diff --git a/th_cli/test_run/logging.py b/th_cli/test_run/logging.py
index 0ad6e64..58c1938 100644
--- a/th_cli/test_run/logging.py
+++ b/th_cli/test_run/logging.py
@@ -13,6 +13,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 #
+import datetime
 import os
 
 from loguru import logger
@@ -27,13 +28,22 @@
 PYTHON_TEST_LEVEL = "PYTHON_TEST"
 logger.level(PYTHON_TEST_LEVEL, no=22, icon="🐍", color="<cyan>")
 
+_LOG_TIMESTAMP_FORMAT = "%Y-%m-%d-%H-%M-%S"
 
 def configure_logger_for_run(title: str) -> str:
     # Reset (Remove all sinks from logger)
     logger.remove()
 
-    log_path = os.path.join(config.log_config.output_log_path, f"test_run_{title}.log")
-
-    logger.add(log_path, enqueue=True, format=config.log_config.format)
+    # Replace colons so the default timestamp-style title does not produce
+    # filenames that are invalid on Windows (e.g. when logs are shared across
+    # systems for triage).
+    safe_title = title.replace(":", "-")
+    timestamp = datetime.datetime.now().strftime(_LOG_TIMESTAMP_FORMAT)
+    log_path = os.path.join(
+        config.log_config.output_log_path,
+        f"test_run_{safe_title}_{timestamp}.log",
+    )
+
+    logger.add(log_path, enqueue=True, format=config.log_config.format, mode="w")
 
     return log_path