diff --git a/apps/web/components/plain/PlainContactForm.tsx b/apps/web/components/plain/PlainContactForm.tsx
index e0b6e726c3..039d19f5cf 100644
--- a/apps/web/components/plain/PlainContactForm.tsx
+++ b/apps/web/components/plain/PlainContactForm.tsx
@@ -1,6 +1,6 @@
 "use client";
 
-import { useState } from "react";
+import { Dispatch, SetStateAction, useState } from "react";
 
 import { Button } from "@calcom/ui/components/button";
 import { FileUploader, type FileData } from "@calcom/ui/components/file-uploader";
@@ -9,8 +9,7 @@ import { Icon } from "@calcom/ui/components/icon";
 import { Popover, PopoverContent, PopoverTrigger } from "@calcom/ui/components/popover";
 import { showToast } from "@calcom/ui/components/toast";
 
-const PlainContactForm = () => {
-  const [isOpen, setIsOpen] = useState(false);
+const PlainContactForm = ({ open, setIsOpen }: { open: boolean, setIsOpen: Dispatch<SetStateAction<boolean>> }) => {
   const [isSubmitting, setIsSubmitting] = useState(false);
   const [isSubmitted, setIsSubmitted] = useState(false);
   const [isUploadingImage, setIsUploadingImage] = useState(false);
@@ -55,6 +54,7 @@ const PlainContactForm = () => {
       setIsUploadingImage(false);
 
       const formData = new FormData();
+      // eslint-disable-next-line @typescript-eslint/no-explicit-any
       uploadFormData.forEach(({ key, value }: any) => {
         formData.append(key, value);
       });
@@ -138,7 +138,7 @@ const PlainContactForm = () => {
 
   return (
     <div className="fixed bottom-[1rem] right-[1rem] z-50">
-      <Popover open={isOpen} onOpenChange={setIsOpen}>
+      <Popover open={open} onOpenChange={setIsOpen}>
         <PopoverTrigger asChild className="enabled:hover:bg-subtle bg-subtle shadow-none">
           <Button
             onClick={() => setIsOpen(true)}
diff --git a/apps/web/components/plain/__tests__/PlainContactForm.test.tsx b/apps/web/components/plain/__tests__/PlainContactForm.test.tsx
index 1cf11ec26a..df0a87b290 100644
--- a/apps/web/components/plain/__tests__/PlainContactForm.test.tsx
+++ b/apps/web/components/plain/__tests__/PlainContactForm.test.tsx
@@ -17,11 +17,15 @@ vi.mock("@calcom/ui/components/toast", () => ({
 const mockUseSession = vi.mocked(useSession);
 const mockShowToast = vi.mocked(showToast);
 const mockFetch = vi.fn();
-global.fetch = mockFetch;
+global.fetch = mockFetch as unknown as typeof fetch;
 
 describe("PlainContactForm", () => {
+  let mockSetIsOpen: ReturnType<typeof vi.fn>;
+
   beforeEach(() => {
     vi.clearAllMocks();
+    mockSetIsOpen = vi.fn();
+
     mockUseSession.mockReturnValue({
       data: {
         hasValidLicense: true,
@@ -35,42 +39,42 @@ describe("PlainContactForm", () => {
       },
       status: "authenticated",
       update: vi.fn(),
-    });
+    } as any);
   });
 
-  it("should render contact button when closed", () => {
-    render(<PlainContactForm />);
+  it("renders the contact button when closed", () => {
+    render(<PlainContactForm open={false} setIsOpen={mockSetIsOpen} />);
 
     const button = screen.getByRole("button");
     expect(button).toBeInTheDocument();
   });
 
-  it("should open contact form when button is clicked", () => {
-    render(<PlainContactForm />);
+  it("opens when the launcher button is clicked (calls setIsOpen(true))", () => {
+    render(<PlainContactForm open={false} setIsOpen={mockSetIsOpen} />);
 
     const button = screen.getByRole("button");
     fireEvent.click(button);
 
+    expect(mockSetIsOpen).toHaveBeenCalledWith(true);
+  });
+
+  it("shows the form when open=true", () => {
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
+
     expect(screen.getByText("Contact support")).toBeInTheDocument();
     expect(screen.getByLabelText("Describe the issue")).toBeInTheDocument();
     expect(screen.getByText("Attachments (optional)")).toBeInTheDocument();
   });
 
-  it("should show empty form initially", () => {
-    render(<PlainContactForm />);
-
-    const button = screen.getByRole("button");
-    fireEvent.click(button);
+  it("shows empty form initially", () => {
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     const messageInput = screen.getByLabelText("Describe the issue") as HTMLTextAreaElement;
     expect(messageInput.value).toBe("");
   });
 
-  it("should close form when X button is clicked", () => {
-    render(<PlainContactForm />);
-
-    const openButton = screen.getByRole("button");
-    fireEvent.click(openButton);
+  it("closes when X button is clicked (calls setIsOpen(false))", () => {
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     const buttons = screen.getAllByRole("button");
     const closeButton = buttons.find((button) => button.querySelector('svg use[href="#x"]'));
@@ -78,19 +82,16 @@ describe("PlainContactForm", () => {
 
     fireEvent.click(closeButton!);
 
-    expect(screen.queryByText("Contact support")).not.toBeInTheDocument();
+    expect(mockSetIsOpen).toHaveBeenCalledWith(false);
   });
 
-  it("should handle form submission successfully", async () => {
+  it("handles form submission successfully", async () => {
     mockFetch.mockResolvedValueOnce({
       ok: true,
       json: () => Promise.resolve({ success: true }),
     });
 
-    render(<PlainContactForm />);
-
-    const openButton = screen.getByRole("button");
-    fireEvent.click(openButton);
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     fireEvent.change(screen.getByLabelText("Describe the issue"), {
       target: { value: "Test message" },
@@ -115,14 +116,11 @@ describe("PlainContactForm", () => {
     });
   });
 
-  it("should show loading state during submission", async () => {
-    // eslint-disable-next-line @typescript-eslint/no-empty-function
+  it("shows loading state during submission", async () => {
+    // never resolves → stays loading
     mockFetch.mockImplementation(() => new Promise((_resolve) => {}));
 
-    render(<PlainContactForm />);
-
-    const openButton = screen.getByRole("button");
-    fireEvent.click(openButton);
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     fireEvent.change(screen.getByLabelText("Describe the issue"), {
       target: { value: "Test message" },
@@ -135,23 +133,19 @@ describe("PlainContactForm", () => {
     await expect(submitButton).toBeDisabled();
   });
 
-  it("should reset form after successful submission", async () => {
+  it("resets form after successful submission", async () => {
     mockFetch.mockResolvedValueOnce({
       ok: true,
       json: () => Promise.resolve({ success: true }),
     });
 
-    render(<PlainContactForm />);
-
-    const openButton = screen.getByRole("button");
-    fireEvent.click(openButton);
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     fireEvent.change(screen.getByLabelText("Describe the issue"), {
       target: { value: "Test message" },
     });
 
-    const submitButton = screen.getByRole("button", { name: /send message/i });
-    fireEvent.click(submitButton);
+    fireEvent.click(screen.getByRole("button", { name: /send message/i }));
 
     await waitFor(() => {
       expect(screen.getByText("Message Sent")).toBeInTheDocument();
@@ -166,27 +160,21 @@ describe("PlainContactForm", () => {
     });
   });
 
-  it("should handle missing user session", () => {
+  it("handles missing user session", () => {
     mockUseSession.mockReturnValue({
       data: null,
       status: "unauthenticated",
       update: vi.fn(),
-    });
+    } as any);
 
-    render(<PlainContactForm />);
-
-    const openButton = screen.getByRole("button");
-    fireEvent.click(openButton);
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     const messageInput = screen.getByLabelText("Describe the issue") as HTMLTextAreaElement;
     expect(messageInput.value).toBe("");
   });
 
-  it("should require message field", async () => {
-    render(<PlainContactForm />);
-
-    const openButton = screen.getByRole("button");
-    fireEvent.click(openButton);
+  it("requires message field", async () => {
+    render(<PlainContactForm open={true} setIsOpen={mockSetIsOpen} />);
 
     await expect(screen.getByLabelText("Describe the issue")).toHaveAttribute("required");
   });
diff --git a/apps/web/components/plain/plainChat.tsx b/apps/web/components/plain/plainChat.tsx
index 9e79e60179..d981cbecc5 100644
--- a/apps/web/components/plain/plainChat.tsx
+++ b/apps/web/components/plain/plainChat.tsx
@@ -83,6 +83,7 @@ const PlainChat = IS_PLAIN_CHAT_ENABLED
   ? ({ nonce }: { nonce: string | undefined }) => {
       const [config, setConfig] = useState<PlainChatConfig | null>(null);
       const [isSmallScreen, setIsSmallScreen] = useState(false);
+      const [isOpen, setIsOpen] = useState(false);
       const { data: session } = useSession();
       const pathname = usePathname();
       const searchParams = useSearchParams();
@@ -269,10 +270,19 @@ const PlainChat = IS_PLAIN_CHAT_ENABLED
 
         checkScreenSize();
         window.addEventListener("resize", checkScreenSize);
-        initConfig();
-
+        if (isPaidUser) {
+          initConfig();
+        } else if (typeof window !== "undefined" && !window.Plain) {
+          window.Plain = {
+            // eslint-disable-next-line @typescript-eslint/no-empty-function
+            init: () => {},
+            open: () => {
+              setIsOpen(true);
+            }
+          };
+        }
         return () => window.removeEventListener("resize", checkScreenSize);
-      }, [isAppDomain, checkScreenSize, initConfig, userEmail]);
+      }, [isAppDomain, checkScreenSize, initConfig, userEmail, isPaidUser]);
 
       const plainChatScript = `
         window.plainScriptLoaded = function() {
@@ -289,7 +299,7 @@ const PlainChat = IS_PLAIN_CHAT_ENABLED
       if (!isAppDomain || isSmallScreen || typeof window === "undefined") return null;
 
       if (!isPaidUser) {
-        return <PlainContactForm />;
+        return <PlainContactForm open={isOpen} setIsOpen={setIsOpen} />;
       }
 
       if (!config) return null;
diff --git a/apps/web/lib/hooks/useIsBookingPage.ts b/apps/web/lib/hooks/useIsBookingPage.ts
index 2ecec817f8..beca240e3f 100644
--- a/apps/web/lib/hooks/useIsBookingPage.ts
+++ b/apps/web/lib/hooks/useIsBookingPage.ts
@@ -14,10 +14,11 @@ export default function useIsBookingPage(): boolean {
     "/apps/routing-forms/routing-link", // Routing Form page
     "/forms/", // Rewrites to /apps/routing-forms/routing-link
   ].some((route) => pathname?.startsWith(route));
+  const isBookingsListPage = ["/upcoming", "/unconfirmed", "/recurring", "/cancelled", "/past"].some((route) => pathname?.endsWith(route));
 
   const searchParams = useCompatSearchParams();
   const isUserBookingPage = Boolean(searchParams?.get("user"));
   const isUserBookingTypePage = Boolean(searchParams?.get("user") && searchParams?.get("type"));
 
-  return isBookingPage || isUserBookingPage || isUserBookingTypePage;
+  return (isBookingPage && !isBookingsListPage) || isUserBookingPage || isUserBookingTypePage;
 }
diff --git a/packages/features/shell/user-dropdown/UserDropdown.tsx b/packages/features/shell/user-dropdown/UserDropdown.tsx
index ee6aa16f34..aeea9cb4a8 100644
--- a/packages/features/shell/user-dropdown/UserDropdown.tsx
+++ b/packages/features/shell/user-dropdown/UserDropdown.tsx
@@ -56,11 +56,19 @@ export function UserDropdown({ small }: UserDropdownProps) {
 
   const [menuOpen, setMenuOpen] = useState(false);
 
-  const handleHelpClick = () => {
-    if (window.Plain) {
-      window.Plain.open();
-    }
+  const handleHelpClick = (e?: React.MouseEvent) => {
+    e?.preventDefault();
+    e?.stopPropagation();
+
     setMenuOpen(false);
+
+    // Defer to next frame to avoid the originating click closing the dialog
+    requestAnimationFrame(() => {
+      // double RAF is extra-safe if your dropdown unmounts with a transition
+      requestAnimationFrame(() => {
+        if (window.Plain) window.Plain.open();
+      });
+    });
   };
 
   // Prevent rendering dropdown if user isn't available.