diff --git a/insight/reporter.py b/insight/reporter.py
index 92e0c5a..8b25c15 100644
--- a/insight/reporter.py
+++ b/insight/reporter.py
@@ -1,7 +1,15 @@
 import os
 
+
+def _report_filename(file_path):
+    normalized_path = os.path.normpath(file_path)
+    if os.altsep:
+        normalized_path = normalized_path.replace(os.altsep, "_")
+    return normalized_path.replace(os.sep, "_").replace(":", "_") + ".md"
+
+
 def save_file_report(file_info, output_dir):
-    filename = os.path.basename(file_info["file"]) + ".md"
+    filename = _report_filename(file_info["file"])
     filepath = os.path.join(output_dir, filename)
     with open(filepath, "w") as f:
         f.write(f"# Report for `{file_info['file']}`\n\n")
@@ -30,5 +38,5 @@ def generate_report(analysis, output_dir="report"):
         f.write(f"**Total lines of code:** {total_lines}\n\n")
         f.write("## Files Included\n")
         for file_info in analysis:
-            short_name = os.path.basename(file_info["file"])
-            f.write(f"- [{short_name}]({short_name}.md) ({file_info['total_lines']} lines)\n")
+            report_name = _report_filename(file_info["file"])
+            f.write(f"- [{report_name}]({report_name}) ({file_info['total_lines']} lines)\n")
diff --git a/tests/test_reporter.py b/tests/test_reporter.py
new file mode 100644
index 0000000..c4eb73e
--- /dev/null
+++ b/tests/test_reporter.py
@@ -0,0 +1,31 @@
+from pathlib import Path
+
+from insight.reporter import generate_report
+
+
+def test_reports_keep_same_basenames_distinct_and_linkable(tmp_path: Path) -> None:
+    analysis = [
+        {
+            "file": "pkg_a/user.py",
+            "total_lines": 1,
+            "explanation": "first file",
+            "preview": [],
+        },
+        {
+            "file": "pkg_b/user.py",
+            "total_lines": 2,
+            "explanation": "second file",
+            "preview": [],
+        },
+    ]
+
+    generate_report(analysis, tmp_path)
+
+    first_report = tmp_path / "pkg_a_user.py.md"
+    second_report = tmp_path / "pkg_b_user.py.md"
+    summary = (tmp_path / "summary.md").read_text(encoding="utf-8")
+
+    assert first_report.read_text(encoding="utf-8").count("first file") == 1
+    assert second_report.read_text(encoding="utf-8").count("second file") == 1
+    assert "- [pkg_a_user.py.md](pkg_a_user.py.md) (1 lines)" in summary
+    assert "- [pkg_b_user.py.md](pkg_b_user.py.md) (2 lines)" in summary