diff --git a/src/test/py/bazel/bzlmod/repo_contents_cache_test.py b/src/test/py/bazel/bzlmod/repo_contents_cache_test.py
index 204f676710c940..93d015b257387f 100644
--- a/src/test/py/bazel/bzlmod/repo_contents_cache_test.py
+++ b/src/test/py/bazel/bzlmod/repo_contents_cache_test.py
@@ -101,6 +101,23 @@ def assertRepoNotCached(self, repo_dir):
     except OSError:
       pass  # Not a symlink means not cached, which is expected
 
+  def _rmtreeWithRetry(self, path, attempts=10, delay=0.5):
+    """Like shutil.rmtree, but retries on Windows file-lock errors.
+
+    `bazel shutdown` returns before the OS has finished releasing file
+    handles in the output base, so a follow-up rmtree may transiently hit
+    PermissionError on Windows. We retry a few times before giving up.
+    """
+    last_err = None
+    for _ in range(attempts):
+      try:
+        shutil.rmtree(path)
+        return
+      except OSError as e:
+        last_err = e
+        time.sleep(delay)
+    raise last_err
+
   def testCachedAfterCleanExpunge(self):
     self.ScratchFile(
         'MODULE.bazel',
@@ -763,6 +780,191 @@ def testCachedRepoWithSymlinks_symlinksEnabledOnWindows(self):
     # by the replanting logic, so cross-repo symlinks prevent caching.
     self.doTestCachedRepoWithSymlinks(expect_cross_repo_cached=False)
 
+  def doTestRepoWithWorkspaceSymlinkSurvivesWorkspaceMove(self):
+    """Regression test for https://github.com/bazelbuild/bazel/issues/29515.
+
+    A reproducible repo that symlinks a file from the main workspace has those
+    symlinks replanted to relative paths through `../_main/...`. On Windows
+    (which resolves symlinks logically) those targets dangle when the repo is
+    read through the execroot unless a corresponding `_main` symlink exists
+    under `<execroot>/external/` too. After the fix, the build must succeed
+    even when the cached repo is reused from a completely different workspace
+    (with the original workspace and output base nuked between builds).
+
+    The workspace is set up under a subdirectory of `_test_cwd` (rather than
+    in `_test_cwd` itself) so that we can delete it without breaking the
+    `tempfile.TemporaryFile(dir=self._test_cwd)` calls inside `RunBazel`.
+    """
+    # Files that make up the workspace. Each file is written to both the
+    # original and the new workspace; the original is later deleted entirely.
+    ws_files = {
+        'payload/BUILD.bazel': [],
+        'payload/hello.txt': ['Hello from workspace!'],
+        'MODULE.bazel': [
+            'ext = use_extension("extension.bzl", "ext")',
+            'use_repo(ext, "linked", "same_repo_only")',
+        ],
+        'extension.bzl': [
+            'def _linked_impl(ctx):',
+            '    ctx.file("REPO.bazel")',
+            '    # Workspace symlink: replantSymlinks rewrites this as',
+            '    # ../_main/payload/hello.txt before the repo is (potentially)',
+            '    # placed in the contents cache.',
+            '    ctx.symlink(',
+            '        ctx.path(Label("@@//payload:hello.txt")),',
+            '        "linked_hello.txt",',
+            '    )',
+            '    ctx.file("BUILD", "exports_files([\\"linked_hello.txt\\"])")',
+            '    return ctx.repo_metadata(reproducible = True)',
+            'linked = repository_rule(implementation = _linked_impl)',
+            '',
+            'def _same_repo_only_impl(ctx):',
+            '    ctx.file("REPO.bazel")',
+            '    ctx.file("data", "Hello from same-repo!")',
+            '    # Same-repo absolute symlink: replanted to a portable relative',
+            '    # path, so this repo is eligible for the contents cache.',
+            '    ctx.symlink(ctx.path("data"), "sym_same_repo")',
+            '    ctx.file("BUILD", "exports_files([\\"sym_same_repo\\"])")',
+            '    return ctx.repo_metadata(reproducible = True)',
+            'same_repo_only = repository_rule(',
+            '    implementation = _same_repo_only_impl,',
+            ')',
+            '',
+            'def _ext_impl(ctx):',
+            '    linked(name = "linked")',
+            '    same_repo_only(name = "same_repo_only")',
+            'ext = module_extension(implementation = _ext_impl)',
+        ],
+        'BUILD': [
+            'genrule(',
+            '    name = "use_linked",',
+            '    srcs = [',
+            '        "@linked//:linked_hello.txt",',
+            '        "@same_repo_only//:sym_same_repo",',
+            '    ],',
+            '    outs = ["output.txt"],',
+            # cmd_bat uses native cmd.exe with execroot-relative Windows paths
+            # to match the original reproducer; on Windows the bug only
+            # manifests through that resolver, not through MSYS bash/cat which
+            # dereferences symlinks differently.
+            '    cmd = "cat $(execpath @linked//:linked_hello.txt) '
+            '$(execpath @same_repo_only//:sym_same_repo) > $@",',
+            '    cmd_bat = "type $(execpath @linked//:linked_hello.txt) '
+            '$(execpath @same_repo_only//:sym_same_repo) > $@",',
+            ')',
+        ],
+    }
+    for rel_path, lines in ws_files.items():
+      self.ScratchFile('original_ws/' + rel_path, lines)
+
+    # First build in the original workspace: fetches and (where eligible)
+    # caches the repos. Use an explicit output base so we can delete it.
+    original_ws = os.path.join(self._test_cwd, 'original_ws')
+    original_output_base = tempfile.mkdtemp(dir=self._tests_root)
+    self.RunBazel(
+        [
+            f'--output_base={original_output_base}',
+            'build',
+            '//:use_linked',
+        ],
+        cwd=original_ws,
+    )
+    output = os.path.join(original_ws, 'bazel-bin/output.txt')
+    self.AssertFileContentContains(output, 'Hello from workspace!')
+    self.AssertFileContentContains(output, 'Hello from same-repo!')
+
+    # Let Bazel itself delete the output base via `clean --expunge` (which
+    # also shuts the server down). On Windows direct rmtree of a still-warm
+    # output base races with the OS releasing file handles, but the Bazel
+    # client knows how to wait for its own server to fully exit.
+    self.RunBazel(
+        [f'--output_base={original_output_base}', 'clean', '--expunge'],
+        cwd=original_ws,
+    )
+
+    # Set up a fresh workspace from scratch (no copy from the original to
+    # ensure the original's bazel-* convenience symlinks don't leak in).
+    new_ws = os.path.join(self._test_cwd, 'new_ws')
+    for rel_path, lines in ws_files.items():
+      self.ScratchFile('new_ws/' + rel_path, lines)
+
+    # Nuke the original workspace. The original output base is already gone
+    # (clean --expunge above). After this point only the contents cache and
+    # the new workspace remain on disk.
+    shutil.rmtree(original_ws)
+    if os.path.exists(original_output_base):
+      # clean --expunge may leave behind an empty shell on some platforms;
+      # remove what's left, retrying a few times for Windows file-handle lag.
+      self._rmtreeWithRetry(original_output_base)
+
+    # Build from the new workspace with a fresh output base. The
+    # `same_repo_only` repo must come straight from the cache; the
+    # `linked` repo with the workspace symlink must work (either from the
+    # cache or refetched) and resolve correctly against the new workspace.
+    new_output_base = tempfile.mkdtemp(dir=self._tests_root)
+    self.RunBazel(
+        [
+            f'--output_base={new_output_base}',
+            'build',
+            '//:use_linked',
+        ],
+        cwd=new_ws,
+    )
+    output = os.path.join(new_ws, 'bazel-bin/output.txt')
+    self.AssertFileContentContains(output, 'Hello from workspace!')
+    self.AssertFileContentContains(output, 'Hello from same-repo!')
+
+    # On platforms that natively support symbolic links (always on Unix; on
+    # Windows only with Developer Mode), the fix materializes a `_main`
+    # symlink under `<execroot>/external/` pointing at the workspace, so the
+    # relative `../_main/...` targets that replantSymlinks produces resolve
+    # correctly when read through the execroot. Verify it's there.
+    #
+    # The behavioral check above (the build itself) only catches the bug on
+    # Windows with real symlinks (which Bazel CI Windows runners don't have),
+    # so this structural assertion is what actually guards the fix on the
+    # Linux/macOS test runs.
+    _, stdout, _ = self.RunBazel(
+        [f'--output_base={new_output_base}', 'info', 'execution_root'],
+        cwd=new_ws,
+    )
+    execroot = stdout[0].strip()
+    workspace_link = os.path.join(execroot, 'external', '_main')
+    if not self.IsWindows() or self._realSymlinksWork():
+      self.assertTrue(
+          os.path.lexists(workspace_link),
+          msg=f'expected workspace symlink to be planted at {workspace_link}',
+      )
+
+  def _realSymlinksWork(self):
+    """Best-effort check for whether the OS can create a real symlink here."""
+    probe_dir = tempfile.mkdtemp(dir=self._tests_root)
+    target = os.path.join(probe_dir, 'target')
+    os.mkdir(target)
+    link = os.path.join(probe_dir, 'link')
+    try:
+      os.symlink(target, link, target_is_directory=True)
+      return True
+    except OSError:
+      return False
+
+  def testRepoWithWorkspaceSymlinkSurvivesWorkspaceMove(self):
+    self.doTestRepoWithWorkspaceSymlinkSurvivesWorkspaceMove()
+
+  def testRepoWithWorkspaceSymlinkSurvivesWorkspaceMove_symlinksEnabledOnWindows(
+      self,
+  ):
+    if not self.IsWindows():
+      self.skipTest('This test is only relevant on Windows')
+    self.ScratchFile(
+        '.bazelrc',
+        [
+            'startup --windows_enable_symlinks',
+        ],
+        mode='a',
+    )
+    self.doTestRepoWithWorkspaceSymlinkSurvivesWorkspaceMove()
+
 
 if __name__ == '__main__':
   absltest.main()