diff --git a/src/cleveragents/cli/commands/plan.py b/src/cleveragents/cli/commands/plan.py
index a53a2df72..15c7e2528 100644
--- a/src/cleveragents/cli/commands/plan.py
+++ b/src/cleveragents/cli/commands/plan.py
@@ -31,6 +31,7 @@ from datetime import datetime
 from pathlib import Path
 from typing import TYPE_CHECKING, Annotated, Any, Literal, cast
 
+import structlog
 import typer
 from rich.console import Console
 from rich.panel import Panel
@@ -39,13 +40,18 @@ from rich.table import Table
 from sqlalchemy.exc import SQLAlchemyError
 
 from cleveragents.a2a.models import A2aRequest
+from cleveragents.application.container import get_container
 from cleveragents.cli.formatting import OutputFormat, format_output
 from cleveragents.core.exceptions import (
     CleverAgentsError,
+    NotFoundError,
     PlanError,
     ValidationError,
 )
 from cleveragents.domain.models.core.plan import PlanPhase, ProcessingState
+from cleveragents.infrastructure.sandbox.git_worktree import (
+    GitWorktreeSandbox,
+)
 
 # Regex for validating namespaced actor names (namespace/name format)
 _NAMESPACED_ACTOR_RE = re.compile(r"^[a-z][a-z0-9-]*/[a-z][a-z0-9._-]*$")
@@ -1349,6 +1355,9 @@ def _get_lifecycle_service():
     return container.plan_lifecycle_service()
 
 
+_cleanup_logger = structlog.get_logger("cleveragents.cli.commands.plan.cleanup")
+
+
 def _cleanup_sandbox_for_plan(
     plan_id: str,
     service: PlanLifecycleService,
@@ -1361,19 +1370,33 @@ def _cleanup_sandbox_for_plan(
 
     Used by ``plan cancel`` to prevent resource leaks.
     """
-    from cleveragents.application.container import get_container
-    from cleveragents.infrastructure.sandbox.git_worktree import (
-        GitWorktreeSandbox,
-    )
+    if not plan_id or not plan_id.strip():
+        _cleanup_logger.warning("cleanup_sandbox.skipped", reason="empty plan_id")
+        return
 
     container = get_container()
-    plan = service.get_plan(plan_id)
+
+    try:
+        plan = service.get_plan(plan_id)
+    except (NotFoundError, CleverAgentsError) as exc:
+        _cleanup_logger.warning(
+            "cleanup_sandbox.plan_not_found",
+            plan_id=plan_id,
+            error=str(exc),
+        )
+        return
+
     project_names = [pl.project_name for pl in getattr(plan, "project_links", [])]
 
     for project_name in project_names:
         try:
             project = container.namespaced_project_repo().get(project_name)
-        except Exception:
+        except (NotFoundError, CleverAgentsError, SQLAlchemyError) as exc:
+            _cleanup_logger.debug(
+                "cleanup_sandbox.project_lookup_failed",
+                project_name=project_name,
+                error=str(exc),
+            )
             continue
         if project is None:
             continue
@@ -1382,7 +1405,12 @@ def _cleanup_sandbox_for_plan(
                 resource = container.resource_registry_service().show_resource(
                     lr.resource_id,
                 )
-            except Exception:
+            except (NotFoundError, CleverAgentsError, SQLAlchemyError) as exc:
+                _cleanup_logger.debug(
+                    "cleanup_sandbox.resource_lookup_failed",
+                    resource_id=lr.resource_id,
+                    error=str(exc),
+                )
                 continue
             if (
                 resource.resource_type_name not in ("git-checkout", "git")
diff --git a/src/cleveragents/infrastructure/sandbox/git_worktree.py b/src/cleveragents/infrastructure/sandbox/git_worktree.py
index b5651d849..7a61779af 100644
--- a/src/cleveragents/infrastructure/sandbox/git_worktree.py
+++ b/src/cleveragents/infrastructure/sandbox/git_worktree.py
@@ -226,9 +226,11 @@ class GitWorktreeSandbox:
                 branch_name,
             )
 
+        branch_deleted = True
         try:
             _run_git(["branch", "-D", branch_name], cwd=repo_path)
         except (subprocess.CalledProcessError, subprocess.TimeoutExpired):
+            branch_deleted = False
             logger.warning(
                 "Failed to delete stale branch %s",
                 branch_name,
@@ -240,8 +242,14 @@ class GitWorktreeSandbox:
         ):
             _run_git(["worktree", "prune"], cwd=repo_path)
 
-        logger.info("Stale sandbox branch cleaned up: branch=%s", branch_name)
-        return True
+        if branch_deleted:
+            logger.info("Stale sandbox branch cleaned up: branch=%s", branch_name)
+        else:
+            logger.warning(
+                "Partial cleanup: worktree removed but branch persists: branch=%s",
+                branch_name,
+            )
+        return True  # Branch was found; cleanup attempted (even if partial)
 
     # -- protocol methods ----------------------------------------------------