diff --git a/src/managers/builtin/main.ts b/src/managers/builtin/main.ts
index 7171b78f..f9b588b5 100644
--- a/src/managers/builtin/main.ts
+++ b/src/managers/builtin/main.ts
@@ -9,6 +9,8 @@ import { UvProjectCreator } from './uvProjectCreator';
 import { isUvInstalled } from './helpers';
 import { createFileSystemWatcher, onDidDeleteFiles } from '../../common/workspace.apis';
 import { createSimpleDebounce } from '../../common/utils/debounce';
+import { onDidEndTerminalShellExecution } from '../../common/window.apis';
+import { isPipInstallCommand } from './pipUtils';
 
 export async function registerSystemPythonFeatures(
     nativeFinder: NativePythonFinder,
@@ -43,6 +45,18 @@ export async function registerSystemPythonFeatures(
         }),
     );
 
+    disposables.push(
+        onDidEndTerminalShellExecution(async (e) => {
+            const cwd = e.terminal.shellIntegration?.cwd;
+            if (isPipInstallCommand(e.execution.commandLine.value) && cwd) {
+                const env = await venvManager.get(cwd);
+                if (env) {
+                    await pkgManager.refresh(env);
+                }
+            }
+        }),
+    );
+
     setImmediate(async () => {
         if (await isUvInstalled(log)) {
             disposables.push(api.registerPythonProjectCreator(new UvProjectCreator(api, log)));
diff --git a/src/managers/builtin/pipUtils.ts b/src/managers/builtin/pipUtils.ts
index c6912ab1..f41682c7 100644
--- a/src/managers/builtin/pipUtils.ts
+++ b/src/managers/builtin/pipUtils.ts
@@ -207,3 +207,17 @@ export async function getProjectInstallable(
     );
     return installable;
 }
+
+export function isPipInstallCommand(command: string): boolean {
+    // Regex to match pip install commands, capturing variations like:
+    // pip install package
+    // python -m pip install package
+    // pip3 install package
+    // py -m pip install package
+    // pip install -r requirements.txt
+    // uv pip install package
+    // poetry run pip install package
+    // pipx run pip install package
+    // Any other tool that might wrap pip install
+    return /(?:^|\s)(?:\S+\s+)*(?:pip\d*)\s+(install|uninstall)\b/.test(command);
+}