diff --git a/src-tauri/Cargo.lock b/src-tauri/Cargo.lock
index ea1796d6..003ca0f5 100644
--- a/src-tauri/Cargo.lock
+++ b/src-tauri/Cargo.lock
@@ -514,6 +514,25 @@ dependencies = [
  "generic-array",
 ]
 
+[[package]]
+name = "block-sys"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "ae85a0696e7ea3b835a453750bf002770776609115e6d25c6d2ff28a8200f7e7"
+dependencies = [
+ "objc-sys",
+]
+
+[[package]]
+name = "block2"
+version = "0.4.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e58aa60e59d8dbfcc36138f5f18be5f24394d33b38b24f7fd0b1caa33095f22f"
+dependencies = [
+ "block-sys",
+ "objc2",
+]
+
 [[package]]
 name = "block2"
 version = "0.5.1"
@@ -2420,6 +2439,16 @@ dependencies = [
  "png",
 ]
 
+[[package]]
+name = "icrate"
+version = "0.1.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3fb69199826926eb864697bddd27f73d9fddcffc004f5733131e15b465e30642"
+dependencies = [
+ "block2 0.4.0",
+ "objc2",
+]
+
 [[package]]
 name = "ident_case"
 version = "1.0.1"
@@ -3292,7 +3321,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e4e89ad9e3d7d297152b17d39ed92cd50ca8063a89a9fa569046d41568891eff"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "libc",
  "objc2",
  "objc2-core-data",
@@ -3308,7 +3337,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "74dd3b56391c7a0596a295029734d3c1c5e7e510a4cb30245f8221ccea96b009"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-core-location",
  "objc2-foundation",
@@ -3320,7 +3349,7 @@ version = "0.2.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a5ff520e9c33812fd374d8deecef01d4a840e7b41862d849513de77e44aa4889"
 dependencies = [
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-foundation",
 ]
@@ -3332,7 +3361,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "617fbf49e071c178c0b24c080767db52958f716d9eabdf0890523aeae54773ef"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-foundation",
 ]
@@ -3343,7 +3372,7 @@ version = "0.2.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "55260963a527c99f1819c4f8e3b47fe04f9650694ef348ffd2227e8196d34c80"
 dependencies = [
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-foundation",
  "objc2-metal",
@@ -3355,7 +3384,7 @@ version = "0.2.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "000cfee34e683244f284252ee206a27953279d370e309649dc3ee317b37e5781"
 dependencies = [
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-contacts",
  "objc2-foundation",
@@ -3374,7 +3403,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0ee638a5da3799329310ad4cfa62fbf045d5f56e3ef5ba4149e7452dcf89d5a8"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "dispatch",
  "libc",
  "objc2",
@@ -3386,7 +3415,7 @@ version = "0.2.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "a1a1ae721c5e35be65f01a03b6d2ac13a54cb4fa70d8a5da293d7b0020261398"
 dependencies = [
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-app-kit",
  "objc2-foundation",
@@ -3399,11 +3428,23 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "dd0cba1276f6023976a406a14ffa85e1fdd19df6b0f737b063b95f6c8c7aadd6"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-foundation",
 ]
 
+[[package]]
+name = "objc2-osa-kit"
+version = "0.2.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6788b04a18ea31e3dc3ab256b8546639e5bbae07c1a0dc4ea8615252bc6aee9a"
+dependencies = [
+ "bitflags 2.6.0",
+ "objc2",
+ "objc2-app-kit",
+ "objc2-foundation",
+]
+
 [[package]]
 name = "objc2-quartz-core"
 version = "0.2.2"
@@ -3411,7 +3452,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e42bee7bff906b14b167da2bac5efe6b6a07e6f7c0a21a7308d40c960242dc7a"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-foundation",
  "objc2-metal",
@@ -3434,7 +3475,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "b8bb46798b20cd6b91cbd113524c490f1686f4c4e8f49502431415f3512e2b6f"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-cloud-kit",
  "objc2-core-data",
@@ -3454,7 +3495,7 @@ version = "0.2.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "44fa5f9748dbfe1ca6c0b79ad20725a11eca7c2218bceb4b005cb1be26273bfe"
 dependencies = [
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-foundation",
 ]
@@ -3466,7 +3507,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "76cfcbf642358e8689af64cee815d139339f3ed8ad05103ed5eaf73db8d84cb3"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-core-location",
  "objc2-foundation",
@@ -3479,7 +3520,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "68bc69301064cebefc6c4c90ce9cba69225239e4b8ff99d445a2b5563797da65"
 dependencies = [
  "bitflags 2.6.0",
- "block2",
+ "block2 0.5.1",
  "objc2",
  "objc2-app-kit",
  "objc2-foundation",
@@ -3611,6 +3652,20 @@ dependencies = [
  "windows-sys 0.59.0",
 ]
 
+[[package]]
+name = "osakit"
+version = "0.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "35366a452fce3f8947eb2f33226a133aaf0cacedef2af67ade348d58be7f85d0"
+dependencies = [
+ "icrate",
+ "objc2-foundation",
+ "objc2-osa-kit",
+ "serde",
+ "serde_json",
+ "thiserror 1.0.63",
+]
+
 [[package]]
 name = "pad"
 version = "0.1.6"
@@ -4513,7 +4568,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "8af382a047821a08aa6bfc09ab0d80ff48d45d8726f7cd8e44891f7cb4a4278e"
 dependencies = [
  "ashpd",
- "block2",
+ "block2 0.5.1",
  "glib-sys",
  "gobject-sys",
  "gtk-sys",
@@ -5980,17 +6035,18 @@ dependencies = [
 
 [[package]]
 name = "tauri-plugin-updater"
-version = "2.4.0"
+version = "2.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ad3de2b9203bb00b9765e637a9878aaace34df40ae484878b8cea7a5bd5f9188"
+checksum = "ebf3da08c36fb03c98c76e5563d4e74d9a590df0f40978cbe07f39cb52833f7c"
 dependencies = [
  "base64 0.22.1",
- "dirs 5.0.1",
+ "dirs 6.0.0",
  "flate2",
  "futures-util",
  "http",
  "infer",
  "minisign-verify",
+ "osakit",
  "percent-encoding",
  "reqwest",
  "semver",
@@ -7544,7 +7600,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1e644bf458e27b11b0ecafc9e5633d1304fdae82baca1d42185669752fe6ca4f"
 dependencies = [
  "base64 0.22.1",
- "block2",
+ "block2 0.5.1",
  "cookie",
  "crossbeam-channel",
  "dpi",
diff --git a/src-tauri/Cargo.toml b/src-tauri/Cargo.toml
index 08d864f5..5b9c4bc6 100644
--- a/src-tauri/Cargo.toml
+++ b/src-tauri/Cargo.toml
@@ -67,7 +67,7 @@ tauri-plugin-opener = "2.2.5"
 tauri-plugin-os = "2.2.0"
 tauri-plugin-shell = { workspace = true }
 tauri-plugin-single-instance = "2.2.1"
-tauri-plugin-updater = "2.4.0"
+tauri-plugin-updater = "2.5.0"
 tauri-plugin-window-state = "2.2.1"
 tokio = { version = "1.43.0", features = ["sync"] }
 tokio-stream = "0.1.17"
diff --git a/src-web/components/GitDropdown.tsx b/src-web/components/GitDropdown.tsx
index 059ed2da..83d6f198 100644
--- a/src-web/components/GitDropdown.tsx
+++ b/src-web/components/GitDropdown.tsx
@@ -336,12 +336,14 @@ function SetupSyncDropdown({ workspaceMeta }: { workspaceMeta: WorkspaceMeta })
           label: banner,
         },
         {
+          color: 'success',
           label: 'Open Workspace Settings',
           leftSlot: <Icon icon="settings" />,
           onSelect() {
             openWorkspaceSettings.mutate({ openSyncMenu: true });
           },
         },
+        { type: 'separator' },
         {
           label: 'Hide This Message',
           leftSlot: <Icon icon="eye_closed" />,
@@ -396,8 +398,8 @@ function SetupGitDropdown({
           leftSlot: <Icon icon="magic_wand" />,
           onSelect: initRepo,
         },
+        { type: 'separator' },
         {
-          color: 'warning',
           label: 'Hide This Message',
           leftSlot: <Icon icon="eye_closed" />,
           async onSelect() {
diff --git a/src-web/components/LicenseBadge.tsx b/src-web/components/LicenseBadge.tsx
index 06dfedc6..45ca9057 100644
--- a/src-web/components/LicenseBadge.tsx
+++ b/src-web/components/LicenseBadge.tsx
@@ -1,14 +1,14 @@
-import { openUrl } from '@tauri-apps/plugin-opener';
 import type { LicenseCheckStatus } from '@yaakapp-internal/license';
 import { useLicense } from '@yaakapp-internal/license';
 import type { ReactNode } from 'react';
+import { openSettings } from '../commands/openSettings';
 import { appInfo } from '../hooks/useAppInfo';
+import { useLicenseConfirmation } from '../hooks/useLicenseConfirmation';
 import type { ButtonProps } from './core/Button';
 import { Button } from './core/Button';
 import { Icon } from './core/Icon';
 import { HStack } from './core/Stacks';
-import { openSettings } from '../commands/openSettings';
-import {SettingsTab} from "./Settings/SettingsTab";
+import { SettingsTab } from './Settings/SettingsTab';
 
 const details: Record<
   LicenseCheckStatus['type'] | 'dev' | 'beta',
@@ -26,22 +26,30 @@ const details: Record<
   dev: { label: 'Develop', color: 'secondary' },
   commercial_use: null,
   invalid_license: { label: 'License Error', color: 'danger' },
-  personal_use: { label: 'Personal Use', color: 'primary' },
-  trialing: { label: 'Personal Use', color: 'primary' },
+  personal_use: { label: 'Personal Use', color: 'success' },
+  trialing: { label: 'Active Trial', color: 'success' },
 };
 
 export function LicenseBadge() {
   const { check } = useLicense();
+  const [licenseDetails, setLicenseDetails] = useLicenseConfirmation();
 
-  if (check.data == null) {
+  // Hasn't loaded yet
+  if (licenseDetails == null || check.data == null) {
     return null;
   }
 
-  const checkType = appInfo.version.includes('beta')
-    ? 'beta'
-    : appInfo.isDev
-      ? 'dev'
-      : check.data.type;
+  // User has confirmed they are using Yaak for personal use only, so hide badge
+  if (licenseDetails.confirmedPersonalUse) {
+    return null;
+  }
+
+  // User is trialing but has already seen the message, so hide badge
+  if (check.data.type === 'trialing' && licenseDetails.hasDismissedTrial) {
+    return null;
+  }
+
+  const checkType = appInfo.version.includes('beta') ? 'beta' : check.data.type;
   const detail = details[checkType];
   if (detail == null) {
     return null;
@@ -53,11 +61,13 @@ export function LicenseBadge() {
       variant="border"
       className="!rounded-full mx-1"
       onClick={async () => {
-        if (checkType === 'beta') {
-          await openUrl('https://feedback.yaak.app');
-        } else {
-          openSettings.mutate(SettingsTab.License);
+        if (check.data.type === 'trialing') {
+          await setLicenseDetails((v) => ({
+            ...v,
+            dismissedTrial: true,
+          }));
         }
+        openSettings.mutate(SettingsTab.License);
       }}
       color={detail.color}
       event={{ id: 'license-badge', status: check.data.type }}
diff --git a/src-web/components/Settings/SettingsLicense.tsx b/src-web/components/Settings/SettingsLicense.tsx
index 7d57d40b..9cb58c90 100644
--- a/src-web/components/Settings/SettingsLicense.tsx
+++ b/src-web/components/Settings/SettingsLicense.tsx
@@ -1,47 +1,75 @@
+import { openUrl } from '@tauri-apps/plugin-opener';
 import { useLicense } from '@yaakapp-internal/license';
 import { formatDistanceToNowStrict } from 'date-fns';
 import React, { useState } from 'react';
+import { useLicenseConfirmation } from '../../hooks/useLicenseConfirmation';
 import { useToggle } from '../../hooks/useToggle';
 import { Banner } from '../core/Banner';
 import { Button } from '../core/Button';
+import { Checkbox } from '../core/Checkbox';
 import { Icon } from '../core/Icon';
 import { Link } from '../core/Link';
 import { PlainInput } from '../core/PlainInput';
 import { HStack, VStack } from '../core/Stacks';
-import { openUrl } from '@tauri-apps/plugin-opener';
 
 export function SettingsLicense() {
   const { check, activate } = useLicense();
   const [key, setKey] = useState<string>('');
   const [activateFormVisible, toggleActivateFormVisible] = useToggle(false);
+  const [licenseDetails, setLicenseDetails] = useLicenseConfirmation();
+  const [checked, setChecked] = useState<boolean>(false);
 
   if (check.isPending) {
     return null;
   }
 
   return (
-    <div className="flex flex-col gap-6">
+    <div className="flex flex-col gap-6 max-w-lg">
       {check.data?.type === 'commercial_use' ? (
         <Banner color="success">
           <strong>License active!</strong> Enjoy using Yaak for commercial use.
         </Banner>
-      ) : (
-        <Banner color="primary" className="flex flex-col gap-3 max-w-lg">
-          {check.data?.type === 'trialing' && (
-            <p className="select-text">
-              <strong>
-                You have {formatDistanceToNowStrict(check.data.end)} remaining on your trial.
-              </strong>
-            </p>
-          )}
+      ) : check.data?.type == 'trialing' ? (
+        <Banner color="success" className="flex flex-col gap-3 max-w-lg">
           <p className="select-text">
-            A commercial license is required if using Yaak within a for-profit organization.{' '}
-            <Link href="https://yaak.app/pricing" className="text-notice">
-              Learn More
-            </Link>
+            <strong>{formatDistanceToNowStrict(check.data.end)} days remaining</strong> on your
+            commercial use trial
           </p>
         </Banner>
-      )}
+      ) : check.data?.type == 'personal_use' && !licenseDetails?.confirmedPersonalUse ? (
+        <Banner color="success" className="flex flex-col gap-3 max-w-lg">
+          <p className="select-text">
+            Your 30-day trial has ended. Please activate a license or confirm how you&apos;re using
+            Yaak.
+          </p>
+          <form
+            className="flex flex-col gap-3 items-start"
+            onSubmit={async (e) => {
+              e.preventDefault();
+              await setLicenseDetails((v) => ({
+                ...v,
+                confirmedPersonalUse: true,
+              }));
+            }}
+          >
+            <Checkbox
+              checked={checked}
+              onChange={setChecked}
+              title="I am only using Yaak for personal use"
+            />
+            <Button type="submit" disabled={!checked} size="xs" variant="border" color="success">
+              Confirm
+            </Button>
+          </form>
+        </Banner>
+      ) : null}
+
+      <p className="select-text">
+        A commercial license is required if using Yaak within a for-profit organization.{' '}
+        <Link href="https://yaak.app/pricing" className="text-notice">
+          Learn More
+        </Link>
+      </p>
 
       {check.error && <Banner color="danger">{check.error}</Banner>}
       {activate.error && <Banner color="danger">{activate.error}</Banner>}
@@ -80,7 +108,7 @@ export function SettingsLicense() {
           <Button
             color="secondary"
             size="sm"
-            onClick={() => open('https://yaak.app/pricing?ref=app.yaak.desktop')}
+            onClick={() => openUrl('https://yaak.app/pricing?ref=app.yaak.desktop')}
             rightSlot={<Icon icon="external_link" />}
             event="license.purchase"
           >
diff --git a/src-web/components/SettingsDropdown.tsx b/src-web/components/SettingsDropdown.tsx
index 492e0faa..ab73951c 100644
--- a/src-web/components/SettingsDropdown.tsx
+++ b/src-web/components/SettingsDropdown.tsx
@@ -65,7 +65,7 @@ export function SettingsDropdown() {
           label: 'Feedback',
           leftSlot: <Icon icon="chat" />,
           rightSlot: <Icon icon="external_link" />,
-          onSelect: () => openUrl('https://yaak.app/roadmap'),
+          onSelect: () => openUrl('https://yaak.app/feedback'),
         },
         {
           label: 'Changelog',
diff --git a/src-web/components/core/Dropdown.tsx b/src-web/components/core/Dropdown.tsx
index 2a639b3d..f3e6982c 100644
--- a/src-web/components/core/Dropdown.tsx
+++ b/src-web/components/core/Dropdown.tsx
@@ -55,7 +55,7 @@ export type DropdownItemDefault = {
   label: ReactNode;
   hotKeyAction?: HotkeyAction;
   hotKeyLabelOnly?: boolean;
-  color?: 'default' | 'danger' | 'info' | 'warning' | 'notice';
+  color?: 'default' | 'danger' | 'info' | 'warning' | 'notice' | 'success';
   disabled?: boolean;
   hidden?: boolean;
   leftSlot?: ReactNode;
@@ -111,20 +111,23 @@ export const Dropdown = forwardRef<DropdownRef, DropdownProps>(function Dropdown
   const buttonRef = useRef<HTMLButtonElement>(null);
   const menuRef = useRef<Omit<DropdownRef, 'open'>>(null);
 
-  const setIsOpen = useCallback((o: SetStateAction<boolean>) => {
-    jotaiStore.set(openAtom, (prevId) => {
-      const prevIsOpen = prevId === id.current;
-      const newIsOpen = typeof o === 'function' ? o(prevIsOpen) : o;
-      // Persist background color of button until we close the dropdown
-      if (newIsOpen) {
-        onOpen?.();
-        buttonRef.current!.style.backgroundColor = window
-          .getComputedStyle(buttonRef.current!)
-          .getPropertyValue('background-color');
-      }
-      return newIsOpen ? id.current : null; // Set global atom to current ID to signify open state
-    });
-  }, [onOpen]);
+  const setIsOpen = useCallback(
+    (o: SetStateAction<boolean>) => {
+      jotaiStore.set(openAtom, (prevId) => {
+        const prevIsOpen = prevId === id.current;
+        const newIsOpen = typeof o === 'function' ? o(prevIsOpen) : o;
+        // Persist background color of button until we close the dropdown
+        if (newIsOpen) {
+          onOpen?.();
+          buttonRef.current!.style.backgroundColor = window
+            .getComputedStyle(buttonRef.current!)
+            .getPropertyValue('background-color');
+        }
+        return newIsOpen ? id.current : null; // Set global atom to current ID to signify open state
+      });
+    },
+    [onOpen],
+  );
 
   // Because a different dropdown can cause ours to close, a useEffect([isOpen]) is the only method
   // we have of detecting the dropdown closed, to do cleanup.
@@ -642,6 +645,7 @@ function MenuItem({ className, focused, onFocus, item, onSelect, ...props }: Men
         'min-w-[8rem] outline-none px-2 mx-1.5 flex whitespace-nowrap',
         'focus:bg-surface-highlight focus:text rounded',
         item.color === 'danger' && '!text-danger',
+        item.color === 'success' && '!text-success',
         item.color === 'warning' && '!text-warning',
         item.color === 'notice' && '!text-notice',
         item.color === 'info' && '!text-info',
diff --git a/src-web/hooks/useHotKey.ts b/src-web/hooks/useHotKey.ts
index 54e1da4f..3b0b8362 100644
--- a/src-web/hooks/useHotKey.ts
+++ b/src-web/hooks/useHotKey.ts
@@ -115,7 +115,6 @@ export function useHotKey(
       if (e.metaKey) currentKeysWithModifiers.add('Meta');
       if (e.shiftKey) currentKeysWithModifiers.add('Shift');
 
-      console.log('down', currentKeysWithModifiers);
       for (const [hkAction, hkKeys] of Object.entries(hotkeys) as [HotkeyAction, string[]][]) {
         if (
           (e.target instanceof HTMLInputElement || e.target instanceof HTMLTextAreaElement) &&
diff --git a/src-web/hooks/useLicenseConfirmation.ts b/src-web/hooks/useLicenseConfirmation.ts
new file mode 100644
index 00000000..fe40cd05
--- /dev/null
+++ b/src-web/hooks/useLicenseConfirmation.ts
@@ -0,0 +1,15 @@
+import { useKeyValue } from './useKeyValue';
+
+interface LicenseConfirmation {
+  hasDismissedTrial: boolean;
+  confirmedPersonalUse: boolean;
+}
+
+export function useLicenseConfirmation() {
+  const { set, value } = useKeyValue<LicenseConfirmation>({
+    key: 'license_confirmation',
+    fallback: { hasDismissedTrial: false, confirmedPersonalUse: false },
+  });
+
+  return [value, set] as const;
+}