diff --git a/build.py b/build.py
index 58bd80c..6ba966a 100644
--- a/build.py
+++ b/build.py
@@ -400,9 +400,20 @@ def cleanup_old_releases():
     keep = set([first] + last_5)
 
     removed = []
+    _flags = subprocess.CREATE_NO_WINDOW if sys.platform == "win32" else 0
     for f in all_exes:
         if f not in keep:
-            os.remove(f)
+            # Use git rm so deletion is staged for commit
+            try:
+                subprocess.run(
+                    ["git", "rm", "-f", "--quiet", f],
+                    cwd=PROJECT_DIR, creationflags=_flags,
+                    capture_output=True,
+                )
+            except Exception:
+                # Fallback: just delete the file
+                if os.path.exists(f):
+                    os.remove(f)
             removed.append(os.path.basename(f))
 
     if removed:
diff --git a/releases/ServerManager-v1.8.100-win-x64.exe b/releases/ServerManager-v1.8.100-win-x64.exe
deleted file mode 100644
index c0ea656..0000000
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diff --git a/releases/ServerManager-v1.8.101-win-x64.exe b/releases/ServerManager-v1.8.101-win-x64.exe
deleted file mode 100644
index 0b964ff..0000000
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diff --git a/releases/ServerManager-v1.8.98-win-x64.exe b/releases/ServerManager-v1.8.98-win-x64.exe
deleted file mode 100644
index d0a56c3..0000000
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diff --git a/releases/ServerManager-v1.8.99-win-x64.exe b/releases/ServerManager-v1.8.99-win-x64.exe
deleted file mode 100644
index 10993c9..0000000
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diff --git a/releases/ServerManager-v1.9.0-win-x64.exe b/releases/ServerManager-v1.9.0-win-x64.exe
deleted file mode 100644
index 98d0253..0000000
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diff --git a/releases/ServerManager-v1.9.1-win-x64.exe b/releases/ServerManager-v1.9.1-win-x64.exe
deleted file mode 100644
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diff --git a/releases/ServerManager-v1.9.2-win-x64.exe b/releases/ServerManager-v1.9.2-win-x64.exe
deleted file mode 100644
index 1536f79..0000000
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diff --git a/releases/ServerManager-v1.9.3-win-x64.exe b/releases/ServerManager-v1.9.3-win-x64.exe
deleted file mode 100644
index b9e9cca..0000000
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diff --git a/releases/ServerManager-v1.9.4-win-x64.exe b/releases/ServerManager-v1.9.4-win-x64.exe
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index d9892c0..0000000
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diff --git a/releases/ServerManager-v1.9.5-win-x64.exe b/releases/ServerManager-v1.9.5-win-x64.exe
deleted file mode 100644
index f308c00..0000000
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diff --git a/releases/ServerManager-v1.9.6-win-x64.exe b/releases/ServerManager-v1.9.6-win-x64.exe
deleted file mode 100644
index ef97878..0000000
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diff --git a/releases/ServerManager-v1.9.7-win-x64.exe b/releases/ServerManager-v1.9.7-win-x64.exe
deleted file mode 100644
index 16d33be..0000000
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