diff --git a/lib/crewai/src/crewai/agents/agent_builder/base_agent.py b/lib/crewai/src/crewai/agents/agent_builder/base_agent.py
index dbff05e4d6..de9379d096 100644
--- a/lib/crewai/src/crewai/agents/agent_builder/base_agent.py
+++ b/lib/crewai/src/crewai/agents/agent_builder/base_agent.py
@@ -39,7 +39,7 @@
 from crewai.rag.embeddings.types import EmbedderConfig
 from crewai.security.security_config import SecurityConfig
 from crewai.skills.models import Skill
-from crewai.state.checkpoint_config import CheckpointConfig
+from crewai.state.checkpoint_config import CheckpointConfig, _coerce_checkpoint
 from crewai.tools.base_tool import BaseTool, Tool
 from crewai.types.callback import SerializableCallable
 from crewai.utilities.config import process_config
@@ -300,7 +300,10 @@ def _validate_agent_executor(cls, v: Any) -> Any:
         default_factory=SecurityConfig,
         description="Security configuration for the agent, including fingerprinting.",
     )
-    checkpoint: CheckpointConfig | bool | None = Field(
+    checkpoint: Annotated[
+        CheckpointConfig | bool | None,
+        BeforeValidator(_coerce_checkpoint),
+    ] = Field(
         default=None,
         description="Automatic checkpointing configuration. "
         "True for defaults, False to opt out, None to inherit.",
diff --git a/lib/crewai/src/crewai/crew.py b/lib/crewai/src/crewai/crew.py
index 4f9ebab5dc..e630ec5b00 100644
--- a/lib/crewai/src/crewai/crew.py
+++ b/lib/crewai/src/crewai/crew.py
@@ -104,7 +104,7 @@ def get_supported_content_types(provider: str, api: str | None = None) -> list[s
 from crewai.security.fingerprint import Fingerprint
 from crewai.security.security_config import SecurityConfig
 from crewai.skills.models import Skill
-from crewai.state.checkpoint_config import CheckpointConfig
+from crewai.state.checkpoint_config import CheckpointConfig, _coerce_checkpoint
 from crewai.task import Task
 from crewai.tasks.conditional_task import ConditionalTask
 from crewai.tasks.task_output import TaskOutput
@@ -341,7 +341,10 @@ class Crew(FlowTrackable, BaseModel):
         default_factory=SecurityConfig,
         description="Security configuration for the crew, including fingerprinting.",
     )
-    checkpoint: CheckpointConfig | bool | None = Field(
+    checkpoint: Annotated[
+        CheckpointConfig | bool | None,
+        BeforeValidator(_coerce_checkpoint),
+    ] = Field(
         default=None,
         description="Automatic checkpointing configuration. "
         "True for defaults, False to opt out, None to inherit.",
diff --git a/lib/crewai/src/crewai/flow/flow.py b/lib/crewai/src/crewai/flow/flow.py
index 76a96b3f94..60d03b0693 100644
--- a/lib/crewai/src/crewai/flow/flow.py
+++ b/lib/crewai/src/crewai/flow/flow.py
@@ -113,7 +113,7 @@
 )
 from crewai.memory.memory_scope import MemoryScope, MemorySlice
 from crewai.memory.unified_memory import Memory
-from crewai.state.checkpoint_config import CheckpointConfig
+from crewai.state.checkpoint_config import CheckpointConfig, _coerce_checkpoint
 
 
 if TYPE_CHECKING:
@@ -921,7 +921,10 @@ class Flow(BaseModel, Generic[T], metaclass=FlowMeta):
     max_method_calls: int = Field(default=100)
 
     execution_context: ExecutionContext | None = Field(default=None)
-    checkpoint: CheckpointConfig | bool | None = Field(default=None)
+    checkpoint: Annotated[
+        CheckpointConfig | bool | None,
+        BeforeValidator(_coerce_checkpoint),
+    ] = Field(default=None)
 
     @classmethod
     def from_checkpoint(
diff --git a/lib/crewai/src/crewai/state/checkpoint_config.py b/lib/crewai/src/crewai/state/checkpoint_config.py
index 4c5499ff45..84c48bd4e9 100644
--- a/lib/crewai/src/crewai/state/checkpoint_config.py
+++ b/lib/crewai/src/crewai/state/checkpoint_config.py
@@ -2,9 +2,9 @@
 
 from __future__ import annotations
 
-from typing import Literal
+from typing import Any, Literal
 
-from pydantic import BaseModel, Field
+from pydantic import BaseModel, Field, model_validator
 
 from crewai.state.provider.core import BaseProvider
 from crewai.state.provider.json_provider import JsonProvider
@@ -158,6 +158,20 @@
 ]
 
 
+def _coerce_checkpoint(v: Any) -> Any:
+    """BeforeValidator for checkpoint fields on Crew/Flow/Agent.
+
+    Converts True to CheckpointConfig and triggers handler registration.
+    """
+    if v is True:
+        v = CheckpointConfig()
+    if isinstance(v, CheckpointConfig):
+        from crewai.state.checkpoint_listener import _ensure_handlers_registered
+
+        _ensure_handlers_registered()
+    return v
+
+
 class CheckpointConfig(BaseModel):
     """Configuration for automatic checkpointing.
 
@@ -185,6 +199,13 @@ class CheckpointConfig(BaseModel):
         "each write. None means keep all.",
     )
 
+    @model_validator(mode="after")
+    def _register_handlers(self) -> CheckpointConfig:
+        from crewai.state.checkpoint_listener import _ensure_handlers_registered
+
+        _ensure_handlers_registered()
+        return self
+
     @property
     def trigger_all(self) -> bool:
         return "*" in self.on_events