uploaded-local"))
+        status_value = str(created.get("status", "uploaded-local"))
+        redirect_url = "/assignments/upload?submitted=" + str(created["id"]) + "&file_count=" + str(bundle["file_count"]) + "&artifact_kind=" + str(created.get("artifact_kind", "document")) + "&paperless_status=" + status_value
+        if auto_confirmed and auto_confirmed.get("error_detail"):
+            redirect_url += "&paperless_error=" + quote_plus(str(auto_confirmed["error_detail"]))
         return RedirectResponse(url=redirect_url, status_code=303)
     return response_payload
 
diff --git a/home/doris-schoolhouse/app/templates/assignment_upload.html b/home/doris-schoolhouse/app/templates/assignment_upload.html
index 64f27ea..cc6cd33 100644
--- a/home/doris-schoolhouse/app/templates/assignment_upload.html
+++ b/home/doris-schoolhouse/app/templates/assignment_upload.html
@@ -1,12 +1,19 @@
 {% extends 'base.html' %}
 {% block content %}
 {% if request.query_params.get('submitted') %}
-<section class="card form-card notice-card success-card evidence-board">
-  <div class="case-legend"><span class="section-label">Submission packet</span><span class="pill">Filed</span></div>
-  <h2>Submission Created</h2>
+{% set paperless_status = request.query_params.get('paperless_status', 'uploaded-local') %}
+<section class="card form-card notice-card {{ 'success-card' if paperless_status == 'paperless-queued' else '' }} evidence-board">
+  <div class="case-legend"><span class="section-label">Submission packet</span><span class="pill">{{ 'Filed' if paperless_status == 'paperless-queued' else 'Saved locally' }}</span></div>
+  <h2>{{ 'Submission Created' if paperless_status == 'paperless-queued' else 'Submission Saved, Archive Pending' }}</h2>
   <p>Submission {{ request.query_params.get('submitted') }} was created successfully.</p>
   <p class="muted">Artifact: {{ request.query_params.get('artifact_kind', 'document') }} · Files: {{ request.query_params.get('file_count', '1') }}</p>
-  <p class="muted">Paperless status: {{ request.query_params.get('paperless_status', 'uploaded-local') }}</p>
+  <p class="muted">Paperless status: {{ paperless_status }}</p>
+  {% if paperless_status != 'paperless-queued' %}
+  <p class="muted">Schoolhouse kept the submission locally, but the archive handoff failed this time.</p>
+  {% if request.query_params.get('paperless_error') %}
+  <p class="muted">Error: {{ request.query_params.get('paperless_error') }}</p>
+  {% endif %}
+  {% endif %}
 </section>
 {% endif %}
 <section class="card form-card evidence-board">