diff --git a/scripts/test-extension-trial.ts b/scripts/test-extension-trial.ts
new file mode 100644
index 0000000..263d91a
--- /dev/null
+++ b/scripts/test-extension-trial.ts
@@ -0,0 +1,159 @@
+import { config } from "dotenv";
+
+config({ path: ".env.local" });
+
+async function main() {
+  const { db } = await import("@/lib/db");
+  const { createExtensionRequest, approveExtensionRequest } = await import(
+    "@/lib/extension-requests"
+  );
+  const { ACTIVATE_STATUSES, ACCOUNT_TYPES, REQUEST_STATUSES } = await import(
+    "@/lib/constants"
+  );
+
+  const scenarios = [
+    {
+      label: "TRIAL status + paid tier (BASIC_20)",
+      accountType: ACCOUNT_TYPES.BASIC_20,
+    },
+    {
+      label: "TRIAL status + trial tier (STUDENT_TRIAL)",
+      accountType: ACCOUNT_TYPES.STUDENT_TRIAL,
+    },
+  ];
+
+  let failures = 0;
+
+  for (const scenario of scenarios) {
+    const stamp = Date.now();
+    const testName = `__TEST_TRIAL_EXT_${stamp}__`.slice(0, 50);
+    const initialAvailable = new Date(2000, 0, 1);
+    let maestroID: number | null = null;
+
+    console.log(`\n=== Scenario: ${scenario.label} ===`);
+
+    try {
+      const created = await db.maestro.create({
+        data: {
+          Name: testName,
+          Password: "",
+          Email: `${stamp}@test.invalid`.slice(0, 50),
+          AccountType: scenario.accountType,
+          ActivateStatus: ACTIVATE_STATUSES.TRIAL,
+          AvailableActivateDateTime: initialAvailable,
+          PlayerCount: 0,
+          AcceptClausesDateTime: new Date(),
+          AllowEditEnterCode: 0,
+        },
+        select: { MaestroID: true },
+      });
+      maestroID = created.MaestroID;
+      console.log(`  seeded maestro MaestroID=${maestroID}`);
+
+      const requestResult = await createExtensionRequest(maestroID);
+      console.log(
+        `  createExtensionRequest → maestroExtensionID=${requestResult.maestroExtensionID}, status=${requestResult.status}`
+      );
+
+      if (requestResult.status !== REQUEST_STATUSES.REQUESTED) {
+        throw new Error(
+          `expected new request status=${REQUEST_STATUSES.REQUESTED}, got ${requestResult.status}`
+        );
+      }
+
+      const approveResult = await approveExtensionRequest(
+        requestResult.maestroExtensionID
+      );
+      console.log(
+        `  approveExtensionRequest → availableActivateDateTime=${approveResult.availableActivateDateTime}`
+      );
+
+      const afterApprove = await db.maestro.findUniqueOrThrow({
+        where: { MaestroID: maestroID },
+        select: {
+          ActivateStatus: true,
+          AvailableActivateDateTime: true,
+          AccountType: true,
+        },
+      });
+      const requestRow = await db.maestro_extension.findUniqueOrThrow({
+        where: { MaestroExtensionID: requestResult.maestroExtensionID },
+        select: { Status: true, AccountType: true },
+      });
+      const logRows = await db.maestro_log.findMany({
+        where: { MaestroID: maestroID },
+        select: { Type: true },
+        orderBy: { MaestroLogID: "asc" },
+      });
+
+      const today = new Date();
+      today.setHours(0, 0, 0, 0);
+      const expectedYear = today.getFullYear() + 1;
+      const actualAvailable = afterApprove.AvailableActivateDateTime;
+      const actualYear = actualAvailable.getFullYear();
+
+      const checks: Array<[string, boolean, string]> = [
+        [
+          "maestro.ActivateStatus becomes ACTIVE",
+          afterApprove.ActivateStatus === ACTIVATE_STATUSES.ACTIVE,
+          `got ${afterApprove.ActivateStatus}`,
+        ],
+        [
+          "maestro.AccountType preserved",
+          afterApprove.AccountType === scenario.accountType,
+          `got ${afterApprove.AccountType}`,
+        ],
+        [
+          "AvailableActivateDateTime = today +1 year (initial was in the past)",
+          actualYear === expectedYear,
+          `got year=${actualYear}, expected ${expectedYear}`,
+        ],
+        [
+          "extension request Status becomes APPLIED",
+          requestRow.Status === REQUEST_STATUSES.APPLIED,
+          `got ${requestRow.Status}`,
+        ],
+        [
+          "logs include request_extension_maestro",
+          logRows.some((l) => l.Type === "request_extension_maestro"),
+          JSON.stringify(logRows.map((l) => l.Type)),
+        ],
+        [
+          "logs include extension_maestro",
+          logRows.some((l) => l.Type === "extension_maestro"),
+          JSON.stringify(logRows.map((l) => l.Type)),
+        ],
+      ];
+
+      for (const [name, passed, detail] of checks) {
+        console.log(`  ${passed ? "PASS" : "FAIL"}  ${name}  (${detail})`);
+        if (!passed) failures += 1;
+      }
+    } catch (error) {
+      failures += 1;
+      console.error(`  ERROR:`, error);
+    } finally {
+      if (maestroID !== null) {
+        await db.maestro_extension.deleteMany({ where: { MaestroID: maestroID } });
+        await db.maestro_log.deleteMany({ where: { MaestroID: maestroID } });
+        await db.maestro.delete({ where: { MaestroID: maestroID } });
+        console.log(`  cleanup: removed rows for MaestroID=${maestroID}`);
+      }
+    }
+  }
+
+  await db.$disconnect();
+
+  if (failures > 0) {
+    console.error(`\n${failures} check(s) failed.`);
+    process.exitCode = 1;
+  } else {
+    console.log(`\nAll checks passed.`);
+  }
+}
+
+main().catch((error) => {
+  console.error("Test run failed");
+  console.error(error);
+  process.exitCode = 1;
+});