diff --git a/python_modules/dagster/dagster/_core/definitions/instigation_logger.py b/python_modules/dagster/dagster/_core/definitions/instigation_logger.py
index e54cfe59db44e..996e4de9b8d85 100644
--- a/python_modules/dagster/dagster/_core/definitions/instigation_logger.py
+++ b/python_modules/dagster/dagster/_core/definitions/instigation_logger.py
@@ -1,5 +1,6 @@
 import json
 import logging
+import sys
 import threading
 import traceback
 from contextlib import ExitStack
@@ -10,6 +11,7 @@
 from dagster._core.log_manager import LOG_RECORD_METADATA_ATTR
 from dagster._core.storage.compute_log_manager import ComputeIOType, ComputeLogManager
 from dagster._core.utils import coerce_valid_log_level
+from dagster._utils.error import serializable_error_info_from_exc_info
 from dagster._utils.log import create_console_logger
 
 
@@ -66,7 +68,12 @@ def emit(self, record: logging.LogRecord):
         if exc_info:
             record_dict["exc_info"] = "".join(traceback.format_exception(*exc_info))
 
-        self._write_stream.write(_seven.json.dumps(record_dict) + "\n")
+        try:
+            self._write_stream.write(_seven.json.dumps(record_dict) + "\n")
+        except Exception:
+            sys.stderr.write(
+                f"Exception writing to logger event stream: {serializable_error_info_from_exc_info(sys.exc_info())}\n"
+            )
 
 
 class InstigationLogger(logging.Logger):
@@ -107,18 +114,30 @@ def __enter__(self):
             and self._instance
             and isinstance(self._instance.compute_log_manager, ComputeLogManager)
         ):
-            write_stream = self._exit_stack.enter_context(
-                self._instance.compute_log_manager.open_log_stream(
-                    self._log_key, ComputeIOType.STDERR
+            try:
+                write_stream = self._exit_stack.enter_context(
+                    self._instance.compute_log_manager.open_log_stream(
+                        self._log_key, ComputeIOType.STDERR
+                    )
                 )
-            )
+            except Exception:
+                sys.stderr.write(
+                    f"Exception initializing logger write stream: {serializable_error_info_from_exc_info(sys.exc_info())}\n"
+                )
+                write_stream = None
+
             if write_stream:
                 self._capture_handler = CapturedLogHandler(write_stream)
                 self.addHandler(self._capture_handler)
         return self
 
     def __exit__(self, _exception_type, _exception_value, _traceback):
-        self._exit_stack.close()
+        try:
+            self._exit_stack.close()
+        except Exception:
+            sys.stderr.write(
+                f"Exception closing logger write stream: {serializable_error_info_from_exc_info(sys.exc_info())}\n"
+            )
 
     def _annotate_record(self, record: logging.LogRecord) -> logging.LogRecord:
         if self._repository_name and self._instigator_name:
diff --git a/python_modules/dagster/dagster_tests/storage_tests/test_instigation_logger.py b/python_modules/dagster/dagster_tests/storage_tests/test_instigation_logger.py
index 926f2eedece42..a21d1b8e60beb 100644
--- a/python_modules/dagster/dagster_tests/storage_tests/test_instigation_logger.py
+++ b/python_modules/dagster/dagster_tests/storage_tests/test_instigation_logger.py
@@ -1,4 +1,9 @@
+from contextlib import contextmanager
+from unittest import mock
+
 from dagster._core.definitions.instigation_logger import InstigationLogger
+from dagster._core.storage.noop_compute_log_manager import NoOpComputeLogManager
+from dagster._core.test_utils import instance_for_test
 
 
 def test_gets_correct_logger():
@@ -9,3 +14,63 @@ def test_gets_correct_logger():
 
     instigation_logger = InstigationLogger(logger_name=custom_logger_name)
     assert instigation_logger.name == custom_logger_name
+
+
+class CrashyStartupComputeLogManager(NoOpComputeLogManager):
+    @contextmanager
+    def open_log_stream(self, log_key, io_type):
+        raise Exception("OOPS")
+        yield None
+
+
+class MockLogStreamComputeLogManager(NoOpComputeLogManager):
+    @contextmanager
+    def open_log_stream(self, log_key, io_type):
+        yield mock.MagicMock()
+        raise Exception("OOPS ON EXIT")
+
+
+def test_instigation_logger_start_failure(capsys):
+    with instance_for_test(
+        overrides={
+            "compute_logs": {
+                "module": "dagster_tests.storage_tests.test_instigation_logger",
+                "class": "CrashyStartupComputeLogManager",
+            }
+        }
+    ) as instance:
+        with InstigationLogger(log_key="foo", instance=instance) as logger:
+            captured = capsys.readouterr()
+            assert (
+                captured.err.count("Exception initializing logger write stream: Exception: OOPS")
+                == 1
+            )
+            logger.info("I can log without failing")
+
+
+def test_instigation_logger_log_failure(capsys):
+    with instance_for_test(
+        overrides={
+            "compute_logs": {
+                "module": "dagster_tests.storage_tests.test_instigation_logger",
+                "class": "MockLogStreamComputeLogManager",
+            }
+        }
+    ) as instance:
+        with InstigationLogger(log_key="foo", instance=instance) as logger:
+            mock_write_stream = logger._capture_handler._write_stream  # type: ignore # noqa
+            mock_write_stream.write.side_effect = Exception("OOPS")
+
+            logger.info("HELLO")
+            captured = capsys.readouterr()
+
+            assert (
+                captured.err.count("Exception writing to logger event stream: Exception: OOPS") == 1
+            )
+
+        captured = capsys.readouterr()
+
+        assert (
+            captured.err.count("Exception closing logger write stream: Exception: OOPS ON EXIT")
+            == 1
+        )