diff --git a/alembic/versions/2025_07_28_1606-1d0a10ae2a13_add_webhook_failure_reason.py b/alembic/versions/2025_07_28_1606-1d0a10ae2a13_add_webhook_failure_reason.py
new file mode 100644
index 00000000..c6e38d5a
--- /dev/null
+++ b/alembic/versions/2025_07_28_1606-1d0a10ae2a13_add_webhook_failure_reason.py
@@ -0,0 +1,35 @@
+"""add_webhook_failure_reason
+
+Revision ID: 1d0a10ae2a13
+Revises: 044b4a3c3dbc
+Create Date: 2025-07-28 16:06:57.319749+00:00
+
+"""
+
+from typing import Sequence, Union
+
+import sqlalchemy as sa
+
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision: str = "1d0a10ae2a13"
+down_revision: Union[str, None] = "044b4a3c3dbc"
+branch_labels: Union[str, Sequence[str], None] = None
+depends_on: Union[str, Sequence[str], None] = None
+
+
+def upgrade() -> None:
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.add_column("observer_cruises", sa.Column("webhook_failure_reason", sa.String(), nullable=True))
+    op.add_column("tasks", sa.Column("webhook_failure_reason", sa.String(), nullable=True))
+    op.add_column("workflow_runs", sa.Column("webhook_failure_reason", sa.String(), nullable=True))
+    # ### end Alembic commands ###
+
+
+def downgrade() -> None:
+    # ### commands auto generated by Alembic - please adjust! ###
+    op.drop_column("workflow_runs", "webhook_failure_reason")
+    op.drop_column("tasks", "webhook_failure_reason")
+    op.drop_column("observer_cruises", "webhook_failure_reason")
+    # ### end Alembic commands ###
diff --git a/skyvern/forge/agent.py b/skyvern/forge/agent.py
index f57c66f9..282e2a75 100644
--- a/skyvern/forge/agent.py
+++ b/skyvern/forge/agent.py
@@ -2315,6 +2315,11 @@ class ForgeAgent:
                     resp_code=resp.status_code,
                     resp_text=resp.text,
                 )
+                await app.DATABASE.update_task(
+                    task_id=task.task_id,
+                    organization_id=task.organization_id,
+                    webhook_failure_reason="",
+                )
             else:
                 LOG.info(
                     "Webhook failed",
@@ -2323,6 +2328,11 @@ class ForgeAgent:
                     resp_code=resp.status_code,
                     resp_text=resp.text,
                 )
+                await app.DATABASE.update_task(
+                    task_id=task.task_id,
+                    organization_id=task.organization_id,
+                    webhook_failure_reason=f"Webhook failed with status code {resp.status_code}, error message: {resp.text}",
+                )
         except Exception as e:
             raise FailedToSendWebhook(task_id=task.task_id) from e
 
@@ -2542,6 +2552,7 @@ class ForgeAgent:
         status: TaskStatus,
         extracted_information: dict[str, Any] | list | str | None = None,
         failure_reason: str | None = None,
+        webhook_failure_reason: str | None = None,
     ) -> Task:
         # refresh task from db to get the latest status
         task_from_db = await app.DATABASE.get_task(task_id=task.task_id, organization_id=task.organization_id)
diff --git a/skyvern/forge/sdk/db/client.py b/skyvern/forge/sdk/db/client.py
index 924bf47f..a40865ad 100644
--- a/skyvern/forge/sdk/db/client.py
+++ b/skyvern/forge/sdk/db/client.py
@@ -614,6 +614,7 @@ class AgentDB:
         task_id: str,
         status: TaskStatus | None = None,
         extracted_information: dict[str, Any] | list | str | None = None,
+        webhook_failure_reason: str | None = None,
         failure_reason: str | None = None,
         errors: list[dict[str, Any]] | None = None,
         max_steps_per_run: int | None = None,
@@ -625,6 +626,7 @@ class AgentDB:
             and failure_reason is None
             and errors is None
             and max_steps_per_run is None
+            and webhook_failure_reason is None
         ):
             raise ValueError(
                 "At least one of status, extracted_information, or failure_reason must be provided to update the task"
@@ -652,6 +654,8 @@ class AgentDB:
                         task.errors = errors
                     if max_steps_per_run is not None:
                         task.max_steps_per_run = max_steps_per_run
+                    if webhook_failure_reason is not None:
+                        task.webhook_failure_reason = webhook_failure_reason
                     await session.commit()
                     updated_task = await self.get_task(task_id, organization_id=organization_id)
                     if not updated_task:
@@ -1590,21 +1594,29 @@ class AgentDB:
             raise
 
     async def update_workflow_run(
-        self, workflow_run_id: str, status: WorkflowRunStatus, failure_reason: str | None = None
+        self,
+        workflow_run_id: str,
+        status: WorkflowRunStatus | None = None,
+        failure_reason: str | None = None,
+        webhook_failure_reason: str | None = None,
     ) -> WorkflowRun:
         async with self.Session() as session:
             workflow_run = (
                 await session.scalars(select(WorkflowRunModel).filter_by(workflow_run_id=workflow_run_id))
             ).first()
             if workflow_run:
-                workflow_run.status = status
-                workflow_run.failure_reason = failure_reason
-                if status == WorkflowRunStatus.queued and workflow_run.queued_at is None:
+                if status:
+                    workflow_run.status = status
+                if status and status == WorkflowRunStatus.queued and workflow_run.queued_at is None:
                     workflow_run.queued_at = datetime.utcnow()
-                if status == WorkflowRunStatus.running and workflow_run.started_at is None:
+                if status and status == WorkflowRunStatus.running and workflow_run.started_at is None:
                     workflow_run.started_at = datetime.utcnow()
-                if status.is_final() and workflow_run.finished_at is None:
+                if status and status.is_final() and workflow_run.finished_at is None:
                     workflow_run.finished_at = datetime.utcnow()
+                if failure_reason:
+                    workflow_run.failure_reason = failure_reason
+                if webhook_failure_reason is not None:
+                    workflow_run.webhook_failure_reason = webhook_failure_reason
                 await session.commit()
                 await session.refresh(workflow_run)
                 await save_workflow_run_logs(workflow_run_id)
@@ -2667,6 +2679,7 @@ class AgentDB:
         summary: str | None = None,
         output: dict[str, Any] | None = None,
         organization_id: str | None = None,
+        webhook_failure_reason: str | None = None,
     ) -> TaskV2:
         async with self.Session() as session:
             task_v2 = (
@@ -2699,6 +2712,8 @@ class AgentDB:
                     task_v2.summary = summary
                 if output:
                     task_v2.output = output
+                if webhook_failure_reason is not None:
+                    task_v2.webhook_failure_reason = webhook_failure_reason
                 await session.commit()
                 await session.refresh(task_v2)
                 return TaskV2.model_validate(task_v2)
diff --git a/skyvern/forge/sdk/db/models.py b/skyvern/forge/sdk/db/models.py
index 46f75451..5f8577c6 100644
--- a/skyvern/forge/sdk/db/models.py
+++ b/skyvern/forge/sdk/db/models.py
@@ -65,6 +65,7 @@ class TaskModel(Base):
     browser_session_id = Column(String, nullable=True, index=True)
     status = Column(String, index=True)
     webhook_callback_url = Column(String)
+    webhook_failure_reason = Column(String, nullable=True)
     totp_verification_url = Column(String)
     totp_identifier = Column(String)
     title = Column(String)
@@ -263,6 +264,7 @@ class WorkflowRunModel(Base):
     failure_reason = Column(String)
     proxy_location = Column(String)
     webhook_callback_url = Column(String)
+    webhook_failure_reason = Column(String, nullable=True)
     totp_verification_url = Column(String)
     totp_identifier = Column(String)
     max_screenshot_scrolling_times = Column(Integer, nullable=True)
@@ -639,6 +641,7 @@ class TaskV2Model(Base):
     summary = Column(String, nullable=True)
     output = Column(JSON, nullable=True)
     webhook_callback_url = Column(String, nullable=True)
+    webhook_failure_reason = Column(String, nullable=True)
     totp_verification_url = Column(String, nullable=True)
     totp_identifier = Column(String, nullable=True)
     proxy_location = Column(String, nullable=True)
diff --git a/skyvern/forge/sdk/db/utils.py b/skyvern/forge/sdk/db/utils.py
index 9ee309b4..1829de2a 100644
--- a/skyvern/forge/sdk/db/utils.py
+++ b/skyvern/forge/sdk/db/utils.py
@@ -120,6 +120,7 @@ def convert_to_task(task_obj: TaskModel, debug_enabled: bool = False, workflow_p
         terminate_criterion=task_obj.terminate_criterion,
         include_action_history_in_verification=task_obj.include_action_history_in_verification,
         webhook_callback_url=task_obj.webhook_callback_url,
+        webhook_failure_reason=task_obj.webhook_failure_reason,
         totp_verification_url=task_obj.totp_verification_url,
         totp_identifier=task_obj.totp_identifier,
         navigation_goal=task_obj.navigation_goal,
@@ -276,6 +277,7 @@ def convert_to_workflow_run(
             ProxyLocation(workflow_run_model.proxy_location) if workflow_run_model.proxy_location else None
         ),
         webhook_callback_url=workflow_run_model.webhook_callback_url,
+        webhook_failure_reason=workflow_run_model.webhook_failure_reason,
         totp_verification_url=workflow_run_model.totp_verification_url,
         totp_identifier=workflow_run_model.totp_identifier,
         queued_at=workflow_run_model.queued_at,
diff --git a/skyvern/forge/sdk/schemas/task_v2.py b/skyvern/forge/sdk/schemas/task_v2.py
index 5169504f..c83a7351 100644
--- a/skyvern/forge/sdk/schemas/task_v2.py
+++ b/skyvern/forge/sdk/schemas/task_v2.py
@@ -42,6 +42,7 @@ class TaskV2(BaseModel):
     totp_identifier: str | None = None
     proxy_location: ProxyLocation | None = None
     webhook_callback_url: str | None = None
+    webhook_failure_reason: str | None = None
     extracted_information_schema: dict | list | str | None = None
     error_code_mapping: dict | None = None
     model: dict[str, Any] | None = None
diff --git a/skyvern/forge/sdk/schemas/tasks.py b/skyvern/forge/sdk/schemas/tasks.py
index c69ed153..5b0f6557 100644
--- a/skyvern/forge/sdk/schemas/tasks.py
+++ b/skyvern/forge/sdk/schemas/tasks.py
@@ -38,6 +38,10 @@ class TaskBase(BaseModel):
         description="The URL to call when the task is completed.",
         examples=["https://my-webhook.com"],
     )
+    webhook_failure_reason: str | None = Field(
+        default=None,
+        description="The reason for the webhook failure.",
+    )
     totp_verification_url: str | None = None
     totp_identifier: str | None = None
     navigation_goal: str | None = Field(
@@ -314,6 +318,7 @@ class Task(TaskBase):
             finished_at=self.finished_at,
             extracted_information=self.extracted_information,
             failure_reason=failure_reason or self.failure_reason,
+            webhook_failure_reason=self.webhook_failure_reason,
             action_screenshot_urls=action_screenshot_urls,
             screenshot_url=screenshot_url,
             recording_url=recording_url,
@@ -341,6 +346,7 @@ class TaskResponse(BaseModel):
     downloaded_files: list[FileInfo] | None = None
     downloaded_file_urls: list[str] | None = None
     failure_reason: str | None = None
+    webhook_failure_reason: str | None = None
     errors: list[dict[str, Any]] = []
     max_steps_per_run: int | None = None
     workflow_run_id: str | None = None
diff --git a/skyvern/forge/sdk/workflow/models/workflow.py b/skyvern/forge/sdk/workflow/models/workflow.py
index e959247b..2beefe8b 100644
--- a/skyvern/forge/sdk/workflow/models/workflow.py
+++ b/skyvern/forge/sdk/workflow/models/workflow.py
@@ -116,6 +116,7 @@ class WorkflowRun(BaseModel):
     extra_http_headers: dict[str, str] | None = None
     proxy_location: ProxyLocation | None = None
     webhook_callback_url: str | None = None
+    webhook_failure_reason: str | None = None
     totp_verification_url: str | None = None
     totp_identifier: str | None = None
     failure_reason: str | None = None
@@ -151,6 +152,7 @@ class WorkflowRunResponseBase(BaseModel):
     failure_reason: str | None = None
     proxy_location: ProxyLocation | None = None
     webhook_callback_url: str | None = None
+    webhook_failure_reason: str | None = None
     totp_verification_url: str | None = None
     totp_identifier: str | None = None
     extra_http_headers: dict[str, str] | None = None
diff --git a/skyvern/forge/sdk/workflow/service.py b/skyvern/forge/sdk/workflow/service.py
index 5090c73f..63613dd6 100644
--- a/skyvern/forge/sdk/workflow/service.py
+++ b/skyvern/forge/sdk/workflow/service.py
@@ -1226,6 +1226,7 @@ class WorkflowService:
             failure_reason=workflow_run.failure_reason,
             proxy_location=workflow_run.proxy_location,
             webhook_callback_url=workflow_run.webhook_callback_url,
+            webhook_failure_reason=workflow_run.webhook_failure_reason,
             totp_verification_url=workflow_run.totp_verification_url,
             totp_identifier=workflow_run.totp_identifier,
             extra_http_headers=workflow_run.extra_http_headers,
@@ -1390,6 +1391,10 @@ class WorkflowService:
                     resp_code=resp.status_code,
                     resp_text=resp.text,
                 )
+                await app.DATABASE.update_workflow_run(
+                    workflow_run_id=workflow_run.workflow_run_id,
+                    webhook_failure_reason="",
+                )
             else:
                 LOG.info(
                     "Webhook failed",
@@ -1400,6 +1405,10 @@ class WorkflowService:
                     resp_code=resp.status_code,
                     resp_text=resp.text,
                 )
+                await app.DATABASE.update_workflow_run(
+                    workflow_run_id=workflow_run.workflow_run_id,
+                    webhook_failure_reason=f"Webhook failed with status code {resp.status_code}, error message: {resp.text}",
+                )
         except Exception as e:
             raise FailedToSendWebhook(
                 workflow_id=workflow_id,
diff --git a/skyvern/services/task_v2_service.py b/skyvern/services/task_v2_service.py
index 27328c13..b725403a 100644
--- a/skyvern/services/task_v2_service.py
+++ b/skyvern/services/task_v2_service.py
@@ -1726,6 +1726,11 @@ async def send_task_v2_webhook(task_v2: TaskV2) -> None:
                 resp_code=resp.status_code,
                 resp_text=resp.text,
             )
+            await app.DATABASE.update_task_v2(
+                task_v2_id=task_v2.observer_cruise_id,
+                organization_id=task_v2.organization_id,
+                webhook_failure_reason="",
+            )
         else:
             LOG.info(
                 "Task v2 webhook failed",
@@ -1734,5 +1739,10 @@ async def send_task_v2_webhook(task_v2: TaskV2) -> None:
                 resp_code=resp.status_code,
                 resp_text=resp.text,
             )
+            await app.DATABASE.update_task_v2(
+                task_v2_id=task_v2.observer_cruise_id,
+                organization_id=task_v2.organization_id,
+                webhook_failure_reason=f"Webhook failed with status code {resp.status_code}, error message: {resp.text}",
+            )
     except Exception as e:
         raise FailedToSendWebhook(task_v2_id=task_v2.observer_cruise_id) from e