diff --git a/crates/vite_global_cli/src/commands/global/install.rs b/crates/vite_global_cli/src/commands/global/install.rs
index c998dd5ab2..f559bb65a2 100644
--- a/crates/vite_global_cli/src/commands/global/install.rs
+++ b/crates/vite_global_cli/src/commands/global/install.rs
@@ -195,6 +195,16 @@ pub async fn install(
             continue;
         };
         let mut backup = backup;
+        let stale_bin_names = match stale_bin_names_for_package(&package_name, &bin_names).await {
+            Ok(bin_names) => bin_names,
+            Err(error) => {
+                let _ = cleanup_failed_install(&package_name, backup.take()).await;
+                if first_error.is_none() {
+                    first_error = Some(package_error(&package_name, error));
+                }
+                continue;
+            }
+        };
 
         let mut conflicts = Vec::<(String, String)>::new();
         let mut finalize_blocked = false;
@@ -336,12 +346,35 @@ pub async fn install(
             continue;
         }
 
-        // 4.5 Commit the install by discarding the backup and reporting the installed bins.
+        // 4.5 Remove shims for binaries the package used to expose but no longer declares.
+        for bin_name in stale_bin_names {
+            let result = async {
+                remove_package_shim(&bin_dir, &bin_name).await?;
+                BinConfig::delete(&bin_name).await?;
+                Ok::<(), Error>(())
+            }
+            .await;
+
+            if let Err(error) = result.map_err(|error| package_error(&package_name, error)) {
+                let _ = cleanup_failed_install(&package_name, backup.take()).await;
+                if first_error.is_none() {
+                    first_error = Some(error);
+                }
+                finalized = false;
+                break;
+            }
+        }
+
+        if !finalized {
+            continue;
+        }
+
+        // 4.6 Commit the install by discarding the backup and reporting the installed bins.
         if let Some(backup) = backup {
             backup.discard().await;
         }
 
-        // 4.6 Print success message
+        // 4.7 Print success message
         output::success(&format!(
             "{} {} {}{}",
             operation_past,
@@ -552,6 +585,23 @@ async fn cleanup_installed_package(package_name: &str) -> Result<(), Error> {
     Ok(())
 }
 
+async fn stale_bin_names_for_package(
+    package_name: &str,
+    current_bin_names: &[String],
+) -> Result<Vec<String>, Error> {
+    let current_bin_names: HashSet<_> = current_bin_names.iter().cloned().collect();
+    let mut previous_bin_names = HashSet::new();
+
+    if let Some(metadata) = PackageMetadata::load(package_name).await? {
+        previous_bin_names.extend(metadata.bins);
+    }
+
+    previous_bin_names.extend(BinConfig::find_by_package(package_name).await?);
+    previous_bin_names.retain(|bin_name| !current_bin_names.contains(bin_name));
+
+    Ok(previous_bin_names.into_iter().collect())
+}
+
 /// Uninstall a global package.
 ///
 /// Uses two-phase uninstall:
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/check-stale-binary.js b/packages/cli/snap-tests-global/env-install-stale-bin/check-stale-binary.js
new file mode 100644
index 0000000000..747f500736
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/check-stale-binary.js
@@ -0,0 +1,9 @@
+const fs = require('fs');
+const path = require('path');
+
+const shimSuffix = process.platform === 'win32' ? '.exe' : '';
+const shim = path.join(process.env.VP_HOME, 'bin', 'env-install-stale-drop' + shimSuffix);
+const config = path.join(process.env.VP_HOME, 'bins/env-install-stale-drop.json');
+
+console.log(fs.existsSync(shim) ? 'stale shim exists' : 'stale shim removed');
+console.log(fs.existsSync(config) ? 'stale config exists' : 'stale config removed');
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/cli-drop.js b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/cli-drop.js
new file mode 100644
index 0000000000..1007ca7b47
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/cli-drop.js
@@ -0,0 +1,2 @@
+#!/usr/bin/env node
+console.log('env-install-stale-drop ok');
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/cli-keep.js b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/cli-keep.js
new file mode 100644
index 0000000000..8524f7cc95
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/cli-keep.js
@@ -0,0 +1,2 @@
+#!/usr/bin/env node
+console.log('env-install-stale-keep ok');
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/package.json b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/package.json
new file mode 100644
index 0000000000..bc1de7dce4
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v1/package.json
@@ -0,0 +1,8 @@
+{
+  "name": "env-install-stale-bin-pkg",
+  "version": "1.0.0",
+  "bin": {
+    "env-install-stale-drop": "./cli-drop.js",
+    "env-install-stale-keep": "./cli-keep.js"
+  }
+}
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v2/cli-keep.js b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v2/cli-keep.js
new file mode 100644
index 0000000000..8524f7cc95
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v2/cli-keep.js
@@ -0,0 +1,2 @@
+#!/usr/bin/env node
+console.log('env-install-stale-keep ok');
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v2/package.json b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v2/package.json
new file mode 100644
index 0000000000..f6086a76aa
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/env-install-stale-bin-pkg-v2/package.json
@@ -0,0 +1,7 @@
+{
+  "name": "env-install-stale-bin-pkg",
+  "version": "2.0.0",
+  "bin": {
+    "env-install-stale-keep": "./cli-keep.js"
+  }
+}
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/snap.txt b/packages/cli/snap-tests-global/env-install-stale-bin/snap.txt
new file mode 100644
index 0000000000..ddf6aa1e7c
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/snap.txt
@@ -0,0 +1,20 @@
+> vp install -g ./env-install-stale-bin-pkg-v1 # Install package with two binaries
+info: Installing 1 global package with Node.js <semver>
+✓ Installed env-install-stale-bin-pkg <semver>
+  Bins: env-install-stale-drop, env-install-stale-keep
+
+> env-install-stale-keep && env-install-stale-drop # Both binaries should be callable
+env-install-stale-keep ok
+env-install-stale-drop ok
+
+> vp install -g ./env-install-stale-bin-pkg-v2 # Reinstall package version that removed one binary
+info: Installing 1 global package with Node.js <semver>
+✓ Installed env-install-stale-bin-pkg <semver>
+  Bins: env-install-stale-keep
+
+> env-install-stale-keep # Remaining binary should still be callable
+env-install-stale-keep ok
+
+> node check-stale-binary.js
+stale shim removed
+stale config removed
diff --git a/packages/cli/snap-tests-global/env-install-stale-bin/steps.json b/packages/cli/snap-tests-global/env-install-stale-bin/steps.json
new file mode 100644
index 0000000000..8e2adf1354
--- /dev/null
+++ b/packages/cli/snap-tests-global/env-install-stale-bin/steps.json
@@ -0,0 +1,11 @@
+{
+  "env": {},
+  "commands": [
+    "vp install -g ./env-install-stale-bin-pkg-v1 # Install package with two binaries",
+    "env-install-stale-keep && env-install-stale-drop # Both binaries should be callable",
+    "vp install -g ./env-install-stale-bin-pkg-v2 # Reinstall package version that removed one binary",
+    "env-install-stale-keep # Remaining binary should still be callable",
+    "node check-stale-binary.js"
+  ],
+  "after": ["vp remove -g env-install-stale-bin-pkg"]
+}