diff --git a/app/Console/Commands/Concerns/FindsUsersWithLegacyEncryption.php b/app/Console/Commands/Concerns/FindsUsersWithLegacyEncryption.php
index 2c931a9d..4aa40eac 100644
--- a/app/Console/Commands/Concerns/FindsUsersWithLegacyEncryption.php
+++ b/app/Console/Commands/Concerns/FindsUsersWithLegacyEncryption.php
@@ -5,6 +5,7 @@ namespace App\Console\Commands\Concerns;
 use App\Models\User;
 use Illuminate\Database\Eloquent\Builder;
 use Illuminate\Support\Collection;
+use Laravel\Cashier\Subscription;
 
 trait FindsUsersWithLegacyEncryption
 {
@@ -33,11 +34,32 @@ trait FindsUsersWithLegacyEncryption
      * Drop users who are still being billed. These accounts must never be emailed a
      * deletion warning nor deleted while a subscription or trial is active.
      *
+     * Unlike {@see User::hasActiveSubscriptionOrTrial()}, this check is intentionally
+     * independent of the `subscriptions.enabled` feature flag: that flag controls whether
+     * the paywall is enforced, not whether real Stripe subscriptions exist. A destructive
+     * command must never delete a paying customer just because the flag is off in the
+     * runtime that happens to execute it.
+     *
      * @param  Collection<int, User>  $users
      * @return Collection<int, User>
      */
     protected function excludeBilledUsers(Collection $users): Collection
     {
-        return $users->reject(fn (User $user): bool => $user->hasActiveSubscriptionOrTrial())->values();
+        return $users->reject(fn (User $user): bool => $this->isBilled($user))->values();
+    }
+
+    /**
+     * Whether the user is on a generic trial or holds a subscription that is still
+     * valid and not merely coasting through its grace period (it will not renew).
+     */
+    private function isBilled(User $user): bool
+    {
+        if ($user->onGenericTrial()) {
+            return true;
+        }
+
+        return $user->subscriptions->contains(
+            fn (Subscription $subscription): bool => $subscription->valid() && ! $subscription->onGracePeriod()
+        );
     }
 }
diff --git a/tests/Feature/Console/DeleteEncryptedDataAccountsCommandTest.php b/tests/Feature/Console/DeleteEncryptedDataAccountsCommandTest.php
index cf1b2c03..ab5fcc99 100644
--- a/tests/Feature/Console/DeleteEncryptedDataAccountsCommandTest.php
+++ b/tests/Feature/Console/DeleteEncryptedDataAccountsCommandTest.php
@@ -28,8 +28,8 @@ test('it soft-deletes users with encrypted data who did not sign in within the g
     expect(User::whereKey($clean->id)->exists())->toBeTrue();
 });
 
-test('it never deletes a subscribed user', function () {
-    config(['subscriptions.enabled' => true]);
+test('it never deletes a subscribed user even when the subscriptions flag is off', function () {
+    config(['subscriptions.enabled' => false]);
 
     $subscribed = User::factory()->create(['last_active_at' => now()->subDays(30)]);
     Transaction::factory()->for($subscribed)->create();
diff --git a/tests/Feature/Console/NotifyEncryptedDataRemovalCommandTest.php b/tests/Feature/Console/NotifyEncryptedDataRemovalCommandTest.php
index 80f34244..1981a431 100644
--- a/tests/Feature/Console/NotifyEncryptedDataRemovalCommandTest.php
+++ b/tests/Feature/Console/NotifyEncryptedDataRemovalCommandTest.php
@@ -28,8 +28,8 @@ test('it queues a warning email for users with encrypted transactions or account
     Queue::assertNotPushed(SendUpdateEmailJob::class, fn (SendUpdateEmailJob $job) => $job->user->is($clean));
 });
 
-test('it never warns a subscribed user', function () {
-    config(['subscriptions.enabled' => true]);
+test('it never warns a subscribed user even when the subscriptions flag is off', function () {
+    config(['subscriptions.enabled' => false]);
 
     $subscribed = User::factory()->create();
     Transaction::factory()->for($subscribed)->create();