diff --git a/build/scripts/build_windows.py b/build/scripts/build_windows.py
index 6031d38..87df6e9 100644
--- a/build/scripts/build_windows.py
+++ b/build/scripts/build_windows.py
@@ -91,8 +91,30 @@ class WindowsBuilder:
         print(f"📦 Output: {exe_path}")
         print(f"   Size: {exe_path.stat().st_size / 1024 / 1024:.1f} MB")
 
+        # Generate SHA256 checksum
+        self.generate_checksum(exe_path)
+
         return True
 
+    def generate_checksum(self, file_path: Path) -> None:
+        """Generate SHA256 checksum for file."""
+        import hashlib
+
+        print("\n📝 Generating SHA256 checksum...")
+        sha256_hash = hashlib.sha256()
+
+        with open(file_path, "rb") as f:
+            for byte_block in iter(lambda: f.read(4096), b""):
+                sha256_hash.update(byte_block)
+
+        checksum = sha256_hash.hexdigest()
+        checksum_file = file_path.parent / f"{file_path.name}.sha256"
+
+        checksum_file.write_text(checksum)
+        print(f"✅ Checksum generated")
+        print(f"   File: {checksum_file}")
+        print(f"   Hash: {checksum}")
+
     def create_msi(self) -> bool:
         """Create MSI installer using WiX Toolset.
 
diff --git a/build/scripts/upload_to_packages.ps1 b/build/scripts/upload_to_packages.ps1
index 8bad813..413b937 100644
--- a/build/scripts/upload_to_packages.ps1
+++ b/build/scripts/upload_to_packages.ps1
@@ -103,7 +103,9 @@ try {
         -Method PUT `
         -Headers $headers `
         -InFile $ExePath `
-        -ContentType "application/octet-stream"
+        -ContentType "application/octet-stream" `
+        -TimeoutSec 600 `
+        -ErrorAction Stop
     
     Write-Host "[OK] Executable uploaded successfully" -ForegroundColor Green
 }