diff --git a/apps/web/playwright/booking-duplicate-api-calls.e2e.ts b/apps/web/playwright/booking-duplicate-api-calls.e2e.ts
index fb8030f1d7..41ce78aa48 100644
--- a/apps/web/playwright/booking-duplicate-api-calls.e2e.ts
+++ b/apps/web/playwright/booking-duplicate-api-calls.e2e.ts
@@ -1,45 +1,120 @@
 import { expect } from "@playwright/test";
+import type { Page } from "@playwright/test";
 
 import { createTeamEventType } from "./fixtures/users";
 import { test } from "./lib/fixtures";
 
+async function testDuplicateAPICalls(
+  page: Page,
+  url: string,
+  testDate?: Date
+): Promise<{ totalCalls: number; trpcCalls: number; apiV2Calls: number }> {
+  const trpcCalls: string[] = [];
+  const apiV2Calls: string[] = [];
+
+  if (testDate) {
+    await page.clock.install({ time: testDate });
+  }
+
+  await page.route("**/api/trpc/slots/getSchedule**", async (route) => {
+    trpcCalls.push(route.request().url());
+    await route.continue();
+  });
+
+  await page.route("**/api/v2/slots/available**", async (route) => {
+    apiV2Calls.push(route.request().url());
+    await route.continue();
+  });
+
+  await page.goto(url);
+  await page.waitForTimeout(5000);
+
+  return {
+    totalCalls: trpcCalls.length + apiV2Calls.length,
+    trpcCalls: trpcCalls.length,
+    apiV2Calls: apiV2Calls.length,
+  };
+}
+
 test.describe("Duplicate API Calls Prevention", () => {
   test.afterEach(({ users }) => users.deleteAll());
 
-  test("should detect when schedule endpoints are called multiple times for individual user events", async ({
+  test("should detect when schedule endpoints are called multiple times for individual user events - beginning of month", async ({
     page,
     users,
   }) => {
     const user = await users.create();
     const eventType = user.eventTypes.find((e) => e.slug === "30-min");
+    const beginningOfMonth = new Date();
+    beginningOfMonth.setDate(5);
 
-    const trpcCalls: string[] = [];
-    const apiV2Calls: string[] = [];
-
-    // Intercept tRPC getSchedule calls - pattern matches /api/trpc/slots/getSchedule
-    await page.route("**/api/trpc/slots/getSchedule**", async (route) => {
-      trpcCalls.push(route.request().url());
-      await route.continue();
-    });
-
-    await page.route("**/api/v2/slots/available**", async (route) => {
-      apiV2Calls.push(route.request().url());
-      await route.continue();
-    });
-
-    await page.goto(`/${user.username}/${eventType?.slug}`);
-
-    await page.waitForTimeout(5000);
-
-    const totalCalls = trpcCalls.length + apiV2Calls.length;
+    const { totalCalls, trpcCalls, apiV2Calls } = await testDuplicateAPICalls(
+      page,
+      `/${user.username}/${eventType?.slug}`,
+      beginningOfMonth
+    );
 
     expect(totalCalls).toBeGreaterThan(0);
     expect(totalCalls).toBeLessThanOrEqual(1);
-    expect(trpcCalls.length).toBeLessThanOrEqual(1);
-    expect(apiV2Calls.length).toBeLessThanOrEqual(1);
+    expect(trpcCalls).toBeLessThanOrEqual(1);
+    expect(apiV2Calls).toBeLessThanOrEqual(1);
   });
 
-  test("should detect when schedule endpoints are called multiple times for team events", async ({
+  test("should detect when schedule endpoints are called multiple times for individual user events - end of month", async ({
+    page,
+    users,
+  }) => {
+    const user = await users.create();
+    const eventType = user.eventTypes.find((e) => e.slug === "30-min");
+    const endOfMonth = new Date();
+    endOfMonth.setDate(20);
+
+    const { totalCalls, trpcCalls, apiV2Calls } = await testDuplicateAPICalls(
+      page,
+      `/${user.username}/${eventType?.slug}`,
+      endOfMonth
+    );
+
+    expect(totalCalls).toBeGreaterThan(0);
+    expect(totalCalls).toBeLessThanOrEqual(1);
+    expect(trpcCalls).toBeLessThanOrEqual(1);
+    expect(apiV2Calls).toBeLessThanOrEqual(1);
+  });
+
+  test("should detect when schedule endpoints are called multiple times for team events - beginning of month", async ({
+    page,
+    users,
+  }) => {
+    const teamOwner = await users.create(
+      { name: "Team Owner" },
+      {
+        hasTeam: true,
+        teammates: [{ name: "teammate-1" }],
+      }
+    );
+    const beginningOfMonth = new Date();
+    beginningOfMonth.setDate(5);
+
+    const { team } = await teamOwner.getFirstTeamMembership();
+    const teamEvent = await createTeamEventType(
+      { id: teamOwner.id },
+      { id: team.id },
+      { teamEventSlug: "team-event-test", teamEventTitle: "Team Event Test" }
+    );
+
+    const { totalCalls, trpcCalls, apiV2Calls } = await testDuplicateAPICalls(
+      page,
+      `/team/${team.slug}/${teamEvent.slug}`,
+      beginningOfMonth
+    );
+
+    expect(totalCalls).toBeGreaterThan(0);
+    expect(totalCalls).toBeLessThanOrEqual(1);
+    expect(trpcCalls).toBeLessThanOrEqual(1);
+    expect(apiV2Calls).toBeLessThanOrEqual(1);
+  });
+
+  test("should detect when schedule endpoints are called multiple times for team events - end of month", async ({
     page,
     users,
   }) => {
@@ -57,33 +132,22 @@ test.describe("Duplicate API Calls Prevention", () => {
       { id: team.id },
       { teamEventSlug: "team-event-test", teamEventTitle: "Team Event Test" }
     );
+    const endOfMonth = new Date();
+    endOfMonth.setDate(20);
 
-    const trpcCalls: string[] = [];
-    const apiV2Calls: string[] = [];
-
-    await page.route("**/api/trpc/slots/getSchedule**", async (route) => {
-      trpcCalls.push(route.request().url());
-      await route.continue();
-    });
-
-    await page.route("**/api/v2/slots/available**", async (route) => {
-      apiV2Calls.push(route.request().url());
-      await route.continue();
-    });
-
-    await page.goto(`/team/${team.slug}/${teamEvent.slug}`);
-
-    await page.waitForTimeout(5000);
-
-    const totalCalls = trpcCalls.length + apiV2Calls.length;
+    const { totalCalls, trpcCalls, apiV2Calls } = await testDuplicateAPICalls(
+      page,
+      `/team/${team.slug}/${teamEvent.slug}`,
+      endOfMonth
+    );
 
     expect(totalCalls).toBeGreaterThan(0);
     expect(totalCalls).toBeLessThanOrEqual(1);
-    expect(trpcCalls.length).toBeLessThanOrEqual(1);
-    expect(apiV2Calls.length).toBeLessThanOrEqual(1);
+    expect(trpcCalls).toBeLessThanOrEqual(1);
+    expect(apiV2Calls).toBeLessThanOrEqual(1);
   });
 
-  test("should detect when schedule endpoints are called multiple times for organization team events", async ({
+  test("should detect when schedule endpoints are called multiple times for organization team events - beginning of month", async ({
     page,
     users,
   }) => {
@@ -105,29 +169,55 @@ test.describe("Duplicate API Calls Prevention", () => {
       { id: team.id },
       { teamEventSlug: "org-team-event", teamEventTitle: "Org Team Event" }
     );
+    const beginningOfMonth = new Date();
+    beginningOfMonth.setDate(5);
 
-    const trpcCalls: string[] = [];
-    const apiV2Calls: string[] = [];
-
-    await page.route("**/api/trpc/slots/getSchedule**", async (route) => {
-      trpcCalls.push(route.request().url());
-      await route.continue();
-    });
-
-    await page.route("**/api/v2/slots/available**", async (route) => {
-      apiV2Calls.push(route.request().url());
-      await route.continue();
-    });
-
-    await page.goto(`/org/${org.slug}/${team.slug}/${teamEvent.slug}`);
-
-    await page.waitForTimeout(5000);
-
-    const totalCalls = trpcCalls.length + apiV2Calls.length;
+    const { totalCalls, trpcCalls, apiV2Calls } = await testDuplicateAPICalls(
+      page,
+      `/org/${org.slug}/${team.slug}/${teamEvent.slug}`,
+      beginningOfMonth
+    );
 
     expect(totalCalls).toBeGreaterThan(0);
     expect(totalCalls).toBeLessThanOrEqual(1);
-    expect(trpcCalls.length).toBeLessThanOrEqual(1);
-    expect(apiV2Calls.length).toBeLessThanOrEqual(1);
+    expect(trpcCalls).toBeLessThanOrEqual(1);
+    expect(apiV2Calls).toBeLessThanOrEqual(1);
+  });
+
+  test("should detect when schedule endpoints are called multiple times for organization team events - end of month", async ({
+    page,
+    users,
+  }) => {
+    const orgOwner = await users.create(
+      { name: "Org Owner" },
+      {
+        hasTeam: true,
+        teammates: [{ name: "teammate-1" }],
+        isOrg: true,
+        isOrgVerified: true,
+        hasSubteam: true,
+      }
+    );
+
+    const { team } = await orgOwner.getFirstTeamMembership();
+    const { team: org } = await orgOwner.getOrgMembership();
+    const teamEvent = await createTeamEventType(
+      { id: orgOwner.id },
+      { id: team.id },
+      { teamEventSlug: "org-team-event", teamEventTitle: "Org Team Event" }
+    );
+    const endOfMonth = new Date();
+    endOfMonth.setDate(20);
+
+    const { totalCalls, trpcCalls, apiV2Calls } = await testDuplicateAPICalls(
+      page,
+      `/org/${org.slug}/${team.slug}/${teamEvent.slug}`,
+      endOfMonth
+    );
+
+    expect(totalCalls).toBeGreaterThan(0);
+    expect(totalCalls).toBeLessThanOrEqual(1);
+    expect(trpcCalls).toBeLessThanOrEqual(1);
+    expect(apiV2Calls).toBeLessThanOrEqual(1);
   });
 });