diff --git a/src/backend/asset_matcher.rs b/src/backend/asset_matcher.rs
index fab411e431..1c7e99ac20 100644
--- a/src/backend/asset_matcher.rs
+++ b/src/backend/asset_matcher.rs
@@ -353,6 +353,11 @@ impl AssetPicker {
             penalty -= 50;
         }
 
+        // Penalize .vsix files
+        if asset.ends_with(".vsix") {
+            penalty -= 100;
+        }
+
         // Penalize metadata/checksum/signature files
         if asset.ends_with(".asc")
             || asset.ends_with(".sig")
@@ -1368,4 +1373,16 @@ abc123def456abc123def456abc123def456abc123def456abc123def456abcd  tool-darwin.ta
             "Should return the only provenance file available"
         );
     }
+
+    #[test]
+    fn test_vsix_vs_gz() {
+        let picker = AssetPicker::with_libc("macos".to_string(), "x86_64".to_string(), None);
+        let assets = vec![
+            "rust-analyzer-x86_64-apple-darwin.gz".to_string(),
+            "rust-analyzer-x86_64-apple-darwin.vsix".to_string(),
+        ];
+
+        let picked = picker.pick_best_asset(&assets).unwrap();
+        assert_eq!(picked, "rust-analyzer-x86_64-apple-darwin.gz");
+    }
 }