diff --git a/packages/server-runtime-injection/src/register.ts b/packages/server-runtime-injection/src/register.ts
index 881da139417f..7c437e2980c0 100644
--- a/packages/server-runtime-injection/src/register.ts
+++ b/packages/server-runtime-injection/src/register.ts
@@ -29,44 +29,82 @@ function hasStableSyncModuleHooks(isDeno: boolean): boolean {
 }
 
 /**
- * Emit a single, always-on warning that runtime channel injection is disabled, with the actionable
- * fix. Unlike `debug.warn` (gated behind `debug: true`), this reaches every user — otherwise the
- * SDK silently records no channel-based spans.
+ * Emit an always-on warning. Unlike `debug.warn` (gated behind `debug: true`), this reaches every
+ * user — otherwise a broken transform silently records no channel-based spans.
  */
-function warnRuntimeUnavailable(message: string): void {
+function warn(message: string): void {
   consoleSandbox(() => {
     // oxlint-disable-next-line no-console
-    console.warn(`[Sentry] ${message} See ${BUNDLING_DOCS_URL}`);
+    console.warn(`[Sentry] ${message}`);
   });
 }
 
-// One broken transformer breaks every module, so state the fix once.
+/** As {@link warn}, but appends the bundling/troubleshooting docs link for the build-fix cases. */
+function warnRuntimeUnavailable(message: string): void {
+  warn(`${message} See ${BUNDLING_DOCS_URL}`);
+}
+
+// A systemic transformer failure breaks every module, so the "bundled" fix is stated once.
 let warnedTransformerUnavailable = false;
+// Isolated per-module failures are unrelated to bundling, so they warn once per module.
+const warnedModuleFailures = new Set<string>();
 
 /**
- * Warn that the vendored code transformer could not run, so `moduleName` loaded uninstrumented.
- *
- * This package ships the transformer (meriyah/astring/source-map) inline and is meant to run from
- * `node_modules`. A bundler that inlines and tree-shakes `@sentry/server-runtime-injection` strips it, so every
- * transform throws `TypeError: parse is not a function` — swallowed inside the loader, once per
- * module, visible only with `debug: true`.
+ * A module's transform threw. Two very different causes reach this callback, so distinguish them
+ * instead of always blaming bundling — and always include the underlying error, so the message is
+ * self-diagnosing rather than asserting a cause the reader can't check (`debug: true` still logs
+ * the full error and stack).
  *
- * Warning from here rather than probing the transformer at `init()` keeps the check honest. A
- * module only reaches this callback by coming through Node's loader, which means the build-time
- * bundler plugin did not cover it, which means the instrumentation really is lost. Probing at
- * `init()` instead has to guess at that from a global the plugin's entry banner may not have
- * written yet.
+ * - The transform pipeline itself is gone → a bare `TypeError: <name> is not a function`. That is
+ *   the fingerprint of a bundler inlining and tree-shaking `@sentry/server-runtime-injection`,
+ *   which drops its vendored meriyah `parse` / astring `generate` (both module-level imports): it
+ *   fails EVERY module the same way and is app-wide, with an actionable build fix. The identifier is
+ *   NOT matched, because the same bundle renames it beyond recognition — esbuild deconflicts to
+ *   `parse2`, rollup/vite to `parse$1`, and production minifiers to a short opaque `n` — so we match
+ *   the *shape* (a bare `<ident> is not a function`) plus the fact that nothing was ever
+ *   instrumented (a transformer that has already instrumented something is provably not stripped).
+ * - Any other transform `TypeError` (e.g. `transform is not a function`, from a config whose
+ *   operator is not registered at runtime — `transform` is a local dispatch, not a stripped import,
+ *   so an unbundled install throws with its real, unmangled name) is not a bundling problem — even
+ *   when it is the first module to load — so it gets a scoped message that points at reporting it,
+ *   not changing the build. A member-expression failure (`x.y is not a function`) is likewise an
+ *   ordinary per-module bug, not a stripped top-level binding, so the bare-identifier anchor
+ *   excludes it.
  */
-function warnTransformerUnavailable(moduleName: string): void {
+function warnTransformFailed(moduleName: string, error: unknown): void {
+  const reason = error instanceof Error ? error.message : String(error);
+
+  // A stripped pipeline throws `<ident> is not a function` for a *bare* identifier (the renamed
+  // `parse`/`generate` binding); the anchors exclude member-expression failures like `x.y is ...`.
+  const barePrimitiveMissing = /^[\w$]+ is not a function$/.test(reason);
+  // The operator dispatch is a local, only missing when a config operator is unregistered, and an
+  // unbundled install reads it under its real name — never a stripped-transformer symptom.
+  const isolatedOperatorFailure = reason === 'transform is not a function';
+  // A non-empty `runtime` list (something was already instrumented) proves the pipeline works.
+  const nothingInstrumentedYet = (GLOBAL_OBJ.__SENTRY_ORCHESTRION__?.runtime?.length ?? 0) === 0;
+  const pipelineStripped = barePrimitiveMissing && !isolatedOperatorFailure && nothingInstrumentedYet;
+
+  if (!pipelineStripped) {
+    if (warnedModuleFailures.has(moduleName)) {
+      return;
+    }
+    warnedModuleFailures.add(moduleName);
+    warn(
+      `Could not instrument \`${moduleName}\` (${reason}). Other instrumented dependencies are ` +
+        `unaffected, so this is not a bundling problem. If \`${moduleName}\` should be traced, please report it.`,
+    );
+    return;
+  }
+
   if (warnedTransformerUnavailable) {
     return;
   }
   warnedTransformerUnavailable = true;
-
   warnRuntimeUnavailable(
-    `\`@sentry/server-runtime-injection\` was bundled into your application, so ${moduleName} and any other ` +
-      'instrumented dependency load uninstrumented. Keep `@sentry/server-runtime-injection` external in your ' +
-      'server bundle, or use the Sentry bundler plugin for build-time instrumentation.',
+    `\`@sentry/server-runtime-injection\` was bundled into your application, so \`${moduleName}\` and any ` +
+      `other instrumented dependency load uninstrumented (${reason}). Keep ` +
+      '`@sentry/server-runtime-injection` external in your server bundle, or use the Sentry bundler ' +
+      'plugin for build-time instrumentation.',
   );
 }
 
@@ -99,11 +137,11 @@ export function registerDiagnosticsChannelInjection(): void {
 
   setDiagnosticsHook(({ url, moduleName, error }): void => {
     if (error) {
-      // A stripped transformer surfaces as a `TypeError` (`parse`/`generate` are `undefined`) and
-      // costs the user this module's instrumentation, so it is worth an always-on warning. Every
-      // other transform failure stays debug-only.
+      // A transform throwing a `TypeError` costs this module its instrumentation, so it is worth an
+      // always-on warning; `warnTransformFailed` decides whether that is systemic (bundling) or
+      // isolated. Every other transform failure stays debug-only.
       if (error instanceof TypeError) {
-        warnTransformerUnavailable(moduleName);
+        warnTransformFailed(moduleName, error);
       }
       debug.warn(`[instrumentation] failed to inject diagnostics-channel into ${moduleName}:`, error);
     } else {
diff --git a/packages/server-runtime-injection/test/register.test.ts b/packages/server-runtime-injection/test/register.test.ts
index 2170f3b4de8d..18307c0073eb 100644
--- a/packages/server-runtime-injection/test/register.test.ts
+++ b/packages/server-runtime-injection/test/register.test.ts
@@ -36,12 +36,14 @@ vi.mock('@sentry/core', async importOriginal => {
 });
 
 import { GLOBAL_OBJ } from '@sentry/core';
-import { registerDiagnosticsChannelInjection } from '../src/register';
+import type * as RegisterModule from '../src/register';
 
 type DiagnosticsCallback = (event: { moduleName: string; error?: unknown }) => void;
 
 describe('registerDiagnosticsChannelInjection - bundled/tree-shaken detection', () => {
   let warnSpy: ReturnType<typeof vi.spyOn>;
+  // Re-imported per test (see `beforeEach`) so the one-warning-per-process module state is fresh.
+  let registerDiagnosticsChannelInjection: typeof RegisterModule.registerDiagnosticsChannelInjection;
 
   /**
    * The bundling warnings only. Registration itself can warn for unrelated reasons in this
@@ -51,6 +53,11 @@ describe('registerDiagnosticsChannelInjection - bundled/tree-shaken detection',
     return warnSpy.mock.calls.map(([message]) => String(message)).filter(m => m.includes('was bundled into'));
   }
 
+  /** The isolated per-module failure warnings only (a transform failure that is not a stripped transformer). */
+  function moduleFailureWarnings(): string[] {
+    return warnSpy.mock.calls.map(([message]) => String(message)).filter(m => m.includes('Could not instrument'));
+  }
+
   /** The callback the registration handed to tracing-hooks. */
   function diagnosticsCallback(): DiagnosticsCallback {
     const [callback] = setDiagnosticsHookMock.mock.lastCall ?? [];
@@ -64,8 +71,11 @@ describe('registerDiagnosticsChannelInjection - bundled/tree-shaken detection',
     delete GLOBAL_OBJ.__SENTRY_ORCHESTRION__;
     setDiagnosticsHookMock.mockClear();
     warnSpy = vi.spyOn(console, 'warn').mockImplementation(() => undefined);
-    // The one-warning-per-process flag is module state, so each test needs a fresh module.
+    // The one-warning-per-process flags are module state, so each test needs a fresh module — hence
+    // the dynamic re-import below rather than a static top-level one (`resetModules` cannot refresh
+    // an already-bound static import).
     vi.resetModules();
+    ({ registerDiagnosticsChannelInjection } = await import('../src/register'));
   });
 
   afterEach(() => {
@@ -77,13 +87,83 @@ describe('registerDiagnosticsChannelInjection - bundled/tree-shaken detection',
     registerDiagnosticsChannelInjection();
     const onDiagnostics = diagnosticsCallback();
 
-    // A tree-shaken chain: `parse`/`generate` are `undefined`, so the transform throws a TypeError.
-    onDiagnostics({ moduleName: 'mysql2', error: new TypeError('parse is not a function') });
-    onDiagnostics({ moduleName: 'pg', error: new TypeError('parse is not a function') });
+    // A tree-shaken chain: the vendored `parse`/`generate` are `undefined`, so the transform throws
+    // a TypeError. The bundler that stripped them also renames these module-level imports while
+    // merging modules — esbuild emits `parse3` — so the fingerprint must not hinge on the name.
+    onDiagnostics({ moduleName: 'mysql2', error: new TypeError('parse3 is not a function') });
+    onDiagnostics({ moduleName: 'pg', error: new TypeError('parse3 is not a function') });
 
     expect(bundlingWarnings()).toHaveLength(1);
     expect(bundlingWarnings()[0]).toContain('mysql2');
     expect(bundlingWarnings()[0]).toContain('docs.sentry.io');
+    // The underlying error is surfaced so the warning is self-diagnosing.
+    expect(bundlingWarnings()[0]).toContain('parse3 is not a function');
+  });
+
+  it.each([
+    // Rollup/Vite deconflict merged bindings with a `$N` suffix, not a bare number.
+    ['rollup/vite `$N` suffix', 'generate$1 is not a function'],
+    // Production minifiers rename the stripped import to a short opaque identifier.
+    ['minified short name', 'e is not a function'],
+  ])('detects a tree-shaken transformer whose primitive was renamed (%s)', (_label, reason) => {
+    registerDiagnosticsChannelInjection();
+
+    diagnosticsCallback()({ moduleName: 'mysql2', error: new TypeError(reason) });
+
+    expect(bundlingWarnings()).toHaveLength(1);
+    expect(bundlingWarnings()[0]).toContain('mysql2');
+    expect(bundlingWarnings()[0]).toContain(reason);
+  });
+
+  it('treats a member-expression TypeError as an isolated failure, not bundling', () => {
+    registerDiagnosticsChannelInjection();
+
+    // `x.y is not a function` is an ordinary per-module bug, not a stripped bare top-level binding,
+    // so even as the first failing module it must not be blamed on bundling.
+    diagnosticsCallback()({ moduleName: 'lib-member', error: new TypeError('node.foo is not a function') });
+
+    expect(bundlingWarnings()).toEqual([]);
+    expect(moduleFailureWarnings()).toHaveLength(1);
+    expect(moduleFailureWarnings()[0]).toContain('lib-member');
+  });
+
+  it('reports a non-stripped transform TypeError as an isolated failure, not bundling', () => {
+    registerDiagnosticsChannelInjection();
+
+    // `transform is not a function` (a config operator not registered at runtime) is not the
+    // stripped-parser fingerprint, so even as the first and only failing module it must not be
+    // blamed on bundling.
+    diagnosticsCallback()({ moduleName: 'lib-op-missing', error: new TypeError('transform is not a function') });
+
+    expect(bundlingWarnings()).toEqual([]);
+    expect(moduleFailureWarnings()).toHaveLength(1);
+    expect(moduleFailureWarnings()[0]).toContain('lib-op-missing');
+    expect(moduleFailureWarnings()[0]).toContain('transform is not a function');
+  });
+
+  it('treats a stripped-parser error as isolated once another module has been instrumented', () => {
+    registerDiagnosticsChannelInjection();
+    const onDiagnostics = diagnosticsCallback();
+
+    // A successful transform proves the transformer works, so a later `parse is not a function`
+    // cannot be a tree-shaken transformer — it is isolated to that module.
+    onDiagnostics({ moduleName: 'lib-ok' });
+    onDiagnostics({ moduleName: 'lib-guarded', error: new TypeError('parse is not a function') });
+
+    expect(bundlingWarnings()).toEqual([]);
+    expect(moduleFailureWarnings()).toHaveLength(1);
+    expect(moduleFailureWarnings()[0]).toContain('lib-guarded');
+  });
+
+  it('warns once per module for isolated failures', () => {
+    registerDiagnosticsChannelInjection();
+    const onDiagnostics = diagnosticsCallback();
+
+    onDiagnostics({ moduleName: 'lib-dup', error: new TypeError('transform is not a function') });
+    onDiagnostics({ moduleName: 'lib-dup', error: new TypeError('transform is not a function') });
+    onDiagnostics({ moduleName: 'lib-other', error: new TypeError('transform is not a function') });
+
+    expect(moduleFailureWarnings()).toHaveLength(2);
   });
 
   it('stays quiet for transform failures that are not a stripped transformer', () => {