diff --git a/packages/angular_devkit/build_angular/src/tools/esbuild/global-scripts.ts b/packages/angular_devkit/build_angular/src/tools/esbuild/global-scripts.ts
index d3ca2c0c3d85..cdac82c34924 100644
--- a/packages/angular_devkit/build_angular/src/tools/esbuild/global-scripts.ts
+++ b/packages/angular_devkit/build_angular/src/tools/esbuild/global-scripts.ts
@@ -89,15 +89,16 @@ export function createGlobalScriptsBundleOptions(
               let fileContent;
               try {
                 // Attempt to read as a relative path from the workspace root
-                fileContent = await readFile(path.join(workspaceRoot, filename), 'utf-8');
-                watchFiles.push(filename);
+                const fullPath = path.join(workspaceRoot, filename);
+                fileContent = await readFile(fullPath, 'utf-8');
+                watchFiles.push(fullPath);
               } catch (e) {
                 assertIsError(e);
                 if (e.code !== 'ENOENT') {
                   throw e;
                 }
 
-                // If not found attempt to resolve as a module specifier
+                // If not found, attempt to resolve as a module specifier
                 const resolveResult = await build.resolve(filename, {
                   kind: 'entry-point',
                   resolveDir: workspaceRoot,
@@ -114,7 +115,7 @@ export function createGlobalScriptsBundleOptions(
                   };
                 }
 
-                watchFiles.push(path.relative(resolveResult.path, workspaceRoot));
+                watchFiles.push(resolveResult.path);
                 fileContent = await readFile(resolveResult.path, 'utf-8');
               }
 
diff --git a/packages/angular_devkit/build_angular/src/tools/esbuild/load-result-cache.ts b/packages/angular_devkit/build_angular/src/tools/esbuild/load-result-cache.ts
index 981623be07ec..dd80342c270b 100644
--- a/packages/angular_devkit/build_angular/src/tools/esbuild/load-result-cache.ts
+++ b/packages/angular_devkit/build_angular/src/tools/esbuild/load-result-cache.ts
@@ -7,6 +7,7 @@
  */
 
 import type { OnLoadResult, PluginBuild } from 'esbuild';
+import { normalize } from 'node:path';
 
 export interface LoadResultCache {
   get(path: string): OnLoadResult | undefined;
@@ -50,10 +51,12 @@ export class MemoryLoadResultCache implements LoadResultCache {
     this.#loadResults.set(path, result);
     if (result.watchFiles) {
       for (const watchFile of result.watchFiles) {
-        let affected = this.#fileDependencies.get(watchFile);
+        // Normalize the watch file path to ensure OS consistent paths
+        const normalizedWatchFile = normalize(watchFile);
+        let affected = this.#fileDependencies.get(normalizedWatchFile);
         if (affected === undefined) {
           affected = new Set();
-          this.#fileDependencies.set(watchFile, affected);
+          this.#fileDependencies.set(normalizedWatchFile, affected);
         }
         affected.add(path);
       }