diff --git a/tests/examples/conftest.py b/tests/examples/conftest.py
index dc712079..a7f1dfa2 100644
--- a/tests/examples/conftest.py
+++ b/tests/examples/conftest.py
@@ -113,25 +113,61 @@ def _run_once(self, args: str, *, timeout: int, until: list[str] | None) -> str:
 
         return ''.join(lines)
 
-    def start(self, args: str, *, wait: int = 5) -> None:
+    def start(self, args: str, *, wait: int = 5, port_bind_retries: int = 3) -> None:
         """Start a long-lived background service.
 
         Use this for servers/subscribers that must stay alive while a second
         process runs via ``run()``. Call ``stop()`` to terminate and collect
         output. Stdout is written to a temp file to avoid pipe-buffer deadlocks.
+
+        Args:
+            args: Arguments passed to ``dapr run``.
+            wait: Seconds to wait for the sidecar to come up before returning.
+            port_bind_retries: Retry count for Dapr sidecar startup failures
+                caused by a transient random-port collision.
         """
-        output_file = tempfile.NamedTemporaryFile(mode='w+', suffix='.log')
-        proc = subprocess.Popen(
-            args=('dapr', 'run', *shlex.split(args)),
-            cwd=self._cwd,
-            stdout=output_file,
-            stderr=subprocess.STDOUT,
-            text=True,
-            **get_kwargs_for_process_group(),
-        )
-        self._bg_process = proc
-        self._bg_output_file = output_file
-        time.sleep(wait)
+        attempts = max(1, port_bind_retries + 1)
+        for attempt in range(attempts):
+            output_file = tempfile.NamedTemporaryFile(mode='w+', suffix='.log')
+            proc = subprocess.Popen(
+                args=('dapr', 'run', *shlex.split(args)),
+                cwd=self._cwd,
+                stdout=output_file,
+                stderr=subprocess.STDOUT,
+                text=True,
+                **get_kwargs_for_process_group(),
+            )
+            time.sleep(wait)
+
+            can_retry = attempt < attempts - 1
+            if can_retry and self._started_with_port_bind_failure(proc, output_file):
+                self._terminate(proc)
+                output_file.close()
+                print(
+                    'Dapr background sidecar failed to bind a random port; '
+                    f'retrying startup after {2**attempt}s '
+                    f'(attempt {attempt + 1}/{attempts})',
+                    flush=True,
+                )
+                time.sleep(2**attempt)
+                continue
+
+            self._bg_process = proc
+            self._bg_output_file = output_file
+            return
+
+    def _started_with_port_bind_failure(
+        self, proc: subprocess.Popen[str], output_file: IO[str]
+    ) -> bool:
+        """Whether a background sidecar already exited from a random-port collision.
+
+        Reads the log only once the process has exited; seeking the temp file
+        while daprd is still writing would corrupt its shared append offset.
+        """
+        if proc.poll() is None:
+            return False
+        output_file.seek(0)
+        return self._is_dapr_port_bind_failure(output_file.read())
 
     def stop(self) -> str:
         """Stop the background service and return its captured output."""
diff --git a/tests/examples/test_dapr_runner.py b/tests/examples/test_dapr_runner.py
index f5aec129..0980952d 100644
--- a/tests/examples/test_dapr_runner.py
+++ b/tests/examples/test_dapr_runner.py
@@ -1,6 +1,7 @@
 import subprocess
 import time
 from pathlib import Path
+from typing import IO
 
 import pytest
 
@@ -19,6 +20,26 @@ def wait(self, timeout: int | None = None) -> int:
         return self.returncode
 
 
+class FakeBackgroundProcess:
+    """Stand-in for a ``dapr run`` background process started via ``start()``.
+
+    A real background sidecar writes to the file object passed as ``stdout`` and
+    keeps running (``poll()`` returns ``None``); a sidecar that died on a port
+    bind has exited (``poll()`` returns a non-``None`` code).
+    """
+
+    def __init__(self, output: str, returncode: int | None, stdout: IO[str]) -> None:
+        stdout.write(output)
+        stdout.flush()
+        self._returncode = returncode
+
+    def poll(self) -> int | None:
+        return self._returncode
+
+    def wait(self, timeout: int | None = None) -> int:
+        return self._returncode or 0
+
+
 def test_run_retries_transient_dapr_port_bind_failure(
     monkeypatch, tmp_path: Path, capsys: pytest.CaptureFixture[str]
 ) -> None:
@@ -65,3 +86,53 @@ def fake_popen(*args, **kwargs) -> FakeProcess:
 
     assert output == 'application failed before printing expected output\n'
     assert len(popen_calls) == 1
+
+
+PORT_BIND_FAILURE_OUTPUT = (
+    'level=error msg="Failed to listen for gRPC server on TCP address :38779 '
+    'with error: listen tcp :38779: bind: address already in use"\n'
+    'level=fatal msg="Fatal error from runtime: failed to start internal gRPC '
+    'server: could not listen on any endpoint"\n'
+)
+
+
+def test_start_retries_transient_dapr_port_bind_failure(
+    monkeypatch, tmp_path: Path, capsys: pytest.CaptureFixture[str]
+) -> None:
+    attempts = [
+        (PORT_BIND_FAILURE_OUTPUT, 1),
+        ('INFO:     Application startup complete.\n', None),
+    ]
+    popen_calls = []
+
+    def fake_popen(*args, **kwargs) -> FakeBackgroundProcess:
+        popen_calls.append((args, kwargs))
+        output, returncode = attempts.pop(0)
+        return FakeBackgroundProcess(output, returncode, kwargs['stdout'])
+
+    monkeypatch.setattr(subprocess, 'Popen', fake_popen)
+    sleeps: list[int] = []
+    monkeypatch.setattr(time, 'sleep', sleeps.append)
+
+    DaprRunner(tmp_path).start('--app-id demo-actor -- uvicorn demo:app', wait=0)
+
+    assert len(popen_calls) == 2
+    assert sleeps == [0, 1, 0]
+    assert (
+        'Dapr background sidecar failed to bind a random port; retrying startup after 1s'
+        in capsys.readouterr().out
+    )
+
+
+def test_start_does_not_retry_non_port_bind_failure(monkeypatch, tmp_path: Path) -> None:
+    popen_calls = []
+
+    def fake_popen(*args, **kwargs) -> FakeBackgroundProcess:
+        popen_calls.append((args, kwargs))
+        return FakeBackgroundProcess('app crashed for an unrelated reason\n', 1, kwargs['stdout'])
+
+    monkeypatch.setattr(subprocess, 'Popen', fake_popen)
+
+    DaprRunner(tmp_path).start('--app-id demo-actor -- uvicorn demo:app', wait=0)
+
+    assert len(popen_calls) == 1