diff --git a/apps/desktop/src/components/devtool/trial-begin-modal.tsx b/apps/desktop/src/components/devtool/trial-begin-modal.tsx
new file mode 100644
index 0000000000..bda8c1883e
--- /dev/null
+++ b/apps/desktop/src/components/devtool/trial-begin-modal.tsx
@@ -0,0 +1,118 @@
+import { Brain, Cloud, ExternalLink, Puzzle, Sparkle, X } from "lucide-react";
+import { useEffect } from "react";
+import { createPortal } from "react-dom";
+import { create } from "zustand";
+
+import { cn } from "@hypr/utils";
+
+type TrialBeginModalStore = {
+  isOpen: boolean;
+  open: () => void;
+  close: () => void;
+};
+
+export const useTrialBeginModal = create<TrialBeginModalStore>((set) => ({
+  isOpen: false,
+  open: () => set({ isOpen: true }),
+  close: () => set({ isOpen: false }),
+}));
+
+export function TrialBeginModal() {
+  const { isOpen, close } = useTrialBeginModal();
+
+  useEffect(() => {
+    const handleEscape = (e: KeyboardEvent) => {
+      if (e.key === "Escape" && isOpen) {
+        close();
+      }
+    };
+
+    if (isOpen) {
+      document.addEventListener("keydown", handleEscape);
+    }
+
+    return () => {
+      document.removeEventListener("keydown", handleEscape);
+    };
+  }, [isOpen, close]);
+
+  if (!isOpen) {
+    return null;
+  }
+
+  return createPortal(
+    <>
+      <div
+        className="fixed inset-0 z-[9999] bg-black/50 backdrop-blur-sm"
+        onClick={close}
+      >
+        <div
+          data-tauri-drag-region
+          className="w-full min-h-11"
+          onClick={(e) => e.stopPropagation()}
+        />
+      </div>
+
+      <div className="fixed inset-0 z-[9999] flex items-center justify-center p-4 pointer-events-none">
+        <div
+          className={cn([
+            "relative w-full max-w-lg max-h-full overflow-auto",
+            "bg-background rounded-lg shadow-lg pointer-events-auto",
+          ])}
+          onClick={(e) => e.stopPropagation()}
+        >
+          <button
+            onClick={close}
+            className="absolute right-6 top-6 z-10 rounded-sm opacity-70 ring-offset-background transition-opacity hover:opacity-100 focus:outline-none focus:ring-2 focus:ring-ring focus:ring-offset-2"
+            aria-label="Close"
+          >
+            <X className="h-4 w-4" />
+          </button>
+
+          <div className="flex flex-col items-center gap-10 p-10 text-center">
+            <div className="flex flex-col gap-3 max-w-sm">
+              <h2 className="font-serif text-3xl font-semibold">
+                Welcome to Pro!
+              </h2>
+              <p className="text-muted-foreground">
+                You just gained access to these features
+              </p>
+            </div>
+
+            <div className="flex flex-wrap justify-center gap-2 max-w-md">
+              {[
+                { label: "Pro AI models", icon: Sparkle },
+                { label: "Cloud sync", icon: Cloud },
+                { label: "Memory", icon: Brain },
+                { label: "Integrations", icon: Puzzle },
+                { label: "Shareable links", icon: ExternalLink },
+                { label: "and more", icon: null },
+              ].map(({ label, icon: Icon }) => (
+                <div
+                  key={label}
+                  className={cn([
+                    "px-4 h-8 flex items-center text-sm rounded-full",
+                    "bg-gradient-to-b from-white to-stone-50 border border-neutral-300 text-neutral-700",
+                    "shadow-sm hover:shadow-md hover:scale-[102%] transition-all",
+                    Icon && "gap-2",
+                  ])}
+                >
+                  {Icon && <Icon className="h-4 w-4" />}
+                  {label}
+                </div>
+              ))}
+            </div>
+
+            <button
+              onClick={close}
+              className="px-6 py-2 rounded-full bg-gradient-to-t from-stone-600 to-stone-500 text-white text-sm font-medium transition-opacity duration-150 hover:opacity-90"
+            >
+              Let's go!
+            </button>
+          </div>
+        </div>
+      </div>
+    </>,
+    document.body,
+  );
+}
diff --git a/apps/desktop/src/components/devtool/trial-expired-modal.tsx b/apps/desktop/src/components/devtool/trial-expired-modal.tsx
index 0846a03aed..e74d332ed7 100644
--- a/apps/desktop/src/components/devtool/trial-expired-modal.tsx
+++ b/apps/desktop/src/components/devtool/trial-expired-modal.tsx
@@ -1,7 +1,8 @@
 import { Brain, Cloud, ExternalLink, Puzzle, Sparkle, X } from "lucide-react";
+import { useEffect } from "react";
+import { createPortal } from "react-dom";
 import { create } from "zustand";
 
-import { Modal } from "@hypr/ui/components/ui/modal";
 import { cn } from "@hypr/utils";
 
 import { useBillingAccess } from "../../billing";
@@ -27,58 +28,96 @@ export function TrialExpiredModal() {
     close();
   };
 
-  return (
-    <Modal open={isOpen} onClose={close} preventClose size="lg">
-      <div className="relative flex flex-col">
-        <button
-          onClick={close}
-          className="absolute right-4 top-4 z-10 rounded-sm opacity-70 ring-offset-background transition-opacity hover:opacity-100 focus:outline-none focus:ring-2 focus:ring-ring focus:ring-offset-2"
-          aria-label="Close"
-        >
-          <X className="h-4 w-4" />
-        </button>
+  useEffect(() => {
+    const handleEscape = (e: KeyboardEvent) => {
+      if (e.key === "Escape" && isOpen) {
+        close();
+      }
+    };
 
-        <div className="flex flex-col items-center gap-8 p-6 text-center">
-          <div className="flex flex-col gap-3">
-            <h2 className="font-serif text-3xl font-semibold">
-              Your free trial is over
-            </h2>
-            <p className="text-muted-foreground">
-              You can keep using Hyprnote for free,
-              <br />
-              but here's what you'll be losing
-            </p>
-          </div>
+    if (isOpen) {
+      document.addEventListener("keydown", handleEscape);
+    }
 
-          <div className="flex flex-wrap justify-center gap-3 max-w-md">
-            {[
-              { label: "Pro AI models", icon: Sparkle },
-              { label: "Cloud sync", icon: Cloud },
-              { label: "Memory", icon: Brain },
-              { label: "Integrations", icon: Puzzle },
-              { label: "Shareable links", icon: ExternalLink },
-            ].map(({ label, icon: Icon }) => (
-              <div
-                key={label}
-                className={cn([
-                  "rounded-full border border-border bg-secondary/50 px-4 py-2 text-[12px] text-secondary-foreground",
-                  "flex items-center gap-2",
-                ])}
-              >
-                <Icon className="h-4 w-4" />
-                {label}
-              </div>
-            ))}
-          </div>
+    return () => {
+      document.removeEventListener("keydown", handleEscape);
+    };
+  }, [isOpen, close]);
+
+  if (!isOpen) {
+    return null;
+  }
+
+  return createPortal(
+    <>
+      <div className="fixed inset-0 z-[9999] bg-black/50 backdrop-blur-sm">
+        <div
+          data-tauri-drag-region
+          className="w-full min-h-11"
+          onClick={(e) => e.stopPropagation()}
+        />
+      </div>
 
+      <div className="fixed inset-0 z-[9999] flex items-center justify-center p-4 pointer-events-none">
+        <div
+          className={cn([
+            "relative w-full max-w-lg max-h-full overflow-auto",
+            "bg-background rounded-lg shadow-lg pointer-events-auto",
+          ])}
+          onClick={(e) => e.stopPropagation()}
+        >
           <button
-            onClick={handleUpgrade}
-            className="px-6 py-2 rounded-full bg-gradient-to-t from-stone-600 to-stone-500 text-white text-sm font-medium transition-opacity duration-150 hover:opacity-90"
+            onClick={close}
+            className="absolute right-6 top-6 z-10 rounded-sm opacity-70 ring-offset-background transition-opacity hover:opacity-100 focus:outline-none focus:ring-2 focus:ring-ring focus:ring-offset-2"
+            aria-label="Close"
           >
-            I'd like to keep using <span className="font-serif">Pro</span>
+            <X className="h-4 w-4" />
           </button>
+
+          <div className="flex flex-col items-center gap-10 p-10 text-center">
+            <div className="flex flex-col gap-3">
+              <h2 className="font-serif text-3xl font-semibold">
+                Your free trial is over
+              </h2>
+              <p className="text-muted-foreground">
+                Here's what you just lost access to
+              </p>
+            </div>
+
+            <div className="flex flex-wrap justify-center gap-2 max-w-md">
+              {[
+                { label: "Pro AI models", icon: Sparkle },
+                { label: "Cloud sync", icon: Cloud },
+                { label: "Memory", icon: Brain },
+                { label: "Integrations", icon: Puzzle },
+                { label: "Shareable links", icon: ExternalLink },
+                { label: "and more", icon: null },
+              ].map(({ label, icon: Icon }) => (
+                <div
+                  key={label}
+                  className={cn([
+                    "px-4 h-8 flex items-center text-sm rounded-full",
+                    "bg-gradient-to-b from-white to-stone-50 border border-neutral-300 text-neutral-700",
+                    "shadow-sm hover:shadow-md hover:scale-[102%] transition-all",
+                    Icon && "gap-2",
+                  ])}
+                >
+                  {Icon && <Icon className="h-4 w-4" />}
+                  {label}
+                </div>
+              ))}
+            </div>
+
+            <button
+              onClick={handleUpgrade}
+              className="px-6 py-2 rounded-full bg-gradient-to-t from-stone-600 to-stone-500 text-white text-sm font-medium transition-opacity duration-150 hover:opacity-90"
+            >
+              I'd like to keep using <span className="font-serif">Pro</span>
+            </button>
+          </div>
         </div>
       </div>
-    </Modal>
+    </>,
+    document.body,
   );
 }
diff --git a/apps/desktop/src/components/main-app-layout.tsx b/apps/desktop/src/components/main-app-layout.tsx
index 601301e50b..b8492cbb15 100644
--- a/apps/desktop/src/components/main-app-layout.tsx
+++ b/apps/desktop/src/components/main-app-layout.tsx
@@ -8,6 +8,7 @@ import { AuthProvider } from "../auth";
 import { BillingProvider } from "../billing";
 import { NetworkProvider } from "../contexts/network";
 import { useTabs } from "../store/zustand/tabs";
+import { TrialBeginModal } from "./devtool/trial-begin-modal";
 import { TrialExpiredModal } from "./devtool/trial-expired-modal";
 import { useNewNote } from "./main/shared";
 
@@ -19,6 +20,7 @@ export default function MainAppLayout() {
       <BillingProvider>
         <NetworkProvider>
           <Outlet />
+          <TrialBeginModal />
           <TrialExpiredModal />
         </NetworkProvider>
       </BillingProvider>
diff --git a/apps/desktop/src/components/main/sidebar/devtool.tsx b/apps/desktop/src/components/main/sidebar/devtool.tsx
index 6777194677..59f0e90d5b 100644
--- a/apps/desktop/src/components/main/sidebar/devtool.tsx
+++ b/apps/desktop/src/components/main/sidebar/devtool.tsx
@@ -11,6 +11,7 @@ import {
 } from "../../../store/tinybase/store/main";
 import { useTabs } from "../../../store/zustand/tabs";
 import { type SeedDefinition, seeds } from "../../devtool/seed/index";
+import { useTrialBeginModal } from "../../devtool/trial-begin-modal";
 import { useTrialExpiredModal } from "../../devtool/trial-expired-modal";
 import { getLatestVersion } from "../body/changelog";
 
@@ -313,11 +314,25 @@ function NavigationCard() {
 }
 
 function ModalsCard() {
+  const { open: openTrialBeginModal } = useTrialBeginModal();
   const { open: openTrialExpiredModal } = useTrialExpiredModal();
 
   return (
     <DevtoolCard title="Modals">
       <div className="flex flex-col gap-1.5">
+        <button
+          type="button"
+          onClick={openTrialBeginModal}
+          className={cn([
+            "w-full px-2.5 py-1.5 rounded-md",
+            "text-xs font-medium text-left",
+            "border border-neutral-200 text-neutral-700",
+            "cursor-pointer transition-colors",
+            "hover:bg-neutral-50 hover:border-neutral-300",
+          ])}
+        >
+          Trial Begin
+        </button>
         <button
           type="button"
           onClick={openTrialExpiredModal}
diff --git a/apps/desktop/src/components/onboarding/login.tsx b/apps/desktop/src/components/onboarding/login.tsx
index a94f0e1288..b39e5aacd6 100644
--- a/apps/desktop/src/components/onboarding/login.tsx
+++ b/apps/desktop/src/components/onboarding/login.tsx
@@ -9,6 +9,7 @@ import { getEntitlementsFromToken } from "../../billing";
 import { env } from "../../env";
 import { Route } from "../../routes/app/onboarding/_layout.index";
 import * as settings from "../../store/tinybase/store/settings";
+import { useTrialBeginModal } from "../devtool/trial-begin-modal";
 import { getBack, getNext, type StepProps } from "./config";
 import { STEP_ID_CONFIGURE_NOTICE } from "./configure-notice";
 import { Divider, OnboardingContainer } from "./shared";
@@ -19,6 +20,7 @@ export function Login({ onNavigate }: StepProps) {
   const search = Route.useSearch();
   const auth = useAuth();
   const [callbackUrl, setCallbackUrl] = useState("");
+  const { open: openTrialBeginModal } = useTrialBeginModal();
 
   const setLlmProvider = settings.UI.useSetValueCallback(
     "current_llm_provider",
@@ -78,6 +80,7 @@ export function Login({ onNavigate }: StepProps) {
     onSuccess: (isPro) => {
       if (isPro) {
         setTrialDefaults();
+        openTrialBeginModal();
       }
       const nextSearch = { ...search, pro: isPro };
       onNavigate({ ...nextSearch, step: getNext(nextSearch)! });
diff --git a/apps/desktop/src/components/settings/general/account.tsx b/apps/desktop/src/components/settings/general/account.tsx
index 6de276054a..f84fa84552 100644
--- a/apps/desktop/src/components/settings/general/account.tsx
+++ b/apps/desktop/src/components/settings/general/account.tsx
@@ -20,6 +20,7 @@ import { cn } from "@hypr/utils";
 import { useAuth } from "../../../auth";
 import { useBillingAccess } from "../../../billing";
 import { env } from "../../../env";
+import { useTrialBeginModal } from "../../devtool/trial-begin-modal";
 
 const WEB_APP_BASE_URL = env.VITE_APP_URL ?? "http://localhost:3000";
 
@@ -176,6 +177,7 @@ export function AccountSettings() {
 function BillingButton() {
   const auth = useAuth();
   const { isPro } = useBillingAccess();
+  const { open: openTrialBeginModal } = useTrialBeginModal();
 
   const canTrialQuery = useQuery({
     enabled: !!auth?.session && !isPro,
@@ -218,6 +220,7 @@ function BillingButton() {
         plan: "pro",
       });
       await auth?.refreshSession();
+      openTrialBeginModal();
     },
   });
 
diff --git a/packages/ui/src/components/ui/modal.tsx b/packages/ui/src/components/ui/modal.tsx
index fade9190a9..9ec2a37467 100644
--- a/packages/ui/src/components/ui/modal.tsx
+++ b/packages/ui/src/components/ui/modal.tsx
@@ -54,7 +54,7 @@ export function Modal({
     <>
       {showOverlay && (
         <div
-          className="fixed inset-0 z-50 bg-black/50 backdrop-blur-sm"
+          className="fixed inset-0 z-[100] bg-black/50 backdrop-blur-sm"
           aria-hidden="true"
           onClick={preventClose ? undefined : onClose}
         >
@@ -69,7 +69,7 @@ export function Modal({
         role="dialog"
         aria-modal="true"
         className={cn([
-          "fixed left-1/2 top-1/2 z-50 -translate-x-1/2 -translate-y-1/2",
+          "fixed left-1/2 top-1/2 z-[100] -translate-x-1/2 -translate-y-1/2",
           "overflow-clip rounded-lg bg-background shadow-lg",
           sizeClasses[size],
           className,