diff --git a/lib/crewai/src/crewai/cli/checkpoint_tui.py b/lib/crewai/src/crewai/cli/checkpoint_tui.py
index 8df820412..f5163bda1 100644
--- a/lib/crewai/src/crewai/cli/checkpoint_tui.py
+++ b/lib/crewai/src/crewai/cli/checkpoint_tui.py
@@ -552,14 +552,24 @@ async def _run_checkpoint_tui_async(location: str) -> None:
                     preview = preview[:77] + "..."
                 click.echo(f"  Task {task_idx + 1}: {desc}")
                 click.echo(f"    -> {preview}")
-                # Update the assistant message in the executor's history
-                # so the LLM sees the override in its conversation
                 agent = crew.tasks[task_idx].agent
                 if agent and agent.agent_executor:
-                    for msg in reversed(agent.agent_executor.messages):
-                        if msg.get("role") == "assistant":
-                            msg["content"] = new_output
-                            break
+                    nth = sum(1 for t in crew.tasks[:task_idx] if t.agent is agent)
+                    messages = agent.agent_executor.messages
+                    system_positions = [
+                        i for i, m in enumerate(messages) if m.get("role") == "system"
+                    ]
+                    if nth < len(system_positions):
+                        seg_start = system_positions[nth]
+                        seg_end = (
+                            system_positions[nth + 1]
+                            if nth + 1 < len(system_positions)
+                            else len(messages)
+                        )
+                        for j in range(seg_end - 1, seg_start, -1):
+                            if messages[j].get("role") == "assistant":
+                                messages[j]["content"] = new_output
+                                break
                     overridden_agents.add(id(agent))
 
         earliest = min(task_overrides)
diff --git a/lib/crewai/src/crewai/state/runtime.py b/lib/crewai/src/crewai/state/runtime.py
index 3e8e4f4bd..56790005a 100644
--- a/lib/crewai/src/crewai/state/runtime.py
+++ b/lib/crewai/src/crewai/state/runtime.py
@@ -10,7 +10,6 @@ via ``RuntimeState.model_rebuild()``.
 from __future__ import annotations
 
 import logging
-from pathlib import Path
 from typing import TYPE_CHECKING, Any
 import uuid
 
@@ -38,19 +37,6 @@ if TYPE_CHECKING:
     from crewai import Entity
 
 
-def _base_location(location: str, provider: BaseProvider) -> str:
-    """Extract the base storage location from a restore path.
-
-    For SQLite (``db_path#id``), returns ``db_path``.
-    For JSON (a file path), returns the parent directory.
-    """
-    from crewai.state.provider.sqlite_provider import SqliteProvider
-
-    if isinstance(provider, SqliteProvider):
-        return location.rsplit("#", 1)[0]
-    return str(Path(location).parent)
-
-
 def _sync_checkpoint_fields(entity: object) -> None:
     """Copy private runtime attrs into checkpoint fields before serializing.
 
@@ -125,7 +111,6 @@ class RuntimeState(RootModel):  # type: ignore[type-arg]
     _checkpoint_id: str | None = PrivateAttr(default=None)
     _parent_id: str | None = PrivateAttr(default=None)
     _branch: str = PrivateAttr(default="main")
-    _location: str | None = PrivateAttr(default=None)
     _trigger: str | None = PrivateAttr(default=None)
 
     @property
@@ -253,7 +238,6 @@ class RuntimeState(RootModel):  # type: ignore[type-arg]
         raw = provider.from_checkpoint(location)
         state = cls.model_validate_json(raw, **kwargs)
         state._provider = provider
-        state._location = _base_location(location, provider)
         checkpoint_id = provider.extract_id(location)
         state._checkpoint_id = checkpoint_id
         state._parent_id = checkpoint_id
@@ -281,7 +265,6 @@ class RuntimeState(RootModel):  # type: ignore[type-arg]
         raw = await provider.afrom_checkpoint(location)
         state = cls.model_validate_json(raw, **kwargs)
         state._provider = provider
-        state._location = _base_location(location, provider)
         checkpoint_id = provider.extract_id(location)
         state._checkpoint_id = checkpoint_id
         state._parent_id = checkpoint_id