diff --git a/.github/workflows/typos.toml b/.github/workflows/typos.toml
index f2765a3ec97..88bfebbdc75 100644
--- a/.github/workflows/typos.toml
+++ b/.github/workflows/typos.toml
@@ -10,6 +10,8 @@ MacOS = "macOS"
 AKS = "AKS"
 O_WRONLY = "O_WRONLY"
 AIBridge = "AI Bridge"
+# plural of SIEM, as in security information and event management
+SIEMs = "SIEMs"
 
 [default.extend-words]
 AKS = "AKS"
diff --git a/site/src/components/Paywall/Paywall.tsx b/site/src/components/Paywall/Paywall.tsx
index 4d1a1c81001..a13ffb3386c 100644
--- a/site/src/components/Paywall/Paywall.tsx
+++ b/site/src/components/Paywall/Paywall.tsx
@@ -1,4 +1,4 @@
-import { ArrowRightIcon, CheckIcon, ExternalLinkIcon } from "lucide-react";
+import { ArrowRightIcon, CheckIcon } from "lucide-react";
 import type React from "react";
 import type { FC } from "react";
 import { type LinkProps, Link as RouterLink } from "react-router";
@@ -14,10 +14,9 @@ export const PREMIUM_FEATURES = [
 ];
 
 export const PREMIUM_PAGE_PATH = "/deployment/premium";
-export const PREMIUM_PRICING_LINK = "https://coder.com/pricing";
 export const PREMIUM_DEFAULT_DESCRIPTION =
 	"You need a Premium license to use this feature.";
-export const PREMIUM_DEFAULT_HERO = "Get Access with Coder Premium";
+export const PREMIUM_DEFAULT_HERO = "Get access with a Coder trial";
 
 export type PaywallProps = React.ComponentProps<"div"> & {
 	message: string;
@@ -113,25 +112,6 @@ export const PaywallDescription: FC<React.ComponentProps<"p">> = ({
 	);
 };
 
-export const PaywallDocumentationLink: FC<React.ComponentProps<"a">> = ({
-	children = "Read the documentation",
-	className,
-	href,
-	...props
-}) => {
-	return (
-		<a
-			href={href}
-			target="_blank"
-			rel="noreferrer"
-			className={cn("text-content-link font-medium mr-4", className)}
-			{...props}
-		>
-			{children} <ExternalLinkIcon className="size-icon-xs" />
-		</a>
-	);
-};
-
 export const PaywallSupergraphic: FC<React.ComponentProps<"div">> = ({
 	className,
 	...props
diff --git a/site/src/components/Paywall/PaywallAIGovernance.stories.tsx b/site/src/components/Paywall/PaywallAIGovernance.stories.tsx
index a7413097af3..58a9dc88dd6 100644
--- a/site/src/components/Paywall/PaywallAIGovernance.stories.tsx
+++ b/site/src/components/Paywall/PaywallAIGovernance.stories.tsx
@@ -10,3 +10,9 @@ export default meta;
 type Story = StoryObj<typeof PaywallAIGovernance>;
 
 export const Default: Story = {};
+
+export const Sessions: Story = {
+	args: {
+		variant: "sessions",
+	},
+};
diff --git a/site/src/components/Paywall/PaywallAIGovernance.tsx b/site/src/components/Paywall/PaywallAIGovernance.tsx
index 5f579b9f4f6..94b85f286a9 100644
--- a/site/src/components/Paywall/PaywallAIGovernance.tsx
+++ b/site/src/components/Paywall/PaywallAIGovernance.tsx
@@ -1,20 +1,46 @@
 import { PaywallSmall } from "#/components/Paywall/PaywallSmall";
 
-const PAYWALL_AIGATEWAY_DESCRIPTION =
-	"AI Gateway provides auditable visibility into user prompts and LLM tool calls from developer tools within Coder Workspaces. AI Gateway requires a Premium license with AI Governance add-on.";
+type PaywallAIGovernanceVariant = "governance" | "sessions";
+
+const PAYWALL_AIGOVERNANCE_COPY: Record<
+	PaywallAIGovernanceVariant,
+	{ description: string; features: string[] }
+> = {
+	governance: {
+		description:
+			"Get a full audit trail of every prompt, tool call, and model response, so AI adoption stays visible, secure, and accountable.",
+		features: [
+			"Centralized auth, no scattered API keys",
+			"Approve MCP servers & tools org-wide",
+			"Per-user token spend & usage tracking",
+		],
+	},
+	sessions: {
+		description:
+			"Trace every AI coding session step by step to see which prompt triggered which tool call, and who was behind it.",
+		features: [
+			"Full session & thread-level detail",
+			"Attribute every action to a user",
+			"Filter by user, project, or date",
+		],
+	},
+};
+
+type PaywallAIGovernanceProps = {
+	variant?: PaywallAIGovernanceVariant;
+};
+
+const PaywallAIGovernance = ({
+	variant = "governance",
+}: PaywallAIGovernanceProps) => {
+	const { description, features } = PAYWALL_AIGOVERNANCE_COPY[variant];
 
-const PaywallAIGovernance = () => {
 	return (
 		<PaywallSmall
 			message="AI Gateway"
 			canViewPremium
-			description={PAYWALL_AIGATEWAY_DESCRIPTION}
-			features={[
-				"Auditable history of user prompts",
-				"Logged LLM tool invocations",
-				"Token usage and consumption visibility",
-				"Centrally-managed MCP servers",
-			]}
+			description={description}
+			features={features}
 		/>
 	);
 };
diff --git a/site/src/components/Paywall/PaywallPremium.stories.tsx b/site/src/components/Paywall/PaywallPremium.stories.tsx
index a72e4fbbced..7344046e2e5 100644
--- a/site/src/components/Paywall/PaywallPremium.stories.tsx
+++ b/site/src/components/Paywall/PaywallPremium.stories.tsx
@@ -1,6 +1,5 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
 import { expect, within } from "storybook/test";
-import { PREMIUM_PRICING_LINK } from "#/components/Paywall/Paywall";
 import { PaywallPremium } from "./PaywallPremium";
 
 const meta: Meta<typeof PaywallPremium> = {
@@ -21,21 +20,20 @@ export const CanViewLicenses: Story = {
 		const canvas = within(canvasElement);
 
 		await expect(
-			canvas.getByRole("heading", { name: /Coder Premium/ }),
+			canvas.getByRole("heading", { name: /Get access with a Coder trial/ }),
+		).toBeVisible();
+		await expect(
+			canvas.getByText("Start an unlimited 30-day trial today"),
 		).toBeVisible();
-		await expect(canvas.getByText("Start a 30-day trial today.")).toBeVisible();
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toBeVisible();
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
 		await expect(cta).not.toHaveAttribute("target", "_blank");
 
-		const pricing = canvas.getByRole("link", {
-			name: "Learn more about premium",
-		});
-		await expect(pricing).toBeVisible();
-		await expect(pricing).toHaveAttribute("href", PREMIUM_PRICING_LINK);
-		await expect(pricing).toHaveAttribute("target", "_blank");
+		await expect(
+			canvas.queryByRole("link", { name: "Learn more about premium" }),
+		).not.toBeInTheDocument();
 
 		await expect(
 			canvas.getByRole("heading", {
@@ -65,8 +63,8 @@ export const CannotViewLicenses: Story = {
 			canvas.queryByRole("link", { name: "Start trial for free" }),
 		).not.toBeInTheDocument();
 		await expect(
-			canvas.getByRole("link", { name: "Learn more about premium" }),
-		).toBeVisible();
+			canvas.queryByRole("link", { name: "Learn more about premium" }),
+		).not.toBeInTheDocument();
 	},
 };
 
diff --git a/site/src/components/Paywall/PaywallPremium.tsx b/site/src/components/Paywall/PaywallPremium.tsx
index cc3638cb76c..a480efa66ad 100644
--- a/site/src/components/Paywall/PaywallPremium.tsx
+++ b/site/src/components/Paywall/PaywallPremium.tsx
@@ -1,4 +1,3 @@
-import { ExternalLinkIcon } from "lucide-react";
 import type { FC } from "react";
 import { Supergraphic } from "#/components/Supergraphic/Supergraphic";
 import { cn } from "#/utils/cn";
@@ -13,10 +12,9 @@ import {
 	PREMIUM_DEFAULT_HERO,
 	PREMIUM_FEATURES,
 	PREMIUM_PAGE_PATH,
-	PREMIUM_PRICING_LINK,
 } from "./Paywall";
 
-const DEFAULT_HERO_SUBTITLE = "Start a 30-day trial today.";
+const DEFAULT_HERO_SUBTITLE = "Start an unlimited 30-day trial today";
 
 const PaywallPremiumHeader: FC<React.ComponentProps<"div">> = ({
 	children,
@@ -88,15 +86,6 @@ const PaywallPremium = ({
 					<h3 className="m-0 font-semibold text-base leading-relaxed text-content-primary">
 						{description}
 					</h3>
-					<a
-						href={PREMIUM_PRICING_LINK}
-						target="_blank"
-						rel="noreferrer"
-						className="mt-4 inline-flex items-center gap-1.5 text-sm text-content-link underline underline-offset-2"
-					>
-						Learn more about premium
-						<ExternalLinkIcon aria-hidden="true" className="size-icon-sm" />
-					</a>
 				</div>
 				<PaywallFeatures className="flex-1 px-0" aria-label={message}>
 					{features.map((feature) => (
diff --git a/site/src/components/Paywall/PaywallSmall.stories.tsx b/site/src/components/Paywall/PaywallSmall.stories.tsx
index a0cefd14ba0..b96d238db4c 100644
--- a/site/src/components/Paywall/PaywallSmall.stories.tsx
+++ b/site/src/components/Paywall/PaywallSmall.stories.tsx
@@ -37,8 +37,8 @@ export const CannotViewLicenses: Story = {
 		const canvas = within(canvasElement);
 
 		await expect(
-			canvas.getByRole("link", { name: "Learn more about premium" }),
-		).toBeVisible();
+			canvas.queryByRole("link", { name: "Learn more about premium" }),
+		).not.toBeInTheDocument();
 		await expect(
 			canvas.getByText(/contact your deployment administrator/i),
 		).toBeVisible();
diff --git a/site/src/components/Paywall/PaywallSmall.tsx b/site/src/components/Paywall/PaywallSmall.tsx
index e357840f4d2..5833f3c518d 100644
--- a/site/src/components/Paywall/PaywallSmall.tsx
+++ b/site/src/components/Paywall/PaywallSmall.tsx
@@ -4,7 +4,6 @@ import {
 	PaywallContent,
 	PaywallCTALink,
 	PaywallDescription,
-	PaywallDocumentationLink,
 	PaywallFeature,
 	PaywallFeatures,
 	PaywallGuidance,
@@ -16,7 +15,6 @@ import {
 	PREMIUM_DEFAULT_HERO,
 	PREMIUM_FEATURES,
 	PREMIUM_PAGE_PATH,
-	PREMIUM_PRICING_LINK,
 } from "./Paywall";
 
 const PaywallSmall = ({
@@ -50,9 +48,6 @@ const PaywallSmall = ({
 				>
 					{description}
 				</PaywallDescription>
-				<PaywallDocumentationLink href={PREMIUM_PRICING_LINK}>
-					Learn more about premium
-				</PaywallDocumentationLink>
 			</PaywallContent>
 			<PaywallStack className={cn(compact && "gap-4")}>
 				<PaywallFeatures className={cn(compact && "pr-0")}>
diff --git a/site/src/pages/AIBridgePage/AIBridgeSessionsLayout.tsx b/site/src/pages/AIBridgePage/AIBridgeSessionsLayout.tsx
index 0f40f32d3ab..31a27c1a1a4 100644
--- a/site/src/pages/AIBridgePage/AIBridgeSessionsLayout.tsx
+++ b/site/src/pages/AIBridgePage/AIBridgeSessionsLayout.tsx
@@ -1,18 +1,22 @@
 import type { FC, PropsWithChildren } from "react";
 import { Outlet } from "react-router";
-import { Link } from "#/components/Link/Link";
 import { Margins } from "#/components/Margins/Margins";
 import {
 	PageHeader,
 	PageHeaderSubtitle,
 	PageHeaderTitle,
 } from "#/components/PageHeader/PageHeader";
+import { SettingsHeaderDocsLink } from "#/components/SettingsHeader/SettingsHeader";
 import { docs } from "#/utils/docs";
 
 const AIBridgeSessionsLayout: FC<PropsWithChildren> = () => {
 	return (
 		<Margins className="pb-12">
-			<PageHeader>
+			<PageHeader
+				actions={
+					<SettingsHeaderDocsLink href={docs("/ai-coder/ai-gateway/audit")} />
+				}
+			>
 				<PageHeaderTitle>
 					<div className="flex items-center gap-2">
 						<span>AI Sessions</span>
@@ -20,14 +24,7 @@ const AIBridgeSessionsLayout: FC<PropsWithChildren> = () => {
 				</PageHeaderTitle>
 				<PageHeaderSubtitle>
 					Review and audit AI activity, token usage, and prompt history across
-					sessions.{" "}
-					<Link
-						href={docs("/ai-coder/ai-gateway/audit")}
-						className="ml-auto"
-						target="_blank"
-					>
-						Learn how to audit AI sessions
-					</Link>
+					sessions.
 				</PageHeaderSubtitle>
 			</PageHeader>
 			<Outlet />
diff --git a/site/src/pages/AIBridgePage/ListSessionsPage/ListSessionsPageView.tsx b/site/src/pages/AIBridgePage/ListSessionsPage/ListSessionsPageView.tsx
index 21299d54c36..534925a5dd3 100644
--- a/site/src/pages/AIBridgePage/ListSessionsPage/ListSessionsPageView.tsx
+++ b/site/src/pages/AIBridgePage/ListSessionsPage/ListSessionsPageView.tsx
@@ -64,7 +64,7 @@ export const ListSessionsPageView: FC<ListSessionsPageViewProps> = ({
 	onSessionRowClick,
 }) => {
 	if (!isAISessionsEntitled) {
-		return <PaywallAIGovernance />;
+		return <PaywallAIGovernance variant="sessions" />;
 	}
 
 	if (!isAISessionsEnabled) {
diff --git a/site/src/pages/AIBridgePage/SessionThreadsPage/SessionThreadsPageView.tsx b/site/src/pages/AIBridgePage/SessionThreadsPage/SessionThreadsPageView.tsx
index ba12f4eca13..0a02cedbfe4 100644
--- a/site/src/pages/AIBridgePage/SessionThreadsPage/SessionThreadsPageView.tsx
+++ b/site/src/pages/AIBridgePage/SessionThreadsPage/SessionThreadsPageView.tsx
@@ -62,7 +62,7 @@ export const SessionThreadsPageView: FC<SessionThreadsPageViewProps> = ({
 	onBackClicked,
 }) => {
 	if (!isAISessionsEntitled) {
-		return <PaywallAIGovernance />;
+		return <PaywallAIGovernance variant="sessions" />;
 	}
 
 	if (!isAISessionsEnabled) {
diff --git a/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.stories.tsx b/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.stories.tsx
index 593263a66c3..cf2d6169770 100644
--- a/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.stories.tsx
+++ b/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.stories.tsx
@@ -5,6 +5,7 @@ import {
 	MockPermissions,
 	mockApiError,
 } from "#/testHelpers/entities";
+import { docs } from "#/utils/docs";
 import { GatewayKeysPageView } from "./GatewayKeysPageView";
 
 const meta: Meta<typeof GatewayKeysPageView> = {
@@ -81,6 +82,12 @@ export const Paywall: Story = {
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
+		await expect(
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute(
+			"href",
+			docs("/ai-coder/ai-gateway/standalone#create-a-gateway-key"),
+		);
 	},
 };
 
diff --git a/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.tsx b/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.tsx
index 6dfde035db3..9708010aaa7 100644
--- a/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.tsx
+++ b/site/src/pages/AISettingsPage/GatewayKeysPage/GatewayKeysPageView.tsx
@@ -3,11 +3,11 @@ import type { FC } from "react";
 import type { AIGatewayKey } from "#/api/typesGenerated";
 import { ErrorAlert } from "#/components/Alert/ErrorAlert";
 import { Button } from "#/components/Button/Button";
-import { Link } from "#/components/Link/Link";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
 import {
 	SettingsHeader,
 	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
 	SettingsHeaderTitle,
 } from "#/components/SettingsHeader/SettingsHeader";
 import {
@@ -47,26 +47,36 @@ export const GatewayKeysPageView: FC<GatewayKeysPageViewProps> = ({
 		<div>
 			<SettingsHeader
 				actions={
-					!showPaywall && (
-						<Button variant="outline" onClick={onCreateKey}>
-							<PlusIcon />
-							Create key
-						</Button>
-					)
+					<div className="flex flex-row gap-2 items-center">
+						<SettingsHeaderDocsLink
+							href={docs(
+								"/ai-coder/ai-gateway/standalone#create-a-gateway-key",
+							)}
+						/>
+						{!showPaywall && (
+							<Button variant="outline" onClick={onCreateKey}>
+								<PlusIcon />
+								Create key
+							</Button>
+						)}
+					</div>
 				}
 			>
 				<SettingsHeaderTitle>AI Gateway Keys</SettingsHeaderTitle>
 				<SettingsHeaderDescription>
 					Keys authenticate standalone AI Gateway replicas to this deployment.
-					The key value is shown only once when created.{" "}
-					<Link href={docs("/ai-coder/ai-gateway")}>View docs</Link>
+					The key value is shown only once when created.
 				</SettingsHeaderDescription>
 			</SettingsHeader>
 
 			{showPaywall && (
 				<PaywallPremium
 					message="AI Gateway"
-					description="Authenticate standalone AI Gateway replicas to your deployment. You need a Premium license with AI Gateway enabled to use this feature."
+					description="Authenticate standalone AI Gateway replicas securely."
+					features={[
+						"Authenticate without shared secrets",
+						"Works inside coderd or standalone",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			)}
diff --git a/site/src/pages/AuditPage/AuditPageView.stories.tsx b/site/src/pages/AuditPage/AuditPageView.stories.tsx
index d9d94536cb0..030ed84c0c5 100644
--- a/site/src/pages/AuditPage/AuditPageView.stories.tsx
+++ b/site/src/pages/AuditPage/AuditPageView.stories.tsx
@@ -18,6 +18,7 @@ import {
 	MockUserOwner,
 } from "#/testHelpers/entities";
 import { pixelWithTablet } from "#/testHelpers/pixel";
+import { docs } from "#/utils/docs";
 import { useResourceTypeFilterMenu } from "./AuditFilter";
 import { AuditPageView } from "./AuditPageView";
 
@@ -100,6 +101,9 @@ export const NotVisible: Story = {
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
+		await expect(
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/security/audit-logs"));
 	},
 };
 
diff --git a/site/src/pages/AuditPage/AuditPageView.tsx b/site/src/pages/AuditPage/AuditPageView.tsx
index 71d0eafe03d..c6f9062253a 100644
--- a/site/src/pages/AuditPage/AuditPageView.tsx
+++ b/site/src/pages/AuditPage/AuditPageView.tsx
@@ -11,11 +11,13 @@ import {
 	type PaginationResult,
 } from "#/components/PaginationWidget/PaginationContainer";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
+import { SettingsHeaderDocsLink } from "#/components/SettingsHeader/SettingsHeader";
 import { Table, TableBody } from "#/components/Table/Table";
 import { TableEmpty } from "#/components/TableEmpty/TableEmpty";
 import { TableLoader } from "#/components/TableLoader/TableLoader";
 import { Timeline } from "#/components/Timeline/Timeline";
 import type { Permissions } from "#/modules/permissions";
+import { docs } from "#/utils/docs";
 import { AuditFilter } from "./AuditFilter";
 import { AuditHelpPopover } from "./AuditHelpPopover";
 import { AuditLogRow } from "./AuditLogRow/AuditLogRow";
@@ -49,7 +51,11 @@ export const AuditPageView: FC<AuditPageViewProps> = ({
 
 	return (
 		<Margins className="pb-12">
-			<PageHeader>
+			<PageHeader
+				actions={
+					<SettingsHeaderDocsLink href={docs("/admin/security/audit-logs")} />
+				}
+			>
 				<PageHeaderTitle>
 					<div className="flex flex-row gap-2 items-center">
 						<span>Audit</span>
@@ -84,7 +90,12 @@ export const AuditPageView: FC<AuditPageViewProps> = ({
 			) : (
 				<PaywallPremium
 					message="Audit logs"
-					description="Audit logs allow you to monitor user operations on your deployment."
+					description="See exactly who changed what and when, with every workspace, template, and user action logged for compliance and incident response."
+					features={[
+						"Configurable retention & auto-purge",
+						"API export to Splunk, Datadog & more",
+						"Meets SOC 2 & HIPAA audit requirements",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			)}
diff --git a/site/src/pages/ConnectionLogPage/ConnectionLogPageView.stories.tsx b/site/src/pages/ConnectionLogPage/ConnectionLogPageView.stories.tsx
index a981770aad9..ff238731a5c 100644
--- a/site/src/pages/ConnectionLogPage/ConnectionLogPageView.stories.tsx
+++ b/site/src/pages/ConnectionLogPage/ConnectionLogPageView.stories.tsx
@@ -17,6 +17,7 @@ import {
 	MockUserOwner,
 } from "#/testHelpers/entities";
 import { pixelWithTablet } from "#/testHelpers/pixel";
+import { docs } from "#/utils/docs";
 import { ConnectionLogPageView } from "./ConnectionLogPageView";
 
 type FilterProps = ComponentProps<typeof ConnectionLogPageView>["filterProps"];
@@ -100,6 +101,9 @@ export const NotVisible: Story = {
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
+		await expect(
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/monitoring/connection-logs"));
 	},
 };
 
diff --git a/site/src/pages/ConnectionLogPage/ConnectionLogPageView.tsx b/site/src/pages/ConnectionLogPage/ConnectionLogPageView.tsx
index aeebf9a073b..c0b9da41b89 100644
--- a/site/src/pages/ConnectionLogPage/ConnectionLogPageView.tsx
+++ b/site/src/pages/ConnectionLogPage/ConnectionLogPageView.tsx
@@ -11,11 +11,13 @@ import {
 	type PaginationResult,
 } from "#/components/PaginationWidget/PaginationContainer";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
+import { SettingsHeaderDocsLink } from "#/components/SettingsHeader/SettingsHeader";
 import { Table, TableBody } from "#/components/Table/Table";
 import { TableEmpty } from "#/components/TableEmpty/TableEmpty";
 import { TableLoader } from "#/components/TableLoader/TableLoader";
 import { Timeline } from "#/components/Timeline/Timeline";
 import type { Permissions } from "#/modules/permissions";
+import { docs } from "#/utils/docs";
 import { ConnectionLogFilter } from "./ConnectionLogFilter";
 import { ConnectionLogHelpPopover } from "./ConnectionLogHelpPopover";
 import { ConnectionLogRow } from "./ConnectionLogRow/ConnectionLogRow";
@@ -48,7 +50,13 @@ export const ConnectionLogPageView: FC<ConnectionLogPageViewProps> = ({
 
 	return (
 		<Margins className="pb-12">
-			<PageHeader>
+			<PageHeader
+				actions={
+					<SettingsHeaderDocsLink
+						href={docs("/admin/monitoring/connection-logs")}
+					/>
+				}
+			>
 				<PageHeaderTitle>
 					<div className="flex flex-row gap-2 items-center">
 						<span>Connection Log</span>
@@ -84,7 +92,12 @@ export const ConnectionLogPageView: FC<ConnectionLogPageViewProps> = ({
 			) : (
 				<PaywallPremium
 					message="Connection logs"
-					description="Connection logs allow you to see how and when users connect to workspaces."
+					description="Track every SSH, IDE & port-forward connection."
+					features={[
+						"Full record of SSH, IDE & app sessions",
+						"Filter by organization, user & type",
+						"Export to Splunk & other SIEMs",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			)}
diff --git a/site/src/pages/DeploymentSettingsPage/AIGovernanceSettingsPage/AIGovernanceSettingsPageView.tsx b/site/src/pages/DeploymentSettingsPage/AIGovernanceSettingsPage/AIGovernanceSettingsPageView.tsx
index 00236f80e4a..f473196315e 100644
--- a/site/src/pages/DeploymentSettingsPage/AIGovernanceSettingsPage/AIGovernanceSettingsPageView.tsx
+++ b/site/src/pages/DeploymentSettingsPage/AIGovernanceSettingsPage/AIGovernanceSettingsPageView.tsx
@@ -31,7 +31,7 @@ export const AIGovernanceSettingsPageView: FC<
 			<div>
 				<SettingsHeader
 					actions={
-						<SettingsHeaderDocsLink href={docs("/ai-coder/ai-gateway")} />
+						<SettingsHeaderDocsLink href={docs("/ai-coder/ai-governance")} />
 					}
 				>
 					<SettingsHeaderTitle hierarchy="secondary" level="h2">
diff --git a/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.stories.tsx b/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.stories.tsx
index c917ccd729d..bc81d061c79 100644
--- a/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.stories.tsx
+++ b/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.stories.tsx
@@ -1,6 +1,7 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
 import { expect, within } from "storybook/test";
 import { MockPermissions } from "#/testHelpers/entities";
+import { docs } from "#/utils/docs";
 import { AppearanceSettingsPageView } from "./AppearanceSettingsPageView";
 
 const meta: Meta<typeof AppearanceSettingsPageView> = {
@@ -56,6 +57,9 @@ export const NotEntitled: Story = {
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
+		await expect(
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/setup/appearance"));
 		await expect(
 			canvas.queryByRole("form", { name: "Appearance settings" }),
 		).not.toBeInTheDocument();
diff --git a/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.tsx b/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.tsx
index 9ee5c1f381f..dce55b3def7 100644
--- a/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.tsx
+++ b/site/src/pages/DeploymentSettingsPage/AppearanceSettingsPage/AppearanceSettingsPageView.tsx
@@ -14,9 +14,11 @@ import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
 import {
 	SettingsHeader,
 	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
 	SettingsHeaderTitle,
 } from "#/components/SettingsHeader/SettingsHeader";
 import { Spinner } from "#/components/Spinner/Spinner";
+import { docs } from "#/utils/docs";
 import { getFormHelpers } from "#/utils/formUtils";
 import { AnnouncementBannerSettings } from "./AnnouncementBannerSettings";
 
@@ -47,7 +49,11 @@ export const AppearanceSettingsPageView: FC<
 
 	return (
 		<div className="flex flex-col gap-8">
-			<SettingsHeader>
+			<SettingsHeader
+				actions={
+					<SettingsHeaderDocsLink href={docs("/admin/setup/appearance")} />
+				}
+			>
 				<SettingsHeaderTitle>Appearance</SettingsHeaderTitle>
 				<SettingsHeaderDescription>
 					Customize the look and feel of your Coder deployment.
@@ -57,7 +63,13 @@ export const AppearanceSettingsPageView: FC<
 			{!isEntitled ? (
 				<PaywallPremium
 					message="Appearance"
-					description="With a Premium license, you can customize branding and announcement banners for your deployment."
+					description="Customize branding and announcement banners for your deployment."
+					features={[
+						"Custom application name and logo",
+						"Site-wide announcement banners for updates",
+						"Custom branded OIDC sign-in button",
+						"Custom support links in dropdown",
+					]}
 					canViewPremium={canViewPremium}
 				/>
 			) : (
diff --git a/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPage.tsx b/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPage.tsx
index cf02bd65710..9b8c35fa2d6 100644
--- a/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPage.tsx
+++ b/site/src/pages/DeploymentSettingsPage/IdpOrgSyncPage/IdpOrgSyncPage.tsx
@@ -7,9 +7,9 @@ import {
 	organizationIdpSyncSettings,
 	patchOrganizationSyncSettings,
 } from "#/api/queries/idpsync";
-import { Link } from "#/components/Link/Link";
 import { Loader } from "#/components/Loader/Loader";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
+import { SettingsHeaderDocsLink } from "#/components/SettingsHeader/SettingsHeader";
 import { useAuthenticated } from "#/hooks/useAuthenticated";
 import { useDashboard } from "#/modules/dashboard/useDashboard";
 import { useFeatureVisibility } from "#/modules/dashboard/useFeatureVisibility";
@@ -70,17 +70,24 @@ const IdpOrgSyncPage: FC = () => {
 						<p className="flex flex-row gap-1 text-sm text-content-secondary font-medium m-0">
 							Automatically assign users to an organization based on their IdP
 							claims.
-							<Link href={docs("/admin/users/idp-sync#organization-sync")}>
-								View docs
-							</Link>
 						</p>
 					</div>
-					<ExportPolicyButton syncSettings={settingsQuery.data} />
+					<div className="flex flex-row gap-2 items-center">
+						<SettingsHeaderDocsLink
+							href={docs("/admin/users/idp-sync#organization-sync")}
+						/>
+						<ExportPolicyButton syncSettings={settingsQuery.data} />
+					</div>
 				</header>
 				{!isIdpSyncEnabled ? (
 					<PaywallPremium
 						message="IdP Organization Sync"
 						description="Configure organization mappings to synchronize claims in your auth provider to organizations within Coder."
+						features={[
+							"Sync groups & roles automatically",
+							"No manual user assignment",
+							"Works with your OIDC provider",
+						]}
 						canViewPremium={permissions.viewAllLicenses}
 					/>
 				) : (
diff --git a/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.stories.tsx b/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.stories.tsx
index 1c397954c8e..87ef677ef32 100644
--- a/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.stories.tsx
+++ b/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.stories.tsx
@@ -2,6 +2,7 @@ import type { Meta, StoryObj } from "@storybook/react-vite";
 import { expect, within } from "storybook/test";
 import type { SerpentGroup } from "#/api/typesGenerated";
 import { MockPermissions } from "#/testHelpers/entities";
+import { docs } from "#/utils/docs";
 import { ObservabilitySettingsPageView } from "./ObservabilitySettingsPageView";
 
 const introspectionGroup: SerpentGroup = {
@@ -82,8 +83,8 @@ export const OSS: Story = {
 			canvas.getByRole("link", { name: "Start trial for free" }),
 		).toHaveAttribute("href", "/deployment/premium");
 		await expect(
-			canvas.getByRole("link", { name: "Learn more about premium" }),
-		).toBeVisible();
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/security/audit-logs"));
 		await expect(
 			canvas.queryByText("Audit Logs Retention"),
 		).not.toBeInTheDocument();
diff --git a/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.tsx b/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.tsx
index 7667e09cdf0..25a5ba91f7a 100644
--- a/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.tsx
+++ b/site/src/pages/DeploymentSettingsPage/ObservabilitySettingsPage/ObservabilitySettingsPageView.tsx
@@ -24,7 +24,9 @@ export const ObservabilitySettingsPageView: FC<
 		<div className="flex flex-col gap-12">
 			<div>
 				<SettingsHeader
-					actions={<SettingsHeaderDocsLink href={docs("/admin/monitoring")} />}
+					actions={
+						<SettingsHeaderDocsLink href={docs("/admin/security/audit-logs")} />
+					}
 				>
 					<SettingsHeaderTitle>Observability</SettingsHeaderTitle>
 				</SettingsHeader>
@@ -45,7 +47,13 @@ export const ObservabilitySettingsPageView: FC<
 				) : (
 					<PaywallPremium
 						message="Audit Logging"
-						description="Audit logging lets auditors monitor user operations across your deployment. You need a Premium license to use this feature."
+						description="Monitor user operations across your deployment."
+						features={[
+							"Track user actions across deployment",
+							"Observe developer and agent activity",
+							"Configurable audit log retention period",
+							"Support compliance and security reviews",
+						]}
 						canViewPremium={canViewPremium}
 					/>
 				)}
diff --git a/site/src/pages/GroupsPage/GroupsPage.tsx b/site/src/pages/GroupsPage/GroupsPage.tsx
index 993f30fc1eb..fcf2eff29e4 100644
--- a/site/src/pages/GroupsPage/GroupsPage.tsx
+++ b/site/src/pages/GroupsPage/GroupsPage.tsx
@@ -14,12 +14,14 @@ import { Loader } from "#/components/Loader/Loader";
 import {
 	SettingsHeader,
 	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
 	SettingsHeaderTitle,
 } from "#/components/SettingsHeader/SettingsHeader";
 import { useAuthenticated } from "#/hooks/useAuthenticated";
 import { usePaginatedQuery } from "#/hooks/usePaginatedQuery";
 import { useFeatureVisibility } from "#/modules/dashboard/useFeatureVisibility";
 import { RequirePermission } from "#/modules/permissions/RequirePermission";
+import { docs } from "#/utils/docs";
 import { pageTitle } from "#/utils/page";
 import { useGroupsSettings } from "./GroupsPageProvider";
 import { GroupsPageView, joinGroupsSpend } from "./GroupsPageView";
@@ -111,15 +113,17 @@ const GroupsPage: FC = () => {
 		<div className="w-full max-w-screen-2xl pb-10">
 			{title}
 
-			<div className="flex max-w-full flex-row items-baseline justify-between gap-4">
-				<SettingsHeader>
-					<SettingsHeaderTitle>Groups</SettingsHeaderTitle>
-					<SettingsHeaderDescription>
-						Manage groups for this{" "}
-						{showOrganizations ? "organization" : "deployment"}.
-					</SettingsHeaderDescription>
-				</SettingsHeader>
-			</div>
+			<SettingsHeader
+				actions={
+					<SettingsHeaderDocsLink href={docs("/admin/users/groups-roles")} />
+				}
+			>
+				<SettingsHeaderTitle>Groups</SettingsHeaderTitle>
+				<SettingsHeaderDescription>
+					Manage groups for this{" "}
+					{showOrganizations ? "organization" : "deployment"}.
+				</SettingsHeaderDescription>
+			</SettingsHeader>
 
 			<GroupsPageView
 				groups={groupsWithSpend}
diff --git a/site/src/pages/GroupsPage/GroupsPageView.tsx b/site/src/pages/GroupsPage/GroupsPageView.tsx
index c9c62aa0029..55b445da185 100644
--- a/site/src/pages/GroupsPage/GroupsPageView.tsx
+++ b/site/src/pages/GroupsPage/GroupsPageView.tsx
@@ -95,7 +95,12 @@ export const GroupsPageView: FC<GroupsPageViewProps> = ({
 		return (
 			<PaywallPremium
 				message="Groups"
-				description="Organize users into groups with restricted access to templates."
+				description="Run isolated business units on one deployment, each with its own users, templates, provisioners, and infrastructure."
+				features={[
+					"Isolate provisioners & infrastructure",
+					"Sync org membership from your IdP",
+					"Manage orgs at scale via Terraform",
+				]}
 				canViewPremium={permissions.viewAllLicenses}
 			/>
 		);
diff --git a/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.stories.tsx b/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.stories.tsx
index 9d2322cb043..453db8c8aca 100644
--- a/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.stories.tsx
+++ b/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.stories.tsx
@@ -1,6 +1,7 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
 import { expect, screen, userEvent, within } from "storybook/test";
 import { MockPermissions, mockApiError } from "#/testHelpers/entities";
+import { docs } from "#/utils/docs";
 import { CreateOrganizationPageView } from "./CreateOrganizationPageView";
 
 const meta: Meta<typeof CreateOrganizationPageView> = {
@@ -35,8 +36,8 @@ export const NotEntitled: Story = {
 		const canvas = within(canvasElement);
 
 		await expect(
-			canvas.getByRole("link", { name: "Learn more about premium" }),
-		).toBeVisible();
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/users/organizations"));
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
 	},
diff --git a/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.tsx b/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.tsx
index 1b0e4cdc6e3..76b4a914861 100644
--- a/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.tsx
+++ b/site/src/pages/OrganizationSettingsPage/CreateOrganizationPageView.tsx
@@ -12,10 +12,12 @@ import { FormField } from "#/components/FormField/FormField";
 import { IconField } from "#/components/IconField/IconField";
 import { Label } from "#/components/Label/Label";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
+import { SettingsHeaderDocsLink } from "#/components/SettingsHeader/SettingsHeader";
 import { Spinner } from "#/components/Spinner/Spinner";
 import { Textarea } from "#/components/Textarea/Textarea";
 import type { Permissions } from "#/modules/permissions";
 import { cn } from "#/utils/cn";
+import { docs } from "#/utils/docs";
 import {
 	displayNameValidator,
 	getFormHelpers,
@@ -74,6 +76,9 @@ export const CreateOrganizationPageView: FC<
 					Go Back
 				</Link>
 			</div>
+			<div className="absolute right-12">
+				<SettingsHeaderDocsLink href={docs("/admin/users/organizations")} />
+			</div>
 			<div className="flex flex-col gap-4 w-full min-w-96 mx-auto">
 				<div className="flex flex-col items-center">
 					{Boolean(error) && !isApiValidationError(error) && (
@@ -100,7 +105,12 @@ export const CreateOrganizationPageView: FC<
 					<div className="mx-auto w-full max-w-4xl">
 						<PaywallPremium
 							message="Organizations"
-							description="Create multiple organizations within a single Coder deployment, allowing several platform teams to operate with isolated users, templates, and distinct underlying infrastructure."
+							description="Run isolated business units on one deployment, each with its own users, templates, provisioners, and infrastructure."
+							features={[
+								"Isolate provisioners & infrastructure",
+								"Sync org membership from your IdP",
+								"Manage orgs at scale via Terraform",
+							]}
 							canViewPremium={permissions.viewAllLicenses}
 						/>
 					</div>
diff --git a/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPage.tsx b/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPage.tsx
index c80cbd8d8d9..611117319c4 100644
--- a/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPage.tsx
+++ b/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPage.tsx
@@ -11,6 +11,7 @@ import { EmptyState } from "#/components/EmptyState/EmptyState";
 import {
 	SettingsHeader,
 	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
 	SettingsHeaderTitle,
 } from "#/components/SettingsHeader/SettingsHeader";
 import { useAuthenticated } from "#/hooks/useAuthenticated";
@@ -18,6 +19,7 @@ import { useDashboard } from "#/modules/dashboard/useDashboard";
 import { useFeatureVisibility } from "#/modules/dashboard/useFeatureVisibility";
 import { useOrganizationSettings } from "#/modules/management/OrganizationSettingsLayout";
 import { RequirePermission } from "#/modules/permissions/RequirePermission";
+import { docs } from "#/utils/docs";
 import { pageTitle } from "#/utils/page";
 import { CustomRolesPageView } from "./CustomRolesPageView";
 
@@ -80,14 +82,16 @@ const CustomRolesPage: FC = () => {
 			<RequirePermission
 				isFeatureVisible={organizationPermissions?.viewOrgRoles ?? false}
 			>
-				<div className="flex flex-row gap-4 items-baseline justify-between">
-					<SettingsHeader>
-						<SettingsHeaderTitle>Roles</SettingsHeaderTitle>
-						<SettingsHeaderDescription>
-							Manage roles for this organization.
-						</SettingsHeaderDescription>
-					</SettingsHeader>
-				</div>
+				<SettingsHeader
+					actions={
+						<SettingsHeaderDocsLink href={docs("/admin/users/groups-roles")} />
+					}
+				>
+					<SettingsHeaderTitle>Roles</SettingsHeaderTitle>
+					<SettingsHeaderDescription>
+						Manage roles for this organization.
+					</SettingsHeaderDescription>
+				</SettingsHeader>
 
 				<CustomRolesPageView
 					organization={organization}
diff --git a/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPageView.tsx b/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPageView.tsx
index b0e5b06fefb..09ad282f3f8 100644
--- a/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPageView.tsx
+++ b/site/src/pages/OrganizationSettingsPage/CustomRolesPage/CustomRolesPageView.tsx
@@ -67,7 +67,12 @@ export const CustomRolesPageView: FC<CustomRolesPageViewProps> = ({
 			{!isCustomRolesEnabled && (
 				<PaywallSmall
 					message="Custom Roles"
-					description="Create custom roles to grant users a tailored set of granular permissions."
+					description="Build roles with the exact permissions your team needs."
+					features={[
+						"Configure roles per organization",
+						"Go beyond the built-in role set",
+						"Assign custom roles to any user",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			)}
diff --git a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx
index 3cb3cb3c252..13e51bf326f 100644
--- a/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx
+++ b/site/src/pages/OrganizationSettingsPage/IdpSyncPage/IdpSyncPage.tsx
@@ -13,8 +13,8 @@ import {
 } from "#/api/queries/organizations";
 import { organizationRoles } from "#/api/queries/roles";
 import { EmptyState } from "#/components/EmptyState/EmptyState";
-import { Link } from "#/components/Link/Link";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
+import { SettingsHeaderDocsLink } from "#/components/SettingsHeader/SettingsHeader";
 import { useAuthenticated } from "#/hooks/useAuthenticated";
 import { useFeatureVisibility } from "#/modules/dashboard/useFeatureVisibility";
 import { useOrganizationSettings } from "#/modules/management/OrganizationSettingsLayout";
@@ -125,14 +125,20 @@ const IdpSyncPage: FC = () => {
 						<p className="flex flex-row gap-1 text-sm text-content-secondary font-medium m-0">
 							Automatically assign groups or roles to a user based on their IdP
 							claims.
-							<Link href={docs("/admin/users/idp-sync")}>View docs</Link>
 						</p>
 					</div>
+					<SettingsHeaderDocsLink href={docs("/admin/users/idp-sync")} />
 				</header>
 				{!isIdpSyncEnabled ? (
 					<PaywallPremium
 						message="IdP Sync"
-						description="Configure group and role mappings to manage permissions outside of Coder."
+						description="Auto-sync groups & roles from your IdP."
+						features={[
+							"Sync groups & roles automatically",
+							"Configured per organization",
+							"No manual user assignment",
+							"Works with your OIDC provider",
+						]}
 						canViewPremium={permissions.viewAllLicenses}
 					/>
 				) : (
diff --git a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.stories.tsx b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.stories.tsx
index 1540a8211d5..ce34141fe94 100644
--- a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.stories.tsx
+++ b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.stories.tsx
@@ -12,6 +12,7 @@ import {
 	MockProvisionerKey,
 	mockApiError,
 } from "#/testHelpers/entities";
+import { docs } from "#/utils/docs";
 import { OrganizationProvisionerKeysPageView } from "./OrganizationProvisionerKeysPageView";
 
 const mockProvisionerKeyDaemons: ProvisionerKeyDaemons[] = [
@@ -99,6 +100,9 @@ export const Paywalled: Story = {
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
+		await expect(
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/provisioners"));
 	},
 };
 
diff --git a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.tsx b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.tsx
index bbab0b5d3ff..9b81750de9d 100644
--- a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.tsx
+++ b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionerKeysPage/OrganizationProvisionerKeysPageView.tsx
@@ -6,11 +6,11 @@ import {
 	ProvisionerKeyIDUserAuth,
 } from "#/api/typesGenerated";
 import { Button } from "#/components/Button/Button";
-import { Link } from "#/components/Link/Link";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
 import {
 	SettingsHeader,
 	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
 	SettingsHeaderTitle,
 } from "#/components/SettingsHeader/SettingsHeader";
 import {
@@ -51,18 +51,25 @@ export const OrganizationProvisionerKeysPageView: FC<
 
 	return (
 		<section className="w-full max-w-screen-2xl pb-10">
-			<SettingsHeader>
+			<SettingsHeader
+				actions={<SettingsHeaderDocsLink href={docs("/admin/provisioners")} />}
+			>
 				<SettingsHeaderTitle>Provisioner Keys</SettingsHeaderTitle>
 				<SettingsHeaderDescription>
-					Manage provisioner keys used to authenticate provisioner instances.{" "}
-					<Link href={docs("/admin/provisioners")}>View docs</Link>
+					Manage provisioner keys used to authenticate provisioner instances.
 				</SettingsHeaderDescription>
 			</SettingsHeader>
 
 			{showPaywall ? (
 				<PaywallPremium
 					message="Provisioners"
-					description="Provisioners run your Terraform to create templates and workspaces. You need a Premium license to use this feature for multiple organizations."
+					description="Scoped authentication keys for org provisioners."
+					features={[
+						"Scoped per organization & tag",
+						"Recommended provisioner authentication",
+						"Rotate keys without downtime",
+						"Fully isolated per organization",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			) : (
diff --git a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.stories.tsx b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.stories.tsx
index 5d953a3acb6..340a75608bd 100644
--- a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.stories.tsx
+++ b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.stories.tsx
@@ -8,6 +8,7 @@ import {
 	MockUserProvisioner,
 	mockApiError,
 } from "#/testHelpers/entities";
+import { docs } from "#/utils/docs";
 import { OrganizationProvisionersPageView } from "./OrganizationProvisionersPageView";
 
 const meta: Meta<typeof OrganizationProvisionersPageView> = {
@@ -75,6 +76,9 @@ export const Paywall: Story = {
 
 		const cta = canvas.getByRole("link", { name: "Start trial for free" });
 		await expect(cta).toHaveAttribute("href", "/deployment/premium");
+		await expect(
+			canvas.getByRole("link", { name: /Read the docs/ }),
+		).toHaveAttribute("href", docs("/admin/provisioners"));
 	},
 };
 
diff --git a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.tsx b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.tsx
index 03626589d08..5d291a40c2d 100644
--- a/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.tsx
+++ b/site/src/pages/OrganizationSettingsPage/OrganizationProvisionersPage/OrganizationProvisionersPageView.tsx
@@ -9,6 +9,7 @@ import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
 import {
 	SettingsHeader,
 	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
 	SettingsHeaderTitle,
 } from "#/components/SettingsHeader/SettingsHeader";
 import {
@@ -60,12 +61,13 @@ export const OrganizationProvisionersPageView: FC<
 }) => {
 	return (
 		<section className="w-full max-w-screen-2xl pb-10">
-			<SettingsHeader>
+			<SettingsHeader
+				actions={<SettingsHeaderDocsLink href={docs("/admin/provisioners")} />}
+			>
 				<SettingsHeaderTitle>Provisioners</SettingsHeaderTitle>
 				<SettingsHeaderDescription>
 					Coder server runs provisioner daemons which execute terraform during
-					workspace and template builds.{" "}
-					<Link href={docs("/admin/provisioners")}>View docs</Link>
+					workspace and template builds.
 				</SettingsHeaderDescription>
 			</SettingsHeader>
 
@@ -99,7 +101,13 @@ export const OrganizationProvisionersPageView: FC<
 			{showPaywall ? (
 				<PaywallPremium
 					message="Provisioners"
-					description="Provisioners run your Terraform to create templates and workspaces. You need a Premium license to use this feature for multiple organizations."
+					description="Provisioners run your Terraform to create templates and workspaces."
+					features={[
+						"Run build jobs in isolation",
+						"Isolate cloud APIs from Coder",
+						"Keep secrets off the Coder host",
+						"Reduce server load and queue times",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			) : (
diff --git a/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPage.tsx b/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPage.tsx
index 5e2ad77e6d4..f2d87a851e6 100644
--- a/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPage.tsx
+++ b/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPage.tsx
@@ -8,8 +8,15 @@ import {
 	templateACL,
 } from "#/api/queries/templates";
 import { PaywallPremium } from "#/components/Paywall/PaywallPremium";
+import {
+	SettingsHeader,
+	SettingsHeaderDescription,
+	SettingsHeaderDocsLink,
+	SettingsHeaderTitle,
+} from "#/components/SettingsHeader/SettingsHeader";
 import { useAuthenticated } from "#/hooks/useAuthenticated";
 import { useFeatureVisibility } from "#/modules/dashboard/useFeatureVisibility";
+import { docs } from "#/utils/docs";
 import { pageTitle } from "#/utils/page";
 import { useTemplateSettings } from "../TemplateSettingsLayout";
 import { TemplatePermissionsPageView } from "./TemplatePermissionsPageView";
@@ -33,155 +40,174 @@ const TemplatePermissionsPage: FC = () => {
 		<>
 			<title>{pageTitle(template.name, "Permissions")}</title>
 
-			{!isTemplateRBACEnabled ? (
-				<PaywallPremium
-					message="Template permissions"
-					description="Control users and groups access to templates."
-					canViewPremium={authPermissions.viewAllLicenses}
-				/>
-			) : (
-				<TemplatePermissionsPageView
-					templateID={template.id}
-					templateACL={templateACLQuery.data}
-					canUpdatePermissions={Boolean(permissions?.canUpdateTemplate)}
-					onAddUser={async (user, role, reset) => {
-						await addUserMutation.mutateAsync({
-							templateId: template.id,
-							userId: user.id,
-							role,
-						});
-						reset();
-					}}
-					isAddingUser={addUserMutation.isPending}
-					onUpdateUser={async (user, role) => {
-						await updateUserMutation.mutateAsync(
-							{
+			<div className="flex flex-col gap-12">
+				<SettingsHeader
+					actions={
+						<SettingsHeaderDocsLink
+							href={docs("/admin/templates/template-permissions")}
+						/>
+					}
+				>
+					<SettingsHeaderTitle>Permissions</SettingsHeaderTitle>
+					<SettingsHeaderDescription>
+						Manage which members and groups can use this template.
+					</SettingsHeaderDescription>
+				</SettingsHeader>
+
+				{!isTemplateRBACEnabled ? (
+					<PaywallPremium
+						message="Template permissions"
+						description="Restrict template access by user or group."
+						features={[
+							"Choose Use or Admin-level access",
+							"Prevent unauthorized template use",
+						]}
+						canViewPremium={authPermissions.viewAllLicenses}
+					/>
+				) : (
+					<TemplatePermissionsPageView
+						templateID={template.id}
+						templateACL={templateACLQuery.data}
+						canUpdatePermissions={Boolean(permissions?.canUpdateTemplate)}
+						onAddUser={async (user, role, reset) => {
+							await addUserMutation.mutateAsync({
 								templateId: template.id,
 								userId: user.id,
 								role,
-							},
-							{
-								onSuccess: () => {
-									toast.success(
-										`Role for "${user.username}" updated to "${role}" successfully.`,
-									);
+							});
+							reset();
+						}}
+						isAddingUser={addUserMutation.isPending}
+						onUpdateUser={async (user, role) => {
+							await updateUserMutation.mutateAsync(
+								{
+									templateId: template.id,
+									userId: user.id,
+									role,
 								},
-								onError: (error) => {
-									toast.error(
-										getErrorMessage(
-											error,
-											`Failed to update role for "${user.username}".`,
-										),
-										{
-											description: getErrorDetail(error),
-										},
-									);
+								{
+									onSuccess: () => {
+										toast.success(
+											`Role for "${user.username}" updated to "${role}" successfully.`,
+										);
+									},
+									onError: (error) => {
+										toast.error(
+											getErrorMessage(
+												error,
+												`Failed to update role for "${user.username}".`,
+											),
+											{
+												description: getErrorDetail(error),
+											},
+										);
+									},
 								},
-							},
-						);
-					}}
-					updatingUserId={
-						updateUserMutation.isPending
-							? updateUserMutation.variables?.userId
-							: undefined
-					}
-					onRemoveUser={async (user) => {
-						await removeUserMutation.mutateAsync(
-							{
-								templateId: template.id,
-								userId: user.id,
-								role: "",
-							},
-							{
-								onSuccess: () => {
-									toast.success(
-										`User "${user.username}" removed successfully.`,
-									);
+							);
+						}}
+						updatingUserId={
+							updateUserMutation.isPending
+								? updateUserMutation.variables?.userId
+								: undefined
+						}
+						onRemoveUser={async (user) => {
+							await removeUserMutation.mutateAsync(
+								{
+									templateId: template.id,
+									userId: user.id,
+									role: "",
 								},
-								onError: (error) => {
-									toast.error(
-										getErrorMessage(
-											error,
-											`Failed to remove user "${user.username}".`,
-										),
-										{
-											description: getErrorDetail(error),
-										},
-									);
+								{
+									onSuccess: () => {
+										toast.success(
+											`User "${user.username}" removed successfully.`,
+										);
+									},
+									onError: (error) => {
+										toast.error(
+											getErrorMessage(
+												error,
+												`Failed to remove user "${user.username}".`,
+											),
+											{
+												description: getErrorDetail(error),
+											},
+										);
+									},
 								},
-							},
-						);
-					}}
-					onAddGroup={async (group, role, reset) => {
-						await addGroupMutation.mutateAsync({
-							templateId: template.id,
-							groupId: group.id,
-							role,
-						});
-						reset();
-					}}
-					isAddingGroup={addGroupMutation.isPending}
-					onUpdateGroup={async (group, role) => {
-						await updateGroupMutation.mutateAsync(
-							{
+							);
+						}}
+						onAddGroup={async (group, role, reset) => {
+							await addGroupMutation.mutateAsync({
 								templateId: template.id,
 								groupId: group.id,
 								role,
-							},
-							{
-								onSuccess: () => {
-									toast.success(
-										`Role for "${group.display_name || group.name}" updated to "${role}" successfully.`,
-									);
+							});
+							reset();
+						}}
+						isAddingGroup={addGroupMutation.isPending}
+						onUpdateGroup={async (group, role) => {
+							await updateGroupMutation.mutateAsync(
+								{
+									templateId: template.id,
+									groupId: group.id,
+									role,
 								},
-								onError: (error) => {
-									toast.error(
-										getErrorMessage(
-											error,
-											`Failed to update role for "${group.display_name || group.name}".`,
-										),
-										{
-											description: getErrorDetail(error),
-										},
-									);
+								{
+									onSuccess: () => {
+										toast.success(
+											`Role for "${group.display_name || group.name}" updated to "${role}" successfully.`,
+										);
+									},
+									onError: (error) => {
+										toast.error(
+											getErrorMessage(
+												error,
+												`Failed to update role for "${group.display_name || group.name}".`,
+											),
+											{
+												description: getErrorDetail(error),
+											},
+										);
+									},
 								},
-							},
-						);
-					}}
-					updatingGroupId={
-						updateGroupMutation.isPending
-							? updateGroupMutation.variables?.groupId
-							: undefined
-					}
-					onRemoveGroup={async (group) => {
-						await removeGroupMutation.mutateAsync(
-							{
-								groupId: group.id,
-								templateId: template.id,
-								role: "",
-							},
-							{
-								onSuccess: () => {
-									toast.success(
-										`Group "${group.display_name || group.name}" removed successfully.`,
-									);
+							);
+						}}
+						updatingGroupId={
+							updateGroupMutation.isPending
+								? updateGroupMutation.variables?.groupId
+								: undefined
+						}
+						onRemoveGroup={async (group) => {
+							await removeGroupMutation.mutateAsync(
+								{
+									groupId: group.id,
+									templateId: template.id,
+									role: "",
 								},
-								onError: (error) => {
-									toast.error(
-										getErrorMessage(
-											error,
-											`Failed to remove group "${group.display_name || group.name}".`,
-										),
-										{
-											description: getErrorDetail(error),
-										},
-									);
+								{
+									onSuccess: () => {
+										toast.success(
+											`Group "${group.display_name || group.name}" removed successfully.`,
+										);
+									},
+									onError: (error) => {
+										toast.error(
+											getErrorMessage(
+												error,
+												`Failed to remove group "${group.display_name || group.name}".`,
+											),
+											{
+												description: getErrorDetail(error),
+											},
+										);
+									},
 								},
-							},
-						);
-					}}
-				/>
-			)}
+							);
+						}}
+					/>
+				)}
+			</div>
 		</>
 	);
 };
diff --git a/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPageView.tsx b/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPageView.tsx
index 764840d3a7e..ee0a9854fa4 100644
--- a/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPageView.tsx
+++ b/site/src/pages/TemplateSettingsPage/TemplatePermissionsPage/TemplatePermissionsPageView.tsx
@@ -24,11 +24,6 @@ import {
 	SelectTrigger,
 	SelectValue,
 } from "#/components/Select/Select";
-import {
-	SettingsHeader,
-	SettingsHeaderDescription,
-	SettingsHeaderTitle,
-} from "#/components/SettingsHeader/SettingsHeader";
 import { Spinner } from "#/components/Spinner/Spinner";
 import {
 	Table,
@@ -227,13 +222,6 @@ export const TemplatePermissionsPageView: FC<
 }) => {
 	return (
 		<div className="flex flex-col gap-12">
-			<SettingsHeader>
-				<SettingsHeaderTitle>Permissions</SettingsHeaderTitle>
-				<SettingsHeaderDescription>
-					Manage which members and groups can use this template.
-				</SettingsHeaderDescription>
-			</SettingsHeader>
-
 			<div className="flex flex-col gap-2.5">
 				{canUpdatePermissions && (
 					<AddTemplateUserOrGroup
diff --git a/site/src/pages/UserSettingsPage/WorkspaceProxyPage/WorkspaceProxyView.tsx b/site/src/pages/UserSettingsPage/WorkspaceProxyPage/WorkspaceProxyView.tsx
index a7162fb0720..235d5b4da60 100644
--- a/site/src/pages/UserSettingsPage/WorkspaceProxyPage/WorkspaceProxyView.tsx
+++ b/site/src/pages/UserSettingsPage/WorkspaceProxyPage/WorkspaceProxyView.tsx
@@ -63,7 +63,13 @@ export const WorkspaceProxyView: FC<WorkspaceProxyViewProps> = ({
 			{showPaywall ? (
 				<PaywallPremium
 					message="Workspace Proxies"
-					description="Workspace proxies provide low-latency connections for geo-distributed teams."
+					description="Provide low-latency connections for geo-distributed teams."
+					features={[
+						"Low-latency connections for global teams",
+						"Automatic lowest-latency proxy selection",
+						"Relay for SSH, apps, and ports",
+						"Per-proxy latency and health metrics",
+					]}
 					canViewPremium={permissions.viewAllLicenses}
 				/>
 			) : (