diff --git a/e2e/webpack/src/webpack.test.ts b/e2e/webpack/src/webpack.test.ts
index cdaaacd44cac7..75b39e95319cf 100644
--- a/e2e/webpack/src/webpack.test.ts
+++ b/e2e/webpack/src/webpack.test.ts
@@ -1,4 +1,5 @@
 import {
+  checkFilesExist,
   cleanupProject,
   fileExists,
   listFiles,
@@ -262,6 +263,34 @@ describe('Webpack Plugin', () => {
 
     fileExists(`dist/apps/${appName}/package.json`);
   });
+
+  it('should resolve assets from executors as relative to workspace root', () => {
+    const appName = uniq('app');
+    runCLI(`generate @nx/web:app ${appName} --bundler webpack`);
+    updateFile('shared/docs/TEST.md', 'TEST');
+    updateJson(`apps/${appName}/project.json`, (json) => {
+      json.targets.build = {
+        executor: '@nx/webpack:webpack',
+        outputs: ['{options.outputPath}'],
+        options: {
+          assets: [
+            {
+              input: 'shared/docs',
+              glob: 'TEST.md',
+              output: '.',
+            },
+          ],
+          outputPath: `dist/apps/${appName}`,
+          webpackConfig: `apps/${appName}/webpack.config.js`,
+        },
+      };
+      return json;
+    });
+
+    runCLI(`build ${appName}`);
+
+    checkFilesExist(`dist/apps/${appName}/TEST.md`);
+  });
 });
 
 function readMainFile(dir: string): string {
diff --git a/packages/webpack/src/executors/webpack/lib/normalize-options.ts b/packages/webpack/src/executors/webpack/lib/normalize-options.ts
index b2677c537b961..df6b0198897a7 100644
--- a/packages/webpack/src/executors/webpack/lib/normalize-options.ts
+++ b/packages/webpack/src/executors/webpack/lib/normalize-options.ts
@@ -37,7 +37,8 @@ export function normalizeOptions(
       options.assets,
       root,
       sourceRoot,
-      projectRoot
+      projectRoot,
+      false // executor assets are relative to workspace root for consistency
     );
   }
   return normalizedOptions as NormalizedWebpackExecutorOptions;
diff --git a/packages/webpack/src/plugins/nx-webpack-plugin/lib/normalize-options.ts b/packages/webpack/src/plugins/nx-webpack-plugin/lib/normalize-options.ts
index 17529eb5f314d..f28779f79d687 100644
--- a/packages/webpack/src/plugins/nx-webpack-plugin/lib/normalize-options.ts
+++ b/packages/webpack/src/plugins/nx-webpack-plugin/lib/normalize-options.ts
@@ -51,14 +51,16 @@ export function normalizeOptions(
     }
     Object.assign(
       combinedPluginAndMaybeExecutorOptions,
-      buildTargetOptions,
-      options // plugin options take precedence
+      options,
+      // executor options take precedence (especially for overriding with CLI args)
+      buildTargetOptions
     );
   } else {
     Object.assign(
       combinedPluginAndMaybeExecutorOptions,
-      originalTargetOptions,
-      options // plugin options take precedence
+      options,
+      // executor options take precedence (especially for overriding with CLI args)
+      originalTargetOptions
     );
   }
 
@@ -121,7 +123,8 @@ export function normalizeAssets(
   assets: any[],
   root: string,
   sourceRoot: string,
-  projectRoot: string
+  projectRoot: string,
+  resolveRelativePathsToProjectRoot = true
 ): AssetGlobPattern[] {
   return assets.map((asset) => {
     if (typeof asset === 'string') {
@@ -155,7 +158,7 @@ export function normalizeAssets(
 
       const assetPath = normalizePath(asset.input);
       let resolvedAssetPath = resolve(root, assetPath);
-      if (asset.input.startsWith('.')) {
+      if (resolveRelativePathsToProjectRoot && asset.input.startsWith('.')) {
         const resolvedProjectRoot = resolve(root, projectRoot);
         resolvedAssetPath = resolve(resolvedProjectRoot, assetPath);
       }