diff --git a/packages/cli/src/lib/sourcemap/inject.ts b/packages/cli/src/lib/sourcemap/inject.ts
index a8c405275..dfd9d2cf9 100644
--- a/packages/cli/src/lib/sourcemap/inject.ts
+++ b/packages/cli/src/lib/sourcemap/inject.ts
@@ -835,6 +835,41 @@ export async function resolveDirectorySourcemaps(
   return results;
 }
 
+/** Next.js build output: any path with a `.next` directory segment. */
+const NEXT_DIST_DIR_RE = /(?:^|\/)\.next(?:\/|$)/;
+
+/** Next.js server output, whose sourcemaps have separate switches. */
+const NEXT_SERVER_DIR_RE = /(?:^|\/)\.next\/server(?:\/|$)/;
+
+/**
+ * How to make the bundler that built `dir` emit sourcemaps.
+ *
+ * Nearly every zero-pairs report comes from `@sentry/nextjs`, which uploads
+ * `.next/server` and `.next/static/...`. The Vite and webpack settings do not
+ * apply there, so Next.js output gets its own advice (CLI-1FN).
+ */
+function sourcemapSettingHint(dir: string): string {
+  const posixDir = dir.replaceAll("\\", "/");
+  if (NEXT_SERVER_DIR_RE.test(posixDir)) {
+    return (
+      "For Next.js server output, check that next.config does not turn " +
+      "server sourcemaps off, e.g. a custom `webpack()` that sets " +
+      "`config.devtool`, or `experimental.serverSourceMaps: false`."
+    );
+  }
+  if (NEXT_DIST_DIR_RE.test(posixDir)) {
+    return (
+      "For Next.js, remove `productionBrowserSourceMaps: false` from " +
+      "next.config (`withSentryConfig` turns it on), or set " +
+      "`sourcemaps.disable: true` in `withSentryConfig` to skip the upload."
+    );
+  }
+  return (
+    "For Vite/Astro: `vite.environments.client.build.sourcemap: 'hidden'`. " +
+    "For webpack: `devtool: 'hidden-source-map'`."
+  );
+}
+
 /**
  * Build an actionable error for the zero-pairs case, tailored to
  * which side of the JS/map pairing is missing.
@@ -855,9 +890,8 @@ export function buildEmptyDiscoveryError(
   if (jsFiles > 0 && mapFiles === 0) {
     return new ValidationError(
       `Found ${jsFiles} JS file(s) in '${dir}' but no companion .map ` +
-        "files. Your bundler is not emitting sourcemaps. For Vite/Astro: " +
-        "`vite.environments.client.build.sourcemap: 'hidden'`. For webpack: " +
-        "`devtool: 'hidden-source-map'`. Pass --allow-empty to suppress.",
+        "files. Your bundler is not emitting sourcemaps. " +
+        `${sourcemapSettingHint(dir)} Pass --allow-empty to suppress.`,
       "directory",
     );
   }
@@ -871,9 +905,10 @@ export function buildEmptyDiscoveryError(
   }
   return new ValidationError(
     `Found ${jsFiles} JS and ${mapFiles} .map file(s) in '${dir}' but ` +
-      "no JS file has a matching `<name>.map` companion. Check that your " +
-      "bundler emits JS and sourcemaps with matching basenames. Pass " +
-      "--allow-empty to suppress.",
+      "no JS file has a sourcemap: none has a sibling `<name>.map` or a " +
+      "`//# sourceMappingURL=` comment pointing at a map in this " +
+      `directory. ${sourcemapSettingHint(dir)} Pass --allow-empty to ` +
+      "suppress.",
     "directory",
   );
 }
diff --git a/packages/cli/test/commands/sourcemap/upload.test.ts b/packages/cli/test/commands/sourcemap/upload.test.ts
index cfb2a1fc0..4b81582d1 100644
--- a/packages/cli/test/commands/sourcemap/upload.test.ts
+++ b/packages/cli/test/commands/sourcemap/upload.test.ts
@@ -15,6 +15,7 @@ import { uploadCommand } from "../../../src/commands/sourcemap/upload.js";
 import * as sourcemapsApi from "../../../src/lib/api/sourcemaps.js";
 import { ValidationError } from "../../../src/lib/errors.js";
 import { getDebugIdSnippet } from "../../../src/lib/sourcemap/debug-id.js";
+import { buildEmptyDiscoveryError } from "../../../src/lib/sourcemap/inject.js";
 
 type InjectFuncArgs = {
   ext?: string;
@@ -43,6 +44,26 @@ function makeContext() {
   };
 }
 
+describe("buildEmptyDiscoveryError — bundler hint", () => {
+  test.each([
+    ["/app/dist", /vite.*webpack/i],
+    ["/app/.next/static/chunks", /productionBrowserSourceMaps: false/],
+    ["/app/.next/static/immutable/chunks", /productionBrowserSourceMaps/],
+    ["C:\\app\\.next\\static\\chunks", /productionBrowserSourceMaps/],
+    ["/app/.next/server", /serverSourceMaps/],
+    ["/app/not.next/static", /vite.*webpack/i],
+  ])("%s", (dir, hint) => {
+    for (const diag of [
+      { jsFiles: 3, mapFiles: 0 },
+      { jsFiles: 3, mapFiles: 1 },
+    ]) {
+      const msg = buildEmptyDiscoveryError(dir, diag).message;
+      expect(msg).toMatch(hint);
+      expect(msg).toContain("--allow-empty");
+    }
+  });
+});
+
 describe("sourcemap inject command — --allow-empty behavior", () => {
   let dir: string;
   let func: CmdFunc<InjectFuncArgs>;
@@ -126,7 +147,7 @@ describe("sourcemap inject command — --allow-empty behavior", () => {
       const msg = (err as Error).message;
       expect(msg).toContain("1 JS");
       expect(msg).toContain("1 .map");
-      expect(msg).toContain("matching basename");
+      expect(msg).toContain("sourceMappingURL");
     }
   });