diff --git a/news/8676.feature b/news/8676.feature
new file mode 100644
index 000000000..f8da963f6
--- /dev/null
+++ b/news/8676.feature
@@ -0,0 +1,2 @@
+Improve error message friendliness when an environment has packages with
+corrupted metadata.
diff --git a/src/pip/_internal/operations/check.py b/src/pip/_internal/operations/check.py
index 5714915bc..0d5963295 100644
--- a/src/pip/_internal/operations/check.py
+++ b/src/pip/_internal/operations/check.py
@@ -48,8 +48,8 @@ def create_package_set_from_installed(**kwargs):
         name = canonicalize_name(dist.project_name)
         try:
             package_set[name] = PackageDetails(dist.version, dist.requires())
-        except RequirementParseError as e:
-            # Don't crash on broken metadata
+        except (OSError, RequirementParseError) as e:
+            # Don't crash on unreadable or broken metadata
             logger.warning("Error parsing requirements for %s: %s", name, e)
             problems = True
     return package_set, problems