diff --git a/site/src/modules/apps/WorkspaceAppFrame.tsx b/site/src/modules/apps/WorkspaceAppFrame.tsx
index 4ff610f88ac80..bf77bbbe1e961 100644
--- a/site/src/modules/apps/WorkspaceAppFrame.tsx
+++ b/site/src/modules/apps/WorkspaceAppFrame.tsx
@@ -63,7 +63,7 @@ export const WorkspaceAppFrame: FC<WorkspaceAppFrameProps> = ({
 						variant="subtle"
 						onClick={(e) => {
 							e.preventDefault();
-							if (frameRef.current?.contentWindow) {
+							if (link.href && frameRef.current?.contentWindow) {
 								frameRef.current.contentWindow.location.href = link.href;
 							}
 						}}
@@ -83,7 +83,11 @@ export const WorkspaceAppFrame: FC<WorkspaceAppFrameProps> = ({
 						</DropdownMenuTrigger>
 						<DropdownMenuContent align="end">
 							<DropdownMenuItem asChild>
-								<RouterLink to={link.href} target="_blank" rel="noreferrer">
+								<RouterLink
+									to={link.href ?? ""}
+									target="_blank"
+									rel="noreferrer"
+								>
 									<ExternalLinkIcon />
 									Open app in new tab
 								</RouterLink>
diff --git a/site/src/modules/apps/useAppLink.ts b/site/src/modules/apps/useAppLink.ts
index e53ee9cb84611..9aaee91bec984 100644
--- a/site/src/modules/apps/useAppLink.ts
+++ b/site/src/modules/apps/useAppLink.ts
@@ -1,7 +1,8 @@
 import type React from "react";
-import { useQuery } from "react-query";
+import { useMutation } from "react-query";
 import { toast } from "sonner";
-import { apiKey } from "#/api/queries/users";
+import { API } from "#/api/api";
+import { getErrorMessage } from "#/api/errors";
 import type {
 	Workspace,
 	WorkspaceAgent,
@@ -21,10 +22,12 @@ type UseAppLinkParams = {
 };
 
 type AppLink = {
-	href: string;
+	// Token-backed external apps intentionally expose no href: their URL is only
+	// complete once a session token is minted on click.
+	href: string | undefined;
 	onClick: (e: React.MouseEvent) => void;
 	label: string;
-	hasToken: boolean;
+	isLoading: boolean;
 };
 
 export const useAppLink = (
@@ -33,20 +36,100 @@ export const useAppLink = (
 ): AppLink => {
 	const label = app.display_name ?? app.slug;
 	const { proxy } = useProxy();
-	const { data: apiKeyResponse } = useQuery({
-		...apiKey(),
-		enabled: isExternalApp(app) && needsSessionToken(app),
-	});
 
-	const href = getAppHref(app, {
-		agent,
-		workspace,
-		token: apiKeyResponse?.key,
-		path: proxy.preferredPathAppURL,
-		host: proxy.preferredWildcardHostname,
+	// External apps that embed the session token in their URL need a freshly
+	// minted key. We defer minting until the user clicks (see `onClick`) rather
+	// than on mount, so that merely rendering a link no longer mints (and
+	// audits) a session key for an app the user may never open.
+	const requiresSessionToken = isExternalApp(app) && needsSessionToken(app);
+
+	const buildHref = (token: string): string =>
+		getAppHref(app, {
+			agent,
+			workspace,
+			token,
+			path: proxy.preferredPathAppURL,
+			host: proxy.preferredWildcardHostname,
+		});
+
+	// Custom-protocol (non-HTTP) external apps can silently fail when the target
+	// application isn't installed. The browser blurs when it hands control to
+	// the protocol handler, which clears the timeout before the error fires.
+	const notifyOnOpenExternalAppFailed = () => {
+		const openAppExternallyFailedTimeout = 1500;
+		const openAppExternallyFailed = setTimeout(() => {
+			// Check if this is a JetBrains IDE app
+			// starts with "jetbrains-gateway://connect#type=coder" (from https://registry.coder.com/modules/coder/jetbrains-gateway)
+			const isJetBrainsGateway = app.url?.startsWith("jetbrains-gateway:");
+			// starts with "jetbrains://gateway/coder" (from https://registry.coder.com/modules/coder/jetbrains)
+			const isJetBrainsToolbox = app.url?.startsWith("jetbrains:");
+
+			// Check if this is a coder:// URL
+			const isCoderApp = app.url?.startsWith("coder:");
+
+			if (isJetBrainsGateway) {
+				toast.error(`Failed to open "${label}".`, {
+					description: "JetBrains Gateway must be installed.",
+				});
+			} else if (isJetBrainsToolbox) {
+				toast.error(`Failed to open "${label}".`, {
+					description: "JetBrains Toolbox must be installed.",
+				});
+			} else if (isCoderApp) {
+				toast.error(`Failed to open "${label}".`, {
+					description: "Coder Desktop must be installed.",
+				});
+			} else {
+				toast.error(`Failed to open "${label}".`, {
+					description: "The app must be installed first.",
+				});
+			}
+		}, openAppExternallyFailedTimeout);
+		window.addEventListener(
+			"blur",
+			() => {
+				clearTimeout(openAppExternallyFailed);
+			},
+			{ once: true },
+		);
+	};
+
+	// The success/error handlers live on the mutation (not on the `mutate` call)
+	// so they still run when the triggering element unmounts before the request
+	// settles, e.g. a dropdown menu item that closes on select. Callbacks passed
+	// to `mutate` are dropped once the observer unmounts, which would otherwise
+	// swallow both the navigation and the failure toast.
+	const generateKeyMutation = useMutation({
+		mutationFn: () => API.getApiKey(),
+		onSuccess: ({ key }) => {
+			notifyOnOpenExternalAppFailed();
+			location.href = buildHref(key);
+		},
+		onError: (error) => {
+			toast.error(getErrorMessage(error, `Failed to open "${label}".`));
+		},
 	});
 
+	// Token-backed apps expose no navigable href: the token is minted on click
+	// and the final URL is built then. Exposing a tokenless href would let
+	// middle-click or "Open link" launch the custom protocol with an empty
+	// token, so we omit it entirely. Non-token apps still render as anchors.
+	const href = requiresSessionToken ? undefined : buildHref("");
+
 	const onClick = (e: React.MouseEvent) => {
+		// Apps that embed a session token mint it on click instead of on mount.
+		// These are always custom-protocol (non-HTTP) external apps, so we build
+		// the final URL with the freshly minted token and navigate to it via
+		// `location.href`, relying on the browser's protocol handler.
+		if (requiresSessionToken) {
+			e.preventDefault();
+			if (generateKeyMutation.isPending) {
+				return;
+			}
+			generateKeyMutation.mutate();
+			return;
+		}
+
 		if (!e.currentTarget.getAttribute("href")) {
 			return;
 		}
@@ -57,41 +140,7 @@ export const useAppLink = (
 			app.external && app.url && !app.url.startsWith("http");
 
 		if (isExternalProtocolApp) {
-			// When browser recognizes the protocol and is able to navigate to the app,
-			// it will blur away, and will stop the timer. Otherwise,
-			// an error message will be displayed.
-			const openAppExternallyFailedTimeout = 1500;
-			const openAppExternallyFailed = setTimeout(() => {
-				// Check if this is a JetBrains IDE app
-				// starts with "jetbrains-gateway://connect#type=coder" (from https://registry.coder.com/modules/coder/jetbrains-gateway)
-				const isJetBrainsGateway = app.url?.startsWith("jetbrains-gateway:");
-				// starts with "jetbrains://gateway/coder" (from https://registry.coder.com/modules/coder/jetbrains)
-				const isJetBrainsToolbox = app.url?.startsWith("jetbrains:");
-
-				// Check if this is a coder:// URL
-				const isCoderApp = app.url?.startsWith("coder:");
-
-				if (isJetBrainsGateway) {
-					toast.error(`Failed to open "${label}".`, {
-						description: "JetBrains Gateway must be installed.",
-					});
-				} else if (isJetBrainsToolbox) {
-					toast.error(`Failed to open "${label}".`, {
-						description: "JetBrains Toolbox must be installed.",
-					});
-				} else if (isCoderApp) {
-					toast.error(`Failed to open "${label}".`, {
-						description: "Coder Desktop must be installed.",
-					});
-				} else {
-					toast.error(`Failed to open "${label}".`, {
-						description: "The app must be installed first.",
-					});
-				}
-			}, openAppExternallyFailedTimeout);
-			window.addEventListener("blur", () => {
-				clearTimeout(openAppExternallyFailed);
-			});
+			notifyOnOpenExternalAppFailed();
 
 			// Custom protocol external apps don't support open_in since they
 			// rely on the browser's protocol handling.
@@ -101,7 +150,9 @@ export const useAppLink = (
 		switch (app.open_in) {
 			case "slim-window": {
 				e.preventDefault();
-				openAppInNewWindow(href);
+				if (href) {
+					openAppInNewWindow(href);
+				}
 				return;
 			}
 		}
@@ -111,6 +162,6 @@ export const useAppLink = (
 		href,
 		onClick,
 		label,
-		hasToken: Boolean(apiKeyResponse?.key),
+		isLoading: generateKeyMutation.isPending,
 	};
 };
diff --git a/site/src/modules/resources/AppLink/AppLink.stories.tsx b/site/src/modules/resources/AppLink/AppLink.stories.tsx
index 37cd7100b684b..5295c1649c0aa 100644
--- a/site/src/modules/resources/AppLink/AppLink.stories.tsx
+++ b/site/src/modules/resources/AppLink/AppLink.stories.tsx
@@ -1,5 +1,13 @@
 import type { Meta, StoryObj } from "@storybook/react-vite";
-import { expect, screen, spyOn, userEvent, within } from "storybook/test";
+import {
+	expect,
+	screen,
+	spyOn,
+	userEvent,
+	waitFor,
+	within,
+} from "storybook/test";
+import { API } from "#/api/api";
 import { getPreferredProxy } from "#/contexts/ProxyContext";
 import {
 	MockPrimaryWorkspaceProxy,
@@ -257,6 +265,91 @@ export const WithTooltip: Story = {
 	},
 };
 
+// Regression test for DEVEX-460: external apps that embed the session token
+// must not mint an API key on render. The key is minted only when the user
+// clicks the link.
+export const ExternalAppDefersSessionToken: Story = {
+	decorators: [withToaster],
+	// Install the spy before the component renders. `play` runs after render and
+	// its effects, so a regression back to eager (on-mount) minting would fetch a
+	// key before a spy installed in `play` exists, and the later
+	// `not.toHaveBeenCalled()` assertion would still pass.
+	beforeEach: () => {
+		// Never resolve: we only assert whether/when the request fires, and
+		// leaving it pending avoids the subsequent protocol-handler navigation.
+		const getApiKey = spyOn(API, "getApiKey").mockImplementation(
+			() => new Promise(() => {}),
+		);
+		return () => {
+			getApiKey.mockRestore();
+		};
+	},
+	args: {
+		workspace: MockWorkspace,
+		app: {
+			...MockWorkspaceApp,
+			external: true,
+			url: "jetbrains-gateway://connect?token=$SESSION_TOKEN",
+		},
+		agent: MockWorkspaceAgent,
+	},
+	play: async ({ canvasElement, step }) => {
+		const canvas = within(canvasElement);
+		// Token-backed apps expose no href and render as a button (the token is
+		// minted on click), so query by role "button".
+		const trigger = await canvas.findByRole("button");
+		const user = userEvent.setup();
+
+		await step("no API key is minted on render", async () => {
+			expect(API.getApiKey).not.toHaveBeenCalled();
+		});
+
+		await step("clicking mints the API key on demand", async () => {
+			await user.click(trigger);
+			await waitFor(() => expect(API.getApiKey).toHaveBeenCalledTimes(1));
+		});
+	},
+};
+
+// External apps that do not embed the session token must never mint a key,
+// even on click, so we don't create session keys for apps that don't need one.
+export const ExternalAppWithoutSessionTokenNeverMints: Story = {
+	decorators: [withToaster],
+	// Install the spy before render so an on-mount mint would be observed.
+	beforeEach: () => {
+		const getApiKey = spyOn(API, "getApiKey").mockResolvedValue({
+			key: "test-key",
+		});
+		return () => {
+			getApiKey.mockRestore();
+		};
+	},
+	args: {
+		workspace: MockWorkspace,
+		app: {
+			...MockWorkspaceApp,
+			external: true,
+			url: "https://example.com",
+			open_in: "slim-window",
+		},
+		agent: MockWorkspaceAgent,
+	},
+	play: async ({ canvasElement, step }) => {
+		// The app opens in a slim window, so stub window.open to keep the click
+		// from navigating the test frame.
+		spyOn(window, "open").mockReturnValue(null);
+		const canvas = within(canvasElement);
+		const link = await canvas.findByRole("link");
+		const user = userEvent.setup();
+
+		await step("no API key is minted on render or click", async () => {
+			expect(API.getApiKey).not.toHaveBeenCalled();
+			await user.click(link);
+			expect(API.getApiKey).not.toHaveBeenCalled();
+		});
+	},
+};
+
 export const SlimWindowPopupBlocked: Story = {
 	decorators: [withToaster],
 	args: {
diff --git a/site/src/modules/resources/AppLink/AppLink.tsx b/site/src/modules/resources/AppLink/AppLink.tsx
index 7b660ff039bbf..225705ab529bf 100644
--- a/site/src/modules/resources/AppLink/AppLink.tsx
+++ b/site/src/modules/resources/AppLink/AppLink.tsx
@@ -21,8 +21,6 @@ import { useProxy } from "#/contexts/ProxyContext";
 import {
 	isAppBlockedByMissingWildcard,
 	isAppUrlValid,
-	isExternalApp,
-	needsSessionToken,
 } from "#/modules/apps/apps";
 import { useAppLink } from "#/modules/apps/useAppLink";
 import { docs } from "#/utils/docs";
@@ -132,8 +130,11 @@ export const AppLink: FC<AppLinkProps> = ({
 		);
 	}
 
-	if (isExternalApp(app) && needsSessionToken(app) && !link.hasToken) {
-		canClick = false;
+	// The session token for external apps is minted on click, so key generation
+	// no longer gates clickability. While a click is minting a token, show a
+	// spinner to reflect the in-flight request.
+	if (link.isLoading) {
+		icon = <Spinner loading />;
 	}
 
 	if (
@@ -156,32 +157,44 @@ export const AppLink: FC<AppLinkProps> = ({
 				shareIcon: null,
 			};
 
+	// Token-minting external apps expose no navigable href (see useAppLink): the
+	// URL is only complete after the on-click mint. Render them as a button so
+	// they stay interactive. A bare anchor without href is styled and treated as
+	// disabled by AgentButton, and middle-clicking one would otherwise launch
+	// the custom protocol with an empty token.
+	const opensViaClick = link.href === undefined;
+
+	const content = (
+		<>
+			{icon}
+			{link.label}
+			{ShareIcon && <ShareIcon />}
+		</>
+	);
+
+	const trigger = opensViaClick ? (
+		<button
+			type="button"
+			onClick={link.onClick}
+			disabled={!canClick || link.isLoading}
+		>
+			{content}
+		</button>
+	) : (
+		<a
+			href={canClick ? link.href : undefined}
+			onClick={link.onClick}
+			target={app.open_in === "tab" ? "_blank" : undefined}
+			rel={app.open_in === "tab" ? "noreferrer" : undefined}
+		>
+			{content}
+		</a>
+	);
+
 	const button = grouped ? (
-		<DropdownMenuItem asChild>
-			<a
-				href={canClick ? link.href : undefined}
-				onClick={link.onClick}
-				target={app.open_in === "tab" ? "_blank" : undefined}
-				rel={app.open_in === "tab" ? "noreferrer" : undefined}
-			>
-				{icon}
-				{link.label}
-				{ShareIcon && <ShareIcon />}
-			</a>
-		</DropdownMenuItem>
+		<DropdownMenuItem asChild>{trigger}</DropdownMenuItem>
 	) : (
-		<AgentButton asChild>
-			<a
-				href={canClick ? link.href : undefined}
-				onClick={link.onClick}
-				target={app.open_in === "tab" ? "_blank" : undefined}
-				rel={app.open_in === "tab" ? "noreferrer" : undefined}
-			>
-				{icon}
-				{link.label}
-				{ShareIcon && <ShareIcon />}
-			</a>
-		</AgentButton>
+		<AgentButton asChild>{trigger}</AgentButton>
 	);
 
 	if (primaryTooltip || app.tooltip) {
diff --git a/site/src/pages/AgentsPage/components/WorkspacePill.tsx b/site/src/pages/AgentsPage/components/WorkspacePill.tsx
index 1a194ba3da70c..c2a443b8d842a 100644
--- a/site/src/pages/AgentsPage/components/WorkspacePill.tsx
+++ b/site/src/pages/AgentsPage/components/WorkspacePill.tsx
@@ -39,8 +39,6 @@ import { useIsBelowMdViewport } from "#/hooks/useIsBelowMdViewport";
 import {
 	getTerminalHref,
 	getVSCodeHref,
-	isExternalApp,
-	needsSessionToken,
 	openAppInNewWindow,
 } from "#/modules/apps/apps";
 import { useAppLink } from "#/modules/apps/useAppLink";
@@ -338,13 +336,10 @@ const AppMenuItem: FC<{
 }> = ({ app, workspace, agent, isRunning }) => {
 	const link = useAppLink(app, { workspace, agent });
 
-	const canClick =
-		!isExternalApp(app) || !needsSessionToken(app) || link.hasToken;
-
 	return (
-		<DropdownMenuItem asChild disabled={!canClick || !isRunning}>
+		<DropdownMenuItem asChild disabled={!isRunning || link.isLoading}>
 			<a
-				href={canClick && isRunning ? link.href : undefined}
+				href={isRunning ? link.href : undefined}
 				onClick={link.onClick}
 				target="_blank"
 				rel="noreferrer"
diff --git a/site/src/pages/TaskPage/TaskApps.tsx b/site/src/pages/TaskPage/TaskApps.tsx
index d415514be2e77..745fccb93e677 100644
--- a/site/src/pages/TaskPage/TaskApps.tsx
+++ b/site/src/pages/TaskPage/TaskApps.tsx
@@ -172,12 +172,19 @@ const ExternalAppMenuItem: FC<{
 		workspace,
 	});
 
+	// External apps mint their session token on click via `link.onClick`, so we
+	// render a plain anchor (not a RouterLink) and let the hook handle opening.
 	return (
 		<DropdownMenuItem asChild>
-			<RouterLink to={link.href}>
+			<a
+				href={link.href}
+				onClick={link.onClick}
+				target="_blank"
+				rel="noreferrer"
+			>
 				{app.icon ? <ExternalImage src={app.icon} /> : <LayoutGridIcon />}
 				{link.label}
-			</RouterLink>
+			</a>
 		</DropdownMenuItem>
 	);
 };
@@ -201,7 +208,7 @@ const TaskAppTab: FC<TaskAppTabProps> = ({
 	});
 
 	return (
-		<TaskTab active={active} to={link.href} onClick={onClick}>
+		<TaskTab active={active} to={link.href ?? ""} onClick={onClick}>
 			{app.icon ? <ExternalImage src={app.icon} /> : <LayoutGridIcon />}
 			{link.label}
 			{app.health === "unhealthy" && (