diff --git a/crates/integration-tests/tests/integration/versioned.rs b/crates/integration-tests/tests/integration/versioned.rs
index 9f622f7..691fef3 100644
--- a/crates/integration-tests/tests/integration/versioned.rs
+++ b/crates/integration-tests/tests/integration/versioned.rs
@@ -617,6 +617,85 @@ fn test_removing_api_version_fails_check() -> Result<()> {
     Ok(())
 }
 
+/// Test that removing an API version whose document is unparseable fails
+/// the check.
+#[test]
+fn test_removing_api_version_unparseable_doc_fails_check() -> Result<()> {
+    let env = TestEnvironment::new_git()?;
+    let apis = versioned_health_apis()?;
+
+    env.generate_documents(&apis)?;
+    env.commit_documents()?;
+
+    // Conflict markers make the v3 document unparseable.
+    let v3_orphan_path = env
+        .find_versioned_document_path("versioned-health", "3.0.0")?
+        .expect("v3 document exists");
+    let conflict_content = r#"<<<<<<< HEAD
+{
+  "openapi": "3.0.3",
+  "info": {
+    "title": "Versioned Health API",
+    "version": "3.0.0"
+  }
+}
+=======
+{
+  "openapi": "3.0.3",
+  "info": {
+    "title": "Versioned Health API Modified",
+    "version": "3.0.0"
+  }
+}
+>>>>>>> branch
+"#;
+    env.create_file(&v3_orphan_path, conflict_content)?;
+
+    // With the reduced set of API versions, v3 is both orphaned and
+    // unparseable.
+    let reduced_apis = versioned_health_reduced_apis()?;
+
+    let (result, summaries, rendered) =
+        check_apis_with_render(env.environment(), &reduced_apis)?;
+    assert_eq!(result, CheckResult::NeedsUpdate);
+    crate::snapshot::assert_render_snapshot(
+        &env,
+        "orphaned_unparseable_doc.txt",
+        &rendered,
+    );
+    assert_eq!(
+        summaries,
+        [
+            ProblemSummary::new(
+                "versioned-health",
+                "3.0.0",
+                ProblemKind::LocalDocFileOrphaned {
+                    basename: v3_orphan_path
+                        .file_name()
+                        .expect("v3_orphan_path has a file name")
+                        .to_owned()
+                },
+            ),
+            ProblemSummary::for_api(
+                "versioned-health",
+                ProblemKind::LatestLinkStale,
+            ),
+        ],
+    );
+
+    // The fix deletes the unparseable orphaned document.
+    env.generate_documents(&reduced_apis)?;
+    assert!(
+        !env.file_exists(&v3_orphan_path),
+        "unparseable orphaned document should have been deleted"
+    );
+
+    let result = check_apis_up_to_date(env.environment(), &reduced_apis)?;
+    assert_eq!(result, CheckResult::Success);
+
+    Ok(())
+}
+
 /// Test that adding new API versions passes the check.
 #[test]
 fn test_adding_new_api_version_passes_check() -> Result<()> {
diff --git a/crates/integration-tests/tests/output/integration/orphaned_unparseable_doc.txt b/crates/integration-tests/tests/output/integration/orphaned_unparseable_doc.txt
new file mode 100644
index 0000000..6850cb8
--- /dev/null
+++ b/crates/integration-tests/tests/output/integration/orphaned_unparseable_doc.txt
@@ -0,0 +1,35 @@
+     -------
+  Generating OpenAPI documents from API definitions ... 
+     Loading local OpenAPI documents from "<documents dir>" ... 
+     Warning skipping unparseable file: file "versioned-health/versioned-health-3.0.0-05def5.json": parsing as JSON: expected value at line 1 column 1
+     Loading blessed OpenAPI documents from VCS revision "main" path "documents"
+     -------
+    Checking 2 OpenAPI documents...
+       Fresh versioned-health (versioned v1.0.0 (blessed)): Versioned Health API
+       Fresh versioned-health (versioned v2.0.0 (blessed)): Versioned Health API
+       Stale versioned-health "latest" symlink
+     problem: "Latest" symlink for versioned API "versioned-health" is stale:
+              points to versioned-health-3.0.0-05def5.json, but should be
+              versioned-health-2.0.0-511899.json
+         fix: will update symlink to point to versioned-health-2.0.0-511899.json
+
+       Other problems not associated with a specific supported API version:
+     problem: A local OpenAPI document was found that does not correspond to a
+              supported version of this API: versioned-health/versioned-health-
+              3.0.0-05def5.json.  This is unusual, but it could happen if you're
+              either retiring an older version of this API or if you created
+              this version in this branch and later merged with upstream and had
+              to change your local version number.  In either case, this tool
+              can remove the unused file for you.
+         fix: will delete file: versioned-health/versioned-health-3.0.0-
+              05def5.json
+
+        Note API versioned-health version 3.0.0: formerly blessed version has
+             been removed.  This version will no longer be supported!  This will
+             break upgrade from software that still uses this version.  If this
+             is unexpected, check the list of supported versions in Rust for a
+             possible mismerge.
+
+     -------
+       Stale 2 documents checked: 2 fresh, 0 stale, 0 failed, 2 other problems
+             (run test-openapi-manager generate to update)