[Bug] Extended Thinking: Summarized thinking blocks fail signature validation when resent to API

Resolved 💬 2 comments Opened May 28, 2026 by kroqos Closed Jun 30, 2026

Summary

With extended thinking enabled, a thinking block in the assistant message history intermittently gets modified after it was originally produced. Because the API requires thinking/redacted_thinking blocks to be resent byte-for-byte identical (with their original signature), the next request fails with a 400. Once it happens the conversation is permanently unrecoverable: every subsequent message replays the full history including the corrupted block, so it fails identically every time.

Error

API Error: 400 messages.1.content.6: `thinking` or `redacted_thinking` blocks in the latest
assistant message cannot be modified. These blocks must remain as they were in the original response.

Reproduced in a second, unrelated session with a different index:

API Error: 400 messages.7.content.3: `thinking` or `redacted_thinking` blocks in the latest
assistant message cannot be modified. These blocks must remain as they were in the original response.

Environment

| | |
|---|---|
| Claude Code | 2.1.154 (note: ahead of npm stable 2.1.153 — appears to be a pre-release/nightly build) |
| OS | macOS, Darwin 25.5.0, arm64 |
| Model | Opus 4.8 (1M context) — claude-opus-4-8[1m] |

Relevant settings.json:

"alwaysThinkingEnabled": true,
"showThinkingSummaries": true,
"effortLevel": "xhigh"

Conditions / repro

No crisp deterministic repro yet, but both occurrences shared the same conditions:

  • Extended thinking on for every turn (alwaysThinkingEnabled: true) at xhigh effort, so thinking blocks are present on basically every assistant message.
  • Long, tool-heavy sequences with many interleaved thinking blocks (one crash followed a ~13-minute background workflow run).
  • The second crash occurred immediately after a cancelled parallel Bash tool call (one of two parallel calls was cancelled), which looks like a likely moment for the assistant message to be reassembled incorrectly.

Key evidence: the thinking-summarizer's prompt leaked into a thinking block

While showThinkingSummaries was on, this fragment appeared inside one of the displayed thinking summaries:

"I need to see the next thinking to rewrite it. Could you provide the next thinking chunk that follows the current rewritten thinking?"

That is not assistant reasoning — it reads like the summarizer/rewriter process's own prompt bleeding into the stored thinking content.

Hypothesized root cause

(Hypothesis, not confirmed.) The thinking-summary feature (showThinkingSummaries) rewrites raw thinking blocks into shorter summaries for display. It looks like the rewritten/summarized content can end up persisted in place of the original signed block, so when that block is resent to the API its content no longer matches the signature → 400 ... blocks cannot be modified. The likelihood seems to rise with the number of thinking blocks in history (high effort, always-on thinking, long workflows) and possibly with tool-call cancellation/reassembly.

Impact

  • A single corrupted block bricks the entire conversation — it cannot recover by any further messaging, because the full history (including the bad block) is replayed on every request.
  • rewind only helps if the corruption is late in the history; when the bad block is near the start (e.g. messages.1), the whole session is effectively lost.

Workaround

Setting "showThinkingSummaries": false (keeping thinking otherwise enabled) is the suspected fix; falling back to "alwaysThinkingEnabled": false removes thinking blocks entirely so there is nothing to corrupt.

Questions for maintainers

  1. Does showThinkingSummaries write summarized content back into the message array that is later sent to the API, rather than keeping summaries display-only?
  2. Is there extra risk of thinking-block reassembly corruption when a parallel tool call is cancelled mid-flight?
  3. Is 2.1.154 a known pre-release, and is this a regression vs 2.1.153?

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