diff --git a/server/src/infrastructure/sequelize/initializeData.test.ts b/server/src/infrastructure/sequelize/initializeData.test.ts
index a0d0265..aaad435 100644
--- a/server/src/infrastructure/sequelize/initializeData.test.ts
+++ b/server/src/infrastructure/sequelize/initializeData.test.ts
@@ -69,3 +69,13 @@ it("reports connection cleanup errors", async () => {
   connection.close.mockRejectedValue(new Error("synthetic private detail"));
   await expect(initializeData({ ...options, admin: true })).rejects.toThrow("connection cleanup");
 });
+
+it("preserves the original failure when cleanup also fails", async () => {
+  const cause = new Error("Account failed");
+  users.mockRejectedValue(cause);
+  connection.close.mockRejectedValue(new Error("Close failed"));
+  await expect(initializeData({ ...options, admin: true })).rejects.toMatchObject({
+    message: "Data initialization failed during accounts.", cause,
+  });
+  expect(connection.close).toHaveBeenCalledTimes(1);
+});
diff --git a/server/src/infrastructure/sequelize/initializeData.ts b/server/src/infrastructure/sequelize/initializeData.ts
index 90e0448..0e704ff 100644
--- a/server/src/infrastructure/sequelize/initializeData.ts
+++ b/server/src/infrastructure/sequelize/initializeData.ts
@@ -19,6 +19,7 @@ export const initializeData = async (options: DataInitializationOptions): Promis
   }
   let adapter: ReturnType<typeof createSequelizeAdapter> | undefined;
   let stage = "connection";
+  let failure: Error | undefined;
   try {
     // Seed errors and SQL logging must not expose account data or password hashes.
     adapter = createSequelizeAdapter({ logging: false });
@@ -45,12 +46,13 @@ export const initializeData = async (options: DataInitializationOptions): Promis
     }
   } catch (cause) {
     // Only this static message is printed by the CLI; the original cause stays private.
-    throw new Error(`Data initialization failed during ${stage}.`, { cause });
+    failure = new Error(`Data initialization failed during ${stage}.`, { cause });
   } finally {
     try {
       await adapter?.connection.close();
     } catch (cause) {
-      throw new Error("Data initialization failed during connection cleanup.", { cause });
+      failure ??= new Error("Data initialization failed during connection cleanup.", { cause });
     }
   }
+  if (failure) throw failure;
 };