diff --git a/app/layouts/shell.tsx b/app/layouts/shell.tsx
index 5fb903f..76f37cb 100644
--- a/app/layouts/shell.tsx
+++ b/app/layouts/shell.tsx
@@ -63,6 +63,11 @@ export async function loader({
 						return false;
 					}
 
+					if (context.sessions.onboardForSubject(sessionUser.subject)) {
+						// Assume onboarded
+						return true;
+					}
+
 					return subject === sessionUser.subject;
 				});
 
@@ -102,7 +107,8 @@ export default function Shell() {
 	return (
 		<>
 			<Header {...data} />
-			{data.uiAccess ? (
+			{/* Always show the outlet if we are onboarding */}
+			{(data.onboarding ? true : data.uiAccess) ? (
 				<Outlet />
 			) : (
 				<Card className="mx-auto w-fit mt-24">
diff --git a/app/routes.ts b/app/routes.ts
index 845ff15..fd56844 100644
--- a/app/routes.ts
+++ b/app/routes.ts
@@ -15,6 +15,7 @@ export default [
 	// Double nested to separate error propagations
 	layout('layouts/shell.tsx', [
 		route('/onboarding', 'routes/users/onboarding.tsx'),
+		route('/onboarding/skip', 'routes/users/onboarding-skip.tsx'),
 		layout('layouts/dashboard.tsx', [
 			...prefix('/machines', [
 				index('routes/machines/overview.tsx'),
diff --git a/app/routes/users/onboarding-skip.tsx b/app/routes/users/onboarding-skip.tsx
new file mode 100644
index 0000000..06a9837
--- /dev/null
+++ b/app/routes/users/onboarding-skip.tsx
@@ -0,0 +1,16 @@
+import { LoaderFunctionArgs, redirect } from 'react-router';
+import { LoadContext } from '~/server';
+
+export async function loader({
+	request,
+	context,
+}: LoaderFunctionArgs<LoadContext>) {
+	const session = await context.sessions.auth(request);
+	const user = session.get('user');
+	if (!user) {
+		return redirect('/login');
+	}
+
+	context.sessions.overrideOnboarding(user.subject, true);
+	return redirect('/machines');
+}
diff --git a/app/routes/users/onboarding.tsx b/app/routes/users/onboarding.tsx
index 4f7b505..13faca7 100644
--- a/app/routes/users/onboarding.tsx
+++ b/app/routes/users/onboarding.tsx
@@ -1,3 +1,4 @@
+import { ArrowRight } from 'lucide-react';
 import { useEffect } from 'react';
 import { GrApple } from 'react-icons/gr';
 import { ImFinder } from 'react-icons/im';
@@ -335,6 +336,12 @@ export default function Page() {
 						</div>
 					)}
 				</Card>
+				<NavLink to="/onboarding/skip" className="col-span-2 w-max mx-auto">
+					<Button className="flex items-center gap-1">
+						I already know what I'm doing
+						<ArrowRight className="p-1" />
+					</Button>
+				</NavLink>
 			</div>
 		</div>
 	);
diff --git a/app/server/web/sessions.ts b/app/server/web/sessions.ts
index c370ba3..0cc05a0 100644
--- a/app/server/web/sessions.ts
+++ b/app/server/web/sessions.ts
@@ -47,12 +47,12 @@ interface CookieOptions {
 
 class Sessionizer {
 	private storage: SessionStorage<JoinedSession, Error>;
-	private caps: Record<string, Capabilities>;
+	private caps: Record<string, { c: Capabilities; oo?: boolean }>;
 	private capsPath?: string;
 
 	constructor(
 		options: CookieOptions,
-		caps: Record<string, Capabilities>,
+		caps: Record<string, { c: Capabilities; oo?: boolean }>,
 		capsPath?: string,
 	) {
 		this.caps = caps;
@@ -86,7 +86,7 @@ class Sessionizer {
 	}
 
 	roleForSubject(subject: string): keyof typeof Roles | undefined {
-		const role = this.caps[subject];
+		const role = this.caps[subject].c;
 		// We need this in string form based on Object.keys of the roles
 		for (const [key, value] of Object.entries(Roles)) {
 			if (value === role) {
@@ -95,6 +95,10 @@ class Sessionizer {
 		}
 	}
 
+	onboardForSubject(subject: string) {
+		return this.caps[subject].oo ?? false;
+	}
+
 	// Given an OR of capabilities, check if the session has the required
 	// capabilities. If not, return false. Can throw since it calls auth()
 	async check(request: Request, capabilities: Capabilities) {
@@ -120,10 +124,10 @@ class Sessionizer {
 		const role = this.caps[subject];
 		if (!role) {
 			const memberRole = await this.registerSubject(subject);
-			return (capabilities & memberRole) === capabilities;
+			return (capabilities & memberRole.c) === capabilities;
 		}
 
-		return (capabilities & role) === capabilities;
+		return (capabilities & role.c) === capabilities;
 	}
 
 	async checkSubject(subject: string, capabilities: Capabilities) {
@@ -143,10 +147,10 @@ class Sessionizer {
 		const role = this.caps[subject];
 		if (!role) {
 			const memberRole = await this.registerSubject(subject);
-			return (capabilities & memberRole) === capabilities;
+			return (capabilities & memberRole.c) === capabilities;
 		}
 
-		return (capabilities & role) === capabilities;
+		return (capabilities & role.c) === capabilities;
 	}
 
 	// This code is very simple, if the user does not exist in the database
@@ -160,13 +164,13 @@ class Sessionizer {
 
 		if (Object.keys(this.caps).length === 0) {
 			log.debug('auth', 'First user registered as owner: %s', subject);
-			this.caps[subject] = Roles.owner;
+			this.caps[subject] = { c: Roles.owner };
 			await this.flushUserDatabase();
 			return this.caps[subject];
 		}
 
 		log.debug('auth', 'New user registered as member: %s', subject);
-		this.caps[subject] = Roles.member;
+		this.caps[subject] = { c: Roles.member };
 		await this.flushUserDatabase();
 		return this.caps[subject];
 	}
@@ -176,7 +180,11 @@ class Sessionizer {
 			return;
 		}
 
-		const data = Object.entries(this.caps).map(([u, c]) => ({ u, c }));
+		const data = Object.entries(this.caps).map(([u, { c, oo }]) => ({
+			u,
+			c,
+			oo,
+		}));
 		try {
 			const handle = await open(this.capsPath, 'w');
 			await handle.write(JSON.stringify(data));
@@ -193,11 +201,17 @@ class Sessionizer {
 			return false;
 		}
 
-		this.caps[subject] = Roles[role];
+		this.caps[subject].c = Roles[role];
 		await this.flushUserDatabase();
 		return true;
 	}
 
+	// Overrides the onboarding status for a subject
+	async overrideOnboarding(subject: string, onboarding: boolean) {
+		this.caps[subject].oo = onboarding;
+		await this.flushUserDatabase();
+	}
+
 	getOrCreate<T extends JoinedSession = AuthSession>(request: Request) {
 		return this.storage.getSession(request.headers.get('cookie')) as Promise<
 			Session<T, Error>
@@ -217,7 +231,13 @@ export async function createSessionStorage(
 	options: CookieOptions,
 	usersPath?: string,
 ) {
-	const map: Record<string, Capabilities> = {};
+	const map: Record<
+		string,
+		{
+			c: number;
+			oo?: boolean;
+		}
+	> = {};
 	if (usersPath) {
 		// We need to load our users from the file (default to empty map)
 		// We then translate each user into a capability object using the helper
@@ -226,7 +246,10 @@ export async function createSessionStorage(
 		log.debug('config', 'Loaded %d users from database', data.length);
 
 		for (const user of data) {
-			map[user.u] = user.c;
+			map[user.u] = {
+				c: user.c,
+				oo: user.oo,
+			};
 		}
 	}
 
@@ -248,7 +271,11 @@ async function loadUserFile(path: string) {
 
 	try {
 		const data = await readFile(realPath, 'utf8');
-		const users = JSON.parse(data.trim()) as { u?: string; c?: number }[];
+		const users = JSON.parse(data.trim()) as {
+			u?: string;
+			c?: number;
+			oo?: boolean;
+		}[];
 
 		// Never trust user input
 		return users.filter(
@@ -256,6 +283,7 @@ async function loadUserFile(path: string) {
 		) as {
 			u: string;
 			c: number;
+			oo?: boolean;
 		}[];
 	} catch (error) {
 		log.debug('config', 'Error reading user database file: %s', error);