diff --git a/CHANGELOG.md b/CHANGELOG.md
index 02bf2a7..fc1ec4d 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -7,7 +7,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 > **Note**: odd version numbers, for example, `0.13.0`, are not included in this changelog. They are used to test the new features and fixes before the final release.
 
-## [0.25.0] - Unreleased
+## [0.25.1] - Unreleased
 
 ### Added:
 
@@ -17,6 +17,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 - Snippets: Updated all snippets to use `v0.29.0` schema
 - Snippets: Updated all snuppers to use new DLL name, `DevProxy.Plugins.dll`
+- Notification: Upgrade notification invokes package manager to upgrade Dev Proxy
 
 ## [0.24.0] - 2025-06-04
 
diff --git a/README.md b/README.md
index ceeea6e..7a78185 100644
--- a/README.md
+++ b/README.md
@@ -64,6 +64,7 @@ Shown when the active document is a Dev Proxy configuration file
 
 - Not installed
 - New version detection
+- Upgrade Dev Proxy
 
 ### Settings
 
@@ -173,3 +174,4 @@ Shown when the active document is a Dev Proxy configuration file
 - Display tick if Dev Proxy is latest version (check based on `newVersionNotification` config setting in Dev Proxy configuration file)
 - Display radio tower when Dev Proxy is running
 - Display error is Dev Proxy is not installed
+- Upgrade Dev Proxy progress
diff --git a/package-lock.json b/package-lock.json
index 4a6b9c4..2188e43 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "dev-proxy-toolkit",
-  "version": "0.25.0",
+  "version": "0.25.1",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "dev-proxy-toolkit",
-      "version": "0.25.0",
+      "version": "0.25.1",
       "dependencies": {
         "json-to-ast": "^2.1.0"
       },
diff --git a/package.json b/package.json
index 886d926..eaa60ef 100644
--- a/package.json
+++ b/package.json
@@ -2,7 +2,7 @@
   "name": "dev-proxy-toolkit",
   "displayName": "Dev Proxy Toolkit",
   "description": "Makes it easy to create and update Dev Proxy configuration files.",
-  "version": "0.25.0",
+  "version": "0.25.1",
   "publisher": "garrytrinder",
   "engines": {
     "vscode": "^1.101.0"
diff --git a/src/commands.ts b/src/commands.ts
index 9b2e6ac..288f752 100644
--- a/src/commands.ts
+++ b/src/commands.ts
@@ -1,7 +1,7 @@
 import * as vscode from 'vscode';
 import { pluginDocs } from './constants';
 import { VersionPreference } from './enums';
-import { executeCommand, isConfigFile } from './helpers';
+import { executeCommand, isConfigFile, openUpgradeDocumentation, upgradeDevProxyWithPackageManager } from './helpers';
 import { isDevProxyRunning, getDevProxyExe } from './detect';
 
 export const registerCommands = (context: vscode.ExtensionContext, configuration: vscode.WorkspaceConfiguration) => {
@@ -80,8 +80,41 @@ export const registerCommands = (context: vscode.ExtensionContext, configuration
 
     context.subscriptions.push(
         vscode.commands.registerCommand('dev-proxy-toolkit.upgrade', async () => {
-            const url = 'https://aka.ms/devproxy/upgrade';
-            vscode.env.openExternal(vscode.Uri.parse(url));
+            const platform = process.platform;
+            const versionPreference = configuration.get('version') as VersionPreference;
+            
+            // Handle Linux early - always redirect to documentation
+            if (platform === 'linux') {
+                openUpgradeDocumentation();
+                return;
+            }
+            
+            // Handle Windows
+            if (platform === 'win32') {
+                const packageId = versionPreference === VersionPreference.Stable ? 'Microsoft.DevProxy' : 'Microsoft.DevProxy.Beta';
+                const upgradeCommand = `winget upgrade ${packageId} --silent`;
+                
+                const upgraded = await upgradeDevProxyWithPackageManager('winget', packageId, upgradeCommand);
+                if (!upgraded) {
+                    openUpgradeDocumentation();
+                }
+                return;
+            }
+            
+            // Handle macOS
+            if (platform === 'darwin') {
+                const packageId = versionPreference === VersionPreference.Stable ? 'dev-proxy' : 'dev-proxy-beta';
+                const upgradeCommand = `brew upgrade ${packageId}`;
+                
+                const upgraded = await upgradeDevProxyWithPackageManager('brew', packageId, upgradeCommand);
+                if (!upgraded) {
+                    openUpgradeDocumentation();
+                }
+                return;
+            }
+            
+            // Unknown platform - redirect to documentation
+            openUpgradeDocumentation();
         }));
 
     context.subscriptions.push(
diff --git a/src/helpers.ts b/src/helpers.ts
index 59fd632..eaf8325 100644
--- a/src/helpers.ts
+++ b/src/helpers.ts
@@ -116,3 +116,55 @@ export const executeCommand = async (cmd: string, options: ExecOptions = {}): Pr
     });
   });
 };
+
+export const upgradeDevProxyWithPackageManager = async (
+  packageManager: string,
+  packageId: string,
+  upgradeCommand: string,
+): Promise<boolean> => {
+  try {
+    // Check if package manager is available
+    await executeCommand(`${packageManager} --version`);
+
+    // Check if Dev Proxy is installed via package manager
+    const listCommand =
+      packageManager === 'winget'
+        ? `winget list ${packageId}`
+        : 'brew list --formula';
+    const listOutput = await executeCommand(listCommand);
+
+    if (!listOutput.includes(packageId)) {
+      return false;
+    }
+
+    // Proceed with upgrade
+    const statusMessage = vscode.window.setStatusBarMessage(
+      'Upgrading Dev Proxy...',
+    );
+
+    try {
+      await executeCommand(upgradeCommand);
+      statusMessage.dispose();
+
+      const result = await vscode.window.showInformationMessage(
+        'Dev Proxy has been successfully upgraded!',
+        'Reload Window',
+      );
+      if (result === 'Reload Window') {
+        await vscode.commands.executeCommand('workbench.action.reloadWindow');
+      }
+      return true;
+    } catch (error) {
+      statusMessage.dispose();
+      vscode.window.showErrorMessage(`Failed to upgrade Dev Proxy: ${error}`);
+      return false;
+    }
+  } catch (error) {
+    return false;
+  }
+};
+
+export const openUpgradeDocumentation = () => {
+  const url = 'https://aka.ms/devproxy/upgrade';
+  vscode.env.openExternal(vscode.Uri.parse(url));
+};