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Desktop official OAuth sessions inject a token into a long-lived CLI process to avoid OS credential prompts. After Windows sleep/wake that env token can become stale, so the server now pushes a refreshed token before each resumed user turn and the CLI clears its OAuth cache when the env token changes. The retry path also disables keep-alive after ECONNRESET/EPIPE by default, matching the stale pooled-socket failure mode reported on #651. Constraint: Real Win11 sleep/wake cannot be physically reproduced in this macOS worktree Rejected: Restart the CLI before every user turn | would add latency and discard useful process continuity Confidence: medium Scope-risk: moderate Directive: Keep official OAuth env-token updates paired with CLI-side OAuth cache invalidation Tested: bun test src/server/__tests__/conversation-service.test.ts --timeout 30000 Tested: bun test src/cli/__tests__/structuredIO.test.ts --timeout 30000 Tested: bun test src/services/api/withRetry.test.ts --timeout 30000 Tested: bun run check:server Tested: git diff --check Not-tested: Real Win11 sleep/wake with Claude official OAuth Not-tested: External ccswitch reqwest pool reset path when the reset is hidden behind the proxy Related: #658 Related: #651