diff --git a/dandi/download.py b/dandi/download.py
index 10e7ab568..235381420 100644
--- a/dandi/download.py
+++ b/dandi/download.py
@@ -7,6 +7,7 @@
 from enum import Enum
 from functools import partial
 import hashlib
+import inspect
 import json
 import os
 import os.path as op
@@ -153,11 +154,24 @@ def download(
 
     gen_ = (r for dl in downloaders for r in dl.download_generator())
 
+    # Constructs to capture errors and handle them at the end
     errors = []
 
+    def p4e_gen(callback):
+        for v in callback:
+            yield p4e(v)
+
     def p4e(out):
         if out.get("status") == "error":
-            errors.append(out)
+            if out not in errors:
+                errors.append(out)
+        else:
+            # If generator was yielded, we need to wrap it also with
+            # our handling
+            for k, v in out.items():
+                if inspect.isgenerator(v):
+                    rec[k] = p4e_gen(v)
+
         return out
 
     # TODOs:
@@ -199,7 +213,9 @@ def p4e(out):
                 else:
                     break
     if errors:
-        raise RuntimeError(f"Encountered {len(errors)} errors while downloading.")
+        raise RuntimeError(
+            f"Encountered {pluralize(len(errors), 'error')} while downloading."
+        )
 
 
 @dataclass
diff --git a/dandi/tests/test_download.py b/dandi/tests/test_download.py
index 6e89d0dec..a06d94aec 100644
--- a/dandi/tests/test_download.py
+++ b/dandi/tests/test_download.py
@@ -72,9 +72,10 @@ def test_download_000027(
         download(url, tmp_path, format=DownloadFormat.DEBUG)
     assert "FileExistsError" not in capsys.readouterr().out
     # Generic error should be raised if we are using pyout/parallelization
-    with pytest.raises(RuntimeError):
+    with pytest.raises(RuntimeError) as exc:
         download(url, tmp_path)
     assert "FileExistsError" in capsys.readouterr().out
+    assert "Encountered 1 error while downloading" in str(exc)
 
     # TODO: somehow get that status report about what was downloaded and what not
     download(url, tmp_path, existing=DownloadExisting.SKIP)  # TODO: check that skipped