diff --git a/.changes/unreleased/Fixes-20230331-095428.yaml b/.changes/unreleased/Fixes-20230331-095428.yaml
new file mode 100644
index 00000000000..772ce077b7d
--- /dev/null
+++ b/.changes/unreleased/Fixes-20230331-095428.yaml
@@ -0,0 +1,6 @@
+kind: Fixes
+body: Improved failed event serialization handling and associated tests
+time: 2023-03-31T09:54:28.701963-07:00
+custom:
+  Author: QMalcolm
+  Issue: 7113 7108 6568
diff --git a/core/dbt/context/base.py b/core/dbt/context/base.py
index ed2d6548d16..8d70a5a057c 100644
--- a/core/dbt/context/base.py
+++ b/core/dbt/context/base.py
@@ -556,6 +556,10 @@ def log(msg: str, info: bool = False) -> str:
               {{ log("Running some_macro: " ~ arg1 ~ ", " ~ arg2) }}
             {% endmacro %}"
         """
+
+        if not isinstance(msg, str):
+            msg = str(msg)
+
         if info:
             fire_event(MacroEventInfo(msg=msg))
         else:
diff --git a/test/unit/test_base_context.py b/test/unit/test_base_context.py
new file mode 100644
index 00000000000..0dc2d93ddca
--- /dev/null
+++ b/test/unit/test_base_context.py
@@ -0,0 +1,22 @@
+import os
+
+from dbt.context.base import BaseContext
+from jinja2.runtime import Undefined
+
+
+class TestBaseContext:
+    def test_log_jinja_undefined(self):
+        # regression test for CT-2259
+        try:
+            os.environ["DBT_ENV_SECRET_LOG_TEST"] = "cats_are_cool"
+            BaseContext.log(msg=Undefined(), info=True)
+        except Exception as e:
+            assert False, f"Logging an jinja2.Undefined object raises an exception: {e}"
+
+    def test_log_with_dbt_env_secret(self):
+        # regression test for CT-1783
+        try:
+            os.environ["DBT_ENV_SECRET_LOG_TEST"] = "cats_are_cool"
+            BaseContext.log({"fact1": "I like cats"}, info=True)
+        except Exception as e:
+            assert False, f"Logging while a `DBT_ENV_SECRET` was set raised an exception: {e}"