fix: OAuth token refresh retry and error handling for idle timeout

packages/opencode/src/altimate/plugin/anthropic.ts

@@ -76,29 +76,51 @@ export async function AnthropicAuthPlugin(input: PluginInput): Promise<Hooks> {
             const currentAuth = await getAuth()
             if (currentAuth.type !== "oauth") return fetch(requestInput, init)
 
-            // Refresh token if expired
-            if (!currentAuth.access || currentAuth.expires < Date.now()) {
-              const response = await fetch("https://console.anthropic.com/v1/oauth/token", {
-                method: "POST",
-                headers: { "Content-Type": "application/json" },
-                body: JSON.stringify({
-                  grant_type: "refresh_token",
-                  refresh_token: currentAuth.refresh,
-                  client_id: CLIENT_ID,
-                }),
-              })
-              if (!response.ok) throw new Error(`Token refresh failed: ${response.status}`)
-              const json: TokenResponse = await response.json()
-              await input.client.auth.set({
-                path: { id: "anthropic" },
-                body: {
-                  type: "oauth",
-                  refresh: json.refresh_token,
-                  access: json.access_token,
-                  expires: Date.now() + json.expires_in * 1000,
-                },
-              })
-              currentAuth.access = json.access_token
+            // Refresh token if expired or about to expire (30s buffer)
+            if (!currentAuth.access || currentAuth.expires < Date.now() + 30_000) {
+              let lastError: Error | undefined
+              for (let attempt = 0; attempt < 3; attempt++) {
+                try {
+                  const response = await fetch("https://console.anthropic.com/v1/oauth/token", {
+                    method: "POST",
+                    headers: { "Content-Type": "application/json" },
+                    body: JSON.stringify({
+                      grant_type: "refresh_token",
+                      refresh_token: currentAuth.refresh,
+                      client_id: CLIENT_ID,
+                    }),
+                  })
+                  if (!response.ok) {
+                    const body = await response.text().catch(() => "")
+                    throw new Error(
+                      `Anthropic OAuth token refresh failed (HTTP ${response.status}). ` +
+                        `Try re-authenticating: altimate-code auth login anthropic` +
+                        (body ? ` — ${body.slice(0, 200)}` : ""),
+                    )
+                  }
+                  const json: TokenResponse = await response.json()
+                  await input.client.auth.set({
+                    path: { id: "anthropic" },
+                    body: {
+                      type: "oauth",
+                      refresh: json.refresh_token,
+                      access: json.access_token,
+                      expires: Date.now() + json.expires_in * 1000,
+                    },
+                  })
+                  currentAuth.access = json.access_token
+                  currentAuth.expires = Date.now() + json.expires_in * 1000
+                  lastError = undefined
+                  break
+                } catch (e) {
+                  lastError = e instanceof Error ? e : new Error(String(e))
+                  // Don't retry on 4xx (permanent auth failures) — only retry on network errors / 5xx
+                  const is4xx = lastError.message.includes("HTTP 4")
+                  if (is4xx || attempt >= 2) break
+                  await new Promise((r) => setTimeout(r, 1000 * (attempt + 1)))
+                }
+              }
+              if (lastError) throw lastError
             }
 
             // Build headers from incoming request

packages/opencode/src/plugin/codex.ts

@@ -128,19 +128,36 @@ async function exchangeCodeForTokens(code: string, redirectUri: string, pkce: Pk
 }
 
 async function refreshAccessToken(refreshToken: string): Promise<TokenResponse> {
-  const response = await fetch(`${ISSUER}/oauth/token`, {
-    method: "POST",
-    headers: { "Content-Type": "application/x-www-form-urlencoded" },
-    body: new URLSearchParams({
-      grant_type: "refresh_token",
-      refresh_token: refreshToken,
-      client_id: CLIENT_ID,
-    }).toString(),
-  })
-  if (!response.ok) {
-    throw new Error(`Token refresh failed: ${response.status}`)
+  let lastError: Error | undefined
+  for (let attempt = 0; attempt < 3; attempt++) {
+    try {
+      const response = await fetch(`${ISSUER}/oauth/token`, {
+        method: "POST",
+        headers: { "Content-Type": "application/x-www-form-urlencoded" },
+        body: new URLSearchParams({
+          grant_type: "refresh_token",
+          refresh_token: refreshToken,
+          client_id: CLIENT_ID,
+        }).toString(),
+      })
+      if (!response.ok) {
+        const body = await response.text().catch(() => "")
+        throw new Error(
+          `Codex OAuth token refresh failed (HTTP ${response.status}). ` +
+            `Try re-authenticating: altimate-code auth login openai` +
+            (body ? ` — ${body.slice(0, 200)}` : ""),
+        )
+      }
+      return response.json()
+    } catch (e) {
+      lastError = e instanceof Error ? e : new Error(String(e))
+      // Don't retry on 4xx (permanent auth failures) — only retry on network errors / 5xx
+      const is4xx = lastError.message.includes("HTTP 4")
+      if (is4xx || attempt >= 2) break
+      await new Promise((r) => setTimeout(r, 1000 * (attempt + 1)))
+    }
   }
-  return response.json()
+  throw lastError ?? new Error("Token refresh failed after retries")
 }
 
 const HTML_SUCCESS = `<!doctype html>
@@ -436,8 +453,8 @@ export async function CodexAuthPlugin(input: PluginInput): Promise<Hooks> {
             // Cast to include accountId field
             const authWithAccount = currentAuth as typeof currentAuth & { accountId?: string }
 
-            // Check if token needs refresh
-            if (!currentAuth.access || currentAuth.expires < Date.now()) {
+            // Check if token needs refresh (30s buffer to avoid edge-case expiry during request)
+            if (!currentAuth.access || currentAuth.expires < Date.now() + 30_000) {
               log.info("refreshing codex access token")
               const tokens = await refreshAccessToken(currentAuth.refresh)
               const newAccountId = extractAccountId(tokens) || authWithAccount.accountId

packages/opencode/src/session/message-v2.ts

@@ -882,8 +882,22 @@ export namespace MessageV2 {
           },
           { cause: e },
         ).toObject()
-      case e instanceof Error:
-        return new NamedError.Unknown({ message: e.toString() }, { cause: e }).toObject()
+      case e instanceof Error: {
+        const msg = e.message || e.name || "Unknown error"
+        // Token refresh failures should surface as auth errors with recovery instructions
+        if (/OAuth token refresh failed/i.test(msg)) {
+          return new MessageV2.AuthError(
+            {
+              providerID: ctx.providerID,
+              message: msg,
+            },
+            { cause: e },
+          ).toObject()
+        }
+        // Include error class name for better diagnostics when message is generic
+        const displayMsg = msg === "Error" || msg === e.name ? `${e.name}: ${e.stack?.split("\n")[0] || "unknown error"}` : msg
+        return new NamedError.Unknown({ message: displayMsg }, { cause: e }).toObject()
+      }
       default:
         try {
           const parsed = ProviderError.parseStreamError(e)

packages/opencode/src/session/retry.ts

@@ -61,6 +61,10 @@ export namespace SessionRetry {
   export function retryable(error: ReturnType<NamedError["toObject"]>) {
     // context overflow errors should not be retried
     if (MessageV2.ContextOverflowError.isInstance(error)) return undefined
+    // auth errors (token refresh failures) should be retried — the token may refresh on next attempt
+    if (MessageV2.AuthError.isInstance(error)) {
+      return `Authentication failed — retrying. If this persists, run: altimate-code auth login ${error.data.providerID}`
+    }
     if (MessageV2.APIError.isInstance(error)) {
       if (!error.data.isRetryable) return undefined
       if (error.data.responseBody?.includes("FreeUsageLimitError"))

packages/opencode/test/session/retry.test.ts

@@ -122,6 +122,29 @@ describe("session.retry.retryable", () => {
 
     expect(SessionRetry.retryable(error)).toBeUndefined()
   })
+
+  test("retries auth errors with recovery message", () => {
+    const error = new MessageV2.AuthError({
+      providerID: "anthropic",
+      message: "Anthropic OAuth token refresh failed (HTTP 401)",
+    }).toObject() as ReturnType<NamedError["toObject"]>
+
+    const result = SessionRetry.retryable(error)
+    expect(result).toBeDefined()
+    expect(result).toContain("Authentication failed")
+    expect(result).toContain("altimate-code auth login anthropic")
+  })
+
+  test("retries auth errors for other providers", () => {
+    const error = new MessageV2.AuthError({
+      providerID: "openai",
+      message: "Codex OAuth token refresh failed (HTTP 403)",
+    }).toObject() as ReturnType<NamedError["toObject"]>
+
+    const result = SessionRetry.retryable(error)
+    expect(result).toBeDefined()
+    expect(result).toContain("altimate-code auth login openai")
+  })
 })
 
 describe("session.message-v2.fromError", () => {
@@ -173,6 +196,41 @@ describe("session.message-v2.fromError", () => {
     expect(retryable).toBe("Connection reset by server")
   })
 
+  test("converts token refresh failure to ProviderAuthError", () => {
+    const error = new Error("Anthropic OAuth token refresh failed (HTTP 401). Try re-authenticating: altimate-code auth login anthropic")
+    const result = MessageV2.fromError(error, { providerID: "anthropic" })
+
+    expect(result.name).toBe("ProviderAuthError")
+    expect((result as any).data.providerID).toBe("anthropic")
+    expect((result as any).data.message).toContain("token refresh failed")
+  })
+
+  test("converts codex token refresh failure to ProviderAuthError", () => {
+    const error = new Error("Codex OAuth token refresh failed (HTTP 403). Try re-authenticating: altimate-code auth login openai")
+    const result = MessageV2.fromError(error, { providerID: "openai" })
+
+    expect(result.name).toBe("ProviderAuthError")
+    expect((result as any).data.providerID).toBe("openai")
+  })
+
+  test("provides descriptive message for generic Error with no message", () => {
+    const error = new Error()
+    const result = MessageV2.fromError(error, { providerID: "test" })
+
+    expect(result.name).toBe("UnknownError")
+    // Should not be just "Error" — should include stack or context
+    expect((result as any).data.message).not.toBe("Error")
+    expect((result as any).data.message.length).toBeGreaterThan(5)
+  })
+
+  test("provides descriptive message for TypeError with no message", () => {
+    const error = new TypeError()
+    const result = MessageV2.fromError(error, { providerID: "test" })
+
+    expect(result.name).toBe("UnknownError")
+    expect((result as any).data.message).toContain("TypeError")
+  })
+
   test("marks OpenAI 404 status codes as retryable", () => {
     const error = new APICallError({
       message: "boom",