diff --git a/frontend/app/auth/callback/route.ts b/frontend/app/auth/callback/route.ts
index fb8cab07..ff8c14ba 100644
--- a/frontend/app/auth/callback/route.ts
+++ b/frontend/app/auth/callback/route.ts
@@ -4,6 +4,7 @@ import { createSupabaseRouteClient, hasSupabaseServerEnv } from "@/lib/supabase/
 import { getConfiguredSiteUrl } from "@/lib/site-url";
 
 const API_BASE = process.env.POLYWEATHER_API_BASE_URL;
+const TERMINAL_CHECKOUT_PATH = "/account?checkout=1";
 
 function normalizeNextPath(input: string | null) {
   const fallback = "/";
@@ -23,6 +24,14 @@ function normalizeAuthError(input: string | null) {
   return raw.slice(0, 240);
 }
 
+function isTerminalNextPath(pathname: string) {
+  return pathname === "/terminal" || pathname.startsWith("/terminal/");
+}
+
+type AuthProfilePayload = {
+  subscription_active?: boolean | null;
+};
+
 function redirectToLoginWithError({
   baseUrl,
   error,
@@ -39,9 +48,9 @@ function redirectToLoginWithError({
   return NextResponse.redirect(loginUrl);
 }
 
-async function warmSignupTrial(accessToken: string) {
+async function warmSignupTrial(accessToken: string): Promise<AuthProfilePayload | null> {
   const token = String(accessToken || "").trim();
-  if (!API_BASE || !token) return;
+  if (!API_BASE || !token) return null;
 
   const headers = new Headers({
     Accept: "application/json",
@@ -55,18 +64,42 @@ async function warmSignupTrial(accessToken: string) {
   const controller = new AbortController();
   const timeoutId = setTimeout(() => controller.abort(), 2500);
   try {
-    await fetch(`${API_BASE.replace(/\/+$/, "")}/api/auth/me?scope=entitlement`, {
+    const response = await fetch(`${API_BASE.replace(/\/+$/, "")}/api/auth/me?scope=entitlement`, {
       cache: "no-store",
       headers,
       signal: controller.signal,
     });
+    if (!response.ok) {
+      return { subscription_active: false };
+    }
+    return await response.json();
   } catch {
     // The account/terminal bootstrap will retry. Callback must not strand login.
+    return null;
   } finally {
     clearTimeout(timeoutId);
   }
 }
 
+async function resolvePostAuthRedirect({
+  accessToken,
+  baseUrl,
+  nextPath,
+}: {
+  accessToken: string;
+  baseUrl: string;
+  nextPath: string;
+}) {
+  const profile = await warmSignupTrial(accessToken);
+  if (!isTerminalNextPath(nextPath)) {
+    return new URL(nextPath, baseUrl);
+  }
+
+  const redirectPath =
+    profile?.subscription_active === false ? TERMINAL_CHECKOUT_PATH : nextPath;
+  return new URL(redirectPath, baseUrl);
+}
+
 export async function GET(request: NextRequest) {
   const siteUrl = getConfiguredSiteUrl();
   if (siteUrl) {
@@ -122,7 +155,12 @@ export async function GET(request: NextRequest) {
         nextPath,
       });
     }
-    await warmSignupTrial(session?.access_token || "");
+    const finalRedirectUrl = await resolvePostAuthRedirect({
+      accessToken: session.access_token,
+      baseUrl,
+      nextPath,
+    });
+    response.headers.set("Location", finalRedirectUrl.toString());
   }
 
   return response;
diff --git a/frontend/components/auth/LoginClient.tsx b/frontend/components/auth/LoginClient.tsx
index a8e71dca..bddbc698 100644
--- a/frontend/components/auth/LoginClient.tsx
+++ b/frontend/components/auth/LoginClient.tsx
@@ -27,6 +27,40 @@ type LoginClientProps = {
   initialMode?: Mode;
 };
 
+const TERMINAL_CHECKOUT_PATH = "/account?checkout=1";
+
+function isTerminalNextPath(pathname: string) {
+  return pathname === "/terminal" || pathname.startsWith("/terminal/");
+}
+
+async function resolvePostLoginRedirect({
+  accessToken,
+  nextPath,
+}: {
+  accessToken?: string | null;
+  nextPath: string;
+}) {
+  if (!isTerminalNextPath(nextPath)) return nextPath;
+  const token = String(accessToken || "").trim();
+  if (!token || typeof fetch !== "function") return TERMINAL_CHECKOUT_PATH;
+  try {
+    const response = await fetch("/api/auth/me?scope=entitlement", {
+      cache: "no-store",
+      headers: {
+        Accept: "application/json",
+        Authorization: `Bearer ${token}`,
+      },
+    });
+    if (!response.ok) return nextPath;
+    const payload = await response.json();
+    return payload?.subscription_active === false
+      ? TERMINAL_CHECKOUT_PATH
+      : nextPath;
+  } catch {
+    return nextPath;
+  }
+}
+
 export function LoginClient({ nextPath, initialError, initialMode }: LoginClientProps) {
   const router = useRouter();
   const { locale } = useI18n();
@@ -214,7 +248,7 @@ export function LoginClient({ nextPath, initialError, initialMode }: LoginClient
     try {
       const supabase = getSupabaseBrowserClient();
       if (mode === "login") {
-        const { error } = await supabase.auth.signInWithPassword({
+        const { data, error } = await supabase.auth.signInWithPassword({
           email: email.trim(),
           password,
         });
@@ -222,7 +256,11 @@ export function LoginClient({ nextPath, initialError, initialMode }: LoginClient
           setErrorText(error.message);
           return;
         }
-        router.replace(nextPath);
+        const redirectPath = await resolvePostLoginRedirect({
+          accessToken: data.session?.access_token,
+          nextPath,
+        });
+        router.replace(redirectPath);
         return;
       }
 
@@ -241,7 +279,11 @@ export function LoginClient({ nextPath, initialError, initialMode }: LoginClient
         return;
       }
       if (data.session?.user) {
-        router.replace(nextPath);
+        const redirectPath = await resolvePostLoginRedirect({
+          accessToken: data.session.access_token,
+          nextPath,
+        });
+        router.replace(redirectPath);
         return;
       }
       setInfoText(copy.signupCheckEmail);
diff --git a/frontend/components/auth/__tests__/terminalCheckoutRedirect.test.ts b/frontend/components/auth/__tests__/terminalCheckoutRedirect.test.ts
new file mode 100644
index 00000000..40eaa53f
--- /dev/null
+++ b/frontend/components/auth/__tests__/terminalCheckoutRedirect.test.ts
@@ -0,0 +1,38 @@
+import fs from "node:fs";
+import path from "node:path";
+
+function assert(condition: unknown, message: string) {
+  if (!condition) throw new Error(message);
+}
+
+export function runTests() {
+  const projectRoot = process.cwd();
+  const loginClientSource = fs.readFileSync(
+    path.join(projectRoot, "components", "auth", "LoginClient.tsx"),
+    "utf8",
+  );
+  const authCallbackSource = fs.readFileSync(
+    path.join(projectRoot, "app", "auth", "callback", "route.ts"),
+    "utf8",
+  );
+
+  assert(
+    loginClientSource.includes("TERMINAL_CHECKOUT_PATH") &&
+      loginClientSource.includes('"/account?checkout=1"') &&
+      loginClientSource.includes("resolvePostLoginRedirect") &&
+      loginClientSource.includes("subscription_active === false") &&
+      loginClientSource.includes("router.replace(redirectPath)") &&
+      !loginClientSource.includes("router.replace(nextPath);\n        return;"),
+    "email/password terminal login must send non-members to the checkout account page instead of blindly returning to /terminal",
+  );
+
+  assert(
+    authCallbackSource.includes("resolvePostAuthRedirect") &&
+      authCallbackSource.includes("TERMINAL_CHECKOUT_PATH") &&
+      authCallbackSource.includes('"/account?checkout=1"') &&
+      authCallbackSource.includes("subscription_active === false") &&
+      authCallbackSource.includes("NextResponse.redirect(redirectUrl)") &&
+      authCallbackSource.includes("await resolvePostAuthRedirect"),
+    "OAuth terminal callback must send non-members to the checkout account page instead of blindly returning to /terminal",
+  );
+}