diff --git a/app/components/tags/TailscaleSSH.tsx b/app/components/tags/TailscaleSSH.tsx
new file mode 100644
index 0000000..96262b9
--- /dev/null
+++ b/app/components/tags/TailscaleSSH.tsx
@@ -0,0 +1,21 @@
+import cn from '~/utils/cn';
+import Chip from '../Chip';
+import Tooltip from '../Tooltip';
+
+export function TailscaleSSHTag() {
+	return (
+		<Tooltip>
+			<Chip
+				text="Tailscale SSH"
+				className={cn(
+					'bg-lime-500 text-lime-900 dark:bg-lime-900 dark:text-lime-500',
+				)}
+			/>
+			<Tooltip.Body>
+				This machine advertises Tailscale SSH, which allows you to authenticate
+				SSH credentials using your Tailscale account and via the Headplane web
+				UI.
+			</Tooltip.Body>
+		</Tooltip>
+	);
+}
diff --git a/app/routes/machines/components/machine-row.tsx b/app/routes/machines/components/machine-row.tsx
index 285e7fb..0dba2d9 100644
--- a/app/routes/machines/components/machine-row.tsx
+++ b/app/routes/machines/components/machine-row.tsx
@@ -12,6 +12,7 @@ import { ExitNodeTag } from '~/components/tags/ExitNode';
 import { ExpiryTag } from '~/components/tags/Expiry';
 import { HeadplaneAgentTag } from '~/components/tags/HeadplaneAgent';
 import { SubnetTag } from '~/components/tags/Subnet';
+import { TailscaleSSHTag } from '~/components/tags/TailscaleSSH';
 import { PopulatedNode } from '~/utils/node-info';
 import toast from '~/utils/toast';
 import MenuOptions from './menu';
@@ -177,6 +178,10 @@ export function uiTagsForNode(node: PopulatedNode, isAgent?: boolean) {
 		uiTags.push('subnet-approved');
 	}
 
+	if (node.hostInfo?.sshHostKeys && node.hostInfo?.sshHostKeys.length > 0) {
+		uiTags.push('tailscale-ssh');
+	}
+
 	if (isAgent === true) {
 		uiTags.push('headplane-agent');
 	}
@@ -205,6 +210,9 @@ export function mapTagsToComponents(node: PopulatedNode, uiTags: string[]) {
 					/>
 				);
 
+			case 'tailscale-ssh':
+				return <TailscaleSSHTag />;
+
 			case 'headplane-agent':
 				return <HeadplaneAgentTag />;
 
diff --git a/app/routes/machines/components/menu.tsx b/app/routes/machines/components/menu.tsx
index 167f92d..c3acf16 100644
--- a/app/routes/machines/components/menu.tsx
+++ b/app/routes/machines/components/menu.tsx
@@ -1,4 +1,4 @@
-import { Cog, Ellipsis } from 'lucide-react';
+import { Cog, Ellipsis, SquareTerminal } from 'lucide-react';
 import { useState } from 'react';
 import Menu from '~/components/Menu';
 import type { User } from '~/types';
@@ -10,7 +10,6 @@ import Move from '../dialogs/move';
 import Rename from '../dialogs/rename';
 import Routes from '../dialogs/routes';
 import Tags from '../dialogs/tags';
-
 interface MenuProps {
 	node: PopulatedNode;
 	users: User[];
@@ -29,6 +28,9 @@ export default function MachineMenu({
 	isDisabled,
 }: MenuProps) {
 	const [modal, setModal] = useState<Modal>(null);
+	const supportsTailscaleSSH =
+		node.hostInfo?.sshHostKeys && node.hostInfo?.sshHostKeys.length > 0;
+
 	return (
 		<>
 			{modal === 'remove' && (
@@ -90,21 +92,69 @@ export default function MachineMenu({
 
 			<Menu isDisabled={isDisabled}>
 				{isFullButton ? (
-					<Menu.Button className="flex items-center gap-x-2">
-						<Cog className="h-5" />
-						<p>Machine Settings</p>
-					</Menu.Button>
+					<div className="flex items-center justify-end gap-1.5 pr-4">
+						{supportsTailscaleSSH ? (
+							<Menu.Button
+								className="flex items-center gap-x-2"
+								variant="heavy"
+								onPress={() => {
+									// We need to use JS to open the SSH URL
+									// in a new WINDOW since href can only
+									// do a new TAB.
+									window.open(
+										// TODO: Use the actual real username lol
+										`${__PREFIX__}/ssh?hostname=${node.name}&username=tale`,
+										'_blank',
+										'noopener,noreferrer,width=800,height=600',
+									);
+								}}
+							>
+								<SquareTerminal className="h-5" />
+								<p>SSH</p>
+							</Menu.Button>
+						) : undefined}
+						<Menu.Button className="flex items-center gap-x-2">
+							<Cog className="h-5" />
+							<p>Machine Settings</p>
+						</Menu.Button>
+					</div>
 				) : (
-					<Menu.IconButton
-						label="Machine Options"
-						className={cn(
-							'py-0.5 w-10 bg-transparent border-transparent',
-							'border group-hover:border-headplane-200',
-							'dark:group-hover:border-headplane-700',
-						)}
-					>
-						<Ellipsis className="h-5" />
-					</Menu.IconButton>
+					<div className="flex items-center justify-end gap-1.5 pr-4">
+						{supportsTailscaleSSH ? (
+							<Menu.Button
+								onPress={() => {
+									// We need to use JS to open the SSH URL
+									// in a new WINDOW since href can only
+									// do a new TAB.
+									window.open(
+										// TODO: Use the actual real username lol
+										`${__PREFIX__}/ssh?hostname=${node.name}&username=tale`,
+										'_blank',
+										'noopener,noreferrer,width=800,height=600',
+									);
+								}}
+								className={cn(
+									'py-0.5 w-fit bg-transparent border-transparent',
+									'border group-hover:border-headplane-200',
+									'dark:group-hover:border-headplane-700',
+									'opacity-0 pointer-events-none group-hover:opacity-100',
+									'group-hover:pointer-events-auto',
+								)}
+							>
+								SSH
+							</Menu.Button>
+						) : undefined}
+						<Menu.IconButton
+							label="Machine Options"
+							className={cn(
+								'py-0.5 w-10 bg-transparent border-transparent',
+								'border group-hover:border-headplane-200',
+								'dark:group-hover:border-headplane-700',
+							)}
+						>
+							<Ellipsis className="h-5" />
+						</Menu.IconButton>
+					</div>
 				)}
 				<Menu.Panel
 					onAction={(key) => setModal(key as Modal)}
diff --git a/app/routes/machines/machine.tsx b/app/routes/machines/machine.tsx
index ae3f892..962ff45 100644
--- a/app/routes/machines/machine.tsx
+++ b/app/routes/machines/machine.tsx
@@ -2,7 +2,6 @@ import { CheckCircle, CircleSlash, Info, UserCircle } from 'lucide-react';
 import { useMemo, useState } from 'react';
 import type { ActionFunctionArgs, LoaderFunctionArgs } from 'react-router';
 import { Link as RemixLink, useLoaderData } from 'react-router';
-import { mapTag } from 'yaml/util';
 import Attribute from '~/components/Attribute';
 import Button from '~/components/Button';
 import Card from '~/components/Card';
diff --git a/app/routes/ssh/console.tsx b/app/routes/ssh/console.tsx
index 0741224..9588f9d 100644
--- a/app/routes/ssh/console.tsx
+++ b/app/routes/ssh/console.tsx
@@ -71,11 +71,8 @@ export async function loader({
 	const qp = new URL(request.url).searchParams;
 	const username = qp.get('username') || undefined;
 	const hostname = qp.get('hostname') || undefined;
-	const port = qp.get('port')
-		? Number.parseInt(qp.get('port')!, 10)
-		: undefined;
-	if (!username || !hostname || !port) {
-		throw data('Missing required parameters: username, hostname, port', 400);
+	if (!username || !hostname) {
+		throw data('Missing required parameters: username, hostname', 400);
 	}
 	// TODO: Verify the Host headers to ensure CORS friendly
 	// TODO: Check if the URL actually resolves correctly