diff --git a/packages/nextjs/src/config/loaders/moduleMetadataInjectionLoader.ts b/packages/nextjs/src/config/loaders/moduleMetadataInjectionLoader.ts
index 96c00569e06f..b26eb452e13b 100644
--- a/packages/nextjs/src/config/loaders/moduleMetadataInjectionLoader.ts
+++ b/packages/nextjs/src/config/loaders/moduleMetadataInjectionLoader.ts
@@ -1,5 +1,5 @@
 import type { LoaderThis } from './types';
-import { SKIP_COMMENT_AND_DIRECTIVE_REGEX } from './valueInjectionLoader';
+import { findInjectionIndexAfterDirectives } from './valueInjectionLoader';
 
 export type ModuleMetadataInjectionLoaderOptions = {
   applicationKey: string;
@@ -39,7 +39,6 @@ export default function moduleMetadataInjectionLoader(
     `e._sentryModuleMetadata[(new e.Error).stack]=Object.assign({},e._sentryModuleMetadata[(new e.Error).stack],${metadata});` +
     '}catch(e){}}();';
 
-  return userCode.replace(SKIP_COMMENT_AND_DIRECTIVE_REGEX, match => {
-    return match + injectedCode;
-  });
+  const injectionIndex = findInjectionIndexAfterDirectives(userCode);
+  return `${userCode.slice(0, injectionIndex)}${injectedCode}${userCode.slice(injectionIndex)}`;
 }
diff --git a/packages/nextjs/src/config/loaders/valueInjectionLoader.ts b/packages/nextjs/src/config/loaders/valueInjectionLoader.ts
index 62cabcf818b8..d388b6bb4dd0 100644
--- a/packages/nextjs/src/config/loaders/valueInjectionLoader.ts
+++ b/packages/nextjs/src/config/loaders/valueInjectionLoader.ts
@@ -1,18 +1,151 @@
-// Rollup doesn't like if we put the directive regex as a literal (?). No idea why.
-/* oxlint-disable sdk/no-regexp-constructor */
-
 import type { LoaderThis } from './types';
 
 export type ValueInjectionLoaderOptions = {
   values: Record<string, unknown>;
 };
 
-// We need to be careful not to inject anything before any `"use strict";`s or "use client"s or really any other directive.
-// As an additional complication directives may come after any number of comments.
-// This regex is shamelessly stolen from: https://github.com/getsentry/sentry-javascript-bundler-plugins/blob/7f984482c73e4284e8b12a08dfedf23b5a82f0af/packages/bundler-plugin-core/src/index.ts#L535-L539
-export const SKIP_COMMENT_AND_DIRECTIVE_REGEX =
-  // Note: CodeQL complains that this regex potentially has n^2 runtime. This likely won't affect realistic files.
-  new RegExp('^(?:\\s*|/\\*(?:.|\\r|\\n)*?\\*/|//.*[\\n\\r])*(?:"[^"]*";?|\'[^\']*\';?)?');
+// We need to be careful not to inject anything before any `"use strict";`s or "use client"s or really any other
+// directives. A small scanner is easier to reason about than the previous regex and avoids regex backtracking concerns.
+export function findInjectionIndexAfterDirectives(userCode: string): number {
+  let index = 0;
+  let lastDirectiveEndIndex: number | undefined;
+
+  while (index < userCode.length) {
+    const statementStartIndex = skipWhitespaceAndComments(userCode, index);
+    if (statementStartIndex === undefined) {
+      return lastDirectiveEndIndex ?? 0;
+    }
+
+    index = statementStartIndex;
+    if (statementStartIndex === userCode.length) {
+      return lastDirectiveEndIndex ?? statementStartIndex;
+    }
+
+    const quote = userCode[statementStartIndex];
+    if (quote !== '"' && quote !== "'") {
+      return lastDirectiveEndIndex ?? statementStartIndex;
+    }
+
+    const stringEndIndex = findStringLiteralEnd(userCode, statementStartIndex);
+    if (stringEndIndex === undefined) {
+      return lastDirectiveEndIndex ?? statementStartIndex;
+    }
+
+    const statementEndIndex = findDirectiveTerminator(userCode, stringEndIndex);
+    if (statementEndIndex === undefined) {
+      return lastDirectiveEndIndex ?? statementStartIndex;
+    }
+
+    index = statementEndIndex;
+    lastDirectiveEndIndex = statementEndIndex;
+  }
+
+  return lastDirectiveEndIndex ?? index;
+}
+
+function skipWhitespaceAndComments(userCode: string, startIndex: number): number | undefined {
+  let index = startIndex;
+
+  while (index < userCode.length) {
+    const char = userCode[index];
+
+    if (char && /\s/.test(char)) {
+      index += 1;
+      continue;
+    }
+
+    if (userCode.startsWith('//', index)) {
+      const newlineIndex = userCode.indexOf('\n', index + 2);
+      index = newlineIndex === -1 ? userCode.length : newlineIndex + 1;
+      continue;
+    }
+
+    if (userCode.startsWith('/*', index)) {
+      const commentEndIndex = userCode.indexOf('*/', index + 2);
+      if (commentEndIndex === -1) {
+        return undefined;
+      }
+
+      index = commentEndIndex + 2;
+      continue;
+    }
+
+    break;
+  }
+
+  return index;
+}
+
+function findStringLiteralEnd(userCode: string, startIndex: number): number | undefined {
+  const quote = userCode[startIndex];
+  let index = startIndex + 1;
+
+  while (index < userCode.length) {
+    const char = userCode[index];
+
+    if (char === '\\') {
+      index += 2;
+      continue;
+    }
+
+    if (char === quote) {
+      return index + 1;
+    }
+
+    if (char === '\n' || char === '\r') {
+      return undefined;
+    }
+
+    index += 1;
+  }
+
+  return undefined;
+}
+
+function findDirectiveTerminator(userCode: string, startIndex: number): number | undefined {
+  let index = startIndex;
+
+  // Only a bare string literal followed by a statement terminator counts as a directive.
+  while (index < userCode.length) {
+    const char = userCode[index];
+
+    if (char === ';') {
+      return index + 1;
+    }
+
+    if (char === '\n' || char === '\r' || char === '}') {
+      return index;
+    }
+
+    if (char && /\s/.test(char)) {
+      index += 1;
+      continue;
+    }
+
+    if (userCode.startsWith('//', index)) {
+      return index;
+    }
+
+    if (userCode.startsWith('/*', index)) {
+      const commentEndIndex = userCode.indexOf('*/', index + 2);
+      if (commentEndIndex === -1) {
+        return undefined;
+      }
+
+      const comment = userCode.slice(index + 2, commentEndIndex);
+      if (comment.includes('\n') || comment.includes('\r')) {
+        return index;
+      }
+
+      index = commentEndIndex + 2;
+      continue;
+    }
+
+    return undefined;
+  }
+
+  return index;
+}
 
 /**
  * Set values on the global/window object at the start of a module.
@@ -36,7 +169,6 @@ export default function valueInjectionLoader(this: LoaderThis<ValueInjectionLoad
       .map(([key, value]) => `globalThis["${key}"] = ${JSON.stringify(value)};`)
       .join('');
 
-  return userCode.replace(SKIP_COMMENT_AND_DIRECTIVE_REGEX, match => {
-    return match + injectedCode;
-  });
+  const injectionIndex = findInjectionIndexAfterDirectives(userCode);
+  return `${userCode.slice(0, injectionIndex)}${injectedCode}${userCode.slice(injectionIndex)}`;
 }
diff --git a/packages/nextjs/test/config/moduleMetadataInjectionLoader.test.ts b/packages/nextjs/test/config/moduleMetadataInjectionLoader.test.ts
index 1a6a2cd14b71..f6c1c613bd00 100644
--- a/packages/nextjs/test/config/moduleMetadataInjectionLoader.test.ts
+++ b/packages/nextjs/test/config/moduleMetadataInjectionLoader.test.ts
@@ -131,4 +131,30 @@ describe('moduleMetadataInjectionLoader', () => {
 
     expect(result).toContain('"_sentryBundlerPluginAppKey:test-key-123":true');
   });
+
+  it('should inject after multiple directives', () => {
+    const loaderThis = createLoaderThis('my-app');
+    const userCode = '"use strict";\n"use client";\nimport React from \'react\';';
+
+    const result = moduleMetadataInjectionLoader.call(loaderThis, userCode);
+
+    const metadataIndex = result.indexOf('_sentryModuleMetadata');
+    const clientDirectiveIndex = result.indexOf('"use client"');
+    const importIndex = result.indexOf("import React from 'react';");
+
+    expect(metadataIndex).toBeGreaterThan(clientDirectiveIndex);
+    expect(metadataIndex).toBeLessThan(importIndex);
+  });
+
+  it('should inject after comments between multiple directives', () => {
+    const loaderThis = createLoaderThis('my-app');
+    const userCode = '"use strict";\n/* keep */\n"use client";\nimport React from \'react\';';
+
+    const result = moduleMetadataInjectionLoader.call(loaderThis, userCode);
+
+    const metadataIndex = result.indexOf('_sentryModuleMetadata');
+    const clientDirectiveIndex = result.indexOf('"use client"');
+
+    expect(metadataIndex).toBeGreaterThan(clientDirectiveIndex);
+  });
 });
diff --git a/packages/nextjs/test/config/valueInjectionLoader.test.ts b/packages/nextjs/test/config/valueInjectionLoader.test.ts
index 57b40b006baa..6d60819c9cd6 100644
--- a/packages/nextjs/test/config/valueInjectionLoader.test.ts
+++ b/packages/nextjs/test/config/valueInjectionLoader.test.ts
@@ -1,7 +1,7 @@
 import { describe, expect, it } from 'vitest';
 import type { LoaderThis } from '../../src/config/loaders/types';
 import type { ValueInjectionLoaderOptions } from '../../src/config/loaders/valueInjectionLoader';
-import valueInjectionLoader from '../../src/config/loaders/valueInjectionLoader';
+import valueInjectionLoader, { findInjectionIndexAfterDirectives } from '../../src/config/loaders/valueInjectionLoader';
 
 const defaultLoaderThis = {
   addDependency: () => undefined,
@@ -149,4 +149,99 @@ describe.each([[clientConfigLoaderThis], [instrumentationLoaderThis]])('valueInj
     expect(result).toMatchSnapshot();
     expect(result).toMatch(';globalThis["foo"] = "bar";');
   });
+
+  it('should correctly insert values after multiple directives', () => {
+    const userCode = `
+      "use strict";
+      "use client";
+      import * as Sentry from '@sentry/nextjs';
+      Sentry.init();
+    `;
+
+    const result = valueInjectionLoader.call(loaderThis, userCode);
+
+    const injectionIndex = result.indexOf(';globalThis["foo"] = "bar";');
+    const clientDirectiveIndex = result.indexOf('"use client"');
+    const importIndex = result.indexOf("import * as Sentry from '@sentry/nextjs';");
+
+    expect(injectionIndex).toBeGreaterThan(clientDirectiveIndex);
+    expect(injectionIndex).toBeLessThan(importIndex);
+  });
+
+  it('should correctly insert values after comments between multiple directives', () => {
+    const userCode = `
+      "use strict";
+      /* keep */
+      "use client";
+      import * as Sentry from '@sentry/nextjs';
+      Sentry.init();
+    `;
+
+    const result = valueInjectionLoader.call(loaderThis, userCode);
+
+    const injectionIndex = result.indexOf(';globalThis["foo"] = "bar";');
+    const clientDirectiveIndex = result.indexOf('"use client"');
+
+    expect(injectionIndex).toBeGreaterThan(clientDirectiveIndex);
+  });
+
+  it('should correctly insert values after semicolon-free directives', () => {
+    const userCode = `
+      "use strict"
+      "use client"
+      import * as Sentry from '@sentry/nextjs';
+      Sentry.init();
+    `;
+
+    const result = valueInjectionLoader.call(loaderThis, userCode);
+
+    const injectionIndex = result.indexOf(';globalThis["foo"] = "bar";');
+    const clientDirectiveIndex = result.indexOf('"use client"');
+
+    expect(injectionIndex).toBeGreaterThan(clientDirectiveIndex);
+  });
+});
+
+describe('findInjectionIndexAfterDirectives', () => {
+  it('returns the position immediately after the last directive', () => {
+    const userCode = '"use strict";\n"use client";\nimport React from \'react\';';
+
+    expect(userCode.slice(findInjectionIndexAfterDirectives(userCode))).toBe("\nimport React from 'react';");
+  });
+
+  it('returns the end of the input when the last directive reaches EOF', () => {
+    const userCode = '"use strict";\n"use client";';
+
+    expect(findInjectionIndexAfterDirectives(userCode)).toBe(userCode.length);
+  });
+
+  it('does not skip a string literal that is not a directive', () => {
+    const userCode = '"use client" + suffix;';
+
+    expect(findInjectionIndexAfterDirectives(userCode)).toBe(0);
+  });
+
+  it('does not treat an escaped quote at EOF as a closed directive', () => {
+    const userCode = '"use client\\"';
+
+    expect(findInjectionIndexAfterDirectives(userCode)).toBe(0);
+  });
+
+  it('returns 0 for an unterminated leading block comment', () => {
+    const userCode = '/* unterminated';
+
+    expect(findInjectionIndexAfterDirectives(userCode)).toBe(0);
+  });
+
+  it('returns the last complete directive when followed by an unterminated block comment', () => {
+    const userCode = '"use client"; /* unterminated';
+
+    expect(findInjectionIndexAfterDirectives(userCode)).toBe('"use client";'.length);
+  });
+
+  it('treats a block comment without a line break as part of the same statement', () => {
+    const userCode = '"use client" /* comment */ + suffix;';
+
+    expect(findInjectionIndexAfterDirectives(userCode)).toBe(0);
+  });
 });