diff --git a/package.json b/package.json
index d4ce4114c9c47..dd7d6036cf087 100644
--- a/package.json
+++ b/package.json
@@ -3583,7 +3583,7 @@
 			},
 			{
 				"command": "gitlens.premium.purchase",
-				"title": "Unlock Premium Features for Private Code...",
+				"title": "Unlock Premium Features for Private Repos...",
 				"category": "GitLens Premium"
 			},
 			{
@@ -10464,18 +10464,28 @@
 			},
 			{
 				"view": "gitlens.views.worktrees",
-				"contents": "Worktrees are a premium feature, which require a free account for public code. [Learn more](https://dev.gitkraken.com/gitlens/premium-features).",
-				"when": "gitlens:premium:upgradeRequired == free+"
+				"contents": "To use premium GitLens features, please verify the email for the account you created.\n\n[Resend verification email](command:gitlens.premium.resendVerification)",
+				"when": "gitlens:premium:requiresVerification"
 			},
 			{
 				"view": "gitlens.views.worktrees",
-				"contents": "Worktrees are a premium feature, which require at least a Pro subscription for private code. [Learn more](https://dev.gitkraken.com/gitlens/premium-features).",
+				"contents": "Worktrees are a premium feature, which require a free account for public repos. [Learn more](https://dev.gitkraken.com/gitlens/premium-features).\n\nYou can try these premium features for free, without an account, for 3 days. All non-premium features will continue to be free without an account.",
+				"when": "gitlens:premium:upgradeRequired == free+ && !gitlens:premium:requiresVerification"
+			},
+			{
+				"view": "gitlens.views.worktrees",
+				"contents": "[Try premium features now](command:gitlens.premium.startPreview)\n\n[Create a free account](command:gitlens.premium.loginOrSignUp)",
+				"when": "gitlens:premium:upgradeRequired == free+ && !gitlens:premium:requiresVerification"
+			},
+			{
+				"view": "gitlens.views.worktrees",
+				"contents": "Worktrees are a premium feature, which require at least a Pro subscription for private repos. [Learn more](https://dev.gitkraken.com/gitlens/premium-features).",
 				"when": "gitlens:premium:upgradeRequired == paid"
 			},
 			{
 				"view": "gitlens.views.worktrees",
-				"contents": "[Unlock Premium Features](command:gitlens.showHomeView)",
-				"when": "gitlens:premium:upgradeRequired"
+				"contents": "[Upgrade your account](command:gitlens.premium.purchase)",
+				"when": "gitlens:premium:upgradeRequired == paid"
 			}
 		],
 		"views": {
diff --git a/src/commands/gitCommands.ts b/src/commands/gitCommands.ts
index 496bfed3f503c..f17221d6691c8 100644
--- a/src/commands/gitCommands.ts
+++ b/src/commands/gitCommands.ts
@@ -709,10 +709,23 @@ export class GitCommandsCommand extends Command {
 										void loadMore();
 										return;
 
+									case Directive.StartPreview:
+										void Container.instance.subscription.startPreview();
+										resolve(undefined);
+										return;
+
 									case Directive.RequiresVerification:
+										void Container.instance.subscription.resendVerification();
+										resolve(undefined);
+										return;
+
 									case Directive.RequiresFreeSubscription:
+										void Container.instance.subscription.loginOrSignUp();
+										resolve(undefined);
+										return;
+
 									case Directive.RequiresPaidSubscription:
-										void Container.instance.subscription.showHomeView();
+										void Container.instance.subscription.purchase();
 										resolve(undefined);
 										return;
 								}
diff --git a/src/commands/quickCommand.steps.ts b/src/commands/quickCommand.steps.ts
index 19712daac6076..500b82caf9c77 100644
--- a/src/commands/quickCommand.steps.ts
+++ b/src/commands/quickCommand.steps.ts
@@ -2236,27 +2236,30 @@ export async function* ensureAccessStep<
 	const access = await Container.instance.git.access(feature, state.repo.path);
 	if (access.allowed) return undefined;
 
-	let directive: Directive;
+	const directives: DirectiveQuickPickItem[] = [];
 	let placeholder: string;
 	if (access.subscription.current.account?.verified === false) {
-		directive = Directive.RequiresVerification;
+		directives.push(DirectiveQuickPickItem.create(Directive.RequiresVerification, true));
 		placeholder = 'You must verify your account email address before you can continue';
 	} else {
 		if (access.subscription.required == null) return undefined;
 
 		if (isPaidSubscriptionPlan(access.subscription.required)) {
-			directive = Directive.RequiresPaidSubscription;
-			placeholder = 'Requires a paid subscription';
+			directives.push(DirectiveQuickPickItem.create(Directive.RequiresPaidSubscription, true));
+			placeholder = 'Premium features require an upgraded account';
 		} else {
-			directive = Directive.RequiresFreeSubscription;
-			placeholder = 'Requires a Free+ account';
+			directives.push(
+				DirectiveQuickPickItem.create(Directive.StartPreview, true),
+				DirectiveQuickPickItem.create(Directive.RequiresFreeSubscription),
+			);
+			placeholder = 'Premium features require an account';
 		}
 	}
 
 	const step = QuickCommand.createPickStep<DirectiveQuickPickItem>({
 		title: appendReposToTitle(context.title, state, context),
 		placeholder: placeholder,
-		items: [DirectiveQuickPickItem.create(directive, true), DirectiveQuickPickItem.create(Directive.Cancel)],
+		items: [...directives, DirectiveQuickPickItem.create(Directive.Cancel)],
 	});
 
 	const selection: StepSelection<typeof step> = yield step;
diff --git a/src/constants.ts b/src/constants.ts
index 08c0496709c1e..eab88e128c3a7 100644
--- a/src/constants.ts
+++ b/src/constants.ts
@@ -243,6 +243,7 @@ export const enum ContextKeys {
 
 	Premium = 'gitlens:premium',
 	PremiumPaid = 'gitlens:premium:paid',
+	PremiumRequiresVerification = 'gitlens:premium:requiresVerification',
 	PremiumUpgradeRequired = 'gitlens:premium:upgradeRequired',
 }
 
diff --git a/src/env/browser/platform.ts b/src/env/browser/platform.ts
index 3b446fceadb13..26eebd814808d 100644
--- a/src/env/browser/platform.ts
+++ b/src/env/browser/platform.ts
@@ -6,3 +6,16 @@ const _userAgent = navigator.userAgent;
 export const isLinux = _platform === 'Linux' || _userAgent.indexOf('Linux') >= 0;
 export const isMac = _platform === 'macOS' || _userAgent.indexOf('Macintosh') >= 0;
 export const isWindows = _platform === 'Windows' || _userAgent.indexOf('Windows') >= 0;
+
+export function getPlatform(): string {
+	if (isWindows) {
+		return 'web-windows';
+	}
+	if (isMac) {
+		return 'web-macOS';
+	}
+	if (isLinux) {
+		return 'web-linux';
+	}
+	return 'web';
+}
diff --git a/src/env/node/platform.ts b/src/env/node/platform.ts
index 7ed8119798b9a..1a0875e3c5e36 100644
--- a/src/env/node/platform.ts
+++ b/src/env/node/platform.ts
@@ -5,3 +5,16 @@ export const isWeb = env.uiKind === UIKind.Web;
 export const isLinux = process.platform === 'linux';
 export const isMac = process.platform === 'darwin';
 export const isWindows = process.platform === 'win32';
+
+export function getPlatform(): string {
+	if (isWindows) {
+		return 'windows';
+	}
+	if (isMac) {
+		return 'macOS';
+	}
+	if (isLinux) {
+		return 'linux';
+	}
+	return isWeb ? 'web' : 'unknown';
+}
diff --git a/src/premium/subscription/subscriptionService.ts b/src/premium/subscription/subscriptionService.ts
index 8018cc070eaf4..d5987562742e3 100644
--- a/src/premium/subscription/subscriptionService.ts
+++ b/src/premium/subscription/subscriptionService.ts
@@ -1,6 +1,7 @@
 import {
 	authentication,
 	AuthenticationSession,
+	version as codeVersion,
 	commands,
 	Disposable,
 	env,
@@ -13,6 +14,7 @@ import {
 	window,
 } from 'vscode';
 import { fetch } from '@env/fetch';
+import { getPlatform } from '@env/platform';
 import { Commands, ContextKeys } from '../../constants';
 import type { Container } from '../../container';
 import { setContext } from '../../context';
@@ -157,6 +159,8 @@ export class SubscriptionService implements Disposable {
 	}
 
 	async loginOrSignUp(): Promise<boolean> {
+		void this.showHomeView();
+
 		const session = await this.ensureSession(true);
 		return Boolean(session);
 	}
@@ -232,10 +236,10 @@ export class SubscriptionService implements Disposable {
 		let { plan, preview } = this._subscription;
 		if (preview != null || plan.effective.id !== SubscriptionPlanId.Free) {
 			if (plan.effective.id === SubscriptionPlanId.Free) {
-				const ok = { title: 'Create Free+ Account' };
+				const ok = { title: 'Extend Trial' };
 				const cancel = { title: 'Cancel' };
 				const result = await window.showInformationMessage(
-					'Your premium feature preview has expired. Please create a Free+ account to extend your trial.',
+					'Your premium feature trial has expired. Please create a free account to extend your trial.',
 					ok,
 					cancel,
 				);
@@ -249,13 +253,16 @@ export class SubscriptionService implements Disposable {
 
 		const startedOn = new Date();
 
+		let days;
 		let expiresOn = new Date(startedOn);
 		if (!this.container.debugging && this.container.env !== 'dev') {
 			// Normalize the date to just before midnight on the same day
 			expiresOn.setHours(23, 59, 59, 999);
 			expiresOn = createFromDateDelta(expiresOn, { days: 3 });
+			days = 3;
 		} else {
 			expiresOn = createFromDateDelta(expiresOn, { minutes: 1 });
+			days = 0;
 		}
 
 		preview = {
@@ -271,6 +278,8 @@ export class SubscriptionService implements Disposable {
 			},
 			preview: preview,
 		});
+
+		void window.showInformationMessage(`You can now try premium GitLens features for ${days} days.`);
 	}
 
 	async validate(): Promise<void> {
@@ -282,12 +291,24 @@ export class SubscriptionService implements Disposable {
 
 	private async checkInAndValidate(session: AuthenticationSession): Promise<void> {
 		try {
+			const checkInData = {
+				id: session.account.id,
+				platform: getPlatform(),
+				gitlensVersion: this.container.version,
+				vscodeEdition: env.appName,
+				vscodeHost: env.appHost,
+				vscodeVersion: codeVersion,
+				previewStartedOn: this._subscription.preview?.startedOn,
+				previewExpiresOn: this._subscription.preview?.expiresOn,
+			};
+
 			const rsp = await fetch(Uri.joinPath(this.baseApiUri, 'gitlens/checkin').toString(), {
 				method: 'POST',
 				headers: {
 					Authorization: `Bearer ${session.accessToken}`,
 					'User-Agent': userAgent,
 				},
+				body: JSON.stringify(checkInData),
 			});
 
 			if (!rsp.ok) {
@@ -506,6 +527,7 @@ export class SubscriptionService implements Disposable {
 
 		void setContext(ContextKeys.Premium, actual.id);
 		void setContext(ContextKeys.PremiumPaid, isPaidSubscriptionPlan(actual.id));
+		void setContext(ContextKeys.PremiumRequiresVerification, this._subscription.account?.verified === false);
 	}
 
 	private updateStatusBar(pending: boolean = false): void {
@@ -530,7 +552,7 @@ export class SubscriptionService implements Disposable {
 				this._statusBarSubscription.text = effective.name;
 				this._statusBarSubscription.command = Commands.ShowHomeView;
 				this._statusBarSubscription.tooltip = new MarkdownString(
-					`You are on **${effective.name}**\n\nClick to upgrade to Free+ for access to premium features for public code`,
+					`You are on **${effective.name}**\n\nClick to upgrade to Free+ for access to premium features for public repos`,
 					true,
 				);
 				break;
diff --git a/src/quickpicks/items/directive.ts b/src/quickpicks/items/directive.ts
index 044d7fafe393c..ef88a5f048dbc 100644
--- a/src/quickpicks/items/directive.ts
+++ b/src/quickpicks/items/directive.ts
@@ -7,8 +7,10 @@ export enum Directive {
 	LoadMore,
 	Noop,
 	RequiresVerification,
+
 	RequiresFreeSubscription,
 	RequiresPaidSubscription,
+	StartPreview,
 }
 
 export namespace Directive {
@@ -43,17 +45,21 @@ export namespace DirectiveQuickPickItem {
 				case Directive.Noop:
 					label = 'Try again';
 					break;
+				case Directive.StartPreview:
+					label = 'Try Premium Features Now';
+					detail = 'Try premium features for free, without an account, for 3 days';
+					break;
 				case Directive.RequiresVerification:
 					label = 'Resend Verification Email';
 					detail = 'You must verify your account email address before you can continue';
 					break;
 				case Directive.RequiresFreeSubscription:
-					label = 'Create a Free+ Account';
-					detail = 'To unlock all premium features for public code';
+					label = 'Create a Free Account';
+					detail = 'To unlock premium features';
 					break;
 				case Directive.RequiresPaidSubscription:
-					label = 'Upgrade to a paid subscription';
-					detail = 'To unlock all premium features for private code';
+					label = 'Upgrade Your Account';
+					detail = 'To unlock premium features for private repos';
 					break;
 			}
 		}
diff --git a/src/webviews/apps/premium/home/home.html b/src/webviews/apps/premium/home/home.html
index 5a1199eaa8662..5888f7ec52a23 100644
--- a/src/webviews/apps/premium/home/home.html
+++ b/src/webviews/apps/premium/home/home.html
@@ -52,7 +52,9 @@ <h3>Welcome to GitLens 12!</h3>
 					individually.
 				</li>
 			</ul>
-			<vscode-button data-action="command:gitlens.home.hideWelcome" appearance="secondary">Hide</vscode-button>
+			<vscode-button data-action="command:gitlens.home.hideWelcome" appearance="secondary"
+				>Dismiss welcome</vscode-button
+			>
 		</section>
 	</template>
 
@@ -62,8 +64,11 @@ <h3>Try GitLens Premium Features</h3>
 			<p>
 				Premium features like <a href="">Git Worktrees</a> and <a href="">Visual File History</a> are available
 				with a free account, with many more features coming soon, including a commit graph and GitHub Enterprise
-				integration. Access to premium features for private code is available with a paid account.
-				<a href="">Learn more</a> about GitLens premium features.
+				integration. Access to premium features for private repos is available with a paid account.
+			</p>
+			<p>
+				<a href="https://dev.gitkraken.com/gitlens/premium-features">Learn more</a> about GitLens premium
+				features.
 			</p>
 			<p>
 				You can try these premium features for free, without an account, for 3 days. All non-premium features
@@ -83,11 +88,14 @@ <h3>Trying Premium Features</h3>
 			<p>
 				You are currently trying premium GitLens features, like <a href="">Git Worktrees</a> and
 				<a href="">Visual File History</a>, for <span data-bind="previewDays">3 more days</span>.
-				<a href="">Learn more</a> about GitLens premium features.
+			</p>
+			<p>
+				<a href="https://dev.gitkraken.com/gitlens/premium-features">Learn more</a> about GitLens premium
+				features.
 			</p>
 			<p>
 				After that time, a free account will be required to continue using these premium features for public
-				code, or you can puchase a paid plan to access premium features for private code.
+				code, or you can puchase a paid plan to access premium features for private repos.
 			</p>
 			<vscode-button data-action="command:gitlens.premium.loginOrSignUp">Create a free account</vscode-button>
 			<vscode-button data-action="command:gitlens.premium.purchase">Purchase a plan</vscode-button>
@@ -101,15 +109,16 @@ <h3>Continue using Premium Features</h3>
 			<p>
 				Premium GitLens features like <a href="">Git Worktrees</a> and <a href="">Visual File History</a>, a
 				commit graph (coming soon), and GitHub Enterprise integration (coming soon) are only available with an
-				account. <a href="">Learn more</a> about GitLens premium features.
+				account.
+			</p>
+			<p>
+				<a href="https://dev.gitkraken.com/gitlens/premium-features">Learn more</a> about GitLens premium
+				features.
 			</p>
 			<p>Create a free account to continue trialing premium features for all code for an additional 7 days.</p>
 			<vscode-button data-action="command:gitlens.premium.loginOrSignUp">Create a free account</vscode-button>
 			<vscode-button data-action="command:gitlens.premium.purchase">Purchase a plan</vscode-button>
 			<p>All non-premium features will continue to be free without an account.</p>
-			<vscode-button data-action="command:gitlens.home.hideSubscription" appearance="secondary"
-				>Close</vscode-button
-			>
 		</section>
 	</template>
 
@@ -118,14 +127,14 @@ <h3>Continue using Premium Features</h3>
 			<h3>Premium Feature Trial</h3>
 			<p>
 				You are currently trialing premium GitLens features like <a href="">Git Worktrees</a> and
-				<a href="">Visual File History</a> for both public and private code. In
-				<span data-bind="trialDays">7 days</span>, accessing these premium features for private code will
+				<a href="">Visual File History</a> for both public and private repos. In
+				<span data-bind="trialDays">7 days</span>, accessing these premium features for private repos will
 				require a paid account.
 			</p>
 			<vscode-button data-action="command:gitlens.premium.purchase">Purchase a plan</vscode-button>
 			<p>
-				With your free account, you will continue to have access to premium features for public code, as well as
-				all non-premium features.
+				With your free account, you will continue to have access to premium features for public repos, as well
+				as all non-premium features.
 			</p>
 			<!-- <vscode-button appearance="secondary">Close</vscode-button> -->
 		</section>
@@ -133,12 +142,12 @@ <h3>Premium Feature Trial</h3>
 
 	<template id="state:verify-email">
 		<section>
-			<h3>Please validate your email</h3>
-			<p>To continue using premium GitLens features, please validate the email for the account you created.</p>
+			<h3>Please verify your email</h3>
+			<p>To continue using premium GitLens features, please verify the email for the account you created.</p>
 			<vscode-button data-action="command:gitlens.premium.resendVerification"
 				>Resend verification email</vscode-button
 			>
-			<vscode-button data-action="command:gitlens.premium.validate">Refresh validation</vscode-button>
+			<vscode-button data-action="command:gitlens.premium.validate">Refresh verification status</vscode-button>
 			<p>All non-premium features will continue to be free without an account.</p>
 		</section>
 	</template>
@@ -148,15 +157,15 @@ <h3>Please validate your email</h3>
 			<h3>GitLens Free+</h3>
 			<p>
 				With your free account, you have access to GitLens Free+, which unlocks premium features like
-				<a href="">Git Worktrees</a> and <a href="">Visual File History</a> for public code. More premium
+				<a href="">Git Worktrees</a> and <a href="">Visual File History</a> for public repos. More premium
 				features like a commit graph and GitHub Enterprise integration are coming soon.
-				<a href="">Learn more</a> about GitLens premium features.
 			</p>
-			<p>Access to premium features for private code requires a paid plan.</p>
+			<p>
+				<a href="https://dev.gitkraken.com/gitlens/premium-features">Learn more</a> about GitLens premium
+				features.
+			</p>
+			<p>Access to premium features for private repos requires a paid plan.</p>
 			<vscode-button data-action="command:gitlens.premium.purchase">Purchase a plan</vscode-button>
-			<vscode-button data-action="command:gitlens.home.hideSubscription" appearance="secondary"
-				>Close</vscode-button
-			>
 		</section>
 	</template>
 
@@ -172,9 +181,6 @@ <h3 data-bind="plan">GitLens Pro</h3>
 				Additional premium featues like a commit graph and GitHub Enterprise integration are coming soon.
 				<a href="">Learn more</a> about GitLens premium features.
 			</p>
-			<vscode-button data-action="command:gitlens.home.hideSubscription" appearance="secondary"
-				>Close</vscode-button
-			>
 		</section>
 	</template>
 </html>