diff --git a/.changelog/fallback-to-charge-for-legacy-sessions.md b/.changelog/fallback-to-charge-for-legacy-sessions.md
new file mode 100644
index 0000000..140a06e
--- /dev/null
+++ b/.changelog/fallback-to-charge-for-legacy-sessions.md
@@ -0,0 +1,5 @@
+---
+wallet-cli: patch
+---
+
+Fall back to compatible charge challenges when servers also offer legacy Tempo sessions.
diff --git a/src/commands/request.ts b/src/commands/request.ts
index b29d5dd..0a5c0ad 100644
--- a/src/commands/request.ts
+++ b/src/commands/request.ts
@@ -5,7 +5,7 @@ import { basename, dirname } from "node:path";
 import { pipeline } from "node:stream/promises";
 import { setTimeout as sleep } from "node:timers/promises";
 
-import { Challenge, Credential, PaymentRequest } from "mppx";
+import { Challenge, Constants, Credential, PaymentRequest } from "mppx";
 import { Mppx, session as tempoSession, tempo } from "mppx/client";
 import { Keystore } from "accounts";
 import { Session as TempoSession } from "mppx/tempo";
@@ -1229,13 +1229,18 @@ async function readOnChainChannel(record: PersistedSessionRecord) {
   };
 }
 
-function sessionChallengeFromHeader(header: string | null) {
+export function sessionChallengeFromHeader(header: string | null) {
   if (!header) return undefined;
   try {
-    const challenges = Challenge.deserializeList(header).filter(
-      (challenge) => challenge.method === "tempo" && challenge.intent === "session",
+    return Challenge.deserializeList(header).find(
+      (challenge) =>
+        challenge.method === "tempo" &&
+        challenge.intent === "session" &&
+        Constants.getMethodDetail(
+          challenge.request.methodDetails,
+          Constants.MethodDetailKeys.sessionProtocol,
+        ) === Constants.SessionProtocols.v2,
     );
-    return challenges[0];
   } catch {
     return undefined;
   }
diff --git a/test/request.test.ts b/test/request.test.ts
index aeaad0a..c68e1c0 100644
--- a/test/request.test.ts
+++ b/test/request.test.ts
@@ -15,6 +15,7 @@ import {
   parseRequestArgs,
   resolvePaymentIdentity,
   runRequest,
+  sessionChallengeFromHeader,
   storedAccessKeyIdentity,
   tempoPaymentChallengeResponse,
 } from "../src/commands/request.js";
@@ -316,6 +317,51 @@ describe("request command", () => {
     expect(Credential.deserialize(credential).payload).toEqual({ ok: true });
   });
 
+  it.each([
+    { name: "unversioned", protocols: [undefined], selectedId: undefined },
+    { name: "v1", protocols: ["v1"], selectedId: undefined },
+    { name: "v2", protocols: ["v2"], selectedId: "session-v2" },
+    { name: "mixed v1 and v2", protocols: ["v1", "v2"], selectedId: "session-v2" },
+  ])(
+    "uses session-first routing only for $name session challenges",
+    ({ protocols, selectedId }) => {
+      const charge = Challenge.from({
+        id: "charge",
+        intent: "charge",
+        method: "tempo",
+        realm: "example",
+        request: {
+          amount: "1",
+          currency: "0x20c000000000000000000000b9537d11c60e8b50",
+          methodDetails: { chainId: 4217 },
+          recipient: "0x0000000000000000000000000000000000000001",
+        },
+      });
+      const sessions = protocols.map((protocol) =>
+        Challenge.from({
+          id: `session-${protocol ?? "unversioned"}`,
+          intent: "session",
+          method: "tempo",
+          realm: "example",
+          request: {
+            amount: "1",
+            currency: "0x20c000000000000000000000b9537d11c60e8b50",
+            methodDetails: {
+              chainId: 4217,
+              ...(protocol ? { sessionProtocol: protocol } : {}),
+            },
+            recipient: "0x0000000000000000000000000000000000000001",
+          },
+        }),
+      );
+      const header = [charge, ...sessions]
+        .map((challenge) => Challenge.serialize(challenge))
+        .join(", ");
+
+      expect(sessionChallengeFromHeader(header)?.id).toBe(selectedId);
+    },
+  );
+
   it("returns E_PAYMENT for non-dry-run 402 responses", async () => {
     const server = await testServer((_request, response) => {
       response.statusCode = 402;