@code-yeongyu/senpi 2026.8.29 → 2026.8.30

package/node_modules/@earendil-works/pi-agent-core/dist/harness/utils/shell-output.js.map

@@ -1 +1 @@
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{ type ExecutionEnv, ExecutionError, err, ok, type Result, type ShellExecOptions, toError } from \"../types.ts\";\nimport { DEFAULT_MAX_BYTES, DEFAULT_MAX_LINES, type TruncationResult, truncateTail } from \"./truncate.ts\";\n\nexport interface ShellCaptureProgress {\n\toutput: string;\n\ttruncation: TruncationResult;\n\tfullOutputPath?: string;\n\tlastLineBytes: number;\n}\n\nexport interface ShellCaptureOptions extends Omit<ShellExecOptions, \"onStdout\" | \"onStderr\"> {\n\tonChunk?: (chunk: string, getProgress: () => ShellCaptureProgress) => void;\n\t/** Return shell execution failures with captured output instead of as a failed Result. */\n\treturnExecutionErrors?: boolean;\n}\n\nexport interface ShellCaptureResult extends ShellCaptureProgress {\n\texitCode: number | undefined;\n\tcancelled: boolean;\n\ttruncated: boolean;\n\texecutionError?: ExecutionError;\n}\n\nfunction toExecutionError(error: unknown): ExecutionError {\n\tif (error instanceof ExecutionError) return error;\n\tconst cause = toError(error);\n\treturn new ExecutionError(\"unknown\", cause.message, cause);\n}\n\nexport function sanitizeBinaryOutput(str: string): string {\n\treturn Array.from(str)\n\t\t.filter((char) => {\n\t\t\tconst code = char.codePointAt(0);\n\t\t\tif (code === undefined) return false;\n\t\t\tif (code === 0x09 || code === 0x0a || code === 0x0d) return true;\n\t\t\tif (code <= 0x1f) return false;\n\t\t\tif (code >= 0xfff9 && code <= 0xfffb) return false;\n\t\t\treturn true;\n\t\t})\n\t\t.join(\"\");\n}\n\nfunction trimToLastUtf8Bytes(text: string, maxBytes: number, encoder: { encode(input?: string): Uint8Array }): string {\n\tconst bytes = encoder.encode(text);\n\tif (bytes.byteLength <= maxBytes) return text;\n\tlet start = bytes.byteLength - maxBytes;\n\twhile (start < bytes.byteLength && ((bytes[start] ?? 0) & 0xc0) === 0x80) start++;\n\treturn new TextDecoder().decode(bytes.subarray(start));\n}\n\nexport async function executeShellWithCapture(\n\tenv: ExecutionEnv,\n\tcommand: string,\n\toptions?: ShellCaptureOptions,\n): Promise<Result<ShellCaptureResult, ExecutionError>> {\n\tlet tailOutput = \"\";\n\tconst maxOutputBytes = DEFAULT_MAX_BYTES * 2;\n\tconst encoder = new TextEncoder();\n\n\tlet totalBytes = 0;\n\tlet completedLines = 0;\n\tlet hasOpenLine = false;\n\tlet currentLineBytes = 0;\n\tlet fullOutputPath: string | undefined;\n\tlet fullOutputRequested = false;\n\tlet acceptingOutput = true;\n\tlet writeChain: Promise<Result<void, ExecutionError>> = Promise.resolve(ok(undefined));\n\tlet captureError: ExecutionError | undefined;\n\n\tconst appendFullOutput = (text: string): void => {\n\t\tif (!fullOutputRequested || captureError) return;\n\t\twriteChain = writeChain.then(async (previous) => {\n\t\t\tif (!previous.ok) return previous;\n\t\t\tif (!fullOutputPath) return err(new ExecutionError(\"unknown\", \"Full output path was not created\"));\n\t\t\tconst appendResult = await env.appendFile(fullOutputPath, text);\n\t\t\treturn appendResult.ok ? ok(undefined) : err(toExecutionError(appendResult.error));\n\t\t});\n\t};\n\n\tconst ensureFullOutputFile = (initialContent: string): void => {\n\t\tif (fullOutputRequested || captureError) return;\n\t\tfullOutputRequested = true;\n\t\twriteChain = writeChain.then(async (previous) => {\n\t\t\tif (!previous.ok) return previous;\n\t\t\tconst tempFile = await env.createTempFile({ prefix: \"bash-\", suffix: \".log\" });\n\t\t\tif (!tempFile.ok) return err(toExecutionError(tempFile.error));\n\t\t\tfullOutputPath = tempFile.value;\n\t\t\tconst appendResult = await env.appendFile(tempFile.value, initialContent);\n\t\t\treturn appendResult.ok ? ok(undefined) : err(toExecutionError(appendResult.error));\n\t\t});\n\t};\n\n\tconst createProgress = (): ShellCaptureProgress => {\n\t\tconst tailTruncation = truncateTail(tailOutput);\n\t\tconst totalLines = completedLines + (hasOpenLine ? 1 : 0);\n\t\tconst truncated = totalLines > DEFAULT_MAX_LINES || totalBytes > DEFAULT_MAX_BYTES;\n\t\tconst truncation: TruncationResult = {\n\t\t\t...tailTruncation,\n\t\t\ttruncated,\n\t\t\ttruncatedBy: truncated\n\t\t\t\t? (tailTruncation.truncatedBy ?? (totalBytes > DEFAULT_MAX_BYTES ? \"bytes\" : \"lines\"))\n\t\t\t\t: null,\n\t\t\ttotalLines,\n\t\t\ttotalBytes,\n\t\t};\n\t\treturn {\n\t\t\toutput: truncated ? truncation.content : tailOutput,\n\t\t\ttruncation,\n\t\t\tfullOutputPath,\n\t\t\tlastLineBytes: currentLineBytes,\n\t\t};\n\t};\n\n\tconst onChunk = (chunk: string): void => {\n\t\tif (!acceptingOutput) return;\n\t\ttry {\n\t\t\tconst text = sanitizeBinaryOutput(chunk).replace(/\\r/g, \"\");\n\t\t\tconst textBytes = encoder.encode(text).byteLength;\n\t\t\ttotalBytes += textBytes;\n\t\t\tconst newlineCount = text.split(\"\\n\").length - 1;\n\t\t\tcompletedLines += newlineCount;\n\t\t\tconst lastNewline = text.lastIndexOf(\"\\n\");\n\t\t\tif (lastNewline >= 0) {\n\t\t\t\tconst trailingText = text.slice(lastNewline + 1);\n\t\t\t\tcurrentLineBytes = encoder.encode(trailingText).byteLength;\n\t\t\t\thasOpenLine = trailingText.length > 0;\n\t\t\t} else if (text.length > 0) {\n\t\t\t\tcurrentLineBytes += textBytes;\n\t\t\t\thasOpenLine = true;\n\t\t\t}\n\n\t\t\ttailOutput += text;\n\t\t\tconst totalLines = completedLines + (hasOpenLine ? 1 : 0);\n\t\t\tif ((totalBytes > DEFAULT_MAX_BYTES || totalLines > DEFAULT_MAX_LINES) && !fullOutputRequested) {\n\t\t\t\tensureFullOutputFile(tailOutput);\n\t\t\t} else if (fullOutputRequested) {\n\t\t\t\tappendFullOutput(text);\n\t\t\t}\n\t\t\ttailOutput = trimToLastUtf8Bytes(tailOutput, maxOutputBytes, encoder);\n\t\t\toptions?.onChunk?.(text, createProgress);\n\t\t} catch (error) {\n\t\t\tcaptureError = toExecutionError(error);\n\t\t}\n\t};\n\n\ttry {\n\t\tconst result = await env.exec(command, {\n\t\t\tcwd: options?.cwd,\n\t\t\tenv: options?.env,\n\t\t\tinheritEnv: options?.inheritEnv,\n\t\t\ttimeout: options?.timeout,\n\t\t\tabortSignal: options?.abortSignal,\n\t\t\tonStdout: onChunk,\n\t\t\tonStderr: onChunk,\n\t\t});\n\t\tacceptingOutput = false;\n\t\tlet progress = createProgress();\n\t\tif (progress.truncation.truncated && !fullOutputRequested) ensureFullOutputFile(tailOutput);\n\t\tconst writeResult = await writeChain;\n\t\tif (!writeResult.ok) return err(writeResult.error);\n\t\tif (captureError) return err(captureError);\n\t\tprogress = createProgress();\n\n\t\tif (!result.ok) {\n\t\t\tif (result.error.code === \"aborted\" || options?.abortSignal?.aborted) {\n\t\t\t\treturn ok({\n\t\t\t\t\t...progress,\n\t\t\t\t\texitCode: undefined,\n\t\t\t\t\tcancelled: true,\n\t\t\t\t\ttruncated: progress.truncation.truncated,\n\t\t\t\t});\n\t\t\t}\n\t\t\tif (options?.returnExecutionErrors) {\n\t\t\t\treturn ok({\n\t\t\t\t\t...progress,\n\t\t\t\t\texitCode: undefined,\n\t\t\t\t\tcancelled: false,\n\t\t\t\t\ttruncated: progress.truncation.truncated,\n\t\t\t\t\texecutionError: result.error,\n\t\t\t\t});\n\t\t\t}\n\t\t\treturn err(result.error);\n\t\t}\n\t\tconst cancelled = options?.abortSignal?.aborted ?? false;\n\t\treturn ok({\n\t\t\t...progress,\n\t\t\texitCode: cancelled ? undefined : result.value.exitCode,\n\t\t\tcancelled,\n\t\t\ttruncated: progress.truncation.truncated,\n\t\t});\n\t} catch (error) {\n\t\tacceptingOutput = false;\n\t\treturn err(toExecutionError(error));\n\t}\n}\n"]}
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ExecutionEnv,\n\tcommand: string,\n\toptions?: ShellCaptureOptions,\n): Promise<Result<ShellCaptureResult, ExecutionError>> {\n\tlet tailOutput = \"\";\n\tconst maxOutputBytes = DEFAULT_MAX_BYTES * 2;\n\tconst encoder = new TextEncoder();\n\n\tlet totalBytes = 0;\n\tlet completedLines = 0;\n\tlet hasOpenLine = false;\n\tlet currentLineBytes = 0;\n\tlet fullOutputPath: string | undefined;\n\tlet fullOutputRequested = false;\n\tlet acceptingOutput = true;\n\tlet writeChain: Promise<Result<void, ExecutionError>> = Promise.resolve(ok(undefined));\n\tlet captureError: ExecutionError | undefined;\n\n\tconst appendFullOutput = (text: string): void => {\n\t\tif (!fullOutputRequested || captureError) return;\n\t\twriteChain = writeChain.then(async (previous) => {\n\t\t\tif (!previous.ok) return previous;\n\t\t\tif (!fullOutputPath) return err(new ExecutionError(\"unknown\", \"Full output path was not created\"));\n\t\t\tconst appendResult = await env.appendFile(fullOutputPath, text);\n\t\t\treturn appendResult.ok ? ok(undefined) : err(toExecutionError(appendResult.error));\n\t\t});\n\t};\n\n\tconst ensureFullOutputFile = (initialContent: string): void => {\n\t\tif (fullOutputRequested || captureError) return;\n\t\tfullOutputRequested = true;\n\t\twriteChain = writeChain.then(async (previous) => {\n\t\t\tif (!previous.ok) return previous;\n\t\t\tconst tempFile = await env.createTempFile({ prefix: \"bash-\", suffix: \".log\" });\n\t\t\tif (!tempFile.ok) return err(toExecutionError(tempFile.error));\n\t\t\tfullOutputPath = tempFile.value;\n\t\t\tconst appendResult = await env.appendFile(tempFile.value, initialContent);\n\t\t\treturn appendResult.ok ? ok(undefined) : err(toExecutionError(appendResult.error));\n\t\t});\n\t};\n\n\tconst cleanupFullOutput = async (): Promise<ExecutionError | undefined> => {\n\t\tif (!fullOutputPath) return undefined;\n\t\tconst result = await env.remove(fullOutputPath, { force: true });\n\t\treturn result.ok ? undefined : toExecutionError(result.error);\n\t};\n\n\tconst withCleanupError = (primary: ExecutionError, cleanupError: ExecutionError | undefined): ExecutionError =>\n\t\tcleanupError\n\t\t\t? new ExecutionError(primary.code, primary.message, new AggregateError([primary, cleanupError]))\n\t\t\t: primary;\n\n\tconst createProgress = (): ShellCaptureProgress => {\n\t\tconst tailTruncation = truncateTail(tailOutput);\n\t\tconst totalLines = completedLines + (hasOpenLine ? 1 : 0);\n\t\tconst truncated = totalLines > DEFAULT_MAX_LINES || totalBytes > DEFAULT_MAX_BYTES;\n\t\tconst truncation: TruncationResult = {\n\t\t\t...tailTruncation,\n\t\t\ttruncated,\n\t\t\ttruncatedBy: truncated\n\t\t\t\t? (tailTruncation.truncatedBy ?? (totalBytes > DEFAULT_MAX_BYTES ? \"bytes\" : \"lines\"))\n\t\t\t\t: null,\n\t\t\ttotalLines,\n\t\t\ttotalBytes,\n\t\t};\n\t\treturn {\n\t\t\toutput: truncated ? truncation.content : tailOutput,\n\t\t\ttruncation,\n\t\t\tfullOutputPath,\n\t\t\tlastLineBytes: currentLineBytes,\n\t\t};\n\t};\n\n\tconst onChunk = async (chunk: string): Promise<void> => {\n\t\tif (!acceptingOutput) return;\n\t\ttry {\n\t\t\tconst text = sanitizeBinaryOutput(chunk).replace(/\\r/g, \"\");\n\t\t\tconst textBytes = encoder.encode(text).byteLength;\n\t\t\ttotalBytes += textBytes;\n\t\t\tconst newlineCount = text.split(\"\\n\").length - 1;\n\t\t\tcompletedLines += newlineCount;\n\t\t\tconst lastNewline = text.lastIndexOf(\"\\n\");\n\t\t\tif (lastNewline >= 0) {\n\t\t\t\tconst trailingText = text.slice(lastNewline + 1);\n\t\t\t\tcurrentLineBytes = encoder.encode(trailingText).byteLength;\n\t\t\t\thasOpenLine = trailingText.length > 0;\n\t\t\t} else if (text.length > 0) {\n\t\t\t\tcurrentLineBytes += textBytes;\n\t\t\t\thasOpenLine = true;\n\t\t\t}\n\n\t\t\ttailOutput += text;\n\t\t\tconst totalLines = completedLines + (hasOpenLine ? 1 : 0);\n\t\t\tif ((totalBytes > DEFAULT_MAX_BYTES || totalLines > DEFAULT_MAX_LINES) && !fullOutputRequested) {\n\t\t\t\tensureFullOutputFile(tailOutput);\n\t\t\t} else if (fullOutputRequested) {\n\t\t\t\tappendFullOutput(text);\n\t\t\t}\n\t\t\ttailOutput = trimToLastUtf8Bytes(tailOutput, maxOutputBytes, encoder);\n\t\t\tawait options?.onChunk?.(text, createProgress);\n\t\t} catch (error) {\n\t\t\tcaptureError = new ExecutionError(\"callback_error\", toError(error).message, error);\n\t\t\t// Keep the harness execution rejected. Merely recording the callback error\n\t\t\t// here turns a failed observer into a fulfilled capture result, preventing\n\t\t\t// the harness abort path from killing the child process.\n\t\t\tthrow error;\n\t\t}\n\t};\n\n\ttry {\n\t\tconst result = await env.exec(command, {\n\t\t\tcwd: options?.cwd,\n\t\t\tenv: options?.env,\n\t\t\tinheritEnv: options?.inheritEnv,\n\t\t\ttimeout: options?.timeout,\n\t\t\tabortSignal: options?.abortSignal,\n\t\t\tonStdout: onChunk,\n\t\t\tonStderr: onChunk,\n\t\t});\n\t\tacceptingOutput = false;\n\t\tlet progress = createProgress();\n\t\tif (progress.truncation.truncated && !fullOutputRequested) ensureFullOutputFile(tailOutput);\n\t\tconst writeResult = await writeChain;\n\t\tif (!writeResult.ok) {\n\t\t\treturn err(withCleanupError(writeResult.error, await cleanupFullOutput()));\n\t\t}\n\t\tif (captureError) {\n\t\t\treturn err(withCleanupError(captureError, await cleanupFullOutput()));\n\t\t}\n\t\tprogress = createProgress();\n\n\t\tif (!result.ok) {\n\t\t\tif (result.error.code === \"aborted\" || options?.abortSignal?.aborted) {\n\t\t\t\tconst cleanupError = await cleanupFullOutput();\n\t\t\t\tif (cleanupError) return err(cleanupError);\n\t\t\t\treturn ok({\n\t\t\t\t\t...progress,\n\t\t\t\t\texitCode: undefined,\n\t\t\t\t\tcancelled: true,\n\t\t\t\t\ttruncated: progress.truncation.truncated,\n\t\t\t\t});\n\t\t\t}\n\t\t\tif (options?.returnExecutionErrors) {\n\t\t\t\treturn ok({\n\t\t\t\t\t...progress,\n\t\t\t\t\texitCode: undefined,\n\t\t\t\t\tcancelled: false,\n\t\t\t\t\ttruncated: progress.truncation.truncated,\n\t\t\t\t\texecutionError: result.error,\n\t\t\t\t});\n\t\t\t}\n\t\t\treturn err(result.error);\n\t\t}\n\t\tconst cancelled = options?.abortSignal?.aborted ?? false;\n\t\treturn ok({\n\t\t\t...progress,\n\t\t\texitCode: cancelled ? undefined : result.value.exitCode,\n\t\t\tcancelled,\n\t\t\ttruncated: progress.truncation.truncated,\n\t\t});\n\t} catch (error) {\n\t\tacceptingOutput = false;\n\t\tconst primaryError = toExecutionError(error);\n\t\treturn err(withCleanupError(primaryError, await cleanupFullOutput()));\n\t}\n}\n"]}

package/node_modules/@earendil-works/pi-agent-core/package.json

@@ -1,6 +1,6 @@
 {
 	"name": "@earendil-works/pi-agent-core",
-	"version": "2026.8.29",
+	"version": "2026.8.30",
 	"description": "General-purpose agent with transport abstraction, state management, and attachment support",
 	"type": "module",
 	"main": "./dist/index.js",
@@ -35,8 +35,8 @@
 		"prepublishOnly": "npm run build"
 	},
 	"dependencies": {
-		"@earendil-works/pi-ai": "npm:@code-yeongyu/senpi-ai@2026.8.29",
-		"@earendil-works/pi-telemetry": "npm:@code-yeongyu/senpi-telemetry@2026.8.29",
+		"@earendil-works/pi-ai": "npm:@code-yeongyu/senpi-ai@2026.8.30",
+		"@earendil-works/pi-telemetry": "npm:@code-yeongyu/senpi-telemetry@2026.8.30",
 		"diff": "9.0.0",
 		"ignore": "7.0.6",
 		"typebox": "1.3.18",

package/node_modules/@earendil-works/pi-ai/dist/api/anthropic-messages.d.ts.map

@@ -1 +1 @@
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+{"version":3,"file":"anthropic-messages.d.ts","sourceRoot":"","sources":["../../src/api/anthropic-messages.ts"],"names":[],"mappings":"AAAA,OAAO,SAAS,MAAM,mBAAmB,CAAC;AAC1C,OAAO,KAAK,EAGX,+BAA+B,EAK/B,MAAM,yCAAyC,CAAC;AAEjD,OAAO,KAAK,EACX,wBAAwB,EAKxB,OAAO,EAGP,KAAK,EAGL,mBAAmB,EAEnB,cAAc,EACd,aAAa,EAOb,MAAM,aAAa,CAAC;AAqCrB,OAAO,EAAE,kBAAkB,EAAE,MAAM,8BAA8B,CAAC;AA6JlE,MAAM,MAAM,eAAe,GAAG,KAAK,GAAG,QAAQ,GAAG,MAAM,GAAG,OAAO,GAAG,KAAK,CAAC;AAE1E,MAAM,MAAM,wBAAwB,GAAG,YAAY,GAAG,SAAS,CAAC;AAyEhE,MAAM,WAAW,gBAAiB,SAAQ,aAAa;IACtD;;;;;;OAMG;IACH,eAAe,CAAC,EAAE,OAAO,CAAC;IAC1B;;;;OAIG;IACH,oBAAoB,CAAC,EAAE,MAAM,CAAC;IAC9B;;;;;;;;;;;OAWG;IACH,MAAM,CAAC,EAAE,eAAe,CAAC;IACzB;;;;;;;;;;;OAWG;IACH,eAAe,CAAC,EAAE,wBAAwB,CAAC;IAC3C;;;;;OAKG;IACH,mBAAmB,CAAC,EAAE,OAAO,CAAC;IAC9B,wEAAwE;IACxE,gBAAgB,CAAC,EAAE,wBAAwB,CAAC;IAC5C;;;;OAIG;IACH,UAAU,CAAC,EAAE,MAAM,GAAG,KAAK,GAAG,MAAM,GAAG;QAAE,IAAI,EAAE,MAAM,CAAC;QAAC,IAAI,EAAE,MAAM,CAAA;KAAE,CAAC;IACtE;;;;OAIG;IACH,MAAM,CAAC,EAAE,SAAS,CAAC;CACnB;AAm4BD,eAAO,MAAM,MAAM,EAAE,cAAc,CAAC,oBAAoB,EAAE,gBAAgB,CAqbzE,CAAC;AA0FF,eAAO,MAAM,YAAY,EAAE,cAAc,CAAC,oBAAoB,EAAE,mBAAmB,CA+ClF,CAAC;AA6IF,wBAAgB,mCAAmC,CAClD,KAAK,EAAE,KAAK,CAAC,oBAAoB,CAAC,EAClC,OAAO,EAAE,OAAO,EAChB,OAAO,CAAC,EAAE,gBAAgB,GACxB,+BAA+B,CAkBjC"}

package/node_modules/@earendil-works/pi-ai/dist/api/anthropic-messages.js

@@ -736,6 +736,48 @@ function sanitizeAdaptiveThinkingPayload(model, params, options) {
 function isCacheableUserContentBlock(block) {
     return block?.type === "text" || block?.type === "image" || block?.type === "tool_result";
 }
+function appendUserBlocks(params, newBlocks) {
+    if (newBlocks.length === 0)
+        return;
+    const lastParam = params[params.length - 1];
+    if (lastParam?.role === "user") {
+        if (typeof lastParam.content === "string") {
+            lastParam.content = [{ type: "text", text: lastParam.content }, ...newBlocks];
+        }
+        else if (Array.isArray(lastParam.content)) {
+            lastParam.content.push(...newBlocks);
+        }
+    }
+    else {
+        params.push({ role: "user", content: newBlocks });
+    }
+}
+function isToolLoopContinuation(messages) {
+    const tail = messages[messages.length - 1];
+    const preceding = messages[messages.length - 2];
+    return (tail?.role === "user" &&
+        Array.isArray(tail.content) &&
+        tail.content.some((block) => block.type === "tool_result") &&
+        preceding?.role === "assistant" &&
+        Array.isArray(preceding.content) &&
+        preceding.content.some((block) => block.type === "tool_use"));
+}
+function markUserMessageCacheCheckpoint(message, cacheControl) {
+    if (message.role !== "user")
+        return false;
+    if (Array.isArray(message.content)) {
+        const lastBlock = message.content[message.content.length - 1];
+        if (!isCacheableUserContentBlock(lastBlock))
+            return false;
+        lastBlock.cache_control = cacheControl;
+        return true;
+    }
+    if (typeof message.content === "string") {
+        message.content = [{ type: "text", text: message.content, cache_control: cacheControl }];
+        return true;
+    }
+    return false;
+}
 const ANTHROPIC_MESSAGE_EVENTS = new Set([
     "message_start",
     "message_delta",
@@ -1535,7 +1577,7 @@ function buildParams(model, context, isOAuthToken, options, unsignedThinkingRepl
             {
                 type: "text",
                 text: "You are Claude Code, Anthropic's official CLI for Claude.",
-                ...(cacheControl ? { cache_control: cacheControl } : {}),
+                ...(!context.systemPrompt && cacheControl ? { cache_control: cacheControl } : {}),
             },
         ];
         if (context.systemPrompt) {
@@ -1701,10 +1743,13 @@ function convertMessages(transformedMessages, model, isOAuthToken, cacheControl,
         if (msg.role === "user") {
             if (typeof msg.content === "string") {
                 if (msg.content.trim().length > 0) {
-                    params.push({
-                        role: "user",
-                        content: sanitizeSurrogates(msg.content),
-                    });
+                    const content = sanitizeSurrogates(msg.content);
+                    if (params[params.length - 1]?.role === "user") {
+                        appendUserBlocks(params, [{ type: "text", text: content }]);
+                    }
+                    else {
+                        params.push({ role: "user", content });
+                    }
                 }
             }
             else {
@@ -1744,10 +1789,7 @@ function convertMessages(transformedMessages, model, isOAuthToken, cacheControl,
                 });
                 if (filteredBlocks.length === 0)
                     continue;
-                params.push({
-                    role: "user",
-                    content: filteredBlocks,
-                });
+                appendUserBlocks(params, filteredBlocks);
             }
         }
         else if (msg.role === "assistant") {
@@ -1862,30 +1904,15 @@ function convertMessages(transformedMessages, model, isOAuthToken, cacheControl,
             if (toolResults.length === 0)
                 continue;
             // Displaced reference-bearing results must follow every tool_result block.
-            params.push({
-                role: "user",
-                content: [...toolResults, ...siblingContent],
-            });
+            appendUserBlocks(params, [...toolResults, ...siblingContent]);
         }
     }
-    // Add cache_control to the last user message to cache conversation history
-    if (cacheControl && params.length > 0) {
-        const lastMessage = params[params.length - 1];
-        if (lastMessage.role === "user") {
-            if (Array.isArray(lastMessage.content)) {
-                const lastBlock = lastMessage.content[lastMessage.content.length - 1];
-                if (isCacheableUserContentBlock(lastBlock)) {
-                    lastBlock.cache_control = cacheControl;
-                }
-            }
-            else if (typeof lastMessage.content === "string") {
-                lastMessage.content = [
-                    {
-                        type: "text",
-                        text: lastMessage.content,
-                        cache_control: cacheControl,
-                    },
-                ];
+    const retainPrecedingCheckpoint = isToolLoopContinuation(params);
+    if (cacheControl && params.length > 0 && markUserMessageCacheCheckpoint(params[params.length - 1], cacheControl)) {
+        if (retainPrecedingCheckpoint) {
+            for (let index = params.length - 2; index >= 0; index--) {
+                if (markUserMessageCacheCheckpoint(params[index], cacheControl))
+                    break;
             }
         }
     }