@juspay/neurolink 9.65.0 → 9.65.2

package/dist/providers/googleVertex.js

@@ -1,10 +1,11 @@
+/* eslint-disable max-lines-per-function */
 // Native SDK imports - no more @ai-sdk/google-vertex dependency
 import fs from "fs";
 import path from "path";
 import os from "os";
 import { ErrorCategory, ErrorSeverity, } from "../constants/enums.js";
 import { BaseProvider } from "../core/baseProvider.js";
-import { DEFAULT_MAX_STEPS, DEFAULT_TOOL_MAX_RETRIES, GLOBAL_LOCATION_MODELS, IMAGE_GENERATION_MODELS, } from "../core/constants.js";
+import { DEFAULT_MAX_STEPS, DEFAULT_TOOL_MAX_RETRIES, GLOBAL_LOCATION_MODELS, IMAGE_GENERATION_MODELS, TOOL_STORAGE_TIMEOUT_MS, } from "../core/constants.js";
 import { ModelConfigurationManager } from "../core/modelConfiguration.js";
 import { createProxyFetch } from "../proxy/proxyFetch.js";
 import { AuthenticationError, InvalidModelError, NetworkError, ProviderError, RateLimitError, } from "../types/index.js";
@@ -16,10 +17,12 @@ import { hasRestrictedOutputLimit, RESTRICTED_OUTPUT_TOKEN_LIMIT, } from "../uti
 import { validateApiKey, createVertexProjectConfig, createGoogleAuthConfig, } from "../utils/providerConfig.js";
 import { convertZodToJsonSchema, inlineJsonSchema, ensureNestedSchemaTypes, } from "../utils/schemaConversion.js";
 import { createNativeThinkingConfig } from "../utils/thinkingConfig.js";
-import { TimeoutError } from "../utils/async/index.js";
-import { prependConversationMessages } from "./googleNativeGemini3.js";
+import { TimeoutError, withTimeout } from "../utils/async/index.js";
+import { parseTimeout } from "../utils/timeout.js";
+import { createTextChannel, extractThoughtSignature, prependConversationMessages, } from "./googleNativeGemini3.js";
 import { ATTR, tracers, withClientSpan, withClientStreamSpan, withSpan, } from "../telemetry/index.js";
 import { calculateCost } from "../utils/pricing.js";
+import { transformToolExecutions } from "../utils/transformationUtils.js";
 // Import proper types for multimodal message handling
 // Dynamic import helper for native Anthropic Vertex SDK
 let anthropicVertexModule = null;
@@ -1125,6 +1128,11 @@ export class GoogleVertexProvider extends BaseProvider {
         let finalText = "";
         let lastStepText = ""; // Track text from last step for maxSteps termination
         const allToolCalls = [];
+        // Mirrors the generate-path shape so StreamResult.toolExecutions can be
+        // populated (parity with AI-SDK-driven providers) and so the storage
+        // hook can persist actual tool outputs rather than the placeholder
+        // "success" string used by flushPendingToolData's default fallback.
+        const toolExecutions = [];
         let step = 0;
         // Track structured output from final_result tool (when using final_result pattern)
         let finalResultStructuredOutput;
@@ -1231,22 +1239,38 @@ export class GoogleVertexProvider extends BaseProvider {
                 });
                 // Execute each function and collect responses
                 const functionResponses = [];
+                // Per-step bookkeeping for conversation-memory storage.
+                const stepStorageCalls = [];
+                const stepStorageResults = [];
+                // Note: tool:start / tool:end events are emitted by ToolsManager's
+                // wrapped `execute` (see ToolsManager.ts:355) — no inline emit needed.
                 for (const call of stepFunctionCalls) {
                     allToolCalls.push({ toolName: call.name, args: call.args });
+                    stepStorageCalls.push({ toolName: call.name, args: call.args });
                     // Check if this tool has already exceeded retry limit
                     const failedInfo = failedTools.get(call.name);
                     if (failedInfo && failedInfo.count >= DEFAULT_TOOL_MAX_RETRIES) {
                         logger.warn(`[GoogleVertex] Tool "${call.name}" has exceeded retry limit (${DEFAULT_TOOL_MAX_RETRIES}), skipping execution`);
+                        const errorPayload = {
+                            error: `TOOL_PERMANENTLY_FAILED: The tool "${call.name}" has failed ${failedInfo.count} times and will not be retried. Last error: ${failedInfo.lastError}. Please proceed without using this tool or inform the user that this functionality is unavailable.`,
+                            status: "permanently_failed",
+                            do_not_retry: true,
+                        };
                         functionResponses.push({
                             functionResponse: {
                                 name: call.name,
-                                response: {
-                                    error: `TOOL_PERMANENTLY_FAILED: The tool "${call.name}" has failed ${failedInfo.count} times and will not be retried. Last error: ${failedInfo.lastError}. Please proceed without using this tool or inform the user that this functionality is unavailable.`,
-                                    status: "permanently_failed",
-                                    do_not_retry: true,
-                                },
+                                response: errorPayload,
                             },
                         });
+                        toolExecutions.push({
+                            name: call.name,
+                            input: call.args,
+                            output: errorPayload,
+                        });
+                        stepStorageResults.push({
+                            toolName: call.name,
+                            output: errorPayload,
+                        });
                         continue;
                     }
                     const execute = executeMap.get(call.name);
@@ -1259,9 +1283,18 @@ export class GoogleVertexProvider extends BaseProvider {
                                 abortSignal: undefined,
                             };
                             const result = await execute(call.args, toolOptions);
+                            toolExecutions.push({
+                                name: call.name,
+                                input: call.args,
+                                output: result,
+                            });
                             functionResponses.push({
                                 functionResponse: { name: call.name, response: { result } },
                             });
+                            stepStorageResults.push({
+                                toolName: call.name,
+                                output: result,
+                            });
                         }
                         catch (error) {
                             const errorMessage = error instanceof Error ? error.message : "Unknown error";
@@ -1276,38 +1309,77 @@ export class GoogleVertexProvider extends BaseProvider {
                             logger.warn(`[GoogleVertex] Tool "${call.name}" failed (attempt ${currentFailInfo.count}/${DEFAULT_TOOL_MAX_RETRIES}): ${errorMessage}`);
                             // Determine if this is a permanent failure
                             const isPermanentFailure = currentFailInfo.count >= DEFAULT_TOOL_MAX_RETRIES;
+                            const errorPayload = {
+                                error: isPermanentFailure
+                                    ? `TOOL_PERMANENTLY_FAILED: The tool "${call.name}" has failed ${currentFailInfo.count} times with error: ${errorMessage}. This tool will not be retried. Please proceed without using this tool or inform the user that this functionality is unavailable.`
+                                    : `TOOL_EXECUTION_ERROR: ${errorMessage}. Retry attempt ${currentFailInfo.count}/${DEFAULT_TOOL_MAX_RETRIES}.`,
+                                status: isPermanentFailure ? "permanently_failed" : "failed",
+                                do_not_retry: isPermanentFailure,
+                                retry_count: currentFailInfo.count,
+                                max_retries: DEFAULT_TOOL_MAX_RETRIES,
+                            };
                             functionResponses.push({
                                 functionResponse: {
                                     name: call.name,
-                                    response: {
-                                        error: isPermanentFailure
-                                            ? `TOOL_PERMANENTLY_FAILED: The tool "${call.name}" has failed ${currentFailInfo.count} times with error: ${errorMessage}. This tool will not be retried. Please proceed without using this tool or inform the user that this functionality is unavailable.`
-                                            : `TOOL_EXECUTION_ERROR: ${errorMessage}. Retry attempt ${currentFailInfo.count}/${DEFAULT_TOOL_MAX_RETRIES}.`,
-                                        status: isPermanentFailure
-                                            ? "permanently_failed"
-                                            : "failed",
-                                        do_not_retry: isPermanentFailure,
-                                        retry_count: currentFailInfo.count,
-                                        max_retries: DEFAULT_TOOL_MAX_RETRIES,
-                                    },
+                                    response: errorPayload,
                                 },
                             });
+                            toolExecutions.push({
+                                name: call.name,
+                                input: call.args,
+                                output: errorPayload,
+                            });
+                            stepStorageResults.push({
+                                toolName: call.name,
+                                output: errorPayload,
+                            });
                         }
                     }
                     else {
                         // Tool not found is a permanent error
+                        const errorPayload = {
+                            error: `TOOL_NOT_FOUND: The tool "${call.name}" does not exist. Do not attempt to call this tool again.`,
+                            status: "permanently_failed",
+                            do_not_retry: true,
+                        };
                         functionResponses.push({
                             functionResponse: {
                                 name: call.name,
-                                response: {
-                                    error: `TOOL_NOT_FOUND: The tool "${call.name}" does not exist. Do not attempt to call this tool again.`,
-                                    status: "permanently_failed",
-                                    do_not_retry: true,
-                                },
+                                response: errorPayload,
                             },
                         });
+                        toolExecutions.push({
+                            name: call.name,
+                            input: call.args,
+                            output: errorPayload,
+                        });
+                        stepStorageResults.push({
+                            toolName: call.name,
+                            output: errorPayload,
+                        });
                     }
                 }
+                // Persist this step's tool calls/results into conversation memory.
+                // Without this, tool_call / tool_result rows never reach Redis and
+                // the chat-history UI loses every tool invocation.
+                //
+                // `thoughtSignature` rides as a sibling on the first call of the
+                // step — Gemini 3 needs it to match thinking patterns when the
+                // conversation is replayed on the next turn.
+                if (stepStorageCalls.length > 0 || stepStorageResults.length > 0) {
+                    const stepThoughtSig = extractThoughtSignature(rawResponseParts);
+                    withTimeout(this.handleToolExecutionStorage(stepStorageCalls.map((c, i) => ({
+                        ...c,
+                        ...(i === 0 && stepThoughtSig
+                            ? { thoughtSignature: stepThoughtSig }
+                            : {}),
+                        stepIndex: step,
+                    })), stepStorageResults.map((r) => ({ ...r, stepIndex: step })), options, new Date()), TOOL_STORAGE_TIMEOUT_MS, "tool storage write timed out").catch((error) => {
+                        logger.warn("[GoogleVertex] Failed to store native Gemini stream tool executions", {
+                            error: error instanceof Error ? error.message : String(error),
+                        });
+                    });
+                }
                 // The @google/genai SDK only accepts "user" and "model" as valid
                 // roles in contents — function/tool responses must use role: "user"
                 // (matching the SDK's automaticFunctionCalling implementation and
@@ -1353,6 +1425,7 @@ export class GoogleVertexProvider extends BaseProvider {
         }
         // Filter out final_result from tool calls as it's an internal pattern
         const externalToolCalls = allToolCalls.filter((tc) => tc.toolName !== "final_result");
+        const externalToolExecutions = toolExecutions.filter((te) => te.name !== "final_result");
         const result = {
             stream: createTextStream(),
             provider: this.providerName,
@@ -1366,6 +1439,12 @@ export class GoogleVertexProvider extends BaseProvider {
                 toolName: tc.toolName,
                 args: tc.args,
             })),
+            // Surface tools-used + execution summary so `hasToolActivity` in
+            // conversationMemory.ts evaluates true for tool-only stream turns
+            // (assistant text empty but tools ran) and downstream consumers see
+            // the same shape AI-SDK-driven providers expose.
+            toolsUsed: externalToolCalls.map((tc) => tc.toolName),
+            toolExecutions: transformToolExecutions(externalToolExecutions),
             metadata: {
                 streamId: `native-vertex-${Date.now()}`,
                 startTime,
@@ -1767,6 +1846,10 @@ export class GoogleVertexProvider extends BaseProvider {
                 });
                 // Execute each function and collect responses
                 const functionResponses = [];
+                const toolCallsBefore = allToolCalls.length;
+                const toolExecsBefore = toolExecutions.length;
+                // Note: tool:start / tool:end events are emitted by ToolsManager's
+                // wrapped `execute` (see ToolsManager.ts:355) — no inline emit needed.
                 for (const call of stepFunctionCalls) {
                     allToolCalls.push({ toolName: call.name, args: call.args });
                     // Check if this tool has already exceeded retry limit
@@ -1869,6 +1952,32 @@ export class GoogleVertexProvider extends BaseProvider {
                         });
                     }
                 }
+                // Persist this step's tool calls/results into conversation memory.
+                // Without this, tool_call / tool_result rows never reach Redis and
+                // the chat-history UI loses every tool invocation. The first call
+                // of the step carries the step's `thoughtSignature` so Gemini 3 can
+                // match thinking patterns on replay.
+                const stepToolCalls = allToolCalls.slice(toolCallsBefore);
+                const stepToolExecs = toolExecutions.slice(toolExecsBefore);
+                if (stepToolCalls.length > 0 || stepToolExecs.length > 0) {
+                    const stepThoughtSig = extractThoughtSignature(rawResponseParts);
+                    withTimeout(this.handleToolExecutionStorage(stepToolCalls.map((tc, i) => ({
+                        toolName: tc.toolName,
+                        args: tc.args,
+                        ...(i === 0 && stepThoughtSig
+                            ? { thoughtSignature: stepThoughtSig }
+                            : {}),
+                        stepIndex: step,
+                    })), stepToolExecs.map((te) => ({
+                        toolName: te.name,
+                        output: te.output,
+                        stepIndex: step,
+                    })), options, new Date()), TOOL_STORAGE_TIMEOUT_MS, "tool storage write timed out").catch((error) => {
+                        logger.warn("[GoogleVertex] Failed to store native Gemini generate tool executions", {
+                            error: error instanceof Error ? error.message : String(error),
+                        });
+                    });
+                }
                 // The @google/genai SDK only accepts "user" and "model" as valid
                 // roles in contents — function/tool responses must use role: "user"
                 // (matching the SDK's automaticFunctionCalling implementation and
@@ -1907,7 +2016,7 @@ export class GoogleVertexProvider extends BaseProvider {
             },
             responseTime,
             toolsUsed: externalToolCalls.map((tc) => tc.toolName),
-            toolExecutions: externalToolExecutions,
+            toolExecutions: transformToolExecutions(externalToolExecutions),
             enhancedWithTools: externalToolCalls.length > 0,
         };
         // Add structured output if final_result tool was used
@@ -1943,7 +2052,15 @@ export class GoogleVertexProvider extends BaseProvider {
         });
         // Build messages from input
         const messages = [];
-        // Add conversation history if present
+        // Add conversation history if present.
+        //
+        // Intentionally text-only. Anthropic's API rejects messages where a
+        // tool_use_id reference appears without its matching tool_use in the
+        // same turn — so synthesising tool_use / tool_result blocks from
+        // stored ChatMessages risks emitting orphaned references that fail
+        // validation. Tool rows are still persisted to Redis (chat-history
+        // UI renders them) but they don't re-enter the model's context on
+        // subsequent turns.
         if (options.conversationMessages &&
             options.conversationMessages.length > 0) {
             for (const msg of options.conversationMessages) {
@@ -2174,157 +2291,270 @@ export class GoogleVertexProvider extends BaseProvider {
                 stop_sequences: options.stopSequences,
             }),
         };
-        // Handle tool calling loop with max steps
+        // ── Real-time streaming via stream.on('text', ...) ────────────────────
+        //
+        // The Anthropic SDK exposes per-delta streaming through `stream.on('text', listener)`:
+        // each content_block_delta SSE event fires the listener synchronously
+        // with that token's text — typically ~10 chars per delta, ~26ms apart
+        // on Claude Haiku. Awaiting `stream.finalMessage()` here would buffer
+        // the entire response before yielding anything; the listener pattern
+        // keeps the wire and the consumer in lockstep instead.
+        //
+        // Structure: push-channel + background agentic loop, returning the
+        // StreamResult immediately so callers can iterate `channel.iterable`
+        // while generation is still in progress. Mirrors the executeStream
+        // pattern in googleAiStudio.ts.
         const maxSteps = options.maxSteps || DEFAULT_MAX_STEPS;
-        let step = 0;
-        let finalText = "";
-        let structuredOutput;
         const allToolCalls = [];
-        // Track each Anthropic text block separately so the returned async
-        // iterable yields multiple chunks. The chunk-count smoke test fails
-        // when an entire response collapses into a single yield, even though
-        // the upstream stream is genuinely incremental.
-        const allTextBlocks = [];
-        let totalInputTokens = 0;
-        let totalOutputTokens = 0;
-        const currentMessages = [...messages];
-        while (step < maxSteps) {
-            step++;
+        const toolExecutions = [];
+        const channel = createTextChannel();
+        // Mutable holders the StreamResult references. Background loop updates
+        // these as state progresses; consumer reads them after iterating the
+        // stream to completion (channel.close() is called AFTER mutations).
+        const usage = { input: 0, output: 0, total: 0 };
+        const metadata = {
+            streamId: `native-anthropic-vertex-${Date.now()}`,
+            startTime,
+            responseTime: 0,
+            totalToolExecutions: 0,
+        };
+        const toolsUsedRef = [];
+        const structuredOutputRef = {};
+        // Track the active Anthropic stream so options.abortSignal can cancel it
+        // mid-flight (pre-rewrite code had no abort handling — fixed for free).
+        let activeStream;
+        const abortHandler = () => {
             try {
-                // Use streaming API
-                const stream = await client.messages.stream({
-                    ...requestParams,
-                    messages: currentMessages,
-                });
-                // Collect the full response
-                const response = await stream.finalMessage();
-                // Update token counts
-                totalInputTokens += response.usage?.input_tokens || 0;
-                totalOutputTokens += response.usage?.output_tokens || 0;
-                // Check if we need to handle tool use
-                const toolUseBlocks = response.content.filter((block) => block.type === "tool_use");
-                // Check for final_result tool call (for structured output)
-                if (useFinalResultTool) {
-                    const finalResultCall = toolUseBlocks.find((block) => block.name === "final_result");
-                    if (finalResultCall) {
-                        // Extract structured output and convert to JSON string for finalText
-                        structuredOutput = finalResultCall.input;
-                        finalText = JSON.stringify(structuredOutput);
-                        logger.debug("[GoogleVertex] Extracted structured output from final_result tool (stream)", { keys: Object.keys(structuredOutput) });
-                        break; // We have the structured output, we're done
-                    }
-                }
-                // Extract text from response
-                const textBlocks = response.content.filter((block) => block.type === "text");
-                const responseText = textBlocks.map((b) => b.text).join("");
-                // Preserve each Anthropic text block separately so the
-                // consumer-visible stream yields multiple chunks (one per block).
-                for (const tb of textBlocks) {
-                    if (tb.text.length > 0) {
-                        allTextBlocks.push(tb.text);
+                activeStream?.controller.abort();
+            }
+            catch {
+                /* ignore — stream may already be finalized */
+            }
+        };
+        options.abortSignal?.addEventListener("abort", abortHandler);
+        // Defensive upper bound: if neither the caller nor the SDK ever fires,
+        // abort the stream after the configured timeout so a stalled
+        // Vertex/Anthropic endpoint can't hang forever. options.timeout wins
+        // if set; otherwise 5 min — generous for tool-heavy turns.
+        const streamTimeoutMs = parseTimeout(options.timeout) ?? 300_000;
+        const streamTimeoutHandle = setTimeout(() => {
+            logger.warn(`[GoogleVertex] Anthropic stream exceeded ${streamTimeoutMs}ms — aborting`);
+            abortHandler();
+        }, streamTimeoutMs);
+        const loopPromise = (async () => {
+            let step = 0;
+            const currentMessages = [...messages];
+            try {
+                while (step < maxSteps) {
+                    if (options.abortSignal?.aborted) {
+                        throw new Error("Stream aborted by caller");
                     }
-                }
-                if (toolUseBlocks.length === 0) {
-                    // No tool calls, we're done
-                    finalText = responseText || finalText;
-                    break;
-                }
-                // Handle tool calls
-                const toolResults = [];
-                for (const toolUse of toolUseBlocks) {
-                    allToolCalls.push({
-                        toolName: toolUse.name,
-                        args: toolUse.input,
+                    step++;
+                    const stream = await client.messages.stream({
+                        ...requestParams,
+                        messages: currentMessages,
                     });
-                    const execute = executeMap.get(toolUse.name);
-                    if (execute) {
-                        try {
-                            const result = await execute(toolUse.input);
-                            toolResults.push({
-                                type: "tool_result",
-                                tool_use_id: toolUse.id,
-                                content: typeof result === "string" ? result : JSON.stringify(result),
-                            });
+                    activeStream = stream;
+                    // Forward each text delta to the consumer as it arrives. The
+                    // Anthropic SDK fires this listener synchronously for every
+                    // content_block_delta SSE event, so the channel sees bytes at
+                    // the same cadence the wire delivers them.
+                    stream.on("text", (delta) => {
+                        if (delta.length > 0) {
+                            channel.push(delta);
                         }
-                        catch (err) {
+                    });
+                    // finalMessage() resolves AFTER message_stop. By then the listener
+                    // has already fired for every delta — awaiting here doesn't block
+                    // visible streaming, it just gives us the structured response
+                    // shape needed for tool_use block extraction.
+                    const response = await stream.finalMessage();
+                    activeStream = undefined;
+                    usage.input += response.usage?.input_tokens || 0;
+                    usage.output += response.usage?.output_tokens || 0;
+                    usage.total = usage.input + usage.output;
+                    const toolUseBlocks = response.content.filter((block) => block.type === "tool_use");
+                    // Structured-output pattern: when the model returns the
+                    // final_result tool call, push its arguments as JSON and stop.
+                    // Single-shot yield so callers consuming the stream still see
+                    // the structured value.
+                    if (useFinalResultTool) {
+                        const finalResultCall = toolUseBlocks.find((block) => block.name === "final_result");
+                        if (finalResultCall) {
+                            structuredOutputRef.value = finalResultCall.input;
+                            channel.push(JSON.stringify(finalResultCall.input));
+                            logger.debug("[GoogleVertex] Extracted structured output from final_result tool (stream)", { keys: Object.keys(finalResultCall.input) });
+                            break;
+                        }
+                    }
+                    // No tools — pure text turn. Listener already pushed all deltas;
+                    // loop terminates and channel.close() flushes the consumer.
+                    if (toolUseBlocks.length === 0) {
+                        break;
+                    }
+                    // Tool execution loop. tool:start / tool:end events fire from
+                    // ToolsManager's wrapped execute (ToolsManager.ts:355) — no inline
+                    // emit needed.
+                    const toolResults = [];
+                    // Per-step bookkeeping for conversation-memory storage.
+                    const stepStorageCalls = [];
+                    const stepStorageResults = [];
+                    // Note: tool:start / tool:end events are emitted by ToolsManager's
+                    // wrapped `execute` (see ToolsManager.ts:355) — no inline emit needed.
+                    for (const toolUse of toolUseBlocks) {
+                        allToolCalls.push({
+                            toolName: toolUse.name,
+                            args: toolUse.input,
+                        });
+                        toolsUsedRef.push(toolUse.name);
+                        stepStorageCalls.push({
+                            toolCallId: toolUse.id,
+                            toolName: toolUse.name,
+                            args: toolUse.input,
+                        });
+                        const execute = executeMap.get(toolUse.name);
+                        if (execute) {
+                            try {
+                                const toolOptions = {
+                                    toolCallId: toolUse.id,
+                                    messages: [],
+                                    abortSignal: options.abortSignal,
+                                };
+                                const result = await execute(toolUse.input, toolOptions);
+                                toolExecutions.push({
+                                    name: toolUse.name,
+                                    input: toolUse.input,
+                                    output: result,
+                                });
+                                // Anthropic requires tool_result.content to be a string.
+                                // JSON.stringify returns undefined for undefined/function/symbol,
+                                // so coerce defensively to keep the follow-up turn valid.
+                                const resultContent = typeof result === "string"
+                                    ? result
+                                    : (JSON.stringify(result ?? null) ?? String(result));
+                                toolResults.push({
+                                    type: "tool_result",
+                                    tool_use_id: toolUse.id,
+                                    content: resultContent,
+                                });
+                                stepStorageResults.push({
+                                    toolCallId: toolUse.id,
+                                    toolName: toolUse.name,
+                                    output: result,
+                                });
+                            }
+                            catch (err) {
+                                const errMsg = `Error executing tool "${toolUse.name}": ${err instanceof Error ? err.message : String(err)}`;
+                                const errorPayload = { error: errMsg };
+                                toolExecutions.push({
+                                    name: toolUse.name,
+                                    input: toolUse.input,
+                                    output: errorPayload,
+                                });
+                                toolResults.push({
+                                    type: "tool_result",
+                                    tool_use_id: toolUse.id,
+                                    content: errMsg,
+                                });
+                                stepStorageResults.push({
+                                    toolCallId: toolUse.id,
+                                    toolName: toolUse.name,
+                                    output: errorPayload,
+                                });
+                            }
+                        }
+                        else {
+                            const errMsg = `TOOL_NOT_FOUND: The tool "${toolUse.name}" does not exist.`;
+                            const errorPayload = { error: errMsg };
+                            toolExecutions.push({
+                                name: toolUse.name,
+                                input: toolUse.input,
+                                output: errorPayload,
+                            });
                             toolResults.push({
                                 type: "tool_result",
                                 tool_use_id: toolUse.id,
-                                content: `Error executing tool: ${err instanceof Error ? err.message : String(err)}`,
+                                content: errMsg,
+                            });
+                            stepStorageResults.push({
+                                toolCallId: toolUse.id,
+                                toolName: toolUse.name,
+                                output: errorPayload,
                             });
                         }
                     }
-                    else {
-                        toolResults.push({
-                            type: "tool_result",
-                            tool_use_id: toolUse.id,
-                            content: `TOOL_NOT_FOUND: The tool "${toolUse.name}" does not exist.`,
+                    // Persist this step's tool calls/results into conversation memory.
+                    // Without this hook, tool rows never land in Redis and the
+                    // chat-history UI loses every tool invocation.
+                    if (stepStorageCalls.length > 0 || stepStorageResults.length > 0) {
+                        withTimeout(this.handleToolExecutionStorage(stepStorageCalls.map((c) => ({ ...c, stepIndex: step })), stepStorageResults.map((r) => ({ ...r, stepIndex: step })), options, new Date()), TOOL_STORAGE_TIMEOUT_MS, "tool storage write timed out").catch((error) => {
+                            logger.warn("[GoogleVertex] Failed to store native Anthropic stream tool executions", {
+                                error: error instanceof Error ? error.message : String(error),
+                            });
                         });
                     }
+                    // Continue the loop: assistant turn + tool_result user turn.
+                    // Filter server_tool_use blocks (Anthropic API rejects them in
+                    // subsequent message turns).
+                    const assistantContent = response.content.filter((block) => block.type !== "server_tool_use");
+                    currentMessages.push({
+                        role: "assistant",
+                        content: assistantContent,
+                    });
+                    currentMessages.push({
+                        role: "user",
+                        content: toolResults,
+                    });
                 }
-                // Add assistant message and tool results to continue the loop
-                // Filter out server_tool_use blocks that the Anthropic API doesn't accept in messages
-                const assistantContent = response.content.filter((block) => block.type !== "server_tool_use");
-                currentMessages.push({
-                    role: "assistant",
-                    content: assistantContent,
-                });
-                currentMessages.push({
-                    role: "user",
-                    content: toolResults,
-                });
-                // Store last text in case we hit max steps
-                if (responseText) {
-                    finalText = responseText;
-                }
-            }
-            catch (error) {
-                logger.error("[GoogleVertex] Native Anthropic SDK stream error", error);
-                throw this.handleProviderError(error);
+                metadata.responseTime = Date.now() - startTime;
+                metadata.totalToolExecutions = allToolCalls.filter((tc) => tc.toolName !== "final_result").length;
+                channel.close();
             }
-        }
-        const responseTime = Date.now() - startTime;
-        // Yield each text block separately so the CLI receives multiple
-        // stream chunks instead of a single coalesced buffer. The Anthropic
-        // SDK gives us discrete text blocks; collapsing them into one chunk
-        // breaks the chunk-count smoke test even though the upstream
-        // streaming is real.
-        const finalContentBlocks = (() => {
-            if (structuredOutput) {
-                return [finalText];
+            catch (err) {
+                logger.error("[GoogleVertex] Native Anthropic SDK stream error", err);
+                channel.error(this.handleProviderError(err));
             }
-            if (allTextBlocks.length > 0) {
-                return allTextBlocks;
+            finally {
+                options.abortSignal?.removeEventListener("abort", abortHandler);
+                clearTimeout(streamTimeoutHandle);
             }
-            return finalText ? [finalText] : [];
         })();
-        async function* createTextStream() {
-            for (const part of finalContentBlocks) {
-                if (part.length > 0) {
-                    yield { content: part };
-                }
-            }
-        }
-        return {
-            stream: createTextStream(),
+        // Suppress unhandled-rejection: errors funnel through channel.error()
+        // and surface when the consumer iterates the stream.
+        loopPromise.catch(() => undefined);
+        // Return StreamResult IMMEDIATELY — caller's for-await can begin
+        // iterating channel.iterable while the background loop is still
+        // generating. usage / metadata / toolCalls / toolExecutions are mutable
+        // references that the loop fills in over time; the consumer reads them
+        // after iteration completes (after channel.close() has fired).
+        const result = {
+            stream: channel.iterable,
             provider: this.providerName,
             model: modelName,
-            usage: {
-                input: totalInputTokens,
-                output: totalOutputTokens,
-                total: totalInputTokens + totalOutputTokens,
-            },
-            toolCalls: allToolCalls.map((tc) => ({
-                toolName: tc.toolName,
-                args: tc.args,
-            })),
-            metadata: {
-                streamId: `native-anthropic-vertex-${Date.now()}`,
-                startTime,
-                responseTime,
-                totalToolExecutions: allToolCalls.length,
-            },
+            usage,
+            metadata,
         };
+        Object.defineProperty(result, "toolCalls", {
+            enumerable: true,
+            configurable: true,
+            get: () => allToolCalls.filter((tc) => tc.toolName !== "final_result"),
+        });
+        Object.defineProperty(result, "toolsUsed", {
+            enumerable: true,
+            configurable: true,
+            get: () => toolsUsedRef.filter((name) => name !== "final_result"),
+        });
+        Object.defineProperty(result, "toolExecutions", {
+            enumerable: true,
+            configurable: true,
+            get: () => transformToolExecutions(toolExecutions.filter((te) => te.name !== "final_result")),
+        });
+        Object.defineProperty(result, "structuredOutput", {
+            enumerable: true,
+            configurable: true,
+            get: () => structuredOutputRef.value,
+        });
+        return result;
     }
     /**
      * Execute generate using native @anthropic-ai/vertex-sdk for Claude models on Vertex AI
@@ -2347,6 +2577,9 @@ export class GoogleVertexProvider extends BaseProvider {
         // the older surface. The Vertex Claude STREAM path already follows this
         // priority — keeping the GENERATE path on `conversationHistory` only
         // would silently drop multi-turn context for memory/loop sessions.
+        // Intentionally text-only: see the stream sibling for the rationale —
+        // synthesising tool_use / tool_result blocks from stored ChatMessages
+        // risks emitting orphaned references that Anthropic's API rejects.
         const historyMessages = options.conversationMessages && options.conversationMessages.length > 0
             ? options.conversationMessages
             : options.conversationHistory;
@@ -2590,10 +2823,14 @@ export class GoogleVertexProvider extends BaseProvider {
         while (step < maxSteps) {
             step++;
             try {
-                const response = await client.messages.create({
+                // Bound the SDK wait so a stalled Vertex/Anthropic call can't hang
+                // generate forever. options.timeout wins if set, otherwise default
+                // to 5 min — generous for tool-heavy turns.
+                const generateTimeoutMs = parseTimeout(options.timeout) ?? 300_000;
+                const response = await withTimeout(client.messages.create({
                     ...requestParams,
                     messages: currentMessages,
-                });
+                }), generateTimeoutMs, "Anthropic generate timed out");
                 // Update token counts
                 totalInputTokens += response.usage?.input_tokens || 0;
                 totalOutputTokens += response.usage?.output_tokens || 0;
@@ -2620,42 +2857,105 @@ export class GoogleVertexProvider extends BaseProvider {
                 }
                 // Handle tool calls
                 const toolResults = [];
+                // Per-step bookkeeping for conversation-memory storage. Tracks calls
+                // and results for ONLY the tools fired in this step so the storage
+                // hook can tag them with the current stepIndex.
+                const stepStorageCalls = [];
+                const stepStorageResults = [];
+                // Note: tool:start / tool:end events are emitted by ToolsManager's
+                // wrapped `execute` (see ToolsManager.ts:355) — no inline emit needed.
                 for (const toolUse of toolUseBlocks) {
                     allToolCalls.push({
                         toolName: toolUse.name,
                         args: toolUse.input,
                     });
+                    stepStorageCalls.push({
+                        toolCallId: toolUse.id,
+                        toolName: toolUse.name,
+                        args: toolUse.input,
+                    });
                     const execute = executeMap.get(toolUse.name);
                     if (execute) {
                         try {
-                            const result = await execute(toolUse.input);
+                            const toolOptions = {
+                                toolCallId: toolUse.id,
+                                messages: [],
+                                abortSignal: options.abortSignal,
+                            };
+                            const result = await execute(toolUse.input, toolOptions);
                             toolExecutions.push({
                                 name: toolUse.name,
                                 input: toolUse.input,
                                 output: result,
                             });
+                            // Anthropic requires tool_result.content to be a string.
+                            // JSON.stringify returns undefined for undefined/function/symbol,
+                            // so coerce defensively to keep the follow-up turn valid.
+                            const resultContent = typeof result === "string"
+                                ? result
+                                : (JSON.stringify(result ?? null) ?? String(result));
                             toolResults.push({
                                 type: "tool_result",
                                 tool_use_id: toolUse.id,
-                                content: typeof result === "string" ? result : JSON.stringify(result),
+                                content: resultContent,
+                            });
+                            stepStorageResults.push({
+                                toolCallId: toolUse.id,
+                                toolName: toolUse.name,
+                                output: result,
                             });
                         }
                         catch (err) {
+                            const errMsg = `Error executing tool "${toolUse.name}": ${err instanceof Error ? err.message : String(err)}`;
+                            const errorPayload = { error: errMsg };
+                            toolExecutions.push({
+                                name: toolUse.name,
+                                input: toolUse.input,
+                                output: errorPayload,
+                            });
                             toolResults.push({
                                 type: "tool_result",
                                 tool_use_id: toolUse.id,
-                                content: `Error executing tool: ${err instanceof Error ? err.message : String(err)}`,
+                                content: errMsg,
+                            });
+                            stepStorageResults.push({
+                                toolCallId: toolUse.id,
+                                toolName: toolUse.name,
+                                output: errorPayload,
                             });
                         }
                     }
                     else {
+                        const errMsg = `TOOL_NOT_FOUND: The tool "${toolUse.name}" does not exist.`;
+                        const errorPayload = { error: errMsg };
+                        toolExecutions.push({
+                            name: toolUse.name,
+                            input: toolUse.input,
+                            output: errorPayload,
+                        });
                         toolResults.push({
                             type: "tool_result",
                             tool_use_id: toolUse.id,
-                            content: `TOOL_NOT_FOUND: The tool "${toolUse.name}" does not exist.`,
+                            content: errMsg,
+                        });
+                        stepStorageResults.push({
+                            toolCallId: toolUse.id,
+                            toolName: toolUse.name,
+                            output: errorPayload,
                         });
                     }
                 }
+                // Persist this step's tool calls/results into conversation memory.
+                // Without this, tool_call / tool_result rows never reach Redis and
+                // the chat-history UI loses every tool invocation.
+                // Fire-and-forget — storage failures must not break generation.
+                if (stepStorageCalls.length > 0 || stepStorageResults.length > 0) {
+                    withTimeout(this.handleToolExecutionStorage(stepStorageCalls.map((c) => ({ ...c, stepIndex: step })), stepStorageResults.map((r) => ({ ...r, stepIndex: step })), options, new Date()), TOOL_STORAGE_TIMEOUT_MS, "tool storage write timed out").catch((error) => {
+                        logger.warn("[GoogleVertex] Failed to store native Anthropic generate tool executions", {
+                            error: error instanceof Error ? error.message : String(error),
+                        });
+                    });
+                }
                 // Add assistant message and tool results to continue the loop
                 // Filter out server_tool_use blocks that the Anthropic API doesn't accept in messages
                 const assistantContent = response.content.filter((block) => block.type !== "server_tool_use");
@@ -2678,6 +2978,8 @@ export class GoogleVertexProvider extends BaseProvider {
             }
         }
         const responseTime = Date.now() - startTime;
+        const externalToolCalls = allToolCalls.filter((tc) => tc.toolName !== "final_result");
+        const externalToolExecutions = toolExecutions.filter((te) => te.name !== "final_result");
         const result = {
             content: finalText,
             provider: this.providerName,
@@ -2688,9 +2990,9 @@ export class GoogleVertexProvider extends BaseProvider {
                 total: totalInputTokens + totalOutputTokens,
             },
             responseTime,
-            toolsUsed: allToolCalls.map((tc) => tc.toolName),
-            toolExecutions,
-            enhancedWithTools: allToolCalls.length > 0,
+            toolsUsed: externalToolCalls.map((tc) => tc.toolName),
+            toolExecutions: transformToolExecutions(externalToolExecutions),
+            enhancedWithTools: externalToolCalls.length > 0,
         };
         // Route through enhanceResult so analytics/evaluation/tracing are picked
         // up the same way the BaseProvider.generate() path picks them up. The