diff --git a/packages/bundler-plugins/src/core/build-plugin-manager.ts b/packages/bundler-plugins/src/core/build-plugin-manager.ts
index a529629e4413..d36e3a4ace38 100644
--- a/packages/bundler-plugins/src/core/build-plugin-manager.ts
+++ b/packages/bundler-plugins/src/core/build-plugin-manager.ts
@@ -554,7 +554,7 @@ export function createSentryBuildPluginManager(
               })),
             );
 
-          await cliInstance.uploadSourcemaps(releaseName, uploadTargets);
+          warnAboutDirectoriesWithoutSourcemaps(logger, await cliInstance.uploadSourcemaps(releaseName, uploadTargets));
         }
 
         if (options.release.setCommits !== false) {
@@ -686,9 +686,9 @@ export function createSentryBuildPluginManager(
                 return;
               }
 
-              await startSpan({ name: 'upload', scope: sentryScope }, async () => {
+              const emptyDirectories = await startSpan({ name: 'upload', scope: sentryScope }, async () => {
                 const cliInstance = new SentryCliAdapter(options);
-                await cliInstance.uploadSourcemaps(
+                return cliInstance.uploadSourcemaps(
                   options.release.name ?? 'undefined',
                   pathsToUpload.map(directory => ({
                     directory,
@@ -698,8 +698,11 @@ export function createSentryBuildPluginManager(
                 );
               });
 
-              uploaded = true;
-              logger.info('Successfully uploaded source maps to Sentry');
+              warnAboutDirectoriesWithoutSourcemaps(logger, emptyDirectories);
+              if (emptyDirectories.length < pathsToUpload.length) {
+                uploaded = true;
+                logger.info('Successfully uploaded source maps to Sentry');
+              }
             } else {
               // Prepare artifacts in temp folder before uploading
               let globAssets: string | string[];
@@ -1029,3 +1032,13 @@ function canUploadSourceMaps(options: NormalizedOptions, logger: Logger, isDevMo
       return true;
   }
 }
+
+function warnAboutDirectoriesWithoutSourcemaps(logger: Logger, directories: string[]): void {
+  for (const directory of directories) {
+    logger.warn(
+      `No source maps found in "${directory}", so nothing was uploaded from it. ` +
+        'This usually means source map generation is not enabled for this build output. ' +
+        'Enable it so Sentry can un-minify stack traces from these files.',
+    );
+  }
+}
diff --git a/packages/bundler-plugins/src/core/cli.ts b/packages/bundler-plugins/src/core/cli.ts
index 2e12bd16b40a..5ecc6603d78d 100644
--- a/packages/bundler-plugins/src/core/cli.ts
+++ b/packages/bundler-plugins/src/core/cli.ts
@@ -120,14 +120,20 @@ export class SentryCliAdapter {
    * array; the new `sourcemap upload` command takes a single directory, so we upload each target
    * separately. A client is created per project because project selection is bound at client
    * creation time.
+   *
+   * Empty directories must not abort the loop: `@sentry/nextjs` uploads `.next/server` first, and
+   * a server build without source maps would otherwise skip every client directory after it.
+   *
+   * @returns The directories that had no source maps to upload.
    */
-  public async uploadSourcemaps(name: string, targets: UploadTarget[]): Promise<void> {
+  public async uploadSourcemaps(name: string, targets: UploadTarget[]): Promise<string[]> {
     const projects = getProjects(this.#options.project) ?? [undefined];
+    const emptyDirectories = new Set<string>();
 
     for (const project of projects) {
       const sdk = this.#createClient(project);
       for (const target of targets) {
-        await sdk.sourcemap.upload({
+        const result = (await sdk.sourcemap.upload({
           directory: target.directory,
           release: name,
           dist: target.dist ?? this.#options.release.dist,
@@ -135,9 +141,15 @@ export class SentryCliAdapter {
           ignore: serializeIgnore(target.ignore),
           ignoreFile: target.ignoreFile,
           urlPrefix: target.urlPrefix,
-        });
+          allowEmpty: true,
+        })) as { filesUploaded?: number } | undefined;
+        if (result?.filesUploaded === 0) {
+          emptyDirectories.add(target.directory);
+        }
       }
     }
+
+    return [...emptyDirectories];
   }
 
   /** Inject debug IDs into the given build artifacts. */
diff --git a/packages/bundler-plugins/test/core/build-plugin-manager.test.ts b/packages/bundler-plugins/test/core/build-plugin-manager.test.ts
index e5105d55f4f8..e2f82a2e1228 100644
--- a/packages/bundler-plugins/test/core/build-plugin-manager.test.ts
+++ b/packages/bundler-plugins/test/core/build-plugin-manager.test.ts
@@ -345,6 +345,50 @@ describe('createSentryBuildPluginManager', () => {
       expect(mockPrepareBundleForDebugIdUpload).not.toHaveBeenCalled();
     });
 
+    it('keeps uploading the other directories when one has no source maps', async () => {
+      mockSourcemapUpload.mockResolvedValueOnce({ filesUploaded: 0 }).mockResolvedValueOnce({ filesUploaded: 4 });
+
+      const manager = createSentryBuildPluginManager(
+        { authToken: 't', org: 'o', project: 'p', release: { name: 'some-release-name' } },
+        { buildTool: 'webpack', loggerPrefix: '[sentry-webpack-plugin]' },
+      );
+      const warnSpy = vi.spyOn(manager.logger, 'warn');
+      const infoSpy = vi.spyOn(manager.logger, 'info');
+
+      const result = await manager.uploadSourcemaps(['.next/server', '.next/static/chunks'], {
+        prepareArtifacts: false,
+      });
+
+      expect(mockSourcemapUpload).toHaveBeenCalledTimes(2);
+      expect(mockSourcemapUpload).toHaveBeenCalledWith(
+        // eslint-disable-next-line @typescript-eslint/no-unsafe-assignment
+        expect.objectContaining({ directory: '.next/server', allowEmpty: true }),
+      );
+      expect(warnSpy).toHaveBeenCalledOnce();
+      expect(warnSpy).toHaveBeenCalledWith(expect.stringContaining('No source maps found in ".next/server"'));
+      expect(infoSpy).toHaveBeenCalledWith('Successfully uploaded source maps to Sentry');
+      expect(result).toEqual({ uploaded: true });
+
+      vi.restoreAllMocks();
+    });
+
+    it('does not report success when no directory has source maps', async () => {
+      mockSourcemapUpload.mockResolvedValue({ filesUploaded: 0 });
+
+      const manager = createSentryBuildPluginManager(
+        { authToken: 't', org: 'o', project: 'p', release: { name: 'some-release-name' } },
+        { buildTool: 'webpack', loggerPrefix: '[sentry-webpack-plugin]' },
+      );
+      const infoSpy = vi.spyOn(manager.logger, 'info');
+
+      const result = await manager.uploadSourcemaps(['.next/server'], { prepareArtifacts: false });
+
+      expect(infoSpy).not.toHaveBeenCalledWith('Successfully uploaded source maps to Sentry');
+      expect(result).toEqual({ uploaded: false });
+
+      vi.restoreAllMocks();
+    });
+
     it('exits early when assets is an empty array', async () => {
       const manager = createSentryBuildPluginManager(
         {
@@ -419,6 +463,7 @@ describe('createSentryBuildPluginManager', () => {
         ignore: undefined,
         ignoreFile: undefined,
         urlPrefix: undefined,
+        allowEmpty: true,
       });
     });
 
diff --git a/packages/bundler-plugins/test/core/cli-contract.test.ts b/packages/bundler-plugins/test/core/cli-contract.test.ts
index f6c1a1d4c50d..51ad7ab86ecd 100644
--- a/packages/bundler-plugins/test/core/cli-contract.test.ts
+++ b/packages/bundler-plugins/test/core/cli-contract.test.ts
@@ -195,6 +195,21 @@ describe('SentryCliAdapter against the real CLI', () => {
     expect(requestsSince(before)).toContain('POST /api/0/organizations/test-org/artifactbundle/assemble/');
   });
 
+  it('skips a directory without source maps and still uploads the next one', async () => {
+    const emptyDir = join(workDir, 'server');
+    mkdirSync(emptyDir);
+    writeFileSync(join(emptyDir, 'page.js'), 'console.log("no map");\n');
+    const before = recordedRequests();
+
+    const emptyDirectories = await createAdapter().uploadSourcemaps('1.0.0', [
+      { directory: emptyDir },
+      { directory: buildDir },
+    ]);
+
+    expect(emptyDirectories).toEqual([emptyDir]);
+    expect(requestsSince(before)).toContain('POST /api/0/organizations/test-org/artifactbundle/assemble/');
+  });
+
   it('resolves the server url, or gives up quietly', async () => {
     const adapter = createAdapter();