diff --git a/releasenotes/notes/fix-reraise-tryagain-underlying-exc-e21a26ee95bad0b3.yaml b/releasenotes/notes/fix-reraise-tryagain-underlying-exc-e21a26ee95bad0b3.yaml
new file mode 100644
index 00000000..ac8f239a
--- /dev/null
+++ b/releasenotes/notes/fix-reraise-tryagain-underlying-exc-e21a26ee95bad0b3.yaml
@@ -0,0 +1,8 @@
+---
+fixes:
+  - |
+    When ``reraise=True`` and ``TryAgain`` is raised from within an ``except``
+    block, the underlying exception that triggered the retry is now reraised
+    once attempts are exhausted, instead of the opaque ``TryAgain`` sentinel.
+    A bare ``TryAgain`` raised without an active exception keeps reraising
+    ``TryAgain`` as before.
diff --git a/tenacity/__init__.py b/tenacity/__init__.py
index 282e6dae..c52d6ba0 100644
--- a/tenacity/__init__.py
+++ b/tenacity/__init__.py
@@ -185,6 +185,14 @@ def __init__(self, last_attempt: "Future") -> None:
 
     def reraise(self) -> t.NoReturn:
         if self.last_attempt.failed:
+            exc = self.last_attempt.exception()
+            # When the user explicitly raises TryAgain (typically from within
+            # an "except" block), surface the underlying exception that caused
+            # the retry rather than the opaque TryAgain sentinel.
+            if isinstance(exc, TryAgain):
+                cause = exc.__cause__ or exc.__context__
+                if cause is not None:
+                    raise cause.with_traceback(cause.__traceback__) from None
             raise self.last_attempt.result()
         raise self
 
diff --git a/tests/test_asyncio.py b/tests/test_asyncio.py
index 7b5c6416..c6d27865 100644
--- a/tests/test_asyncio.py
+++ b/tests/test_asyncio.py
@@ -238,6 +238,29 @@ class CustomError(Exception):
         else:
             raise Exception
 
+    @asynctest
+    async def test_reraise_try_again_with_cause(self) -> None:
+        # When TryAgain is raised from within an "except" block, reraise=True
+        # should surface the underlying exception rather than TryAgain itself.
+        class UnderlyingError(Exception):
+            pass
+
+        async def _test() -> None:
+            try:
+                raise UnderlyingError("boom")
+            except UnderlyingError:
+                # Implicit chaining via __context__ is exactly what we test.
+                raise tenacity.TryAgain  # noqa: B904
+
+        retrying = tasyncio.AsyncRetrying(
+            stop=stop_after_attempt(2),
+            retry=tenacity.retry_never,
+            reraise=True,
+        )
+        with pytest.raises(UnderlyingError):
+            await retrying(_test)
+        self.assertEqual(2, retrying.statistics["attempt_number"])
+
     @asynctest
     async def test_sleeps(self) -> None:
         start = current_time_ms()
diff --git a/tests/test_tenacity.py b/tests/test_tenacity.py
index 6a397392..31e7f432 100644
--- a/tests/test_tenacity.py
+++ b/tests/test_tenacity.py
@@ -857,6 +857,43 @@ def _r() -> None:
         self.assertRaises(tenacity.RetryError, r, _r)
         self.assertEqual(5, r.statistics["attempt_number"])
 
+    def test_retry_try_again_with_cause_reraise(self) -> None:
+        # When TryAgain is raised from within an "except" block, reraise=True
+        # should surface the underlying exception rather than TryAgain itself.
+        class UnderlyingError(Exception):
+            pass
+
+        def _r() -> None:
+            try:
+                raise UnderlyingError("boom")
+            except UnderlyingError:
+                # Implicit chaining via __context__ is exactly what we test.
+                raise tenacity.TryAgain  # noqa: B904
+
+        r = Retrying(
+            stop=tenacity.stop_after_attempt(5),
+            retry=tenacity.retry_never,
+            reraise=True,
+        )
+        self.assertRaises(UnderlyingError, r, _r)
+        self.assertEqual(5, r.statistics["attempt_number"])
+
+    def test_retry_try_again_from_cause_reraise(self) -> None:
+        # An explicit "raise TryAgain from exc" should also be unwrapped.
+        class UnderlyingError(Exception):
+            pass
+
+        def _r() -> None:
+            raise tenacity.TryAgain from UnderlyingError("boom")
+
+        r = Retrying(
+            stop=tenacity.stop_after_attempt(5),
+            retry=tenacity.retry_never,
+            reraise=True,
+        )
+        self.assertRaises(UnderlyingError, r, _r)
+        self.assertEqual(5, r.statistics["attempt_number"])
+
     def test_retry_try_again_forever_reraise(self) -> None:
         def _r() -> None:
             raise tenacity.TryAgain