diff --git a/open-sse/config/kiroConstants.js b/open-sse/config/kiroConstants.js
index 2f97256d..e6408da1 100644
--- a/open-sse/config/kiroConstants.js
+++ b/open-sse/config/kiroConstants.js
@@ -20,6 +20,12 @@ import { effortToBudget } from "../translator/concerns/thinking.js";
 
 export const KIRO_AGENTIC_SUFFIX = "-agentic";
 export const KIRO_THINKING_SUFFIX = "-thinking";
+export const KIRO_TOOL_NAME_MAX_LENGTH = 64;
+export const KIRO_TOOL_DESCRIPTION_MAX_LENGTH = 10237;
+export const KIRO_TOOL_ID_MAX_LENGTH = 64;
+export const KIRO_CODEWHISPERER_TARGET =
+  "AmazonCodeWhispererStreamingService.GenerateAssistantResponse";
+export const KIRO_ENDPOINT_FALLBACK_STATUSES = new Set([401, 403, 404]);
 
 // Public default CodeWhisperer profile ARNs (us-east-1), keyed by auth method.
 // Used when an account cannot resolve its own profileArn. Builder ID and social
diff --git a/open-sse/executors/base.js b/open-sse/executors/base.js
index 71418deb..5a3c4467 100644
--- a/open-sse/executors/base.js
+++ b/open-sse/executors/base.js
@@ -126,7 +126,7 @@ export class BaseExecutor {
     for (let urlIndex = 0; urlIndex < fallbackCount; urlIndex++) {
       const url = this.buildUrl(model, stream, urlIndex, credentials);
       const transformedBody = this.transformRequest(model, body, stream, credentials);
-      const headers = this.buildHeaders(credentials, stream);
+      const headers = this.buildHeaders(credentials, stream, url);
 
       if (!retryAttemptsByUrl[urlIndex]) retryAttemptsByUrl[urlIndex] = 0;
 
diff --git a/open-sse/executors/kiro.js b/open-sse/executors/kiro.js
index 90ec713e..1205522b 100644
--- a/open-sse/executors/kiro.js
+++ b/open-sse/executors/kiro.js
@@ -1,6 +1,10 @@
 import { BaseExecutor } from "./base.js";
 import { PROVIDERS } from "../config/providers.js";
-import { resolveKiroModel } from "../config/kiroConstants.js";
+import {
+  KIRO_CODEWHISPERER_TARGET,
+  KIRO_ENDPOINT_FALLBACK_STATUSES,
+  resolveKiroModel,
+} from "../config/kiroConstants.js";
 import { v4 as uuidv4 } from "uuid";
 import { refreshKiroToken } from "../services/tokenRefresh.js";
 import { SSE_DONE, SSE_HEADERS } from "../utils/sseConstants.js";
@@ -216,12 +220,17 @@ export class KiroExecutor extends BaseExecutor {
     super("kiro", PROVIDERS.kiro);
   }
 
-  buildHeaders(credentials, stream = true) {
+  buildHeaders(credentials, stream = true, url = "") {
     const headers = {
       ...this.config.headers,
       "Amz-Sdk-Request": "attempt=1; max=3",
       "Amz-Sdk-Invocation-Id": uuidv4()
     };
+    if (url.includes("://codewhisperer.")) {
+      headers["X-Amz-Target"] = KIRO_CODEWHISPERER_TARGET;
+    } else {
+      delete headers["X-Amz-Target"];
+    }
 
     // API-key auth: the key is stored as accessToken and sent as a bearer token
     // exactly like an OAuth access token, but with an extra `tokentype: API_KEY`
@@ -236,8 +245,8 @@ export class KiroExecutor extends BaseExecutor {
     const apiKey = credentials?.apiKey || (isApiKey ? credentials?.accessToken : null);
     if (isApiKey && apiKey) {
       headers["Authorization"] = `Bearer ${apiKey}`;
-      headers["tokentype"] = "API_KEY";
-    } else if (credentials.accessToken) {
+      headers["TokenType"] = "API_KEY";
+    } else if (credentials?.accessToken) {
       headers["Authorization"] = `Bearer ${credentials.accessToken}`;
       if (isExternalIdp) {
         headers["TokenType"] = "EXTERNAL_IDP";
@@ -250,14 +259,14 @@ export class KiroExecutor extends BaseExecutor {
   /**
    * Auth-aware endpoint ordering.
    *
-   * API-key Kiro connections store a raw CodeWhisperer credential (validated
-   * against codewhisperer.us-east-1.amazonaws.com via ListAvailableProfiles).
+   * API-key Kiro connections use the Amazon Q surface. The legacy
+   * codewhisperer.* GenerateAssistantResponse endpoint can authenticate the key
+   * but rejects the same valid payload with REQUEST_BODY_INVALID. Since a 400
+   * is terminal in BaseExecutor, putting CodeWhisperer first prevents the working
+   * q.* endpoint from ever being tried. Keep q.* first only for api_key accounts.
+   *
    * The Kiro IDE gateway (runtime.*.kiro.dev) expects Kiro OIDC/social tokens
-   * and rejects an `tokentype: API_KEY` token with 401/403 — which
-   * BaseExecutor.execute() returns immediately (only 429 / network errors fall
-   * through to the next host). So for api-key auth we must try the *.amazonaws.com
-   * CodeWhisperer hosts FIRST, mirroring the Kiro-Go reference fork which never
-   * routes api-key traffic through kiro.dev. External IdP enterprise tokens also
+   * and rejects TokenType=API_KEY. External IdP enterprise tokens instead
    * use the CodeWhisperer surface, with the `TokenType: EXTERNAL_IDP` header.
    * Other OAuth methods keep the default order (kiro.dev first) since their
    * tokens are what that gateway accepts.
@@ -282,6 +291,14 @@ export class KiroExecutor extends BaseExecutor {
 
     const amazon = baseUrls.filter((u) => u.includes("amazonaws.com")).map(regionalize);
     const others = baseUrls.filter((u) => !u.includes("amazonaws.com"));
+    if (authMethod === "api_key") {
+      const q = amazon.filter((u) => u.includes("://q."));
+      const remaining = amazon.filter((u) => !u.includes("://q."));
+      return q.length > 0
+        ? [...q, ...remaining, ...others]
+        : [...amazon, ...others];
+    }
+
     return amazon.length > 0 ? [...amazon, ...others] : baseUrls;
   }
 
@@ -290,6 +307,14 @@ export class KiroExecutor extends BaseExecutor {
     return baseUrls[urlIndex] || baseUrls[0] || this.config.baseUrl;
   }
 
+  // Retry only endpoint/auth-surface failures. Payload-invalid HTTP 400 must be
+  // terminal: sending the same malformed body to every surface cannot repair it.
+  shouldRetry(status, urlIndex) {
+    const hasFallback = urlIndex + 1 < this.getFallbackCount();
+    return super.shouldRetry(status, urlIndex)
+      || (hasFallback && KIRO_ENDPOINT_FALLBACK_STATUSES.has(status));
+  }
+
   transformRequest(model, body, stream, credentials) {
     return body;
   }
diff --git a/open-sse/providers/registry/kiro.js b/open-sse/providers/registry/kiro.js
index 1a47adaa..325745a4 100644
--- a/open-sse/providers/registry/kiro.js
+++ b/open-sse/providers/registry/kiro.js
@@ -29,7 +29,6 @@ export default {
     headers: {
       "Content-Type": "application/json",
       Accept: "application/vnd.amazon.eventstream",
-      "X-Amz-Target": "AmazonCodeWhispererStreamingService.GenerateAssistantResponse",
       "User-Agent": "AWS-SDK-JS/3.0.0 kiro-ide/1.0.0",
       "X-Amz-User-Agent": "aws-sdk-js/3.0.0 kiro-ide/1.0.0",
     },
diff --git a/open-sse/translator/concerns/kiroConversation.js b/open-sse/translator/concerns/kiroConversation.js
new file mode 100644
index 00000000..11d49dc7
--- /dev/null
+++ b/open-sse/translator/concerns/kiroConversation.js
@@ -0,0 +1,435 @@
+import {
+  KIRO_TOOL_DESCRIPTION_MAX_LENGTH,
+  KIRO_TOOL_ID_MAX_LENGTH,
+  KIRO_TOOL_NAME_MAX_LENGTH,
+} from "../../config/kiroConstants.js";
+
+const TOOL_ID_PATTERN = /^[a-zA-Z0-9_-]+$/;
+const TOOL_NAME_PATTERN = /[^a-zA-Z0-9_-]/g;
+
+function clone(value) {
+  return value == null ? value : JSON.parse(JSON.stringify(value));
+}
+
+function text(value) {
+  if (typeof value === "string") return value;
+  if (value == null) return "";
+  try {
+    return JSON.stringify(value);
+  } catch {
+    return String(value);
+  }
+}
+
+function appendText(target, extra) {
+  if (!extra) return;
+  target.content = target.content ? `${target.content}\n\n${extra}` : extra;
+}
+
+function trimCodePoints(value, limit) {
+  return [...String(value || "")].slice(0, limit).join("");
+}
+
+function uniqueName(rawName, index, usedNames) {
+  const cleaned = String(rawName || "")
+    .trim()
+    .replace(TOOL_NAME_PATTERN, "_")
+    .replace(/_+/g, "_")
+    .replace(/^_+|_+$/g, "");
+  const base = trimCodePoints(cleaned || `tool_${index + 1}`, KIRO_TOOL_NAME_MAX_LENGTH);
+  let candidate = base;
+  let suffix = 2;
+  while (usedNames.has(candidate)) {
+    const tail = `_${suffix++}`;
+    candidate = `${base.slice(0, KIRO_TOOL_NAME_MAX_LENGTH - tail.length)}${tail}`;
+  }
+  usedNames.add(candidate);
+  return candidate;
+}
+
+function cleanSchemaValue(value) {
+  if (Array.isArray(value)) return value.map(cleanSchemaValue);
+  if (!value || typeof value !== "object") return value;
+
+  const cleaned = {};
+  for (const [key, child] of Object.entries(value)) {
+    if (key === "additionalProperties") continue;
+    if (key === "required" && Array.isArray(child) && child.length === 0) continue;
+    cleaned[key] = cleanSchemaValue(child);
+  }
+  return cleaned;
+}
+
+function normalizeRootSchema(schema) {
+  const cleaned = cleanSchemaValue(schema && typeof schema === "object" ? clone(schema) : {});
+  cleaned.type = "object";
+  if (!cleaned.properties || typeof cleaned.properties !== "object" || Array.isArray(cleaned.properties)) {
+    cleaned.properties = {};
+  }
+  if (Array.isArray(cleaned.required)) {
+    cleaned.required = [...new Set(cleaned.required.filter(
+      (name) => typeof name === "string" && Object.hasOwn(cleaned.properties, name)
+    ))];
+    if (cleaned.required.length === 0) delete cleaned.required;
+  }
+  return cleaned;
+}
+
+/** Normalize OpenAI- or Claude-shaped tool definitions into Kiro tool specs. */
+export function normalizeKiroToolSpecs(tools) {
+  const specs = [];
+  const nameMap = new Map();
+  const usedNames = new Set();
+
+  for (const [index, tool] of (Array.isArray(tools) ? tools : []).entries()) {
+    if (!tool || typeof tool !== "object") continue;
+    const rawName = tool.function?.name ?? tool.name;
+    if (typeof rawName !== "string" || !rawName.trim()) continue;
+
+    // A repeated definition with the same source name describes the same tool.
+    if (nameMap.has(rawName)) continue;
+    const name = uniqueName(rawName, index, usedNames);
+    nameMap.set(rawName, name);
+
+    const rawDescription = tool.function?.description ?? tool.description ?? `Tool: ${rawName}`;
+    const description = trimCodePoints(
+      String(rawDescription || `Tool: ${rawName}`),
+      KIRO_TOOL_DESCRIPTION_MAX_LENGTH
+    );
+    const schema = tool.function?.parameters ?? tool.parameters ?? tool.input_schema ?? {};
+    specs.push({
+      toolSpecification: {
+        name,
+        description,
+        inputSchema: { json: normalizeRootSchema(schema) },
+      },
+    });
+  }
+
+  return { specs, nameMap };
+}
+
+function toolCallText(toolUse) {
+  return `[Tool call: ${toolUse?.name || "unknown"}(${text(toolUse?.input || {})})]`;
+}
+
+function toolResultText(toolResult) {
+  const content = Array.isArray(toolResult?.content)
+    ? toolResult.content.map((part) => text(part?.text ?? part)).filter(Boolean).join("\n")
+    : text(toolResult?.content);
+  return `[Tool result${toolResult?.status === "error" ? " (error)" : ""}: ${content}]`;
+}
+
+function mergeUser(target, source) {
+  appendText(target, source.content);
+  if (Array.isArray(source.images) && source.images.length > 0) {
+    target.images = [...(target.images || []), ...source.images];
+  }
+  const results = source.userInputMessageContext?.toolResults;
+  if (Array.isArray(results) && results.length > 0) {
+    target.userInputMessageContext ||= {};
+    target.userInputMessageContext.toolResults = [
+      ...(target.userInputMessageContext.toolResults || []),
+      ...results,
+    ];
+  }
+}
+
+function mergeAssistant(target, source) {
+  appendText(target, source.content);
+  if (Array.isArray(source.toolUses) && source.toolUses.length > 0) {
+    target.toolUses = [...(target.toolUses || []), ...source.toolUses];
+  }
+}
+
+function normalizeTurns(history, currentMessage, modelId) {
+  const rawTurns = [...(Array.isArray(history) ? history : [])];
+  if (currentMessage) rawTurns.push(currentMessage);
+  const turns = [];
+
+  for (const raw of rawTurns) {
+    const isUser = !!raw?.userInputMessage;
+    const isAssistant = !!raw?.assistantResponseMessage;
+    if (isUser === isAssistant) continue;
+
+    const turn = isUser
+      ? { userInputMessage: clone(raw.userInputMessage) }
+      : { assistantResponseMessage: clone(raw.assistantResponseMessage) };
+    const previous = turns[turns.length - 1];
+    if (turn.userInputMessage && previous?.userInputMessage) {
+      mergeUser(previous.userInputMessage, turn.userInputMessage);
+    } else if (turn.assistantResponseMessage && previous?.assistantResponseMessage) {
+      mergeAssistant(previous.assistantResponseMessage, turn.assistantResponseMessage);
+    } else {
+      turns.push(turn);
+    }
+  }
+
+  if (turns[0]?.assistantResponseMessage) {
+    turns.unshift({ userInputMessage: { content: "continue", modelId } });
+  }
+  if (turns.length === 0 || turns[turns.length - 1]?.assistantResponseMessage) {
+    turns.push({ userInputMessage: { content: "continue", modelId } });
+  }
+
+  for (const turn of turns) {
+    if (turn.userInputMessage) {
+      turn.userInputMessage.content = text(turn.userInputMessage.content).trim() || "continue";
+      turn.userInputMessage.modelId ||= modelId;
+      if (turn.userInputMessage.userInputMessageContext?.tools) {
+        delete turn.userInputMessage.userInputMessageContext.tools;
+      }
+    } else {
+      turn.assistantResponseMessage.content =
+        text(turn.assistantResponseMessage.content).trim() || "...";
+    }
+  }
+  return turns;
+}
+
+function rawId(value) {
+  return typeof value === "string" ? value : "";
+}
+
+function reserveToolId(value, turnIndex, callIndex, name, usedIds) {
+  const sanitized = rawId(value).replace(/[^a-zA-Z0-9_-]/g, "");
+  const generated = `call_msg${turnIndex}_tc${callIndex}_${name || "tool"}`;
+  const base = trimCodePoints(
+    TOOL_ID_PATTERN.test(sanitized) && sanitized ? sanitized : generated,
+    KIRO_TOOL_ID_MAX_LENGTH
+  );
+  let candidate = base;
+  let suffix = 2;
+  while (usedIds.has(candidate)) {
+    const tail = `_${suffix++}`;
+    candidate = `${base.slice(0, KIRO_TOOL_ID_MAX_LENGTH - tail.length)}${tail}`;
+  }
+  usedIds.add(candidate);
+  return candidate;
+}
+
+function normalizeToolInput(input) {
+  if (input && typeof input === "object" && !Array.isArray(input)) return clone(input);
+  if (typeof input === "string") {
+    try {
+      const parsed = JSON.parse(input);
+      if (parsed && typeof parsed === "object" && !Array.isArray(parsed)) return parsed;
+    } catch {
+      return null;
+    }
+  }
+  return input == null ? {} : null;
+}
+
+function normalizeToolResult(result) {
+  const content = Array.isArray(result?.content)
+    ? result.content.map((part) => ({ text: text(part?.text ?? part) }))
+    : [{ text: text(result?.content) }];
+  return {
+    toolUseId: rawId(result?.toolUseId),
+    status: result?.status === "error" ? "error" : "success",
+    content: content.length > 0 ? content : [{ text: "" }],
+  };
+}
+
+function flattenResults(userMessage, results) {
+  for (const result of results) appendText(userMessage, toolResultText(result));
+}
+
+function cleanUserContext(userMessage) {
+  const context = userMessage.userInputMessageContext;
+  if (!context) return;
+  if (!context.toolResults?.length) delete context.toolResults;
+  if (!context.tools?.length) delete context.tools;
+  if (Object.keys(context).length === 0) delete userMessage.userInputMessageContext;
+}
+
+function reconcileToolPair(assistant, user, turnIndex, nameMap, specNames, usedIds, repairs) {
+  const calls = Array.isArray(assistant.toolUses) ? assistant.toolUses : [];
+  const results = Array.isArray(user.userInputMessageContext?.toolResults)
+    ? user.userInputMessageContext.toolResults.map(normalizeToolResult)
+    : [];
+  if (calls.length === 0) {
+    if (results.length > 0) {
+      flattenResults(user, results);
+      repairs.orphanResults += results.length;
+    }
+    if (user.userInputMessageContext) delete user.userInputMessageContext.toolResults;
+    cleanUserContext(user);
+    return;
+  }
+
+  const callQueues = new Map();
+  const callRecords = calls.map((call, callIndex) => {
+    const key = rawId(call?.toolUseId);
+    const mappedName = nameMap.get(call?.name) || call?.name;
+    const input = normalizeToolInput(call?.input);
+    const record = { call, callIndex, key, mappedName, input, result: null };
+    const queue = callQueues.get(key) || [];
+    queue.push(record);
+    callQueues.set(key, queue);
+    return record;
+  });
+
+  const orphanResults = [];
+  for (const result of results) {
+    const queue = callQueues.get(rawId(result.toolUseId));
+    const record = queue?.find((candidate) => !candidate.result);
+    if (record) record.result = result;
+    else orphanResults.push(result);
+  }
+
+  const keptCalls = [];
+  const keptResults = [];
+  for (const record of callRecords) {
+    const hasSpec = typeof record.mappedName === "string" && specNames.has(record.mappedName);
+    const valid = !!record.result && hasSpec && record.input !== null;
+    if (!valid) {
+      appendText(assistant, toolCallText({ name: record.mappedName, input: record.call?.input }));
+      repairs.missingResults += record.result ? 0 : 1;
+      repairs.invalidToolUses += hasSpec && record.input !== null ? 0 : 1;
+      if (record.result) {
+        flattenResults(user, [record.result]);
+        repairs.orphanResults++;
+      }
+      continue;
+    }
+
+    const toolUseId = reserveToolId(
+      record.key,
+      turnIndex,
+      record.callIndex,
+      record.mappedName,
+      usedIds
+    );
+    keptCalls.push({
+      toolUseId,
+      name: record.mappedName,
+      input: record.input,
+    });
+    keptResults.push({ ...record.result, toolUseId });
+  }
+
+  if (orphanResults.length > 0) {
+    flattenResults(user, orphanResults);
+    repairs.orphanResults += orphanResults.length;
+  }
+
+  if (keptCalls.length > 0) assistant.toolUses = keptCalls;
+  else delete assistant.toolUses;
+  user.userInputMessageContext ||= {};
+  if (keptResults.length > 0) user.userInputMessageContext.toolResults = keptResults;
+  else delete user.userInputMessageContext.toolResults;
+  cleanUserContext(user);
+}
+
+/** Validate the final Kiro wire conversation without mutating it. */
+export function validateKiroConversation(history, currentMessage, toolSpecs = []) {
+  const errors = [];
+  const turns = [...(history || []), currentMessage].filter(Boolean);
+  const specNames = new Set(toolSpecs.map((spec) => spec?.toolSpecification?.name).filter(Boolean));
+  const usedIds = new Set();
+
+  for (let index = 0; index < turns.length; index++) {
+    const expectedUser = index % 2 === 0;
+    const isUser = !!turns[index]?.userInputMessage;
+    if (isUser !== expectedUser) errors.push(`role:${index}`);
+    if (!isUser) {
+      const calls = turns[index].assistantResponseMessage?.toolUses || [];
+      const results = turns[index + 1]?.userInputMessage?.userInputMessageContext?.toolResults || [];
+      const callIds = calls.map((call) => call.toolUseId);
+      const resultIds = results.map((result) => result.toolUseId);
+      if (calls.length !== results.length || callIds.some((id) => !resultIds.includes(id))) {
+        errors.push(`pair:${index}`);
+      }
+      for (const call of calls) {
+        if (!call.toolUseId || usedIds.has(call.toolUseId)) errors.push(`id:${index}`);
+        usedIds.add(call.toolUseId);
+        if (!specNames.has(call.name)) errors.push(`spec:${index}`);
+      }
+    } else if (index === 0) {
+      const results = turns[index].userInputMessage?.userInputMessageContext?.toolResults;
+      if (results?.length) errors.push("orphan:0");
+    }
+  }
+  if (!currentMessage?.userInputMessage?.content) errors.push("current");
+  return { valid: errors.length === 0, errors };
+}
+
+function flattenAllStructuredTools(turns, repairs) {
+  for (const turn of turns) {
+    if (turn.assistantResponseMessage?.toolUses?.length) {
+      for (const call of turn.assistantResponseMessage.toolUses) {
+        appendText(turn.assistantResponseMessage, toolCallText(call));
+      }
+      repairs.invalidToolUses += turn.assistantResponseMessage.toolUses.length;
+      delete turn.assistantResponseMessage.toolUses;
+    }
+    const user = turn.userInputMessage;
+    const results = user?.userInputMessageContext?.toolResults;
+    if (results?.length) {
+      flattenResults(user, results);
+      repairs.orphanResults += results.length;
+      delete user.userInputMessageContext.toolResults;
+      cleanUserContext(user);
+    }
+  }
+}
+
+/**
+ * Produce a strict Kiro conversation: alternating turns, current user message,
+ * adjacent one-to-one tool use/result pairs, and tool specs only on currentMessage.
+ */
+export function canonicalizeKiroConversation({
+  history,
+  currentMessage,
+  modelId,
+  toolSpecs = [],
+  nameMap = new Map(),
+} = {}) {
+  const turns = normalizeTurns(history, currentMessage, modelId);
+  const repairs = { missingResults: 0, orphanResults: 0, invalidToolUses: 0 };
+  const specNames = new Set(toolSpecs.map((spec) => spec?.toolSpecification?.name).filter(Boolean));
+  const usedIds = new Set();
+
+  for (let index = 0; index < turns.length; index += 2) {
+    const user = turns[index].userInputMessage;
+    if (index === 0) {
+      const leadingResults = user.userInputMessageContext?.toolResults || [];
+      if (leadingResults.length > 0) {
+        flattenResults(user, leadingResults);
+        repairs.orphanResults += leadingResults.length;
+        delete user.userInputMessageContext.toolResults;
+        cleanUserContext(user);
+      }
+    }
+    const assistant = turns[index + 1]?.assistantResponseMessage;
+    const nextUser = turns[index + 2]?.userInputMessage;
+    if (assistant && nextUser) {
+      reconcileToolPair(assistant, nextUser, index + 1, nameMap, specNames, usedIds, repairs);
+    }
+  }
+
+  const finalCurrent = turns[turns.length - 1];
+  finalCurrent.userInputMessage.userInputMessageContext ||= {};
+  if (toolSpecs.length > 0) {
+    finalCurrent.userInputMessage.userInputMessageContext.tools = clone(toolSpecs);
+  }
+  cleanUserContext(finalCurrent.userInputMessage);
+
+  let finalHistory = turns.slice(0, -1);
+  let validation = validateKiroConversation(finalHistory, finalCurrent, toolSpecs);
+  if (!validation.valid) {
+    flattenAllStructuredTools(turns, repairs);
+    finalHistory = turns.slice(0, -1);
+    validation = validateKiroConversation(finalHistory, finalCurrent, toolSpecs);
+  }
+
+  return {
+    history: finalHistory,
+    currentMessage: finalCurrent,
+    repairs,
+    valid: validation.valid,
+    errors: validation.errors,
+  };
+}
diff --git a/open-sse/translator/index.js b/open-sse/translator/index.js
index 37e5bde6..48bd1530 100644
--- a/open-sse/translator/index.js
+++ b/open-sse/translator/index.js
@@ -62,8 +62,13 @@ export function translateRequest(sourceFormat, targetFormat, model, body, stream
   // Always ensure tool_calls have id (some providers require it)
   ensureToolCallIds(result);
   
-  // Fix missing tool responses (insert empty tool_result if needed)
-  fixMissingToolResponses(result);
+  // Kiro performs stricter source-aware reconciliation after session replay.
+  // The generic helper inserts OpenAI `role: tool` messages, which a direct
+  // Claude→Kiro translator cannot consume and which cannot repair partial
+  // parallel tool results.
+  if (targetFormat !== FORMATS.KIRO) {
+    fixMissingToolResponses(result);
+  }
 
   // Capture thinking intent from the original (pre-translation) body, before any
   // format conversion strips/renames the fields. Applied after translation.
diff --git a/open-sse/translator/request/claude-to-kiro.js b/open-sse/translator/request/claude-to-kiro.js
index 51b9c7f8..8651e819 100644
--- a/open-sse/translator/request/claude-to-kiro.js
+++ b/open-sse/translator/request/claude-to-kiro.js
@@ -6,17 +6,10 @@
  * direct `claude:kiro` route in ../index.js uses; it is NOT reached through the
  * claude→openai→kiro pivot.
  *
- * It reproduces the two 400-guards that live in openai-to-kiro.js so that a
- * Claude client which omits the `tools` array on a follow-up turn (typical
- * after client-side compaction) does not trip Kiro's schema validator and get
- * "Improperly formed request" (HTTP 400):
- *
- *   1. flattenClaudeToolInteractions — when the client sent NO tools, collapse
- *      every tool_use / tool_result block to plain text so no structured tool
- *      reference survives to trigger the "tools required" rule.
- *   2. reconcileOrphanedToolResults — when tools ARE present, fold any
- *      tool_result whose tool_use_id has no matching tool_use back into the
- *      user text instead of leaving a dangling structured reference.
+ * After session replay it delegates to the shared Kiro conversation
+ * canonicalizer. That layer enforces adjacent one-to-one tool use/results,
+ * repairs partial parallel calls, and flattens compacted structured references
+ * that can no longer be represented safely.
  *
  * It also handles the 9router-synthetic `-agentic` / `-thinking` suffixes and
  * the `<thinking_mode>enabled</thinking_mode>` reasoning trigger, matching
@@ -38,82 +31,17 @@ import {
 } from "../../config/kiroConstants.js";
 import { DEFAULT_IMAGE_MIME } from "../schema/index.js";
 import { ROLE, CLAUDE_BLOCK } from "../schema/index.js";
-
-/** Stringify a tool_use input as a readable line. */
-function toolUseToText(name, input) {
-  let argStr;
-  try {
-    argStr = typeof input === "string" ? input : JSON.stringify(input ?? {});
-  } catch {
-    argStr = "{}";
-  }
-  return `[Tool call: ${name || "unknown"}(${argStr})]`;
-}
-
-/** Render a Claude tool_result block's content as a readable line. */
-function toolResultBlockToText(content) {
-  let text = "";
-  if (typeof content === "string") {
-    text = content;
-  } else if (Array.isArray(content)) {
-    text = content
-      .map((c) => (typeof c === "string" ? c : c?.text || ""))
-      .filter(Boolean)
-      .join("\n");
-  } else if (content) {
-    try {
-      text = JSON.stringify(content);
-    } catch {
-      text = "";
-    }
-  }
-  return `[Tool result: ${text}]`;
-}
-
-/**
- * When the client sent no tools, rewrite every tool_use (assistant) and
- * tool_result (user) content block into plain text. Keeps text + images.
- * Returns a new messages array; never mutates the input.
- */
-function flattenClaudeToolInteractions(messages) {
-  const out = [];
-  for (const msg of messages) {
-    if (!msg) continue;
-
-    if (msg.role === ROLE.ASSISTANT && Array.isArray(msg.content)) {
-      const parts = [];
-      for (const block of msg.content) {
-        if (block.type === CLAUDE_BLOCK.TEXT && block.text) {
-          parts.push(block.text);
-        } else if (block.type === CLAUDE_BLOCK.TOOL_USE) {
-          parts.push(toolUseToText(block.name, block.input));
-        }
-      }
-      out.push({ ...msg, content: parts.join("\n") });
-      continue;
-    }
-
-    if (msg.role === ROLE.USER && Array.isArray(msg.content)) {
-      const newContent = msg.content.map((block) =>
-        block.type === CLAUDE_BLOCK.TOOL_RESULT
-          ? { type: CLAUDE_BLOCK.TEXT, text: toolResultBlockToText(block.content) }
-          : block
-      );
-      out.push({ ...msg, content: newContent });
-      continue;
-    }
-
-    out.push(msg);
-  }
-  return out;
-}
+import {
+  canonicalizeKiroConversation,
+  normalizeKiroToolSpecs,
+} from "../concerns/kiroConversation.js";
 
 /**
  * Convert Claude messages to Kiro history + currentMessage.
  * Kiro requires alternating user/assistant turns; consecutive same-role
  * messages are merged.
  */
-function convertClaudeMessagesToKiro(messages, tools, model) {
+function convertClaudeMessagesToKiro(messages, model) {
   const history = [];
   let currentMessage = null;
 
@@ -122,27 +50,6 @@ function convertClaudeMessagesToKiro(messages, tools, model) {
   let pendingToolResults = [];
   let pendingImages = [];
   let currentRole = null;
-  let toolsInjected = false;
-
-  const clientProvidedTools = Array.isArray(tools) && tools.length > 0;
-
-  const buildToolSpecs = () =>
-    tools.map((t) => {
-      const name = t.name;
-      const description = t.description || `Tool: ${name}`;
-      const schema = t.input_schema || {};
-      const normalizedSchema =
-        Object.keys(schema).length === 0
-          ? { type: "object", properties: {}, required: [] }
-          : { ...schema, required: schema.required ?? [] };
-      return {
-        toolSpecification: {
-          name,
-          description,
-          inputSchema: { json: normalizedSchema },
-        },
-      };
-    });
 
   const flushPending = () => {
     if (currentRole === ROLE.USER) {
@@ -157,15 +64,6 @@ function convertClaudeMessagesToKiro(messages, tools, model) {
           toolResults: pendingToolResults,
         };
       }
-      // Attach tools to the first user turn only.
-      if (clientProvidedTools && !toolsInjected) {
-        if (!userMsg.userInputMessage.userInputMessageContext) {
-          userMsg.userInputMessage.userInputMessageContext = {};
-        }
-        userMsg.userInputMessage.userInputMessageContext.tools = buildToolSpecs();
-        toolsInjected = true;
-      }
-
       history.push(userMsg);
       currentMessage = userMsg;
       pendingUserContent = [];
@@ -209,7 +107,7 @@ function convertClaudeMessagesToKiro(messages, tools, model) {
             }
             pendingToolResults.push({
               toolUseId: block.tool_use_id,
-              status: "success",
+              status: block.is_error ? "error" : "success",
               content: [{ text: resultContent }],
             });
           }
@@ -256,14 +154,7 @@ function convertClaudeMessagesToKiro(messages, tools, model) {
     }
   }
 
-  // Grab tools from the first history user turn before cleanup strips them.
-  const firstHistoryTools =
-    history[0]?.userInputMessage?.userInputMessageContext?.tools;
-
   history.forEach((item) => {
-    if (item.userInputMessage?.userInputMessageContext?.tools) {
-      delete item.userInputMessage.userInputMessageContext.tools;
-    }
     if (
       item.userInputMessage?.userInputMessageContext &&
       Object.keys(item.userInputMessage.userInputMessageContext).length === 0
@@ -307,66 +198,9 @@ function convertClaudeMessagesToKiro(messages, tools, model) {
     currentMessage = { userInputMessage: { content: "", modelId: model } };
   }
 
-  // Inject tools into currentMessage after cleanup if not already present.
-  if (
-    firstHistoryTools?.length > 0 &&
-    !currentMessage.userInputMessage.userInputMessageContext?.tools
-  ) {
-    if (!currentMessage.userInputMessage.userInputMessageContext) {
-      currentMessage.userInputMessage.userInputMessageContext = {};
-    }
-    currentMessage.userInputMessage.userInputMessageContext.tools =
-      firstHistoryTools;
-  }
-
   return { history: mergedHistory, currentMessage };
 }
 
-/**
- * Fold orphaned toolResults (those whose toolUseId has no matching toolUse in
- * any assistant turn) back into the user text, removing the dangling
- * structured reference that makes Kiro 400.
- */
-function reconcileOrphanedToolResults(history, currentMessage) {
-  const validIds = new Set();
-  for (const h of history) {
-    const arm = h.assistantResponseMessage;
-    if (!arm) continue;
-    for (const tu of arm.toolUses || []) {
-      if (tu.toolUseId) validIds.add(tu.toolUseId);
-    }
-  }
-
-  const carriers = currentMessage ? [...history, currentMessage] : history;
-  for (const item of carriers) {
-    const uim = item.userInputMessage;
-    const ctx = uim?.userInputMessageContext;
-    if (!ctx?.toolResults?.length) continue;
-
-    const kept = [];
-    const salvaged = [];
-    for (const tr of ctx.toolResults) {
-      if (validIds.has(tr.toolUseId)) {
-        kept.push(tr);
-      } else {
-        const text = Array.isArray(tr.content)
-          ? tr.content.map((c) => c?.text || "").join("\n")
-          : "";
-        salvaged.push(`[Tool result: ${text}]`);
-      }
-    }
-
-    if (salvaged.length === 0) continue;
-
-    const extra = salvaged.join("\n");
-    uim.content = uim.content ? `${uim.content}\n\n${extra}` : extra;
-    ctx.toolResults = kept;
-    if (kept.length === 0 && !ctx.tools?.length) {
-      delete uim.userInputMessageContext;
-    }
-  }
-}
-
 function extractClaudeSystemText(system) {
   if (!system) return "";
   if (typeof system === "string") return system;
@@ -383,9 +217,8 @@ function extractClaudeSystemText(system) {
  * Build a Kiro payload directly from a Claude Messages API request body.
  */
 export function claudeToKiroRequest(model, body, stream, credentials) {
-  let messages = Array.isArray(body.messages) ? body.messages : [];
+  const messages = Array.isArray(body.messages) ? body.messages : [];
   const tools = Array.isArray(body.tools) ? body.tools : [];
-  const clientProvidedTools = tools.length > 0;
   const maxTokens = body.max_tokens || 32000;
   const temperature = body.temperature;
   const topP = body.top_p;
@@ -397,21 +230,8 @@ export function claudeToKiroRequest(model, body, stream, credentials) {
   const additionalModelRequestFields = buildKiroAdditionalModelRequestFieldsForModel(thinkingBody, upstreamModel);
   const usesNativeGptEffort = usesKiroNativeGptEffort(thinkingBody, upstreamModel);
 
-  // Guard 1: no client tools → flatten all tool interactions to text.
-  if (!clientProvidedTools) {
-    messages = flattenClaudeToolInteractions(messages);
-  }
-
-  const { history, currentMessage } = convertClaudeMessagesToKiro(
-    messages,
-    tools,
-    upstreamModel
-  );
-
-  // Guard 2: tools present → reconcile dangling tool_results.
-  if (clientProvidedTools) {
-    reconcileOrphanedToolResults(history, currentMessage);
-  }
+  const { specs: toolSpecs, nameMap } = normalizeKiroToolSpecs(tools);
+  const { history, currentMessage } = convertClaudeMessagesToKiro(messages, upstreamModel);
 
   // api_key / idc / external_idp must never use the shared default ARN (belongs
   // to another account → 403 "bearer token invalid"); OAuth/social fall back to it.
@@ -460,7 +280,14 @@ export function claudeToKiroRequest(model, body, stream, credentials) {
     history,
     currentMessage,
   });
-  const replayCurrent = replay.currentMessage?.userInputMessage || {};
+  const canonical = canonicalizeKiroConversation({
+    history: replay.history,
+    currentMessage: replay.currentMessage,
+    modelId: upstreamModel,
+    toolSpecs,
+    nameMap,
+  });
+  const replayCurrent = canonical.currentMessage.userInputMessage;
   const userInputMessage = {
     content: replayCurrent.content || "",
     modelId: upstreamModel,
@@ -482,7 +309,7 @@ export function claudeToKiroRequest(model, body, stream, credentials) {
       currentMessage: {
         userInputMessage,
       },
-      history: replay.history,
+      history: canonical.history,
     },
     agentMode: "vibe",
   };
diff --git a/open-sse/translator/request/openai-to-kiro.js b/open-sse/translator/request/openai-to-kiro.js
index 798c827f..aa776949 100644
--- a/open-sse/translator/request/openai-to-kiro.js
+++ b/open-sse/translator/request/openai-to-kiro.js
@@ -20,148 +20,10 @@ import {
 import { parseDataUri } from "../concerns/image.js";
 import { DEFAULT_IMAGE_MIME } from "../schema/index.js";
 import { ROLE, OPENAI_BLOCK, CLAUDE_BLOCK } from "../schema/index.js";
-
-/** Render a single tool call as a readable text line. */
-function toolCallToText(name, input) {
-  let argStr;
-  try {
-    argStr = typeof input === "string" ? input : JSON.stringify(input ?? {});
-  } catch {
-    argStr = "{}";
-  }
-  return `[Tool call: ${name || "unknown"}(${argStr})]`;
-}
-
-/** Render a tool result (string or content-block array) as a text line. */
-function toolResultToText(content) {
-  const text = Array.isArray(content)
-    ? content.map(c => (typeof c === "string" ? c : c.text || "")).join("\n")
-    : (typeof content === "string" ? content : "");
-  return `[Tool result: ${text}]`;
-}
-
-/**
- * Flatten all tool calls/results in a conversation into plain text.
- *
- * Kiro's schema validator requires a non-empty
- * currentMessage.userInputMessageContext.tools array whenever the history
- * references any tool use; otherwise it returns "Improperly formed request"
- * (HTTP 400). A client can hit this by omitting the `tools` array on a
- * follow-up request — typically after client-side compaction (e.g. OpenCode).
- *
- * Rather than fabricate stub tool specs — which would advertise tool-calling
- * capability the client never requested and may not handle, risking a phantom
- * tool call on an otherwise plain turn — we collapse the tool interaction into
- * text. The request stays honest, and since no structured tool content
- * remains, the validator's "tools required" rule never fires.
- *
- * Only invoked when the client did NOT send tools; when tools are present the
- * structured form is preserved.
- */
-function flattenToolInteractions(messages) {
-  const out = [];
-
-  for (const msg of messages) {
-    // OpenAI tool-result message → user text line
-    if (msg.role === ROLE.TOOL) {
-      out.push({ role: ROLE.USER, content: toolResultToText(msg.content) });
-      continue;
-    }
-
-    if (msg.role === ROLE.ASSISTANT) {
-      const parts = [];
-      if (Array.isArray(msg.content)) {
-        for (const c of msg.content) {
-          if (c.type === CLAUDE_BLOCK.TOOL_USE) {
-            parts.push(toolCallToText(c.name, c.input));
-          } else if (c.type === OPENAI_BLOCK.TEXT || c.text) {
-            parts.push(c.text || "");
-          }
-        }
-      } else if (typeof msg.content === "string") {
-        parts.push(msg.content);
-      }
-      for (const tc of msg.tool_calls || []) {
-        parts.push(toolCallToText(tc.function?.name, tc.function?.arguments));
-      }
-      out.push({ role: ROLE.ASSISTANT, content: parts.filter(Boolean).join("\n") });
-      continue;
-    }
-
-    // User messages: replace tool_result blocks with text, keep text + images.
-    if (msg.role === ROLE.USER && Array.isArray(msg.content)) {
-      const newContent = msg.content.map(c =>
-        c.type === CLAUDE_BLOCK.TOOL_RESULT
-          ? { type: OPENAI_BLOCK.TEXT, text: toolResultToText(c.content) }
-          : c
-      );
-      out.push({ ...msg, content: newContent });
-      continue;
-    }
-
-    out.push(msg);
-  }
-
-  return out;
-}
-
-/**
- * Reconcile orphaned toolResults — those whose toolUseId has no matching
- * toolUse in any assistant message. This happens when client-side compaction
- * truncates the conversation and removes the assistant message containing the
- * tool_use, but keeps the user message with the corresponding tool_result.
- *
- * A dangling structured reference makes Kiro return 400, so it must be removed.
- * But the client deliberately kept the result content through compaction, so
- * rather than discard it we fold it back into the user message as text — the
- * same shape flattenToolInteractions() produces. The 400 trigger (the
- * structured reference) is gone; the content survives.
- *
- * `messages` is every carrier that can hold toolResults — both history items
- * and the popped-out currentMessage (orphans can land on either).
- */
-function reconcileOrphanedToolResults(history, currentMessage) {
-  // Phase 1: collect all valid toolUseIds from assistant messages in history.
-  // (currentMessage is always a user turn, so it carries no toolUses.)
-  const validIds = new Set();
-  for (const h of history) {
-    const arm = h.assistantResponseMessage;
-    if (!arm) continue;
-    for (const tu of arm.toolUses || []) {
-      if (tu.toolUseId) validIds.add(tu.toolUseId);
-    }
-  }
-
-  // Phase 2: across history + currentMessage, keep results with a matching
-  // toolUse and salvage the rest as text.
-  const carriers = currentMessage ? [...history, currentMessage] : history;
-  for (const item of carriers) {
-    const uim = item.userInputMessage;
-    const ctx = uim?.userInputMessageContext;
-    if (!ctx?.toolResults?.length) continue;
-
-    const kept = [];
-    const salvaged = [];
-    for (const tr of ctx.toolResults) {
-      if (validIds.has(tr.toolUseId)) {
-        kept.push(tr);
-      } else {
-        salvaged.push(toolResultToText(tr.content));
-      }
-    }
-
-    if (salvaged.length === 0) continue; // no orphans — leave untouched
-
-    // Fold orphaned result content into the user text so it is not lost
-    const extra = salvaged.join("\n");
-    uim.content = uim.content ? `${uim.content}\n\n${extra}` : extra;
-
-    ctx.toolResults = kept;
-    if (kept.length === 0 && !ctx.tools?.length) {
-      delete uim.userInputMessageContext;
-    }
-  }
-}
+import {
+  canonicalizeKiroConversation,
+  normalizeKiroToolSpecs,
+} from "../concerns/kiroConversation.js";
 
 /**
  * Safely parse JSON string, returning fallback on failure.
@@ -177,26 +39,15 @@ function safeJSONParse(str, fallback) {
  *
  * Returns { history, currentMessage }.
  */
-function convertMessages(messages, tools, model) {
+function convertMessages(messages, model) {
   let history = [];
   let currentMessage = null;
 
-  const clientProvidedTools = tools && tools.length > 0;
-
-  // When the client did not send tools, flatten any tool calls/results in the
-  // history into plain text (see flattenToolInteractions). This keeps the
-  // request honest and sidesteps Kiro's "tools required" 400, since no
-  // structured tool content survives to trigger it.
-  if (!clientProvidedTools) {
-    messages = flattenToolInteractions(messages);
-  }
-
   let pendingUserContent = [];
   let pendingAssistantContent = [];
   let pendingToolResults = [];
   let pendingImages = [];
   let currentRole = null;
-  let toolsInjectedToFirstUserMsg = false;
 
   const flushPending = () => {
     if (currentRole === "user") {
@@ -219,39 +70,6 @@ function convertMessages(messages, tools, model) {
         };
       }
 
-      // Add tools to the user message that has no preceding assistant messages,
-      // OR the first user message (whichever comes first after any opening
-      // assistant messages). We track whether any user message has already
-      // received tools via a flag on the history array.
-      if (clientProvidedTools && !toolsInjectedToFirstUserMsg) {
-        if (!userMsg.userInputMessage.userInputMessageContext) {
-          userMsg.userInputMessage.userInputMessageContext = {};
-        }
-        userMsg.userInputMessage.userInputMessageContext.tools = tools.map(t => {
-          const name = t.function?.name || t.name;
-          let description = t.function?.description || t.description || "";
-
-          if (!description.trim()) {
-            description = `Tool: ${name}`;
-          }
-
-          const schema = t.function?.parameters || t.parameters || t.input_schema || {};
-          // Normalize schema: Kiro requires required[] and proper type/properties
-          const normalizedSchema = Object.keys(schema).length === 0
-            ? { type: "object", properties: {}, required: [] }
-            : { ...schema, required: schema.required ?? [] };
-
-          return {
-            toolSpecification: {
-              name,
-              description,
-              inputSchema: { json: normalizedSchema }
-            }
-          };
-        });
-        toolsInjectedToFirstUserMsg = true;
-      }
-
       history.push(userMsg);
       currentMessage = userMsg;
       pendingUserContent = [];
@@ -327,7 +145,7 @@ function convertMessages(messages, tools, model) {
 
             pendingToolResults.push({
               toolUseId: block.tool_use_id,
-              status: "success",
+              status: block.is_error ? "error" : "success",
               content: [{ text: text }]
             });
           });
@@ -339,7 +157,7 @@ function convertMessages(messages, tools, model) {
         const toolContent = typeof msg.content === "string" ? msg.content : "";
         pendingToolResults.push({
           toolUseId: msg.tool_call_id,
-          status: "success",
+          status: msg.is_error || msg.status === "error" ? "error" : "success",
           content: [{ text: toolContent }]
         });
       } else if (content) {
@@ -413,14 +231,8 @@ function convertMessages(messages, tools, model) {
     }
   }
 
-  // Grab tools from first history item BEFORE cleanup removes them
-  const firstHistoryTools = history[0]?.userInputMessage?.userInputMessageContext?.tools;
-
   // Clean up history for Kiro API compatibility
   history.forEach(item => {
-    if (item.userInputMessage?.userInputMessageContext?.tools) {
-      delete item.userInputMessage.userInputMessageContext.tools;
-    }
     if (item.userInputMessage?.userInputMessageContext &&
         Object.keys(item.userInputMessage.userInputMessageContext).length === 0) {
       delete item.userInputMessage.userInputMessageContext;
@@ -473,33 +285,6 @@ function convertMessages(messages, tools, model) {
     };
   }
 
-  // Reconcile orphaned toolResults across history AND currentMessage — when
-  // client-side compaction removes assistant messages containing tool_use but
-  // keeps the tool_result, the dangling reference triggers a Kiro 400. Fold the
-  // content back into the user text instead of discarding it. Run after
-  // currentMessage is finalized (an orphan can be merged into it) and before
-  // tool injection (which may re-add userInputMessageContext).
-  //
-  // Only needed on the tools-present path: when the client sent no tools,
-  // flattenToolInteractions already collapsed every toolResult to text, so
-  // there is nothing structured left to orphan.
-  if (clientProvidedTools) {
-    reconcileOrphanedToolResults(mergedHistory, currentMessage);
-  }
-
-  // Inject tools into currentMessage AFTER cleanup. Tools only exist here when
-  // the client explicitly sent them (otherwise flattenToolInteractions already
-  // collapsed all tool content to text upstream, so there is nothing to carry).
-  const resolvedTools = firstHistoryTools;
-
-  if (resolvedTools?.length > 0 &&
-      !currentMessage.userInputMessage.userInputMessageContext?.tools) {
-    if (!currentMessage.userInputMessage.userInputMessageContext) {
-      currentMessage.userInputMessage.userInputMessageContext = {};
-    }
-    currentMessage.userInputMessage.userInputMessageContext.tools = resolvedTools;
-  }
-
   return { history: mergedHistory, currentMessage };
 }
 
@@ -532,7 +317,8 @@ export function openaiToKiroRequest(model, body, stream, credentials) {
   const additionalModelRequestFields = buildKiroAdditionalModelRequestFieldsForModel(thinkingBody, upstreamModel);
   const usesNativeGptEffort = usesKiroNativeGptEffort(thinkingBody, upstreamModel);
 
-  const { history, currentMessage } = convertMessages(messages, tools, upstreamModel);
+  const { specs: toolSpecs, nameMap } = normalizeKiroToolSpecs(tools);
+  const { history, currentMessage } = convertMessages(messages, upstreamModel);
 
   // API-key (headless) auth uses a raw CodeWhisperer credential whose profile is
   // account-specific. Injecting the shared builder-id/social *default* placeholder
@@ -586,7 +372,14 @@ export function openaiToKiroRequest(model, body, stream, credentials) {
     history,
     currentMessage,
   });
-  const replayCurrent = replay.currentMessage?.userInputMessage || {};
+  const canonical = canonicalizeKiroConversation({
+    history: replay.history,
+    currentMessage: replay.currentMessage,
+    modelId: upstreamModel,
+    toolSpecs,
+    nameMap,
+  });
+  const replayCurrent = canonical.currentMessage.userInputMessage;
 
   const payload = {
     conversationState: {
@@ -607,7 +400,7 @@ export function openaiToKiroRequest(model, body, stream, credentials) {
           })
         }
       },
-      history: replay.history
+      history: canonical.history
     },
     agentMode: "vibe",
   };
diff --git a/open-sse/utils/kiroSessionReplay.js b/open-sse/utils/kiroSessionReplay.js
index 11cae9cd..d758eed6 100644
--- a/open-sse/utils/kiroSessionReplay.js
+++ b/open-sse/utils/kiroSessionReplay.js
@@ -42,6 +42,14 @@ function findFirstUserIndex(history) {
   return history.findIndex((item) => item?.userInputMessage);
 }
 
+function hasToolResults(message) {
+  return !!message?.userInputMessage?.userInputMessageContext?.toolResults?.length;
+}
+
+function canReplaceSessionStart(history, firstUserIndex) {
+  return firstUserIndex === 0 && !hasToolResults(history[firstUserIndex]);
+}
+
 function rememberSessionStart(key, entry) {
   if (sessionStartStore.size >= MAX_SESSION_STARTS) {
     sessionStartStore.delete(sessionStartStore.keys().next().value);
@@ -73,10 +81,13 @@ export function applyKiroSessionReplay({
     existing.lastUsed = Date.now();
     const firstUserIndex = findFirstUserIndex(baseHistory);
     const sessionStart = ensureUserMessageModelId(clone(existing.sessionStart), modelId);
-    if (firstUserIndex >= 0) {
+    if (canReplaceSessionStart(baseHistory, firstUserIndex)) {
       baseHistory[firstUserIndex] = sessionStart;
     } else {
       baseHistory.unshift(sessionStart);
+      if (baseHistory.length === 1) {
+        baseHistory.push({ assistantResponseMessage: { content: "..." } });
+      }
     }
     return {
       history: ensureHistoryModelIds(baseHistory, modelId),
@@ -88,10 +99,18 @@ export function applyKiroSessionReplay({
   const firstUserIndex = findFirstUserIndex(baseHistory);
   let sessionStart;
   let nextCurrent = ensureUserMessageModelId(baseCurrent, modelId);
-  if (firstUserIndex >= 0) {
+  if (canReplaceSessionStart(baseHistory, firstUserIndex)) {
     sessionStart = prefixUserMessage(baseHistory[firstUserIndex], contentPrefix, modelId);
     baseHistory[firstUserIndex] = clone(sessionStart);
     nextCurrent = prefixUserMessage(baseCurrent, currentContentPrefix, modelId);
+  } else if (firstUserIndex >= 0) {
+    sessionStart = prefixUserMessage(
+      { userInputMessage: { content: "", modelId } },
+      contentPrefix,
+      modelId
+    );
+    baseHistory.unshift(clone(sessionStart));
+    nextCurrent = prefixUserMessage(baseCurrent, currentContentPrefix, modelId);
   } else {
     sessionStart = prefixUserMessage(baseCurrent, contentPrefix, modelId);
     nextCurrent = clone(sessionStart);
diff --git a/src/app/api/oauth/kiro/api-key/route.js b/src/app/api/oauth/kiro/api-key/route.js
index 139df9b5..bd2140b3 100644
--- a/src/app/api/oauth/kiro/api-key/route.js
+++ b/src/app/api/oauth/kiro/api-key/route.js
@@ -5,8 +5,8 @@ import { createProviderConnection } from "@/models";
 /**
  * POST /api/oauth/kiro/api-key
  * Import a Kiro API key (headless auth). The key is a long-lived bearer
- * credential — there is no refresh token. It is validated by listing
- * CodeWhisperer profiles, then stored with authMethod="api_key".
+ * credential — there is no refresh token. It is validated against the Amazon
+ * Q model catalog, then stored with authMethod="api_key".
  */
 export async function POST(request) {
   try {
@@ -21,7 +21,7 @@ export async function POST(request) {
 
     const kiroService = new KiroService();
 
-    // Validate the key and resolve its profileArn via ListAvailableProfiles
+    // Validate the key against the same Amazon Q surface used for inference.
     const credential = await kiroService.validateApiKey(
       apiKey,
       region || "us-east-1"
@@ -40,7 +40,7 @@ export async function POST(request) {
       expiresAt: new Date(Date.now() + 365 * 24 * 60 * 60 * 1000).toISOString(),
       email: email || null,
       providerSpecificData: {
-        profileArn: credential.profileArn,
+        ...(credential.profileArn ? { profileArn: credential.profileArn } : {}),
         region: credential.region,
         authMethod: "api_key",
         provider: "API Key",
diff --git a/src/lib/oauth/services/kiro.js b/src/lib/oauth/services/kiro.js
index a739661e..f82089d8 100644
--- a/src/lib/oauth/services/kiro.js
+++ b/src/lib/oauth/services/kiro.js
@@ -260,11 +260,9 @@ export class KiroService {
   }
 
   /**
-   * List available CodeWhisperer profiles for a token (or API key) and return
-   * the best-matching profileArn. AWS SSO OIDC logins return no profileArn, so
-   * it must be fetched separately — the same call works for API-key auth.
-   * Accepts both `arn` and `profileArn` response field names (the API-key
-   * JSON-1.0 surface returns `arn`).
+   * List available CodeWhisperer profiles for OAuth/IDC tokens and return the
+   * best-matching profileArn. API keys use the Amazon Q model catalog instead;
+   * ListAvailableProfiles does not support TokenType=API_KEY.
    */
   async listAvailableProfiles(accessToken, region = "us-east-1") {
     assertValidAwsRegion(region);
@@ -294,10 +292,41 @@ export class KiroService {
   }
 
   /**
-   * Validate an API-key credential by listing profiles with it. API keys are
-   * long-lived bearer tokens (no refresh), so the only way to validate one is
-   * to make an authenticated CodeWhisperer call. Returns a credential object
-   * ready to persist as a "kiro" connection with authMethod="api_key".
+   * Validate an API key against the Amazon Q model catalog. A bearer-only call
+   * to ListAvailableProfiles can return HTTP 200 with an empty list for an
+   * arbitrary key, so it is not proof that the key can run inference.
+   */
+  async listAvailableApiKeyModels(apiKey, region = "us-east-1") {
+    assertValidAwsRegion(region);
+    const params = new URLSearchParams({ origin: "AI_EDITOR" });
+    const endpoint = `https://q.${region}.amazonaws.com/ListAvailableModels?${params}`;
+    const response = await fetch(endpoint, {
+      method: "GET",
+      headers: {
+        "Authorization": `Bearer ${apiKey}`,
+        "TokenType": "API_KEY",
+        "Accept": "application/json",
+        "User-Agent": "AWS-SDK-JS/3.0.0 kiro-ide/1.0.0",
+        "X-Amz-User-Agent": "aws-sdk-js/3.0.0 kiro-ide/1.0.0",
+      },
+    });
+
+    if (!response.ok) {
+      const error = await response.text();
+      throw new Error(`Failed to list API-key models: ${error}`);
+    }
+
+    const data = await response.json();
+    const models = Array.isArray(data?.models) ? data.models : [];
+    if (models.length === 0) {
+      throw new Error("API key returned no available models");
+    }
+    return models;
+  }
+
+  /**
+   * Validate an API-key credential through the same Amazon Q surface used for
+   * inference. API keys are account-bound but do not require a profileArn.
    */
   async validateApiKey(apiKey, region = "us-east-1") {
     if (!apiKey || typeof apiKey !== "string" || !apiKey.trim()) {
@@ -305,9 +334,8 @@ export class KiroService {
     }
     const trimmed = apiKey.trim();
 
-    let profileArn = null;
     try {
-      profileArn = await this.listAvailableProfiles(trimmed, region);
+      await this.listAvailableApiKeyModels(trimmed, region);
     } catch (error) {
       throw new Error(`API key validation failed: ${error.message}`);
     }
@@ -315,7 +343,7 @@ export class KiroService {
     return {
       accessToken: trimmed,
       refreshToken: null,
-      profileArn,
+      profileArn: null,
       region,
       authMethod: "api_key",
     };
diff --git a/tests/unit/kiro-api-key-endpoint-routing.test.js b/tests/unit/kiro-api-key-endpoint-routing.test.js
new file mode 100644
index 00000000..a0750adc
--- /dev/null
+++ b/tests/unit/kiro-api-key-endpoint-routing.test.js
@@ -0,0 +1,67 @@
+import { describe, expect, it } from "vitest";
+import { KiroExecutor } from "../../open-sse/executors/kiro.js";
+
+const RUNTIME = "https://runtime.us-east-1.kiro.dev/generateAssistantResponse";
+const CODEWHISPERER = "https://codewhisperer.us-east-1.amazonaws.com/generateAssistantResponse";
+const Q = "https://q.us-east-1.amazonaws.com/generateAssistantResponse";
+
+function credentials(authMethod, region = "us-east-1") {
+  return { providerSpecificData: { authMethod, region } };
+}
+
+describe("Kiro auth-aware endpoint routing", () => {
+  const executor = new KiroExecutor();
+
+  it("routes API-key inference through Amazon Q before other surfaces", () => {
+    expect(executor.getOrderedBaseUrls(credentials("api_key"))).toEqual([
+      Q,
+      CODEWHISPERER,
+      RUNTIME,
+    ]);
+  });
+
+  it("keeps Builder ID OAuth on the Kiro runtime surface", () => {
+    expect(executor.getOrderedBaseUrls(credentials("builder-id"))).toEqual([
+      RUNTIME,
+      CODEWHISPERER,
+      Q,
+    ]);
+  });
+
+  it("keeps external IdP on CodeWhisperer before Amazon Q", () => {
+    expect(executor.getOrderedBaseUrls(credentials("external_idp"))).toEqual([
+      CODEWHISPERER,
+      Q,
+      RUNTIME,
+    ]);
+  });
+
+  it("regionalizes AWS endpoints for IDC without changing Kiro runtime", () => {
+    expect(executor.getOrderedBaseUrls(credentials("idc", "eu-west-1"))).toEqual([
+      "https://codewhisperer.eu-west-1.amazonaws.com/generateAssistantResponse",
+      "https://q.eu-west-1.amazonaws.com/generateAssistantResponse",
+      RUNTIME,
+    ]);
+  });
+
+  it("retries only endpoint/auth-surface failures, not payload-invalid 400s", () => {
+    expect(executor.shouldRetry(400, 0)).toBe(false);
+    expect(executor.shouldRetry(401, 1)).toBe(true);
+    expect(executor.shouldRetry(403, 2)).toBe(false);
+    expect(executor.shouldRetry(422, 0)).toBe(false);
+  });
+
+  it("builds endpoint-specific headers", () => {
+    const auth = { accessToken: "test-key", providerSpecificData: { authMethod: "api_key" } };
+    const qHeaders = executor.buildHeaders(auth, true, Q);
+    const codeWhispererHeaders = executor.buildHeaders(auth, true, CODEWHISPERER);
+    const runtimeHeaders = executor.buildHeaders(auth, true, RUNTIME);
+
+    expect(qHeaders.TokenType).toBe("API_KEY");
+    expect(qHeaders["X-Amz-Target"]).toBeUndefined();
+    expect(codeWhispererHeaders["X-Amz-Target"]).toBe(
+      "AmazonCodeWhispererStreamingService.GenerateAssistantResponse"
+    );
+    expect(runtimeHeaders["X-Amz-Target"]).toBeUndefined();
+  });
+});
diff --git a/tests/unit/kiro-conversation-canonicalization.test.js b/tests/unit/kiro-conversation-canonicalization.test.js
new file mode 100644
index 00000000..e19984d1
--- /dev/null
+++ b/tests/unit/kiro-conversation-canonicalization.test.js
@@ -0,0 +1,372 @@
+import { beforeEach, describe, expect, it } from "vitest";
+import {
+  canonicalizeKiroConversation,
+  normalizeKiroToolSpecs,
+  validateKiroConversation,
+} from "../../open-sse/translator/concerns/kiroConversation.js";
+import { clearKiroSessionReplayStore } from "../../open-sse/utils/kiroSessionReplay.js";
+import { clearSessionStore } from "../../open-sse/utils/sessionManager.js";
+import { claudeToKiroRequest } from "../../open-sse/translator/request/claude-to-kiro.js";
+import { openaiToKiroRequest } from "../../open-sse/translator/request/openai-to-kiro.js";
+
+const modelId = "claude-opus-5";
+
+function tool(name, schema = { type: "object", properties: {} }) {
+  return { name, description: `Tool ${name}`, input_schema: schema };
+}
+
+function specState(names = ["first", "second"]) {
+  const source = names.map((name) => tool(name));
+  return normalizeKiroToolSpecs(source);
+}
+
+function user(content, toolResults = []) {
+  return {
+    userInputMessage: {
+      content,
+      modelId,
+      ...(toolResults.length > 0 && { userInputMessageContext: { toolResults } }),
+    },
+  };
+}
+
+function assistant(content, toolUses = []) {
+  return {
+    assistantResponseMessage: {
+      content,
+      ...(toolUses.length > 0 && { toolUses }),
+    },
+  };
+}
+
+function result(toolUseId, value, status = "success") {
+  return { toolUseId, status, content: [{ text: value }] };
+}
+
+describe("Kiro conversation canonicalizer", () => {
+  beforeEach(() => {
+    clearKiroSessionReplayStore();
+    clearSessionStore();
+  });
+
+  it("keeps complete parallel tool pairs structured", () => {
+    const { specs, nameMap } = specState();
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [
+          { toolUseId: "t1", name: "first", input: { n: 1 } },
+          { toolUseId: "t2", name: "second", input: { n: 2 } },
+        ]),
+      ],
+      currentMessage: user("continue", [result("t1", "one"), result("t2", "two")]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    const calls = canonical.history[1].assistantResponseMessage.toolUses;
+    const results = canonical.currentMessage.userInputMessage.userInputMessageContext.toolResults;
+    expect(calls.map((call) => call.toolUseId)).toEqual(["t1", "t2"]);
+    expect(results.map((item) => item.toolUseId)).toEqual(["t1", "t2"]);
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("keeps the answered parallel call and flattens only the missing one", () => {
+    const { specs, nameMap } = specState();
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [
+          { toolUseId: "t1", name: "first", input: {} },
+          { toolUseId: "t2", name: "second", input: {} },
+        ]),
+      ],
+      currentMessage: user("continue", [result("t1", "one")]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    const assistantMessage = canonical.history[1].assistantResponseMessage;
+    expect(assistantMessage.toolUses).toHaveLength(1);
+    expect(assistantMessage.toolUses[0].toolUseId).toBe("t1");
+    expect(assistantMessage.content).toContain("[Tool call: second(");
+    expect(canonical.repairs.missingResults).toBe(1);
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("flattens non-adjacent and orphaned tool results", () => {
+    const { specs, nameMap } = specState(["first"]);
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [{ toolUseId: "t1", name: "first", input: {} }]),
+        user("result missing here"),
+        assistant("later"),
+      ],
+      currentMessage: user("late result", [result("t1", "too late")]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    expect(JSON.stringify(canonical)).not.toContain('"toolUseId":"t1"');
+    expect(canonical.history[1].assistantResponseMessage.content).toContain("[Tool call:");
+    expect(canonical.currentMessage.userInputMessage.content).toContain("too late");
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("remaps duplicate tool IDs together with their adjacent results", () => {
+    const { specs, nameMap } = specState();
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [
+          { toolUseId: "duplicate", name: "first", input: {} },
+          { toolUseId: "duplicate", name: "second", input: {} },
+        ]),
+      ],
+      currentMessage: user("continue", [
+        result("duplicate", "one"),
+        result("duplicate", "two"),
+      ]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    const calls = canonical.history[1].assistantResponseMessage.toolUses;
+    const results = canonical.currentMessage.userInputMessage.userInputMessageContext.toolResults;
+    expect(new Set(calls.map((call) => call.toolUseId)).size).toBe(2);
+    expect(results.map((item) => item.toolUseId)).toEqual(calls.map((call) => call.toolUseId));
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("deduplicates extra results without losing their text", () => {
+    const { specs, nameMap } = specState(["first"]);
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [{ toolUseId: "t1", name: "first", input: {} }]),
+      ],
+      currentMessage: user("continue", [result("t1", "one"), result("t1", "duplicate")]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    const current = canonical.currentMessage.userInputMessage;
+    expect(current.userInputMessageContext.toolResults).toHaveLength(1);
+    expect(current.content).toContain("duplicate");
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("flattens a trailing unanswered assistant tool call and creates a current user turn", () => {
+    const { specs, nameMap } = specState(["first"]);
+    const canonical = canonicalizeKiroConversation({
+      history: [user("start")],
+      currentMessage: assistant("run", [{ toolUseId: "t1", name: "first", input: {} }]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    expect(canonical.currentMessage.userInputMessage.content).toBe("continue");
+    expect(canonical.history[1].assistantResponseMessage.toolUses).toBeUndefined();
+    expect(canonical.history[1].assistantResponseMessage.content).toContain("[Tool call:");
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("flattens malformed input and tool uses missing from the current specs", () => {
+    const { specs, nameMap } = specState(["first"]);
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [
+          { toolUseId: "t1", name: "first", input: "{bad json" },
+          { toolUseId: "t2", name: "removed_tool", input: {} },
+        ]),
+      ],
+      currentMessage: user("continue", [result("t1", "one"), result("t2", "two")]),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    expect(canonical.history[1].assistantResponseMessage.toolUses).toBeUndefined();
+    expect(canonical.currentMessage.userInputMessage.userInputMessageContext.toolResults).toBeUndefined();
+    expect(canonical.currentMessage.userInputMessage.content).toContain("one");
+    expect(canonical.currentMessage.userInputMessage.content).toContain("two");
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("repairs a 30-call parallel turn with one missing result", () => {
+    const names = Array.from({ length: 30 }, (_, index) => `tool_${index}`);
+    const { specs, nameMap } = specState(names);
+    const calls = names.map((name, index) => ({
+      toolUseId: `t${index}`,
+      name,
+      input: { index },
+    }));
+    const results = names.slice(0, -1).map((_, index) => result(`t${index}`, `r${index}`));
+    const canonical = canonicalizeKiroConversation({
+      history: [user("start"), assistant("run", calls)],
+      currentMessage: user("continue", results),
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    expect(canonical.history[1].assistantResponseMessage.toolUses).toHaveLength(29);
+    expect(canonical.currentMessage.userInputMessage.userInputMessageContext.toolResults).toHaveLength(29);
+    expect(canonical.repairs.missingResults).toBe(1);
+    expect(canonical.valid).toBe(true);
+  });
+
+  it("flattens structured history when the client sent no tool specs", () => {
+    const canonical = canonicalizeKiroConversation({
+      history: [
+        user("start"),
+        assistant("run", [{ toolUseId: "t1", name: "first", input: {} }]),
+      ],
+      currentMessage: user("continue", [result("t1", "one")]),
+      modelId,
+    });
+
+    expect(JSON.stringify(canonical)).not.toContain("toolUses");
+    expect(JSON.stringify(canonical)).not.toContain("toolResults");
+    expect(canonical.history[1].assistantResponseMessage.content).toContain("[Tool call:");
+    expect(canonical.currentMessage.userInputMessage.content).toContain("[Tool result:");
+  });
+
+  it("normalizes names and recursively removes unsupported schema fields", () => {
+    const longDescription = "x".repeat(11000);
+    const { specs, nameMap } = normalizeKiroToolSpecs([{
+      name: "bad tool/name",
+      description: longDescription,
+      input_schema: {
+        additionalProperties: false,
+        properties: {
+          nested: {
+            type: "object",
+            additionalProperties: true,
+            properties: {},
+            required: [],
+          },
+        },
+        required: [],
+      },
+    }]);
+
+    const specification = specs[0].toolSpecification;
+    expect(nameMap.get("bad tool/name")).toBe("bad_tool_name");
+    expect(specification.name.length).toBeLessThanOrEqual(64);
+    expect(specification.description.length).toBe(10237);
+    expect(JSON.stringify(specification.inputSchema.json)).not.toContain("additionalProperties");
+    expect(JSON.stringify(specification.inputSchema.json)).not.toContain('"required":[]');
+  });
+
+  it("does not mutate the source conversation or tool definitions", () => {
+    const sourceTools = [tool("first")];
+    const sourceHistory = [
+      user("start"),
+      assistant("run", [{ toolUseId: "t1", name: "first", input: {} }]),
+    ];
+    const sourceCurrent = user("continue", [result("t1", "one")]);
+    const before = JSON.stringify({ sourceTools, sourceHistory, sourceCurrent });
+    const { specs, nameMap } = normalizeKiroToolSpecs(sourceTools);
+
+    canonicalizeKiroConversation({
+      history: sourceHistory,
+      currentMessage: sourceCurrent,
+      modelId,
+      toolSpecs: specs,
+      nameMap,
+    });
+
+    expect(JSON.stringify({ sourceTools, sourceHistory, sourceCurrent })).toBe(before);
+  });
+
+  it("preserves Claude tool_result errors", () => {
+    const output = claudeToKiroRequest(modelId, {
+      tools: [tool("first")],
+      messages: [
+        { role: "user", content: "start" },
+        { role: "assistant", content: [{ type: "tool_use", id: "t1", name: "first", input: {} }] },
+        { role: "user", content: [{ type: "tool_result", tool_use_id: "t1", is_error: true, content: "failed" }] },
+      ],
+    }, true, {});
+
+    const item = output.conversationState.currentMessage.userInputMessage
+      .userInputMessageContext.toolResults[0];
+    expect(item.status).toBe("error");
+  });
+
+  it("repairs partial parallel results in both direct translators", () => {
+    const claude = claudeToKiroRequest(modelId, {
+      tools: [tool("first"), tool("second")],
+      messages: [
+        { role: "user", content: "start" },
+        { role: "assistant", content: [
+          { type: "tool_use", id: "t1", name: "first", input: {} },
+          { type: "tool_use", id: "t2", name: "second", input: {} },
+        ] },
+        { role: "user", content: [{ type: "tool_result", tool_use_id: "t1", content: "one" }] },
+      ],
+    }, true, {});
+    const openai = openaiToKiroRequest(modelId, {
+      tools: [
+        { type: "function", function: { name: "first", parameters: { type: "object", properties: {} } } },
+        { type: "function", function: { name: "second", parameters: { type: "object", properties: {} } } },
+      ],
+      messages: [
+        { role: "user", content: "start" },
+        { role: "assistant", content: "", tool_calls: [
+          { id: "t1", type: "function", function: { name: "first", arguments: "{}" } },
+          { id: "t2", type: "function", function: { name: "second", arguments: "{}" } },
+        ] },
+        { role: "tool", tool_call_id: "t1", content: "one" },
+      ],
+    }, true, {});
+
+    for (const payload of [claude, openai]) {
+      const state = payload.conversationState;
+      const validation = validateKiroConversation(
+        state.history,
+        state.currentMessage,
+        state.currentMessage.userInputMessage.userInputMessageContext.tools
+      );
+      expect(validation.valid).toBe(true);
+      expect(state.history[1].assistantResponseMessage.toolUses).toHaveLength(1);
+    }
+  });
+
+  it("does not let session replay replace a tool-result turn", () => {
+    const credentials = {
+      rawHeaders: { "x-session-id": "kiro-replay-tool-result-regression" },
+      connectionId: "kiro-account",
+    };
+    claudeToKiroRequest(modelId, {
+      messages: [{ role: "user", content: "frozen session start" }],
+    }, true, credentials);
+
+    const output = claudeToKiroRequest(modelId, {
+      tools: [tool("first")],
+      messages: [
+        { role: "assistant", content: [{ type: "tool_use", id: "t1", name: "first", input: {} }] },
+        { role: "user", content: [{ type: "tool_result", tool_use_id: "t1", content: "kept" }] },
+      ],
+    }, true, credentials);
+    const state = output.conversationState;
+    const allText = JSON.stringify(state);
+
+    expect(allText).toContain("frozen session start");
+    expect(allText).toContain("kept");
+    expect(validateKiroConversation(
+      state.history,
+      state.currentMessage,
+      state.currentMessage.userInputMessage.userInputMessageContext.tools
+    ).valid).toBe(true);
+  });
+});
diff --git a/tests/unit/kiro-profile-arn.test.js b/tests/unit/kiro-profile-arn.test.js
index 1925582b..bfa3906c 100644
--- a/tests/unit/kiro-profile-arn.test.js
+++ b/tests/unit/kiro-profile-arn.test.js
@@ -4,10 +4,8 @@ import { KiroService } from "../../src/lib/oauth/services/kiro.js";
 /**
  * Regression tests for Kiro API-key auth.
  *
- * KiroService.validateApiKey resolves a profileArn with the key (via
- * CodeWhisperer ListAvailableProfiles) and returns a credential shaped for
- * persistence with authMethod="api_key". The response profile field name
- * varies (`arn` vs `profileArn`) — both are accepted by listAvailableProfiles.
+ * KiroService.validateApiKey validates against the Amazon Q model catalog and
+ * returns an account-bound credential without inventing a profileArn.
  *
  * Note: OAuth (Builder ID / IDC) profileArn resolution is handled upstream by
  * fetchKiroProfileArn in providers.js and is covered there — not here.
@@ -16,11 +14,10 @@ describe("kiro API-key auth (KiroService.validateApiKey)", () => {
   beforeEach(() => vi.restoreAllMocks());
   afterEach(() => vi.restoreAllMocks());
 
-  it("validates an API key and resolves a credential with profileArn", async () => {
-    const expectedArn = "arn:aws:codewhisperer:us-east-1:444:profile/KEY";
+  it("validates an API key against Amazon Q without inventing profileArn", async () => {
     const fetchMock = vi.spyOn(globalThis, "fetch").mockResolvedValue({
       ok: true,
-      json: async () => ({ profiles: [{ arn: expectedArn }] }),
+      json: async () => ({ models: [{ modelId: "claude-opus-5" }] }),
     });
 
     const svc = new KiroService();
@@ -29,17 +26,18 @@ describe("kiro API-key auth (KiroService.validateApiKey)", () => {
     expect(cred).toEqual({
       accessToken: "my-secret-key",
       refreshToken: null,
-      profileArn: expectedArn,
+      profileArn: null,
       region: "us-east-1",
       authMethod: "api_key",
     });
 
     const [url, init] = fetchMock.mock.calls[0];
-    expect(url).toBe("https://codewhisperer.us-east-1.amazonaws.com");
-    expect(init.headers.Authorization).toBe("Bearer my-secret-key");
-    expect(init.headers["x-amz-target"]).toBe(
-      "AmazonCodeWhispererService.ListAvailableProfiles"
+    expect(url).toBe(
+      "https://q.us-east-1.amazonaws.com/ListAvailableModels?origin=AI_EDITOR"
     );
+    expect(init.method).toBe("GET");
+    expect(init.headers.Authorization).toBe("Bearer my-secret-key");
+    expect(init.headers.TokenType).toBe("API_KEY");
   });
 
   it("rejects an empty API key without a network call", async () => {
@@ -60,4 +58,15 @@ describe("kiro API-key auth (KiroService.validateApiKey)", () => {
       /API key validation failed/
     );
   });
+
+  it("rejects a 200 response with an empty model catalog", async () => {
+    vi.spyOn(globalThis, "fetch").mockResolvedValue({
+      ok: true,
+      json: async () => ({ models: [] }),
+    });
+    const svc = new KiroService();
+    await expect(svc.validateApiKey("empty-key")).rejects.toThrow(
+      /returned no available models/
+    );
+  });
 });