diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1d2b812af..595123305 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -54,6 +54,15 @@ The format follows [Keep a Changelog](https://keepachangelog.com/en/1.1.0/).
   message listing available built-in profiles. The resolved profile name is also
   logged at debug level for observability.
 
+- **CheckpointManager rollback_to always returned False** (#7488): Fixed a data
+  integrity bug in `CheckpointManager.create_checkpoint()` where `sandbox_path`
+  was computed from `sandbox.context.sandbox_path` but never stored in the
+  checkpoint metadata. As a result, `rollback_to()` always found
+  `checkpoint.metadata.get("sandbox_path")` returning `None` and silently
+  skipped the rollback, returning `False`. The fix adds `sandbox_path` to the
+  metadata dict before constructing the `SandboxCheckpoint`, enabling
+  `rollback_to()` to correctly restore the sandbox filesystem state.
+
 ### Added
 
 - **TDD Issue-Capture Test Activation** (#7025): Replaced 234 bare `@skip` tags
diff --git a/features/checkpoint_manager_coverage.feature b/features/checkpoint_manager_coverage.feature
index d4334cc58..ee185ae37 100644
--- a/features/checkpoint_manager_coverage.feature
+++ b/features/checkpoint_manager_coverage.feature
@@ -71,6 +71,23 @@ Feature: CheckpointManager full coverage
     When I invoke create_checkpoint with plan "plan-s1" phase "pre_execute" and no metadata
     Then the snapshot directory should contain copies of the sample files
 
+  Scenario: Creating a checkpoint with a real sandbox path stores sandbox_path in metadata
+    Given a freshly created CheckpointManager
+    And a temporary sandbox directory with sample files
+    And a mock sandbox whose context points to the temporary directory
+    When I invoke create_checkpoint with plan "plan-s2" phase "pre_execute" and no metadata
+    Then the returned checkpoint metadata should contain the sandbox path
+
+  Scenario: Rollback succeeds without manually supplying sandbox_path in metadata
+    Given a freshly created CheckpointManager
+    And a temporary sandbox directory with sample files
+    And a mock sandbox whose context points to the temporary directory
+    And a checkpoint was created for the temporary sandbox without explicit sandbox_path metadata
+    And the temporary sandbox files are then modified
+    When I invoke rollback_to on the created checkpoint
+    Then the rollback result should be true
+    And the temporary sandbox should contain the original files
+
   # ---------------------------------------------------------------------------
   # _snapshot_directory – branches
   # ---------------------------------------------------------------------------
diff --git a/features/steps/checkpoint_manager_coverage_steps.py b/features/steps/checkpoint_manager_coverage_steps.py
index 038204418..542ae71c6 100644
--- a/features/steps/checkpoint_manager_coverage_steps.py
+++ b/features/steps/checkpoint_manager_coverage_steps.py
@@ -650,3 +650,43 @@ def step_delete_unknown_cp(context: Context, cp_id: str) -> None:
 @then("the checkpoint delete result should be false")
 def step_assert_delete_false(context: Context) -> None:
     assert context.delete_result is False, "Expected delete to return False"
+
+
+# ===========================================================================
+# Bug fix #7488 — sandbox_path auto-stored in metadata
+# ===========================================================================
+
+
+@then("the returned checkpoint metadata should contain the sandbox path")
+def step_assert_metadata_has_sandbox_path(context: Context) -> None:
+    """Verify that create_checkpoint() automatically stores sandbox_path in metadata."""
+    cp = context.cp_result
+    _register_cleanup(context, os.path.dirname(cp.snapshot_path))
+    assert "sandbox_path" in cp.metadata, (
+        "Expected 'sandbox_path' key in checkpoint metadata, but it was not found. "
+        "Bug #7488: create_checkpoint() must store sandbox_path in metadata."
+    )
+    assert cp.metadata["sandbox_path"] == context.temp_sandbox, (
+        f"Expected sandbox_path={context.temp_sandbox!r}, "
+        f"got {cp.metadata['sandbox_path']!r}"
+    )
+
+
+@given(
+    "a checkpoint was created for the temporary sandbox without explicit sandbox_path metadata"
+)
+def step_create_cp_for_temp_sandbox_no_explicit_path(context: Context) -> None:
+    """Create a checkpoint without manually supplying sandbox_path in metadata.
+
+    After the fix for bug #7488, create_checkpoint() should automatically
+    store sandbox_path in metadata from sandbox.context.sandbox_path.
+    """
+    context.cp_result = context.mgr.create_checkpoint(
+        sandbox=context.mock_sb,
+        plan_id="plan-rb-autopath",
+        phase="pre_execute",
+        # Intentionally NOT passing sandbox_path in metadata — the fix should
+        # auto-populate it from sandbox.context.sandbox_path.
+    )
+    _register_cleanup(context, os.path.dirname(context.cp_result.snapshot_path))
+    context.crafted_cp = context.cp_result
diff --git a/src/cleveragents/infrastructure/sandbox/checkpoint.py b/src/cleveragents/infrastructure/sandbox/checkpoint.py
index cd65b346d..65ffc4ef9 100644
--- a/src/cleveragents/infrastructure/sandbox/checkpoint.py
+++ b/src/cleveragents/infrastructure/sandbox/checkpoint.py
@@ -148,6 +148,9 @@ class CheckpointManager:
         if sandbox.context is not None:
             sandbox_path = sandbox.context.sandbox_path
 
+        if sandbox_path is not None:
+            meta["sandbox_path"] = str(sandbox_path)
+
         snapshot_path = self._snapshot_directory(sandbox_path, checkpoint_id)
 
         checkpoint = SandboxCheckpoint(