diff --git a/src/managers/builtin/pipUtils.ts b/src/managers/builtin/pipUtils.ts
index 9fd540ab..2e7a7f85 100644
--- a/src/managers/builtin/pipUtils.ts
+++ b/src/managers/builtin/pipUtils.ts
@@ -290,12 +290,34 @@ export async function getProjectInstallable(
             const uniqueResults = Array.from(new Map(results.map((uri) => [uri.fsPath, uri])).values());
 
             const fsPaths = projects.map((p) => p.uri.fsPath);
+            // Compute depth relative to the owning project root so ordering reflects
+            // "shallower within the project", independent of where the project lives on disk.
+            const depthFromProject = (uri: Uri): number => {
+                const projectRoot = api.getPythonProject(uri)?.uri.fsPath;
+                if (!projectRoot) {
+                    return Number.MAX_SAFE_INTEGER;
+                }
+                const rel = path.relative(projectRoot, uri.fsPath);
+                if (!rel) {
+                    return 0;
+                }
+                return rel.split(path.sep).filter((segment) => segment.length > 0).length;
+            };
             const filtered = uniqueResults
                 .filter((uri) => {
                     const p = api.getPythonProject(uri)?.uri.fsPath;
                     return p && fsPaths.includes(p);
                 })
-                .sort();
+                .sort((a, b) => {
+                    // Sort by path depth relative to the project root (shallowest first) so
+                    // top-level files like requirements.txt appear before deeply nested ones.
+                    const depthA = depthFromProject(a);
+                    const depthB = depthFromProject(b);
+                    if (depthA !== depthB) {
+                        return depthA - depthB;
+                    }
+                    return a.fsPath.localeCompare(b.fsPath);
+                });
 
             await Promise.all(
                 filtered.map(async (uri) => {
diff --git a/src/test/managers/builtin/pipUtils.unit.test.ts b/src/test/managers/builtin/pipUtils.unit.test.ts
index 5ae58126..f817f6c7 100644
--- a/src/test/managers/builtin/pipUtils.unit.test.ts
+++ b/src/test/managers/builtin/pipUtils.unit.test.ts
@@ -199,4 +199,39 @@ suite('Pip Utils - getProjectInstallable', () => {
         assert.ok(firstResult.uri, 'Should have a URI');
         assert.ok(firstResult.uri.fsPath.startsWith(workspacePath), 'Should be in workspace directory');
     });
+
+    test('should sort shallower files before deeper ones', async () => {
+        // Arrange: Use the shared workspacePath from setup() so paths are platform-safe.
+        const workspacePath = Uri.file('/test/path/root').fsPath;
+        const rootReqPath = path.join(workspacePath, 'requirements.txt');
+        const subdirReqPath = path.join(workspacePath, 'subdir', 'dev-requirements.txt');
+        const deepReqPath = path.join(workspacePath, 'deep', 'nested', 'sub', 'requirements.txt');
+
+        // Return files at different depths, with deeper ones discovered first.
+        findFilesStub.callsFake((pattern: string) => {
+            if (pattern === '**/*requirements*.txt') {
+                return Promise.resolve([Uri.file(deepReqPath), Uri.file(subdirReqPath)]);
+            } else if (pattern === '*requirements*.txt') {
+                return Promise.resolve([Uri.file(rootReqPath)]);
+            } else if (pattern === '**/requirements/*.txt') {
+                return Promise.resolve([]);
+            } else if (pattern === '**/pyproject.toml') {
+                return Promise.resolve([]);
+            }
+            return Promise.resolve([]);
+        });
+
+        // Act
+        const projects = [{ name: 'workspace', uri: Uri.file(workspacePath) }];
+        const result = (await getProjectInstallable(mockApi as PythonEnvironmentApi, projects)).installables;
+
+        // Assert: order by fsPath so the two `requirements.txt` files are unambiguous.
+        assert.strictEqual(result.length, 3);
+        const fsPaths = result.map((r) => r.uri!.fsPath);
+        assert.deepStrictEqual(
+            fsPaths,
+            [rootReqPath, subdirReqPath, deepReqPath],
+            'Files should be ordered by depth relative to the project root',
+        );
+    });
 });