diff --git a/packages/bundler-plugins/src/esbuild/index.ts b/packages/bundler-plugins/src/esbuild/index.ts
index fc17904624be..b369bc67a3ec 100644
--- a/packages/bundler-plugins/src/esbuild/index.ts
+++ b/packages/bundler-plugins/src/esbuild/index.ts
@@ -67,6 +67,7 @@ interface EsbuildPluginBuild {
     options: { filter: RegExp },
     callback: (args: EsbuildOnResolveArgs) => EsbuildOnResolveResult | undefined,
   ) => void;
+  onStart: (callback: () => void) => void;
   onEnd: (callback: (result: EsbuildOnEndArgs) => void | Promise<void>) => void;
 }
 
@@ -156,7 +157,7 @@ export function sentryEsbuildPlugin(userOptions: Options = {}): any {
 
   return {
     name: pluginName,
-    setup({ initialOptions, onLoad, onResolve, onEnd }: EsbuildPluginBuild) {
+    setup({ initialOptions, onLoad, onResolve, onStart, onEnd }: EsbuildPluginBuild) {
       // Release and/or metadata injection
       if (!staticInjectionCode.isEmpty()) {
         const virtualInjectionFilePath = path.resolve('_sentry-injection-stub');
@@ -194,8 +195,9 @@ export function sentryEsbuildPlugin(userOptions: Options = {}): any {
 
       // Debug ID injection - requires per-entry-point unique IDs
       if (sourcemapsEnabled) {
-        // Clear state from previous builds (important for watch mode and test suites)
-        debugIdWrappedPaths.clear();
+        // `setup` runs once per context, `onStart` once per build, so a
+        // rebuild wraps the entry points again.
+        onStart(() => debugIdWrappedPaths.clear());
 
         if (!initialOptions.bundle) {
           logger.warn(
diff --git a/packages/bundler-plugins/test/esbuild/rebuild.test.ts b/packages/bundler-plugins/test/esbuild/rebuild.test.ts
new file mode 100644
index 000000000000..be9b74d558c9
--- /dev/null
+++ b/packages/bundler-plugins/test/esbuild/rebuild.test.ts
@@ -0,0 +1,57 @@
+import * as fs from 'fs';
+import * as os from 'os';
+import * as path from 'path';
+import * as esbuild from 'esbuild';
+import { describe, it, expect, beforeEach, afterEach } from 'vitest';
+import { sentryEsbuildPlugin } from '../../src/esbuild';
+
+const DEBUG_ID_MARKER = /sentry-dbid-([0-9a-f-]{36})/;
+
+describe('rebuilds', () => {
+  let tmpDir: string;
+  let entry: string;
+  let outDir: string;
+
+  beforeEach(() => {
+    tmpDir = fs.mkdtempSync(path.join(os.tmpdir(), 'sentry-esbuild-rebuild-'));
+    entry = path.join(tmpDir, 'entry.js');
+    outDir = path.join(tmpDir, 'dist');
+    fs.writeFileSync(entry, 'export const answer = 42;\nconsole.log(answer);\n');
+  });
+
+  afterEach(() => {
+    fs.rmSync(tmpDir, { recursive: true, force: true });
+  });
+
+  function readDebugIds(): { bundle: string | undefined; map: unknown } {
+    const bundle = fs.readFileSync(path.join(outDir, 'entry.js'), 'utf8');
+    const map = JSON.parse(fs.readFileSync(path.join(outDir, 'entry.js.map'), 'utf8'));
+    return { bundle: bundle.match(DEBUG_ID_MARKER)?.[1], map: map.debug_id };
+  }
+
+  it('injects a debug ID into every rebuild of a context', async () => {
+    const context = await esbuild.context({
+      entryPoints: [entry],
+      bundle: true,
+      sourcemap: true,
+      outdir: outDir,
+      absWorkingDir: tmpDir,
+      plugins: [sentryEsbuildPlugin({ telemetry: false, sourcemaps: { disable: 'disable-upload' } })],
+    });
+
+    try {
+      await context.rebuild();
+      const first = readDebugIds();
+      expect(first.bundle).toBeDefined();
+      expect(first.map).toBe(first.bundle);
+
+      fs.writeFileSync(entry, 'export const answer = 43;\nconsole.log(answer);\n');
+      await context.rebuild();
+      const second = readDebugIds();
+      expect(second.bundle).toBeDefined();
+      expect(second.map).toBe(second.bundle);
+    } finally {
+      await context.dispose();
+    }
+  });
+});