diff --git a/app/(authenticated)/link/_tests/page.test.tsx b/app/(authenticated)/link/_tests/page.test.tsx
new file mode 100644
index 00000000..e05cab14
--- /dev/null
+++ b/app/(authenticated)/link/_tests/page.test.tsx
@@ -0,0 +1,77 @@
+import { renderToStaticMarkup } from "react-dom/server";
+import { beforeEach, describe, expect, it, vi } from "vitest";
+import type { getLinkAccount as readLinkAccount } from "@db/services/auth/link";
+import Page from "../page";
+
+const { getLinkAccount } = vi.hoisted(() => ({
+  getLinkAccount: vi.fn<typeof readLinkAccount>(),
+}));
+
+vi.mock("@db/services/auth/link", () => ({
+  getLinkAccount,
+  linkConfigured: () => true,
+}));
+vi.mock("@web/auth/request-scope", () => ({
+  requireRequestScope: () => ({ userId: "better-auth:phone-user" }),
+}));
+
+beforeEach(() => {
+  getLinkAccount.mockResolvedValue({ id: "wallet-account" });
+});
+
+describe("Link wallet recovery", () => {
+  it("offers reauthentication and returns to the pending wallet request", async () => {
+    const attempt = "6738a4d4-c973-42f4-9e4a-e8339c09687f";
+    const html = renderToStaticMarkup(
+      await Page({
+        params: Promise.resolve({}),
+        searchParams: Promise.resolve({
+          error: "reauthentication_required",
+          attempt,
+        }),
+      })
+    );
+
+    expect(html).toContain("Sign in again before disconnecting your wallet.");
+    expect(html).toContain(
+      `href="/sign-in?reauthenticate=true&amp;callbackUrl=%2Flink%3Fattempt%3D${attempt}"`
+    );
+    expect(html).not.toContain("Disconnect wallet");
+  });
+
+  it("offers a retry for failed revocation without requesting a new sign-in", async () => {
+    const html = renderToStaticMarkup(
+      await Page({
+        params: Promise.resolve({}),
+        searchParams: Promise.resolve({ error: "disconnection_failed" }),
+      })
+    );
+
+    expect(html).toContain("Your wallet could not be disconnected.");
+    expect(html).toContain("It is still connected. Try again shortly.");
+    expect(html).toContain("Disconnect wallet");
+    expect(html).not.toContain("Sign in again");
+  });
+
+  it.each(["disconnection_failed", "reauthentication_required"])(
+    "shows the current disconnected state for a stale %s error",
+    async (code) => {
+      getLinkAccount.mockResolvedValue(undefined);
+      const html = renderToStaticMarkup(
+        await Page({
+          params: Promise.resolve({}),
+          searchParams: Promise.resolve({ error: code }),
+        })
+      );
+
+      expect(html).toContain("Connect Link");
+      expect(html).not.toContain("Disconnect wallet");
+      expect(html).toContain("Your wallet is no longer connected.");
+      expect(html).not.toContain("It is still connected.");
+      expect(html).not.toContain("Sign in again");
+      expect(html).not.toContain(
+        "The wallet connection could not be completed"
+      );
+    }
+  );
+});
diff --git a/app/(authenticated)/link/page.tsx b/app/(authenticated)/link/page.tsx
index fc877767..0501957d 100644
--- a/app/(authenticated)/link/page.tsx
+++ b/app/(authenticated)/link/page.tsx
@@ -21,6 +21,12 @@ export default async function Page({ searchParams }: PageProps<"/link">) {
   const connected =
     configured &&
     Boolean(await getLinkAccount(scope.userId.slice("better-auth:".length)));
+  const reauthenticationRequired =
+    connected && params.error === "reauthentication_required";
+  const disconnectError =
+    params.error === "reauthentication_required" ||
+    params.error === "disconnection_failed";
+  const returnUrl = attempt.success ? `/link?attempt=${attempt.data}` : "/link";
   return (
     <main className="mx-auto flex w-full max-w-xl flex-col gap-6 p-6">
       <div className="space-y-2">
@@ -93,9 +99,13 @@ export default async function Page({ searchParams }: PageProps<"/link">) {
       )}
       {params.error && (
         <p role="alert" className="type-supporting text-destructive">
-          The wallet connection could not be completed. Try again, or sign in
-          again before disconnecting. To use a different wallet, disconnect the
-          current wallet first.
+          {disconnectError && !connected
+            ? "Your wallet is no longer connected."
+            : reauthenticationRequired
+              ? "Sign in again before disconnecting your wallet. Your wallet is still connected."
+              : disconnectError
+                ? "Your wallet could not be disconnected. It is still connected. Try again shortly."
+                : "The wallet connection could not be completed. Try again. To use a different wallet, disconnect the current wallet first."}
         </p>
       )}
       {configured && (
@@ -111,13 +121,27 @@ export default async function Page({ searchParams }: PageProps<"/link">) {
               </Button>
             </form>
           )}
-          {connected && (
-            <form action="/api/link" method="post">
-              <input type="hidden" name="operation" value="disconnect" />
-              <Button type="submit" variant="outline">
-                Disconnect wallet
-              </Button>
-            </form>
+          {reauthenticationRequired ? (
+            <Button
+              nativeButton={false}
+              render={
+                <a
+                  aria-label="Sign in again"
+                  href={`/sign-in?reauthenticate=true&callbackUrl=${encodeURIComponent(returnUrl)}`}
+                />
+              }
+            >
+              Sign in again
+            </Button>
+          ) : (
+            connected && (
+              <form action="/api/link" method="post">
+                <input type="hidden" name="operation" value="disconnect" />
+                <Button type="submit" variant="outline">
+                  Disconnect wallet
+                </Button>
+              </form>
+            )
           )}
         </div>
       )}
diff --git a/app/api/link/route.ts b/app/api/link/route.ts
index c260fa5f..1999475c 100644
--- a/app/api/link/route.ts
+++ b/app/api/link/route.ts
@@ -1,4 +1,5 @@
 import { z } from "zod";
+import { APIError } from "better-auth/api";
 import { getAuth } from "@db/services/auth";
 import { getAuthSession } from "@db/services/auth/session";
 import {
@@ -77,8 +78,14 @@ export async function POST(request: Request) {
         status: 303,
         headers: { ...privateHeaders, location: "/link" },
       });
-    } catch {
-      return connectionFailed(input.data.attempt);
+    } catch (error) {
+      return connectionFailed(
+        input.data.attempt,
+        error instanceof APIError &&
+          (error.body?.code === "SESSION_NOT_FRESH" || error.statusCode === 401)
+          ? "reauthentication_required"
+          : "disconnection_failed"
+      );
     }
   }
   return connectLink(session.user.id, request.headers, input.data.attempt);
@@ -114,9 +121,9 @@ async function connectLink(
   }
 }
 
-function connectionFailed(attempt?: string) {
+function connectionFailed(attempt?: string, error = "connection_failed") {
   const destination = new URL("/link", applicationOrigin());
-  destination.searchParams.set("error", "connection_failed");
+  destination.searchParams.set("error", error);
   if (attempt) destination.searchParams.set("attempt", attempt);
   return new Response(null, {
     status: 303,
diff --git a/app/sign-in/_tests/page.test.tsx b/app/sign-in/_tests/page.test.tsx
new file mode 100644
index 00000000..c8493a4b
--- /dev/null
+++ b/app/sign-in/_tests/page.test.tsx
@@ -0,0 +1,63 @@
+import { createElement } from "react";
+import { renderToStaticMarkup } from "react-dom/server";
+import { describe, expect, it, vi } from "vitest";
+import SignInPage from "../page";
+
+vi.mock("next/headers", () => ({ headers: () => new Headers() }));
+vi.mock("next/navigation", () => ({
+  redirect: (url: string) => {
+    throw new Error(`Redirect: ${url}`);
+  },
+}));
+vi.mock("@db/services/auth/session", () => ({
+  getAuthSession: () => ({ user: { id: "phone-user" } }),
+}));
+vi.mock("@shared/environment", () => ({
+  env: {},
+  localPhoneAuthBypassEnabled: true,
+}));
+vi.mock("@app/sign-in/_components/local-form", () => ({
+  LocalPhoneAuthForm: ({ callbackUrl }: { readonly callbackUrl: string }) =>
+    createElement("form", { action: callbackUrl }),
+}));
+
+describe("phone sign-in reauthentication", () => {
+  it("allows an already signed-in user to verify again and return to Link", async () => {
+    const html = renderToStaticMarkup(
+      await SignInPage({
+        params: Promise.resolve({}),
+        searchParams: Promise.resolve({
+          reauthenticate: "true",
+          callbackUrl: "/link",
+        }),
+      })
+    );
+
+    expect(html).toContain("Sign in again");
+    expect(html).toContain('action="/link"');
+  });
+
+  it("still redirects signed-in users outside the reauthentication flow", async () => {
+    await expect(
+      SignInPage({
+        params: Promise.resolve({}),
+        searchParams: Promise.resolve({ callbackUrl: "/link" }),
+      })
+    ).rejects.toThrow("Redirect: /");
+  });
+
+  it("keeps the reauthentication callback on this app", async () => {
+    const html = renderToStaticMarkup(
+      await SignInPage({
+        params: Promise.resolve({}),
+        searchParams: Promise.resolve({
+          reauthenticate: "true",
+          callbackUrl: "//attacker.example",
+        }),
+      })
+    );
+
+    expect(html).toContain('action="/"');
+    expect(html).not.toContain("attacker.example");
+  });
+});
diff --git a/app/sign-in/page.tsx b/app/sign-in/page.tsx
index 46d19f33..f783789e 100644
--- a/app/sign-in/page.tsx
+++ b/app/sign-in/page.tsx
@@ -9,9 +9,11 @@ import { readLinqOnboardingPhoneNumber } from "@db/services/auth/linq";
 export default async function SignInPage({
   searchParams,
 }: PageProps<"/sign-in">) {
-  if (await getAuthSession(await headers())) redirect("/");
+  const params = await searchParams;
+  const reauthenticate = params.reauthenticate === "true";
+  if (!reauthenticate && (await getAuthSession(await headers()))) redirect("/");
 
-  const callbackValue = (await searchParams).callbackUrl;
+  const callbackValue = params.callbackUrl;
   const requestedCallback = Array.isArray(callbackValue)
     ? callbackValue[0]
     : callbackValue;
@@ -30,7 +32,9 @@ export default async function SignInPage({
     <main className="flex min-h-svh items-center justify-center bg-background px-4 py-8 text-foreground">
       <section className="w-full max-w-sm space-y-6">
         <div className="flex flex-col gap-2">
-          <h1 className="type-page-title">Sign In</h1>
+          <h1 className="type-page-title">
+            {reauthenticate ? "Sign in again" : "Sign In"}
+          </h1>
           <p className="type-supporting-body text-muted-foreground">
             Enter your phone number to sign in.
           </p>
diff --git a/tests/integration/link.test.ts b/tests/integration/link.test.ts
index 98dc2810..716cd93d 100644
--- a/tests/integration/link.test.ts
+++ b/tests/integration/link.test.ts
@@ -333,12 +333,52 @@ describe("Link wallet integration", () => {
         })
       ).rejects.toMatchObject({ cause: { code: "23505" } });
 
-      await expect(link.disconnectLink(userId, headers)).rejects.toThrow(
-        "Unable to revoke Link access"
+      // A valid session older than the freshness window needs a new phone sign-in.
+      await database
+        .update(schema.session)
+        .set({ createdAt: new Date(Date.now() - 25 * 60 * 60_000) })
+        .where(eq(schema.session.userId, userId));
+      expect((await auth.api.getSession({ headers }))?.user.id).toBe(userId);
+      const disconnectRequest = () =>
+        new Request("http://localhost:3000/api/link", {
+          method: "POST",
+          headers,
+          body: new URLSearchParams({ operation: "disconnect" }),
+        });
+      const staleDisconnect = await POST(disconnectRequest());
+      expect(staleDisconnect.status).toBe(303);
+      expect(
+        new URL(staleDisconnect.headers.get("location") ?? "").searchParams.get(
+          "error"
+        )
+      ).toBe("reauthentication_required");
+      expect(revokedTokens).toEqual([]);
+      expect(await link.getLinkAccount(userId)).toBeDefined();
+
+      const reauthenticated = await auth.api.verifyPhoneNumber({
+        body: { phoneNumber: "+12025550123", code: "123456" },
+        headers,
+        returnHeaders: true,
+      });
+      expect(reauthenticated.response.user.id).toBe(userId);
+      expect(reauthenticated.response.token).not.toBe(signedIn.response.token);
+      updateCookies(headers, reauthenticated.headers);
+      const failedDisconnect = await POST(disconnectRequest());
+      expect(failedDisconnect.status).toBe(303);
+      expect(
+        new URL(
+          failedDisconnect.headers.get("location") ?? ""
+        ).searchParams.get("error")
+      ).toBe("disconnection_failed");
+      expect(failedDisconnect.headers.get("cache-control")).toBe("no-store");
+      expect(failedDisconnect.headers.get("referrer-policy")).toBe(
+        "no-referrer"
       );
       expect(await link.getLinkAccount(userId)).toBeDefined();
       revokeSucceeds = true;
-      await link.disconnectLink(userId, headers);
+      const disconnected = await POST(disconnectRequest());
+      expect(disconnected.status).toBe(303);
+      expect(disconnected.headers.get("location")).toBe("/link");
       expect(await link.getLinkAccount(userId)).toBeUndefined();
       expect(revokedTokens).toEqual(["refresh-rotated", "refresh-rotated"]);
       expect((await auth.api.getSession({ headers }))?.user.id).toBe(userId);