diff --git a/apps/web/modules/data-table/components/segment/FilterSegmentSelect.tsx b/apps/web/modules/data-table/components/segment/FilterSegmentSelect.tsx
index 8a54814ec0..71563d447a 100644
--- a/apps/web/modules/data-table/components/segment/FilterSegmentSelect.tsx
+++ b/apps/web/modules/data-table/components/segment/FilterSegmentSelect.tsx
@@ -1,27 +1,25 @@
-import { useSession } from "next-auth/react";
-import { useState, useMemo } from "react";
-
 import { checkAdminOrOwner } from "@calcom/features/auth/lib/checkAdminOrOwner";
+import { useDataTable } from "@calcom/features/data-table/hooks";
+import type {
+  CombinedFilterSegment,
+  FilterSegmentOutput,
+  SystemFilterSegmentInternal,
+  UserFilterSegment,
+} from "@calcom/features/data-table/lib/types";
 import { useLocale } from "@calcom/lib/hooks/useLocale";
 import { Button } from "@calcom/ui/components/button";
 import {
   Dropdown,
   DropdownItem,
-  DropdownMenuPortal,
   DropdownMenuContent,
   DropdownMenuItem,
-  DropdownMenuTrigger,
   DropdownMenuLabel,
+  DropdownMenuPortal,
+  DropdownMenuTrigger,
 } from "@calcom/ui/components/dropdown";
 import { Icon, type IconName } from "@calcom/ui/components/icon";
-
-import { useDataTable } from "@calcom/features/data-table/hooks";
-import type {
-  FilterSegmentOutput,
-  CombinedFilterSegment,
-  SystemFilterSegmentInternal,
-  UserFilterSegment,
-} from "@calcom/features/data-table/lib/types";
+import { useSession } from "next-auth/react";
+import { useMemo, useState } from "react";
 import { DeleteSegmentDialog } from "./DeleteSegmentDialog";
 import { DuplicateSegmentDialog } from "./DuplicateSegmentDialog";
 import { RenameSegmentDialog } from "./RenameSegmentDialog";
@@ -43,7 +41,7 @@ export function FilterSegmentSelect({ shortLabel }: Props = {}) {
   const { t } = useLocale();
   const session = useSession();
   const isAdminOrOwner = checkAdminOrOwner(session.data?.user?.org?.role);
-  const { segments, selectedSegment, segmentId, setSegmentId, isSegmentEnabled } = useDataTable();
+  const { segments, selectedSegment, segmentId, setSegmentId, isSegmentEnabled, clearAll } = useDataTable();
   const [segmentToRename, setSegmentToRename] = useState<FilterSegmentOutput | undefined>();
   const [segmentToDuplicate, setSegmentToDuplicate] = useState<CombinedFilterSegment | undefined>();
   const [segmentToDelete, setSegmentToDelete] = useState<FilterSegmentOutput | undefined>();
@@ -192,7 +190,7 @@ export function FilterSegmentSelect({ shortLabel }: Props = {}) {
                       segment={segment}
                       onSelect={() => {
                         if (segmentId && segmentId.type === segment.type && segmentId.id === segment.id) {
-                          setSegmentId(null);
+                          clearAll();
                         } else {
                           if (segment.type === "system") {
                             setSegmentId({ id: segment.id, type: "system" });
@@ -247,9 +245,7 @@ function DropdownItemWithSubmenu({
   const [isOpen, setIsOpen] = useState(false);
 
   return (
-    <DropdownMenuItem
-      className="cursor-pointer rounded-lg last-of-type:rounded-b-lg"
-      onSelect={onSelect}>
+    <DropdownMenuItem className="cursor-pointer rounded-lg last-of-type:rounded-b-lg" onSelect={onSelect}>
       <div className="flex items-center">
         {children}
         <div className="grow" />
diff --git a/apps/web/playwright/filter-segment.e2e.ts b/apps/web/playwright/filter-segment.e2e.ts
index 2511540de2..b98f223bf9 100644
--- a/apps/web/playwright/filter-segment.e2e.ts
+++ b/apps/web/playwright/filter-segment.e2e.ts
@@ -1,17 +1,18 @@
-import { expect } from "@playwright/test";
-
 import { MembershipRole } from "@calcom/prisma/enums";
+import { expect } from "@playwright/test";
 
 import {
   applySelectFilter,
-  createFilterSegment,
-  selectSegment,
-  deleteSegment,
-  listSegments,
   clearFilters,
-  openSegmentSubmenu,
-  locateSelectedSegmentName,
+  createFilterSegment,
+  deleteSegment,
+  expectSegmentCleared,
+  expectSegmentSelected,
   getByTableColumnText,
+  listSegments,
+  locateSelectedSegmentName,
+  openSegmentSubmenu,
+  selectSegment,
 } from "./filter-helpers";
 import { test } from "./lib/fixtures";
 
@@ -362,4 +363,34 @@ test.describe("Filter Segment Functionality", () => {
       ).toBeHidden();
     });
   });
+
+  test("Deselecting a segment clears all active filters", async ({ page, users }) => {
+    const orgOwner = await users.create(undefined, {
+      hasTeam: true,
+      isOrg: true,
+    });
+    const { team: org } = await orgOwner.getOrgMembership();
+
+    await orgOwner.apiLogin();
+    await page.goto(`/settings/organizations/${org.slug}/members`);
+
+    const dataTable = page.getByTestId("user-list-data-table").first();
+    await expect(dataTable).toBeVisible();
+
+    await applySelectFilter(page, "role", "admin");
+    const segmentName = "Test Deselect Segment";
+    await createFilterSegment(page, segmentName);
+
+    await expectSegmentSelected(page, segmentName);
+    const urlWithSegment = page.url();
+    expect(urlWithSegment).toContain("activeFilters");
+
+    await selectSegment(page, segmentName);
+    await expectSegmentCleared(page);
+
+    const urlAfterDeselect = page.url();
+    expect(urlAfterDeselect).not.toContain("activeFilters");
+
+    await deleteSegment(page, segmentName);
+  });
 });
diff --git a/apps/web/playwright/system-segments.e2e.ts b/apps/web/playwright/system-segments.e2e.ts
index 11ac507727..e4602e8f7e 100644
--- a/apps/web/playwright/system-segments.e2e.ts
+++ b/apps/web/playwright/system-segments.e2e.ts
@@ -1,7 +1,7 @@
-import { expect } from "@playwright/test";
 import type { Page } from "@playwright/test";
+import { expect } from "@playwright/test";
 
-import { addFilter, selectSegment, expectSegmentCleared, expectSegmentSelected } from "./filter-helpers";
+import { addFilter, expectSegmentCleared, expectSegmentSelected, selectSegment } from "./filter-helpers";
 import { test } from "./lib/fixtures";
 
 test.describe.configure({ mode: "parallel" });