diff --git a/bundle/deploy/lock/release.go b/bundle/deploy/lock/release.go
index 26f95edfc..b9ea783f5 100644
--- a/bundle/deploy/lock/release.go
+++ b/bundle/deploy/lock/release.go
@@ -46,12 +46,10 @@ func (m *release) Apply(ctx context.Context, b *bundle.Bundle) diag.Diagnostics
 
 	log.Infof(ctx, "Releasing deployment lock")
 	switch m.goal {
-	case GoalDeploy:
-		return diag.FromErr(b.Locker.Unlock(ctx))
-	case GoalBind, GoalUnbind:
-		return diag.FromErr(b.Locker.Unlock(ctx))
+	case GoalDeploy, GoalBind, GoalUnbind:
+		return diag.FromErrPrefix("failed to unlock: ", b.Locker.Unlock(ctx))
 	case GoalDestroy:
-		return diag.FromErr(b.Locker.Unlock(ctx, locker.AllowLockFileNotExist))
+		return diag.FromErrPrefix("failed to unlock: ", b.Locker.Unlock(ctx, locker.AllowLockFileNotExist))
 	default:
 		return diag.Errorf("unknown goal for lock release: %s", m.goal)
 	}
diff --git a/bundle/permissions/workspace_root.go b/bundle/permissions/workspace_root.go
index 828b12f50..956909420 100644
--- a/bundle/permissions/workspace_root.go
+++ b/bundle/permissions/workspace_root.go
@@ -75,7 +75,7 @@ func setPermissions(ctx context.Context, w workspace.WorkspaceInterface, path st
 
 	obj, err := w.GetStatusByPath(ctx, path)
 	if err != nil {
-		return err
+		return fmt.Errorf("GetStatusByPath(%s) failed: %w", path, err)
 	}
 
 	_, err = w.SetPermissions(ctx, workspace.WorkspaceObjectPermissionsRequest{
@@ -84,7 +84,7 @@ func setPermissions(ctx context.Context, w workspace.WorkspaceInterface, path st
 		AccessControlList:   permissions,
 	})
 
-	return err
+	return fmt.Errorf("SetPermissions(%d) failed: %w", obj.ObjectId, err)
 }
 
 func GetWorkspaceObjectPermissionLevel(bundlePermission string) (workspace.WorkspaceObjectPermissionLevel, error) {
diff --git a/libs/diag/diagnostic.go b/libs/diag/diagnostic.go
index 0c7699b4e..d22e2f87f 100644
--- a/libs/diag/diagnostic.go
+++ b/libs/diag/diagnostic.go
@@ -53,6 +53,19 @@ func FromErr(err error) Diagnostics {
 	}
 }
 
+// FromErrPrefix returns a new error diagnostic from the specified error, if any.
+func FromErrPrefix(prefix string, err error) Diagnostics {
+	if err == nil {
+		return nil
+	}
+	return []Diagnostic{
+		{
+			Severity: Error,
+			Summary:  prefix + err.Error(),
+		},
+	}
+}
+
 // FromErr returns a new warning diagnostic from the specified error, if any.
 func WarningFromErr(err error) Diagnostics {
 	if err == nil {