diff --git a/src/_pytest/recwarn.py b/src/_pytest/recwarn.py
index 334b3b850..5452b7cb9 100644
--- a/src/_pytest/recwarn.py
+++ b/src/_pytest/recwarn.py
@@ -281,6 +281,12 @@ class WarningsChecker(WarningsRecorder):
         self.expected_warning = expected_warning_tup
         self.match_expr = match_expr
 
+    def matches(self, warning: warnings.WarningMessage) -> bool:
+        assert self.expected_warning is not None
+        return issubclass(warning.category, self.expected_warning) and bool(
+            self.match_expr is None or re.search(self.match_expr, str(warning.message))
+        )
+
     def __exit__(
         self,
         exc_type: Optional[Type[BaseException]],
@@ -291,56 +297,39 @@ class WarningsChecker(WarningsRecorder):
 
         __tracebackhide__ = True
 
+        if self.expected_warning is None:
+            # nothing to do in this deprecated case, see WARNS_NONE_ARG above
+            return
+
+        if not (exc_type is None and exc_val is None and exc_tb is None):
+            # We currently ignore missing warnings if an exception is active.
+            # TODO: fix this, because it means things are surprisingly order-sensitive.
+            return
+
         def found_str():
             return pformat([record.message for record in self], indent=2)
 
-        def re_emit() -> None:
-            for r in self:
-                if matches(r):
-                    continue
-
-                assert issubclass(r.message.__class__, Warning)
-
-                warnings.warn_explicit(
-                    str(r.message),
-                    r.message.__class__,
-                    r.filename,
-                    r.lineno,
-                    module=r.__module__,
-                    source=r.source,
+        try:
+            if not any(issubclass(w.category, self.expected_warning) for w in self):
+                fail(
+                    f"DID NOT WARN. No warnings of type {self.expected_warning} were emitted.\n"
+                    f" Emitted warnings: {found_str()}."
                 )
-
-        def matches(warning) -> bool:
-            if self.expected_warning is not None:
-                if issubclass(warning.category, self.expected_warning):
-                    if self.match_expr is not None:
-                        if re.compile(self.match_expr).search(str(warning.message)):
-                            return True
-                        return False
-                    return True
-            return False
-
-        # only check if we're not currently handling an exception
-        if exc_type is None and exc_val is None and exc_tb is None:
-            if self.expected_warning is not None:
-                if not any(issubclass(r.category, self.expected_warning) for r in self):
-                    __tracebackhide__ = True
-                    fail(
-                        f"DID NOT WARN. No warnings of type {self.expected_warning} were emitted.\n"
-                        f"The list of emitted warnings is: {found_str()}."
+            elif not any(self.matches(w) for w in self):
+                fail(
+                    f"DID NOT WARN. No warnings of type {self.expected_warning} matching the regex were emitted.\n"
+                    f" Regex: {self.match_expr}\n"
+                    f" Emitted warnings: {found_str()}."
+                )
+        finally:
+            # Whether or not any warnings matched, we want to re-emit all unmatched warnings.
+            for w in self:
+                if not self.matches(w):
+                    warnings.warn_explicit(
+                        str(w.message),
+                        w.message.__class__,
+                        w.filename,
+                        w.lineno,
+                        module=w.__module__,
+                        source=w.source,
                     )
-                elif self.match_expr is not None:
-                    for r in self:
-                        if issubclass(r.category, self.expected_warning):
-                            if re.compile(self.match_expr).search(str(r.message)):
-                                re_emit()
-                                break
-                    else:
-                        fail(
-                            f"""\
-DID NOT WARN. No warnings of type {self.expected_warning} matching the regex were emitted.
- Regex: {self.match_expr}
- Emitted warnings: {found_str()}"""
-                        )
-                else:
-                    re_emit()
diff --git a/testing/test_recwarn.py b/testing/test_recwarn.py
index d9cd1d778..a423b2001 100644
--- a/testing/test_recwarn.py
+++ b/testing/test_recwarn.py
@@ -376,7 +376,7 @@ class TestWarns:
                 warnings.warn("value must be 42", UserWarning)
 
     def test_one_from_multiple_warns(self) -> None:
-        with pytest.raises(pytest.fail.Exception):
+        with pytest.raises(pytest.fail.Exception, match="DID NOT WARN"):
             with pytest.warns(UserWarning, match=r"aaa"):
                 with pytest.warns(UserWarning, match=r"aaa"):
                     warnings.warn("cccccccccc", UserWarning)
@@ -384,7 +384,7 @@ class TestWarns:
                     warnings.warn("aaaaaaaaaa", UserWarning)
 
     def test_none_of_multiple_warns(self) -> None:
-        with pytest.raises(pytest.fail.Exception):
+        with pytest.raises(pytest.fail.Exception, match="DID NOT WARN"):
             with pytest.warns(UserWarning, match=r"aaa"):
                 warnings.warn("bbbbbbbbbb", UserWarning)
                 warnings.warn("cccccccccc", UserWarning)
@@ -424,13 +424,13 @@ class TestWarns:
                 warnings.warn("some deprecation warning", DeprecationWarning)
 
     def test_re_emit_match_multiple(self) -> None:
-        # with pytest.warns(UserWarning):
-        with pytest.warns(UserWarning, match="user warning"):
-            warnings.warn("first user warning", UserWarning)
-            warnings.warn("second user warning", UserWarning)
+        with warnings.catch_warnings():
+            warnings.simplefilter("error")  # if anything is re-emitted
+            with pytest.warns(UserWarning, match="user warning"):
+                warnings.warn("first user warning", UserWarning)
+                warnings.warn("second user warning", UserWarning)
 
     def test_re_emit_non_match_single(self) -> None:
-        # with pytest.warns(UserWarning):
         with pytest.warns(UserWarning, match="v2 warning"):
             with pytest.warns(UserWarning, match="v1 warning"):
                 warnings.warn("v1 warning", UserWarning)