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fix(sse): demote mid-conversation system roles to user in claude-to-openai translation - #12908

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initguru:fix/claude-mid-system-user-demote
Sep 17, 2026
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diegosouzapw merged 2 commits into
diegosouzapw:release/v3.8.51from
initguru:fix/claude-mid-system-user-demote

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@initguru initguru commented Sep 7, 2026 •

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fix(sse): demote mid-conversation system roles to user in claude-to-openai translation

Summary

Resolve the issue where HCP-Vision-Latest (vLLM via LiteLLM) returns 400 "System message must be at the beginning." when Claude Code hook context (SessionStart ~25KB, PreToolUse) is inserted mid-conversation with role:"system".

  • claude→openai translation preserved mid-conversation system messages in place, but some vLLM chat templates force system to index 0
  • fix: demote systems at output index > 0 to user during the translation loop (preserving content byte-for-byte). Keep the index-0 system (created by the translator + placed directly by the client)
  • Acceptance evidence: among the most recent 300 calls, 138 had the mid-conversation system pattern and 135 returned 200 — demotion is safe for upstreams that accept it as well
  • Live evidence: call log b022ad (400) reproduced translation roles system,user,system,assistant,tool,user,system → after the fix system,user,user,assistant,tool,user,user

Related Issues

Validation

  • Change type: provider / routing
  • Focused tests: node --import tsx/esm --test tests/unit/claude-to-openai-mid-system-user-normalize.test.ts tests/unit/claude-to-openai-system-role-6954.test.ts tests/unit/claude-to-openai-glm-user-turn.test.ts (12/12)
  • RED validation: 3/5 new tests failed on the parent commit (running behavior) → 5/5 after the fix
  • Regression: claude-to-openai import tests 21 files, 169/169
  • npm run typecheck:core — 0 errors
  • Production-code changes include a new or updated automated test in this PR

Tests Added Or Updated

Coverage Notes

  • All new guards/edge cases (index-0 preservation, multiple mid-conversation systems, array return path, no-op) are covered by new tests.

Reviewer Notes

  • Two patches (0019 fix + 0020 test hardening). Apply after PR5 is recommended — shares claude-to-openai.ts.
  • Reviewer validation: demotion is evaluated at push time, giving the correct output-index semantics; downstream (regroupToolMessages, fixMissingToolResponses, ensureUserTurn) does not reintroduce system; confirmed update was required by reproducing RED on the parent commit.
  • Live validation: b022ad real-request replay returned 200 (previously 400)

changelog.d/fixes/12908-mid-system-role-demote.md

- **fix(sse):** demote mid-conversation system roles to user in claude-to-openai translation — stops vLLM upstreams rejecting Claude Code hook-context system turns with "System message must be at the beginning" 400 ([#12908](https://github.com/diegosouzapw/OmniRoute/pull/12908))

Jihyun Son added 2 commits September 7, 2026 13:27
…penai translation

Claude Code hook contexts (SessionStart ~25KB, PreToolUse) arrive as
role:system messages in the middle of the messages array. HCP-Vision-Latest
vLLM (via LiteLLM gateway) rejects any system not at index 0 with
400 "System message must be at the beginning." Demote every system at
output index > 0 to user with content preserved byte-identical; the
index-0 system (translator-made from the top-level system field, or
client-placed first) stays untouched. Other upstreams are unaffected:
135/138 recent mid-system calls to GLM-5.3-Flash / DeepSeek-V4-Flash
already returned 200. Supersedes the pass-through assertion of diegosouzapw#6954
(its intent — systems never misattributed as assistant — still holds).
…nvariant note

Quality-review Minor 1: document the array-return-path invariant in
claudeToOpenAIRequest (convertClaudeMessage arrays are tool/user only, so
no second system element can survive demotion while result.messages is
empty). Minor 2: add the same OMNIROUTE_SYSTEM_INSTRUCTION_APPEND env
guard to the diegosouzapw#6954 test as the new mid-system test for consistency.
APPROVED items, no behavior change.
@diegosouzapw

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Thanks for the well-documented fix — the production call-log evidence (138/300 recent calls
hitting the mid-conversation system pattern) and the RED→GREEN test methodology make this an
easy review. Ran claude-to-openai-mid-system-user-normalize.test.ts and
claude-to-openai-system-role-6954.test.ts at your head: 9/9 pass. Only ask before merge: add
a changelog.d/fixes/ fragment (none of the PRs in this batch have one yet). Also flagging for
the maintainer that this composes cleanly with your other PR #12904 (same root cause, adjacent
lines in the same file, verified conflict-free) — they'll likely land as a pair.

@diegosouzapw
diegosouzapw merged commit f4be5cc into diegosouzapw:release/v3.8.51 Sep 17, 2026
3 checks passed
diegosouzapw added a commit that referenced this pull request Sep 17, 2026
The tip moved 13 commits while the first pass was running and brought its own
reds. All reproduced locally on the merged tree first.

vitest 4.1.11 -> 5.0.0 in the #13661 development-group bump is a major, and
vitest 5 moved `vite` from a dependency to a peerDependency. This repo only ever
declared `vite` under `overrides`, which pins a version but installs nothing, so
`npm ci` stopped providing it and the Vitest job died at startup with
ERR_MODULE_NOT_FOUND. Declared as the devDependency it actually is — the same
^8.0.16 the override already pinned, and what @vitejs/plugin-react asks for as a
peer — and regenerated the lockfile: 684 lines added, none changed.

#12909 filtered a mapped array with `toolCall is JsonRecord`, but the element
type is the tool-call literal or null, and a predicate's type has to be
assignable to the parameter's (TS2677). Narrowed by the element's own type
instead; the literal still satisfies JsonRecord at the return.

#12906 added `|| result.errorCode === "empty_response"` to the stream-failure
condition and Prettier rewrapped it, so the #8928 probe — which located the
branch by an exact four-line string — stopped finding it. It now matches on what
the branch tests rather than how it is typeset, and still fails when the
eviction call is removed.

probe-7293 is the visible half of a real conflict, filed as #13948. #7293 merges
a mid-array system into index 0; #12908, landed later, demotes it to "user" in
place instead. Both target the same constraint and only one can win, and the
combination also reorders: the pre-translation hoist moves the turn forward
expecting it to stay a system message, then the demotion converts it where it
now sits, ahead of the conversation. Choosing between the two strategies is a
product call, not a base-red one, so the test was realigned to assert the half
that protects the caller — the instruction survives, as a user turn — and pins
the current ordering with a pointer to the issue, so the eventual decision shows
up as a deliberate test change instead of a silent regression.

Refs #13866, #13948
diegosouzapw added a commit that referenced this pull request Sep 17, 2026
* fix(quality): clear the release/v3.8.51 base-reds

19 failing unit tests plus the API Route Typecheck and mutation-test-coverage
gates, all reproduced on the clean tip before touching anything.

Ten of the failures share one cause. #13452/#13798 made `*-compatible-*`
buildUrl() refuse a connection with no baseUrl instead of quietly defaulting to
the real OpenAI/Anthropic API — which would ship the operator's stored key to a
public third party. The guard is right; three fixtures still built those
connections unhydrated, and one of them put baseUrl at the top level of
credentials, where the chat path never reads it.

The rest:

- modelDiscovery.ts missed the VertexModelMetadataProvenance cast that its
  read-path twin in db/models/synced.ts already had — both written by #12471.
- A provider-test regexp carried raw 0x00/0x1f bytes, which makes git, GitHub
  and ripgrep treat the file as binary. Same character class, written
  with escapes instead of the bytes themselves.
- #13399 (Agnes AI China) adds "agnes-cn" + "agnescn": the only two provider
  prefixes since the count was last set (412 -> 414). Everything else added in
  that range is model ids.
- The free-tier budget card SVG was stale (443 -> 452 models); regenerated by
  its own script.
- Three new tests were missing from stryker.conf.json tap.testFiles, so the
  mutants they kill did not count.

Three guards asserted syntax rather than the invariant they protect, and broke
when the source legitimately changed. Each was re-expressed and then verified by
mutating the source back:

- #2331 required modelEffort to head the rawEffort chain; #13556 deliberately
  put the server-selected force rule first. The real invariant is relative —
  modelEffort outranks the defaults a client injects — and it still trips when
  explicitReasoning is moved ahead of it.
- The OAuth loopback guard matched the isLocalhost arm literally; #9944 added
  `&& !opts?.manualLoopback`. It now matches the arm whatever guards it, and
  still fails when the hint stops being built.
- The i18n scanner flagged dynamically-built keys — t("effort." + mode) reaches
  it as a literal prefix, never a string. It now accepts a prefix that resolves
  to a namespace holding messages, and still fails when the namespace is gone.

tests/unit/sse-auth.test.ts (#12080) expected a bare null where #13879 now
returns the key-policy diagnostic — the same sentinel shape the terminal-state
path has used since #12441. The assertion was rewritten to the constraint #12080
actually protects: nothing usable comes back and neither connection leaks. The
contract risk that remains — those sentinels are truthy, and executeWebSearch
treats any truthy value as a credential — is filed as #13945 rather than
widened into this PR.

Refs #13866

* fix(quality): clear the second wave of release/v3.8.51 base-reds

The tip moved 13 commits while the first pass was running and brought its own
reds. All reproduced locally on the merged tree first.

vitest 4.1.11 -> 5.0.0 in the #13661 development-group bump is a major, and
vitest 5 moved `vite` from a dependency to a peerDependency. This repo only ever
declared `vite` under `overrides`, which pins a version but installs nothing, so
`npm ci` stopped providing it and the Vitest job died at startup with
ERR_MODULE_NOT_FOUND. Declared as the devDependency it actually is — the same
^8.0.16 the override already pinned, and what @vitejs/plugin-react asks for as a
peer — and regenerated the lockfile: 684 lines added, none changed.

#12909 filtered a mapped array with `toolCall is JsonRecord`, but the element
type is the tool-call literal or null, and a predicate's type has to be
assignable to the parameter's (TS2677). Narrowed by the element's own type
instead; the literal still satisfies JsonRecord at the return.

#12906 added `|| result.errorCode === "empty_response"` to the stream-failure
condition and Prettier rewrapped it, so the #8928 probe — which located the
branch by an exact four-line string — stopped finding it. It now matches on what
the branch tests rather than how it is typeset, and still fails when the
eviction call is removed.

probe-7293 is the visible half of a real conflict, filed as #13948. #7293 merges
a mid-array system into index 0; #12908, landed later, demotes it to "user" in
place instead. Both target the same constraint and only one can win, and the
combination also reorders: the pre-translation hoist moves the turn forward
expecting it to stay a system message, then the demotion converts it where it
now sits, ahead of the conversation. Choosing between the two strategies is a
product call, not a base-red one, so the test was realigned to assert the half
that protects the caller — the instruction survives, as a user turn — and pins
the current ordering with a pointer to the issue, so the eventual decision shows
up as a deliberate test change instead of a silent regression.

Refs #13866, #13948

* fix(quality): allowlist vite, rebaseline tip growth, drop a dead import

Third pass on the release/v3.8.51 base-reds. Declaring `vite` in the previous
commit was correct but incomplete: check-deps is a human review point against
typosquatting, so a newly declared package has to be vouched for by name.
Recorded in dependency-allowlist.json with why it is needed — the official Vite
build tool, already pinned through overrides, and a required peer of both
vitest 5 and @vitejs/plugin-react. That also turns check-deps.test.ts green.

check-file-size went red on nine files. One is mine: sse-auth.test.ts grew when
the #12080 assertion was rewritten. Three of the four assertions I had added
were redundant with the strict deepEqual that follows them, so they are gone and
the file grows by 4 lines instead of 8; the cap absorbs the rest.

The other eight are production and test files this PR does not touch, grown by
other work and never rebaselined — which is the whole reason a base-red drain
exists. Each is attributed to the commit that grew it: #12906 (chat.ts,
chatHelpers.ts, proxyFetch.ts, stream.ts), #12904 + #12910 (chatCore.ts), and
batch_api.test.ts from the same wave. Two of them predate the wave entirely and
were already over cap on 3d5baf1 — imageGeneration.ts (#13748) and
roundRobinCombo.ts (#13776) — so they were base-reds hiding behind a gate that
only surfaced them once the tip was merged in. Both are recorded separately from
the wave so the history stays honest about when each cap actually moved.

Note for whoever reads the gate next: it counts one line more than `wc -l`,
since it measures split length rather than newlines.

Finally, #13290 replaced rmSync with cleanupTempDataDir in
zcode-executor.test.ts but left the import behind, which the frozen-warning
ESLint gate rejects. Removed.

Refs #13866
@initguru
initguru deleted the fix/claude-mid-system-user-demote branch September 25, 2026 14:43
muhamadgalihsaputra pushed a commit to niyatna/NiyatnaRoute that referenced this pull request Sep 27, 2026
…penai translation (diegosouzapw#12908)

* fix(sse): demote mid-conversation system roles to user in claude-to-openai translation

Claude Code hook contexts (SessionStart ~25KB, PreToolUse) arrive as
role:system messages in the middle of the messages array. HCP-Vision-Latest
vLLM (via LiteLLM gateway) rejects any system not at index 0 with
400 "System message must be at the beginning." Demote every system at
output index > 0 to user with content preserved byte-identical; the
index-0 system (translator-made from the top-level system field, or
client-placed first) stays untouched. Other upstreams are unaffected:
135/138 recent mid-system calls to GLM-5.3-Flash / DeepSeek-V4-Flash
already returned 200. Supersedes the pass-through assertion of diegosouzapw#6954
(its intent — systems never misattributed as assistant — still holds).

* test(sse): harden mid-system demotion with env guard and array-path invariant note

Quality-review Minor 1: document the array-return-path invariant in
claudeToOpenAIRequest (convertClaudeMessage arrays are tool/user only, so
no second system element can survive demotion while result.messages is
empty). Minor 2: add the same OMNIROUTE_SYSTEM_INSTRUCTION_APPEND env
guard to the diegosouzapw#6954 test as the new mid-system test for consistency.
APPROVED items, no behavior change.

---------

Co-authored-by: Jihyun Son <jihyun.son@sk.com>
muhamadgalihsaputra pushed a commit to niyatna/NiyatnaRoute that referenced this pull request Sep 27, 2026
* fix(quality): clear the release/v3.8.51 base-reds

19 failing unit tests plus the API Route Typecheck and mutation-test-coverage
gates, all reproduced on the clean tip before touching anything.

Ten of the failures share one cause. diegosouzapw#13452/diegosouzapw#13798 made `*-compatible-*`
buildUrl() refuse a connection with no baseUrl instead of quietly defaulting to
the real OpenAI/Anthropic API — which would ship the operator's stored key to a
public third party. The guard is right; three fixtures still built those
connections unhydrated, and one of them put baseUrl at the top level of
credentials, where the chat path never reads it.

The rest:

- modelDiscovery.ts missed the VertexModelMetadataProvenance cast that its
  read-path twin in db/models/synced.ts already had — both written by diegosouzapw#12471.
- A provider-test regexp carried raw 0x00/0x1f bytes, which makes git, GitHub
  and ripgrep treat the file as binary. Same character class, written
  with escapes instead of the bytes themselves.
- diegosouzapw#13399 (Agnes AI China) adds "agnes-cn" + "agnescn": the only two provider
  prefixes since the count was last set (412 -> 414). Everything else added in
  that range is model ids.
- The free-tier budget card SVG was stale (443 -> 452 models); regenerated by
  its own script.
- Three new tests were missing from stryker.conf.json tap.testFiles, so the
  mutants they kill did not count.

Three guards asserted syntax rather than the invariant they protect, and broke
when the source legitimately changed. Each was re-expressed and then verified by
mutating the source back:

- diegosouzapw#2331 required modelEffort to head the rawEffort chain; diegosouzapw#13556 deliberately
  put the server-selected force rule first. The real invariant is relative —
  modelEffort outranks the defaults a client injects — and it still trips when
  explicitReasoning is moved ahead of it.
- The OAuth loopback guard matched the isLocalhost arm literally; diegosouzapw#9944 added
  `&& !opts?.manualLoopback`. It now matches the arm whatever guards it, and
  still fails when the hint stops being built.
- The i18n scanner flagged dynamically-built keys — t("effort." + mode) reaches
  it as a literal prefix, never a string. It now accepts a prefix that resolves
  to a namespace holding messages, and still fails when the namespace is gone.

tests/unit/sse-auth.test.ts (diegosouzapw#12080) expected a bare null where diegosouzapw#13879 now
returns the key-policy diagnostic — the same sentinel shape the terminal-state
path has used since diegosouzapw#12441. The assertion was rewritten to the constraint diegosouzapw#12080
actually protects: nothing usable comes back and neither connection leaks. The
contract risk that remains — those sentinels are truthy, and executeWebSearch
treats any truthy value as a credential — is filed as diegosouzapw#13945 rather than
widened into this PR.

Refs diegosouzapw#13866

* fix(quality): clear the second wave of release/v3.8.51 base-reds

The tip moved 13 commits while the first pass was running and brought its own
reds. All reproduced locally on the merged tree first.

vitest 4.1.11 -> 5.0.0 in the diegosouzapw#13661 development-group bump is a major, and
vitest 5 moved `vite` from a dependency to a peerDependency. This repo only ever
declared `vite` under `overrides`, which pins a version but installs nothing, so
`npm ci` stopped providing it and the Vitest job died at startup with
ERR_MODULE_NOT_FOUND. Declared as the devDependency it actually is — the same
^8.0.16 the override already pinned, and what @vitejs/plugin-react asks for as a
peer — and regenerated the lockfile: 684 lines added, none changed.

diegosouzapw#12909 filtered a mapped array with `toolCall is JsonRecord`, but the element
type is the tool-call literal or null, and a predicate's type has to be
assignable to the parameter's (TS2677). Narrowed by the element's own type
instead; the literal still satisfies JsonRecord at the return.

diegosouzapw#12906 added `|| result.errorCode === "empty_response"` to the stream-failure
condition and Prettier rewrapped it, so the diegosouzapw#8928 probe — which located the
branch by an exact four-line string — stopped finding it. It now matches on what
the branch tests rather than how it is typeset, and still fails when the
eviction call is removed.

probe-7293 is the visible half of a real conflict, filed as diegosouzapw#13948. diegosouzapw#7293 merges
a mid-array system into index 0; diegosouzapw#12908, landed later, demotes it to "user" in
place instead. Both target the same constraint and only one can win, and the
combination also reorders: the pre-translation hoist moves the turn forward
expecting it to stay a system message, then the demotion converts it where it
now sits, ahead of the conversation. Choosing between the two strategies is a
product call, not a base-red one, so the test was realigned to assert the half
that protects the caller — the instruction survives, as a user turn — and pins
the current ordering with a pointer to the issue, so the eventual decision shows
up as a deliberate test change instead of a silent regression.

Refs diegosouzapw#13866, diegosouzapw#13948

* fix(quality): allowlist vite, rebaseline tip growth, drop a dead import

Third pass on the release/v3.8.51 base-reds. Declaring `vite` in the previous
commit was correct but incomplete: check-deps is a human review point against
typosquatting, so a newly declared package has to be vouched for by name.
Recorded in dependency-allowlist.json with why it is needed — the official Vite
build tool, already pinned through overrides, and a required peer of both
vitest 5 and @vitejs/plugin-react. That also turns check-deps.test.ts green.

check-file-size went red on nine files. One is mine: sse-auth.test.ts grew when
the diegosouzapw#12080 assertion was rewritten. Three of the four assertions I had added
were redundant with the strict deepEqual that follows them, so they are gone and
the file grows by 4 lines instead of 8; the cap absorbs the rest.

The other eight are production and test files this PR does not touch, grown by
other work and never rebaselined — which is the whole reason a base-red drain
exists. Each is attributed to the commit that grew it: diegosouzapw#12906 (chat.ts,
chatHelpers.ts, proxyFetch.ts, stream.ts), diegosouzapw#12904 + diegosouzapw#12910 (chatCore.ts), and
batch_api.test.ts from the same wave. Two of them predate the wave entirely and
were already over cap on 8a95ffa — imageGeneration.ts (diegosouzapw#13748) and
roundRobinCombo.ts (diegosouzapw#13776) — so they were base-reds hiding behind a gate that
only surfaced them once the tip was merged in. Both are recorded separately from
the wave so the history stays honest about when each cap actually moved.

Note for whoever reads the gate next: it counts one line more than `wc -l`,
since it measures split length rather than newlines.

Finally, diegosouzapw#13290 replaced rmSync with cleanupTempDataDir in
zcode-executor.test.ts but left the import behind, which the frozen-warning
ESLint gate rejects. Removed.

Refs diegosouzapw#13866
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