@@ -108,6 +108,9 @@ class TestResult:
     # short descriptions of how the test altered the execution environment
     env_changed_reasons: list[str] | None = None
 
+    # test file, set once the test module is imported
+    filename: str | None = None
+
     def is_failed(self, fail_env_changed: bool) -> bool:
         if self.state == State.ENV_CHANGED:
             return fail_env_changed
@@ -205,23 +208,24 @@ def format_github_summary(self, expand: bool) -> str:
         return "".join(f"{block}\n\n" for block in blocks)
 
     def print_github_annotation(self, runtests: RunTests) -> None:
-        """Print github error annotation line for each failure."""
-        if not (runtests.github_annotations
-                and self.is_failed(runtests.fail_env_changed)):
+        """Annotate a failed test file without failed test cases."""
+        if (not runtests.github_annotations
+                or not self.is_failed(runtests.fail_env_changed)
+                or self.failed_test_cases):
             return
-        # Convert python import test name to relative file path.
-        # Ex: "test.test_x.test_y" is test_x/test_y.py
-        name = self.test_name.removeprefix("test.")
-        path = pathlib.Path(findtestdir(runtests.test_dir), *name.split("."))
-        filename = path.with_suffix(".py")
-        if not filename.exists():
-            filename = path / "__init__.py"
-        annotations = self.failed_test_cases
-        if not annotations:
-            message = "\n".join([str(self), *(self.env_changed_reasons or ())])
-            annotations = [(self.test_name, message)]
-        for title, message in annotations:
-            print_github_annotation(title, message, str(filename))
+        filename = self.filename
+        if not filename:
+            # The worker crashed or timed out before reporting the test file:
+            # convert python import test name to relative file path.
+            # Ex: "test.test_x.test_y" is test_x/test_y.py
+            name = self.test_name.removeprefix("test.")
+            path = pathlib.Path(findtestdir(runtests.test_dir),
+                                *name.split("."))
+            filename = path.with_suffix(".py")
+            if not filename.exists():
+                filename = path / "__init__.py"
+        message = "\n".join([str(self), *(self.env_changed_reasons or ())])
+        print_github_annotation(self.test_name, message, str(filename))
 
     def set_env_changed(self, *reasons):
         if self.state is None or self.state == State.PASSED:
 
@@ -12,6 +12,7 @@
 
 from .filter import set_match_tests
 from .runtests import RunTests
+lazy from .testresult import RegressionTestResult
 from .utils import (
     setup_unraisable_hook, setup_threading_excepthook,
     adjust_rlimit_nofile)
@@ -112,9 +113,9 @@ def setup_tests(runtests: RunTests) -> None:
 
     set_match_tests(runtests.match_tests)
 
+    RegressionTestResult.GITHUB_ANNOTATIONS = runtests.github_annotations
     if runtests.use_junit:
         support.junit_xml_list = []
-        from .testresult import RegressionTestResult
         RegressionTestResult.USE_XML = True
     else:
         support.junit_xml_list = None
 
@@ -153,6 +153,7 @@ def _load_run_test(result: TestResult, runtests: RunTests) -> None:
     test_name = result.test_name
     module_name = abs_module_name(test_name, runtests.test_dir)
     test_mod = importlib.import_module(module_name)
+    result.filename = test_mod.__file__
 
     if hasattr(test_mod, "test_main"):
         # https://github.com/python/cpython/issues/89392
 
@@ -9,10 +9,11 @@
 import traceback
 import unittest
 from test import support
-from test.libregrtest.utils import sanitize_xml
+from test.libregrtest.utils import print_github_annotation, sanitize_xml
 
 class RegressionTestResult(unittest.TextTestResult):
     USE_XML = False
+    GITHUB_ANNOTATIONS = False
 
     def __init__(self, stream, descriptions, verbosity):
         super().__init__(stream=stream, descriptions=descriptions,
@@ -130,6 +131,14 @@ def addUnexpectedSuccess(self, test):
         self._add_result(test, outcome='UNEXPECTED_SUCCESS')
         super().addUnexpectedSuccess(test)
 
+    def printErrorList(self, flavour, errors):
+        for test, err in errors:
+            super().printErrorList(flavour, [(test, err)])
+            # Annotate just after the failure report, so that the annotation
+            # links to the report in the job log
+            if self.GITHUB_ANNOTATIONS:
+                print_github_annotation(str(test), err, stream=self.stream)
+
     def get_xml_element(self):
         if not self.USE_XML:
             raise ValueError("USE_XML is false")
@@ -146,6 +155,11 @@ def __init__(self, stream, buffer=False):
 
     def run(self, test):
         test(self.result)
+        # Failures are not reported in quiet mode: annotate them at the end
+        if self.result.GITHUB_ANNOTATIONS:
+            for test, err in self.result.errors + self.result.failures:
+                print_github_annotation(str(test), err,
+                                        stream=self.result.stream)
         return self.result
 
 def get_test_runner_class(verbosity, buffer=False):
 
@@ -148,19 +148,21 @@ def print_warning(msg: str) -> None:
                                                              ",": "%2C"})
 
 
-def print_github_annotation(title: str, message: str, filename: str) -> None:
+def print_github_annotation(title: str, message: str,
+                            filename: str | None = None,
+                            stream=None) -> None:
     """Print a GitHub Actions error annotation for the failure."""
-    if not filename:
-        raise ValueError(f"missing filename to annotate {title!r}")
     message = decolor(message)
 
-    # Try to get a line number from backtrace.
+    # Try to get a file + line number from backtrace.
     line = None
     if frames := re.findall(r'^ *File "(.*)", line (\d+)', message,
                             re.MULTILINE):
         test_frames = [frame for frame in frames
                        if pathlib.Path(frame[0]).name.startswith('test_')]
         filename, line = test_frames[-1] if test_frames else frames[0]
+    if not filename:
+        raise ValueError(f"missing filename to annotate {title!r}")
 
     # Normalize stdlib path to be relative inside the repository checkout.
     path = pathlib.Path(filename)
@@ -175,7 +177,7 @@ def print_github_annotation(title: str, message: str, filename: str) -> None:
     props_text = ",".join(f"{key}={value.translate(GITHUB_ESCAPE_PROPERTY)}"
                           for key, value in props.items() if value)
     print(f"::error {props_text}::{message.translate(GITHUB_ESCAPE_DATA)}",
-          flush=True)
+          file=stream, flush=True)
 
 
 def regrtest_unraisable_hook(unraisable) -> None: