diff --git a/packages/cli/src/services/check-parser/__tests__/bundler.spec.ts b/packages/cli/src/services/check-parser/__tests__/bundler.spec.ts
new file mode 100644
index 00000000..e96a04fc
--- /dev/null
+++ b/packages/cli/src/services/check-parser/__tests__/bundler.spec.ts
@@ -0,0 +1,113 @@
+import { mkdir, mkdtemp, rm, symlink, writeFile } from 'node:fs/promises'
+import { tmpdir } from 'node:os'
+import path from 'node:path'
+
+import { list } from 'tar'
+import { afterEach, beforeEach, describe, expect, it } from 'vitest'
+
+import { Bundler } from '../bundler.js'
+
+describe('Bundler', () => {
+  let root: string
+
+  beforeEach(async () => {
+    root = await mkdtemp(path.join(tmpdir(), 'checkly-bundler-'))
+  })
+
+  afterEach(async () => {
+    await rm(root, { recursive: true, force: true })
+  })
+
+  it('does not archive a symlink when files below it are selected', async () => {
+    const packagePath = path.join(root, 'packages', 'shared-package')
+    const linkedPackagePath = path.join(
+      root,
+      'packages',
+      'app',
+      'node_modules',
+      '@workspace',
+      'shared-package',
+    )
+    const packageJsonPath = path.join(packagePath, 'package.json')
+    const sourcePath = path.join(packagePath, 'src', 'index.js')
+    const linkedPackageJsonPath = path.join(linkedPackagePath, 'package.json')
+    const linkedSourcePath = path.join(linkedPackagePath, 'src', 'index.js')
+
+    await mkdir(path.dirname(linkedPackagePath), { recursive: true })
+    await mkdir(path.dirname(sourcePath), { recursive: true })
+    await writeFile(packageJsonPath, '{"name":"@workspace/shared-package"}')
+    await writeFile(sourcePath, 'export const value = true\n')
+    await symlink('../../../shared-package', linkedPackagePath, 'dir')
+
+    const bundler = await Bundler.create({
+      cacheHash: 'cache-hash',
+      tempDir: root,
+      stripPrefix: root,
+    })
+    bundler.registerFiles(
+      { filePath: packageJsonPath, physical: true },
+      { filePath: sourcePath, physical: true },
+      { filePath: linkedPackagePath, physical: true },
+      { filePath: linkedPackageJsonPath, physical: true },
+      { filePath: linkedSourcePath, physical: true },
+    )
+
+    const archive = await bundler.finalize()
+    const archivePaths: string[] = []
+    await list({
+      file: archive.archiveFile,
+      onReadEntry: entry => archivePaths.push(entry.path),
+    })
+
+    expect(archivePaths.sort()).toEqual([
+      'packages/app/node_modules/@workspace/shared-package/package.json',
+      'packages/app/node_modules/@workspace/shared-package/src/index.js',
+      'packages/shared-package/package.json',
+      'packages/shared-package/src/index.js',
+    ])
+  })
+
+  it('archives a symlink when no files below it are selected', async () => {
+    const packagePath = path.join(root, 'packages', 'shared-package')
+    const linkedPackagePath = path.join(
+      root,
+      'packages',
+      'app',
+      'node_modules',
+      '@workspace',
+      'shared-package',
+    )
+
+    await mkdir(path.dirname(linkedPackagePath), { recursive: true })
+    await mkdir(packagePath, { recursive: true })
+    await symlink('../../../shared-package', linkedPackagePath, 'dir')
+
+    const bundler = await Bundler.create({
+      cacheHash: 'cache-hash',
+      tempDir: root,
+      stripPrefix: root,
+    })
+    bundler.registerFiles({ filePath: linkedPackagePath, physical: true })
+
+    const archive = await bundler.finalize()
+    const archiveEntries: Array<{
+      path: string
+      type: string
+      linkpath: string
+    }> = []
+    await list({
+      file: archive.archiveFile,
+      onReadEntry: entry => archiveEntries.push({
+        path: entry.path,
+        type: entry.type,
+        linkpath: entry.linkpath,
+      }),
+    })
+
+    expect(archiveEntries).toEqual([{
+      path: 'packages/app/node_modules/@workspace/shared-package',
+      type: 'SymbolicLink',
+      linkpath: '../../../shared-package',
+    }])
+  })
+})
diff --git a/packages/cli/src/services/check-parser/bundler.ts b/packages/cli/src/services/check-parser/bundler.ts
index d8c2ccb8..d654e6ae 100644
--- a/packages/cli/src/services/check-parser/bundler.ts
+++ b/packages/cli/src/services/check-parser/bundler.ts
@@ -14,6 +14,7 @@ import { File } from './parser.js'
 import { Workspace } from './package-files/workspace.js'
 
 const debug = Debug('checkly:cli:services:check-parser:bundler')
+const FILESYSTEM_CONCURRENCY = 32
 
 export interface CreateBundleArchiveOptions {
   tempDir?: string
@@ -307,22 +308,59 @@ export class Bundler {
   }
 
   async finalize (): Promise<FinalizedBundleArchive> {
+    let files = Array.from(this.#files.values())
+    files.sort((a, b) => {
+      return a.filePath.localeCompare(b.filePath)
+    })
+    files = await omitSymlinksWithSelectedDescendants(files)
+
     const archive = await BundleArchive.create({
       tempDir: this.#tempDir,
       stripPrefix: this.#stripPrefix,
     })
 
-    const files = Array.from(this.#files.values())
-    files.sort((a, b) => {
-      return a.filePath.localeCompare(b.filePath)
-    })
-
     await archive.add(...files)
 
     return await archive.finalize()
   }
 }
 
+async function omitSymlinksWithSelectedDescendants (files: File[]): Promise<File[]> {
+  const physicalFiles = files.filter(file => file.physical)
+  const symlinkPaths = new Set<string>()
+  for (let offset = 0; offset < physicalFiles.length; offset += FILESYSTEM_CONCURRENCY) {
+    const batch = physicalFiles.slice(offset, offset + FILESYSTEM_CONCURRENCY)
+    const symlinks = await Promise.all(batch.map(async file => {
+      if (!(await fs.lstat(file.filePath)).isSymbolicLink()) {
+        return undefined
+      }
+
+      return path.resolve(file.filePath)
+    }))
+    for (const symlink of symlinks) {
+      if (symlink !== undefined) {
+        symlinkPaths.add(symlink)
+      }
+    }
+  }
+
+  const symlinksWithSelectedDescendants = new Set<string>()
+  for (const file of files) {
+    const filePath = path.resolve(file.filePath)
+    let parentPath = path.dirname(filePath)
+    while (parentPath !== path.dirname(parentPath)) {
+      if (symlinkPaths.has(parentPath)) {
+        symlinksWithSelectedDescendants.add(parentPath)
+      }
+      parentPath = path.dirname(parentPath)
+    }
+  }
+
+  return files.filter(file => {
+    return !symlinksWithSelectedDescendants.has(path.resolve(file.filePath))
+  })
+}
+
 async function createArchiver (): Promise<Archiver> {
   // Dynamic import for CommonJs so it doesn't break when using checkly/playwright-reporter archiver
   // The custom Checkly fork of archiver exports TarArchive class instead of a default function