diff --git a/airflow-core/pyproject.toml b/airflow-core/pyproject.toml
index 3f3cfd996e49e..588cb536ca720 100644
--- a/airflow-core/pyproject.toml
+++ b/airflow-core/pyproject.toml
@@ -229,8 +229,8 @@ exclude = [
 "../shared/module_loading/src/airflow_shared/module_loading" = "src/airflow/_shared/module_loading"
 "../shared/observability/src/airflow_shared/observability" = "src/airflow/_shared/observability"
 "../shared/secrets_backend/src/airflow_shared/secrets_backend" = "src/airflow/_shared/secrets_backend"
-"../shared/secrets_masker/src/airflow_shared/secrets_masker" = "src/airflow/_shared/secrets_masker"
-"../shared/timezones/src/airflow_shared/timezones" = "src/airflow/_shared/timezones"
+    "../shared/secrets_masker/src/airflow_shared/secrets_masker" = "src/airflow/_shared/secrets_masker"
+    "../shared/timezones/src/airflow_shared/timezones" = "src/airflow/_shared/timezones"
 
 [tool.hatch.build.targets.custom]
 path = "./hatch_build.py"
diff --git a/airflow-core/src/airflow/serialization/helpers.py b/airflow-core/src/airflow/serialization/helpers.py
index 723c113709a87..c0f3a2e59d056 100644
--- a/airflow-core/src/airflow/serialization/helpers.py
+++ b/airflow-core/src/airflow/serialization/helpers.py
@@ -19,7 +19,8 @@
 from __future__ import annotations
 
 import contextlib
-from typing import TYPE_CHECKING, Any
+from typing import TYPE_CHECKING, Any, Union
+from collections.abc import Sequence
 
 from airflow._shared.secrets_masker import redact
 from airflow.configuration import conf
@@ -29,6 +30,34 @@
     from airflow.timetables.base import Timetable as CoreTimetable
 
 
+def truncate_rendered_value(rendered: Any, max_length: int) -> str:
+    """
+    Truncate rendered value with a reasonable minimum length to avoid edge cases.
+    
+    Args:
+        rendered: The rendered value to truncate
+        max_length: The maximum allowed length for the output
+        
+    Returns:
+        Truncated string that respects the max_length constraint
+    """
+    # Set a reasonable minimum to avoid complex edge cases with very small values
+    if max_length < 100:
+        max_length = 100
+
+    prefix = "Truncated. You can change this behaviour in [core]max_templated_field_length. "
+    suffix = "... "
+    
+    # Apply repr() to the content first to account for quotes that will be added
+    content_repr = repr(rendered)
+    available_length = max_length - len(prefix) - len(suffix)
+    if available_length <= 0:
+        return (prefix + suffix)[:max_length]
+    
+    content_part = content_repr[:available_length]
+    return f"{prefix}{content_part}{suffix}"
+
+
 def serialize_template_field(template_field: Any, name: str) -> str | dict | list | int | float:
     """
     Return a serializable representation of the templated field.
@@ -74,10 +103,7 @@ def sort_dict_recursively(obj: Any) -> Any:
             serialized = str(template_field)
         if len(serialized) > max_length:
             rendered = redact(serialized, name)
-            return (
-                "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-                f"{rendered[: max_length - 79]!r}... "
-            )
+            return truncate_rendered_value(rendered, max_length)
         return serialized
     if not template_field and not isinstance(template_field, tuple):
         # Avoid unnecessary serialization steps for empty fields unless they are tuples
@@ -91,10 +117,7 @@ def sort_dict_recursively(obj: Any) -> Any:
     serialized = str(template_field)
     if len(serialized) > max_length:
         rendered = redact(serialized, name)
-        return (
-            "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-            f"{rendered[: max_length - 79]!r}... "
-        )
+        return truncate_rendered_value(rendered, max_length)
     return template_field
 
 
diff --git a/task-sdk/pyproject.toml b/task-sdk/pyproject.toml
index 7c26f1babb58a..8f671094fb811 100644
--- a/task-sdk/pyproject.toml
+++ b/task-sdk/pyproject.toml
@@ -119,10 +119,10 @@ path = "src/airflow/sdk/__init__.py"
 "../shared/dagnode/src/airflow_shared/dagnode" = "src/airflow/sdk/_shared/dagnode"
 "../shared/logging/src/airflow_shared/logging" = "src/airflow/sdk/_shared/logging"
 "../shared/module_loading/src/airflow_shared/module_loading" = "src/airflow/sdk/_shared/module_loading"
-"../shared/observability/src/airflow_shared/observability" = "src/airflow/_shared/observability"
-"../shared/secrets_backend/src/airflow_shared/secrets_backend" = "src/airflow/sdk/_shared/secrets_backend"
-"../shared/secrets_masker/src/airflow_shared/secrets_masker" = "src/airflow/sdk/_shared/secrets_masker"
-"../shared/timezones/src/airflow_shared/timezones" = "src/airflow/sdk/_shared/timezones"
+"../shared/observability/src/airflow_shared/observability" = "src/airflow/sdk/_shared/observability"
+    "../shared/secrets_backend/src/airflow_shared/secrets_backend" = "src/airflow/sdk/_shared/secrets_backend"
+    "../shared/secrets_masker/src/airflow_shared/secrets_masker" = "src/airflow/sdk/_shared/secrets_masker"
+    "../shared/timezones/src/airflow_shared/timezones" = "src/airflow/sdk/_shared/timezones"
 
 [tool.hatch.build.targets.wheel]
 packages = ["src/airflow"]
diff --git a/task-sdk/src/airflow/sdk/execution_time/task_runner.py b/task-sdk/src/airflow/sdk/execution_time/task_runner.py
index 703cecf509cb2..77238dcc01d0d 100644
--- a/task-sdk/src/airflow/sdk/execution_time/task_runner.py
+++ b/task-sdk/src/airflow/sdk/execution_time/task_runner.py
@@ -25,12 +25,12 @@
 import os
 import sys
 import time
-from collections.abc import Callable, Iterable, Iterator, Mapping
+from collections.abc import Callable, Iterable, Iterator, Mapping, Sequence
 from contextlib import suppress
 from datetime import datetime, timezone
 from itertools import product
 from pathlib import Path
-from typing import TYPE_CHECKING, Annotated, Any, Literal
+from typing import TYPE_CHECKING, Annotated, Any, Literal, Union
 from urllib.parse import quote
 
 import attrs
@@ -104,6 +104,7 @@
     TriggerDagRun,
     ValidateInletsAndOutlets,
 )
+
 from airflow.sdk.execution_time.context import (
     ConnectionAccessor,
     InletEventsAccessors,
@@ -136,6 +137,35 @@ class TaskRunnerMarker:
     """Marker for listener hooks, to properly detect from which component they are called."""
 
 
+def truncate_rendered_value(rendered: Any, max_length: int) -> str:
+    """
+    Truncate rendered value with a reasonable minimum length to avoid edge cases.
+    
+    Args:
+        rendered: The rendered value to truncate
+        max_length: The maximum allowed length for the output
+        
+    Returns:
+        Truncated string that respects the max_length constraint
+    """
+    # Set a reasonable minimum to avoid complex edge cases with very small values
+    if max_length < 100:
+        max_length = 100
+
+    prefix = "Truncated. You can change this behaviour in [core]max_templated_field_length. "
+    suffix = "... "
+    
+    # Apply repr() to the content first to account for quotes that will be added
+    content_repr = repr(rendered)
+    available_length = max_length - len(prefix) - len(suffix)
+    if available_length <= 0:
+        return (prefix + suffix)[:max_length]
+    
+    content_part = content_repr[:available_length]
+    return f"{prefix}{content_part}{suffix}"
+
+
+
 # TODO: Move this entire class into a separate file:
 #  `airflow/sdk/execution_time/task_instance.py`
 #   or `airflow/sdk/execution_time/runtime_ti.py`
@@ -877,10 +907,7 @@ def sort_dict_recursively(obj: Any) -> Any:
             serialized = str(template_field)
         if len(serialized) > max_length:
             rendered = redact(serialized, name)
-            return (
-                "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-                f"{rendered[: max_length - 79]!r}... "
-            )
+            return truncate_rendered_value(rendered, max_length)
         return serialized
     if not template_field and not isinstance(template_field, tuple):
         # Avoid unnecessary serialization steps for empty fields unless they are tuples
@@ -894,10 +921,7 @@ def sort_dict_recursively(obj: Any) -> Any:
     serialized = str(template_field)
     if len(serialized) > max_length:
         rendered = redact(serialized, name)
-        return (
-            "Truncated. You can change this behaviour in [core]max_templated_field_length. "
-            f"{rendered[: max_length - 79]!r}... "
-        )
+        return truncate_rendered_value(rendered, max_length)
     return template_field
 
 
@@ -1683,4 +1707,4 @@ def reinit_supervisor_comms() -> None:
 
 
 if __name__ == "__main__":
-    main()
+    main()
\ No newline at end of file