gsd-pi 2.78.0 → 2.78.1-dev.2ff77b0ce

package/packages/pi-ai/dist/utils/repair-tool-json.js.map

@@ -1 +1 @@
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Used Web Notification API...,\n *   \"keyFiles\": - src-tauri/src/lib.rs — Extended...\n *\n * instead of valid JSON arrays:\n *\n *   \"keyDecisions\": [\"Used Web Notification API...\"],\n *   \"keyFiles\": [\"src-tauri/src/lib.rs — Extended...\"]\n *\n * This module detects and repairs such patterns before JSON.parse is called.\n *\n * @see https://github.com/gsd-build/gsd-2/issues/2660\n */\n\n/**\n * Detect whether a JSON string contains YAML-style bullet-list values\n * (i.e. `\"key\": - item` instead of `\"key\": [\"item\"]`).\n */\nexport function hasYamlBulletLists(json: string): boolean {\n\t// Match: \"key\": followed by whitespace then a dash-space pattern (YAML bullet)\n\t// The negative lookahead excludes negative numbers (e.g. \"key\": -1)\n\treturn /\"\\s*:\\s*-\\s+(?!\\d)/.test(json);\n}\n\n/**\n * Detect whether a JSON string contains XML parameter tags\n * (i.e. `<parameter name=\"X\">value</parameter>`).\n *\n * Some models mix XML tool-call syntax into JSON string values,\n * producing hybrid output that fails JSON.parse.\n *\n * @see https://github.com/gsd-build/gsd-2/issues/3403\n */\nexport function hasXmlParameterTags(json: string): boolean {\n\treturn /<\\/?parameter[\\s>]/.test(json);\n}\n\n/**\n * Detect whether a JSON string contains truncated numeric values\n * (e.g. `\"exitCode\": -,` or `\"durationMs\": ,`).\n *\n * Smaller models sometimes emit incomplete numbers when the value\n * is cut off mid-generation.\n *\n * @see https://github.com/gsd-build/gsd-2/issues/3464\n */\nexport function hasTruncatedNumbers(json: string): boolean {\n\t// Match: colon, optional whitespace, then a comma or } without a value\n\t// Or: colon, optional whitespace, bare minus sign followed by comma/}\n\treturn /:\\s*,/.test(json) || /:\\s*-\\s*[,}]/.test(json);\n}\n\ntype XmlParameterBlock = {\n\tname: string;\n\tvalue: unknown;\n};\n\nconst xmlParameterBlockPattern = /<parameter\\s+name=\"([^\"]+)\"\\s*>([\\s\\S]*?)<\\/parameter>/g;\n\nfunction parseXmlParameterValue(raw: string): unknown {\n\tconst trimmed = raw.trim();\n\tif (trimmed === \"\") return \"\";\n\ttry {\n\t\treturn JSON.parse(trimmed);\n\t} catch {\n\t\treturn trimmed;\n\t}\n}\n\nfunction extractXmlParameterBlocks(text: string): XmlParameterBlock[] {\n\tconst blocks: XmlParameterBlock[] = [];\n\tfor (const match of text.matchAll(xmlParameterBlockPattern)) {\n\t\tblocks.push({\n\t\t\tname: match[1],\n\t\t\tvalue: parseXmlParameterValue(match[2] ?? \"\"),\n\t\t});\n\t}\n\treturn blocks;\n}\n\nfunction trimLeakedXmlTail(fieldName: string, value: string): string {\n\tlet cut = value.length;\n\tconst parameterIndex = value.indexOf(\"<parameter\");\n\tif (parameterIndex >= 0) cut = Math.min(cut, parameterIndex);\n\n\tconst closingTagIndex = value.indexOf(`</${fieldName}>`);\n\tif (closingTagIndex >= 0) cut = Math.min(cut, closingTagIndex);\n\n\treturn value.slice(0, cut).trimEnd();\n}\n\n/**\n * Strip XML `<parameter>` tags from a JSON string, leaving only the\n * text content. This handles the case where the LLM mixes XML\n * tool-call format into JSON string values.\n */\nfunction stripXmlParameterTags(json: string): string {\n\t// Remove opening tags: <parameter name=\"X\">\n\tlet cleaned = json.replace(/<parameter\\s+name=\"[^\"]*\"\\s*>/g, \"\");\n\t// Remove closing tags: </parameter>\n\tcleaned = cleaned.replace(/<\\/parameter>/g, \"\");\n\treturn cleaned;\n}\n\nfunction promoteXmlParametersToTopLevel(json: string): string {\n\ttry {\n\t\tconst parsed = JSON.parse(json) as Record<string, unknown>;\n\t\tif (!parsed || typeof parsed !== \"object\" || Array.isArray(parsed)) {\n\t\t\treturn stripXmlParameterTags(json);\n\t\t}\n\n\t\tlet changed = false;\n\t\tfor (const [fieldName, value] of Object.entries(parsed)) {\n\t\t\tif (typeof value !== \"string\" || !hasXmlParameterTags(value)) continue;\n\n\t\t\tconst blocks = extractXmlParameterBlocks(value);\n\t\t\tif (blocks.length === 0) continue;\n\n\t\t\tparsed[fieldName] = trimLeakedXmlTail(fieldName, value);\n\t\t\tfor (const block of blocks) {\n\t\t\t\tif (!(block.name in parsed)) {\n\t\t\t\t\tparsed[block.name] = block.value;\n\t\t\t\t}\n\t\t\t}\n\t\t\tchanged = true;\n\t\t}\n\n\t\treturn changed ? JSON.stringify(parsed) : stripXmlParameterTags(json);\n\t} catch {\n\t\treturn stripXmlParameterTags(json);\n\t}\n}\n\n/**\n * Replace truncated numeric values with 0.\n * Handles: `\"key\": ,` → `\"key\": 0,` and `\"key\": -,` → `\"key\": 0,`\n */\nfunction repairTruncatedNumbers(json: string): string {\n\t// Bare comma after colon (missing value entirely)\n\tlet repaired = json.replace(/:\\s*,/g, \": 0,\");\n\t// Bare minus sign followed by comma or closing brace\n\trepaired = repaired.replace(/:\\s*-\\s*([,}])/g, \": 0$1\");\n\treturn repaired;\n}\n\n/**\n * Attempt to repair malformed JSON in LLM tool-call arguments.\n *\n * Handles three categories of malformation:\n *\n * 1. **YAML bullet lists** (#2660): `\"key\": - item1\\n  - item2` → `\"key\": [\"item1\", \"item2\"]`\n * 2. **XML parameter tags** (#3403): `<parameter name=\"X\">value</parameter>` → stripped to content\n * 3. **Truncated numbers** (#3464): `\"exitCode\": -,` → `\"exitCode\": 0,`\n *\n * Returns the original string unchanged if no patterns are detected\n * or if the repair itself would produce invalid JSON.\n */\nexport function repairToolJson(json: string): string {\n\tlet repaired = json;\n\n\t// Phase 1: Strip XML parameter tags\n\tif (hasXmlParameterTags(repaired)) {\n\t\trepaired = promoteXmlParametersToTopLevel(repaired);\n\t}\n\n\t// Phase 2: Repair truncated numbers\n\tif (hasTruncatedNumbers(repaired)) {\n\t\trepaired = repairTruncatedNumbers(repaired);\n\t}\n\n\t// Phase 3: Repair YAML bullet lists\n\tif (!hasYamlBulletLists(repaired)) {\n\t\treturn repaired;\n\t}\n\n\t// Strategy: find each `\"key\": - item1\\n  - item2\\n  - item3` region and\n\t// wrap items in a JSON array.\n\t//\n\t// We work on the raw string because the JSON is not parseable yet.\n\t// The pattern we target:\n\t//   \"someKey\":\\s*- item text (possibly multiline)\n\t//   optionally followed by more `- item` lines\n\t//   terminated by the next `\"key\":` or `}` or end of string.\n\n\t// Match a key followed by YAML-style bullet list.\n\t// Capture: (1) the key portion including colon, (2) the bullet-list body,\n\t// (3) the separator (comma or empty) before the next key/bracket.\n\t// The bullet list body ends at the next `\"key\":` or `}` or `]` or end of string.\n\tconst keyBulletPattern =\n\t\t/(\"(?:[^\"\\\\]|\\\\.)*\"\\s*:\\s*)(- .+?)(,?\\s*)(?=\"(?:[^\"\\\\]|\\\\.)*\"\\s*:|[}\\]]|$)/gs;\n\n\trepaired = repaired.replace(\n\t\tkeyBulletPattern,\n\t\t(_match, keyPart: string, bulletBody: string, separator: string) => {\n\t\t\t// Split the bullet body into individual items on `- ` boundaries.\n\t\t\t// Items may contain embedded newlines for multi-line values.\n\t\t\tconst items = bulletBody\n\t\t\t\t.split(/\\n?\\s*- /)\n\t\t\t\t.filter((s) => s.trim().length > 0)\n\t\t\t\t.map((s) => s.replace(/,\\s*$/, \"\").trim());\n\n\t\t\t// JSON-encode each item as a string, then wrap in an array.\n\t\t\tconst jsonArray = \"[\" + items.map((item) => JSON.stringify(item)).join(\", \") + \"]\";\n\n\t\t\t// Re-emit the separator (comma) so the next key is properly delimited\n\t\t\tconst sep = separator.trim() ? separator : (/^\\s*\"/.test(separator + \"x\") ? \", \" : \"\");\n\t\t\treturn keyPart + jsonArray + sep;\n\t\t},\n\t);\n\n\t// Strip trailing commas before } or ] (common in repaired JSON)\n\trepaired = repaired.replace(/,(\\s*[}\\]])/g, \"$1\");\n\n\treturn repaired;\n}\n"]}
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closingTagIndex);\n\n\treturn value.slice(0, cut).trimEnd();\n}\n\n/**\n * Strip XML `<parameter>` tags from a JSON string, leaving only the\n * text content. This handles the case where the LLM mixes XML\n * tool-call format into JSON string values.\n */\nfunction stripXmlParameterTags(json: string): string {\n\t// Remove opening tags: <parameter name=\"X\">\n\tlet cleaned = json.replace(/<parameter\\s+name=\"[^\"]*\"\\s*>/g, \"\");\n\t// Remove closing tags: </parameter>\n\tcleaned = cleaned.replace(/<\\/parameter>/g, \"\");\n\treturn cleaned;\n}\n\nfunction promoteXmlParametersToTopLevel(json: string): string {\n\ttry {\n\t\tconst parsed = JSON.parse(json) as Record<string, unknown>;\n\t\tif (!parsed || typeof parsed !== \"object\" || Array.isArray(parsed)) {\n\t\t\treturn stripXmlParameterTags(json);\n\t\t}\n\n\t\tlet changed = false;\n\t\tfor (const [fieldName, value] of Object.entries(parsed)) {\n\t\t\tif (typeof value !== \"string\" || !hasXmlParameterTags(value)) continue;\n\n\t\t\tconst blocks = extractXmlParameterBlocks(value);\n\t\t\tif (blocks.length === 0) continue;\n\n\t\t\tparsed[fieldName] = trimLeakedXmlTail(fieldName, value);\n\t\t\tfor (const block of blocks) {\n\t\t\t\tif (!(block.name in parsed)) {\n\t\t\t\t\tparsed[block.name] = block.value;\n\t\t\t\t}\n\t\t\t}\n\t\t\tchanged = true;\n\t\t}\n\n\t\treturn changed ? JSON.stringify(parsed) : stripXmlParameterTags(json);\n\t} catch {\n\t\treturn stripXmlParameterTags(json);\n\t}\n}\n\n/**\n * Replace truncated numeric values with 0.\n * Handles: `\"key\": ,` → `\"key\": 0,` and `\"key\": -,` → `\"key\": 0,`\n */\nfunction repairTruncatedNumbers(json: string): string {\n\t// Bare comma after colon (missing value entirely)\n\tlet repaired = json.replace(/:\\s*,/g, \": 0,\");\n\t// Bare minus sign followed by comma or closing brace\n\trepaired = repaired.replace(/:\\s*-\\s*([,}])/g, \": 0$1\");\n\treturn repaired;\n}\n\n/**\n * Attempt to repair malformed JSON in LLM tool-call arguments.\n *\n * Handles three categories of malformation:\n *\n * 1. **YAML bullet lists** (#2660): `\"key\": - item1\\n  - item2` → `\"key\": [\"item1\", \"item2\"]`\n * 2. **XML parameter tags** (#3403): `<parameter name=\"X\">value</parameter>` → stripped to content\n * 3. **Truncated numbers** (#3464): `\"exitCode\": -,` → `\"exitCode\": 0,`\n *\n * Returns the original string unchanged if no patterns are detected\n * or if the repair itself would produce invalid JSON.\n */\nexport function repairToolJson(json: string): string {\n\tlet repaired = json;\n\n\t// Phase 1: Strip XML parameter tags\n\tif (hasXmlParameterTags(repaired)) {\n\t\trepaired = promoteXmlParametersToTopLevel(repaired);\n\t}\n\n\t// Phase 2: Repair truncated numbers\n\tif (hasTruncatedNumbers(repaired)) {\n\t\trepaired = repairTruncatedNumbers(repaired);\n\t}\n\n\t// Phase 3: Repair YAML bullet lists\n\tif (!hasYamlBulletLists(repaired)) {\n\t\treturn repaired;\n\t}\n\n\t// Strategy: find each `\"key\": - item1\\n  - item2\\n  - item3` region and\n\t// wrap items in a JSON array.\n\t//\n\t// We work on the raw string because the JSON is not parseable yet.\n\t// The pattern we target:\n\t//   \"someKey\":\\s*- item text (possibly multiline)\n\t//   optionally followed by more `- item` lines\n\t//   terminated by the next `\"key\":` or `}` or end of string.\n\n\t// Match a key followed by YAML-style bullet list.\n\t// Capture: (1) the key portion including colon, (2) the bullet-list body,\n\t// (3) the separator (comma or empty) before the next key/bracket.\n\t// The bullet list body ends at the next `\"key\":` or `}` or `]` or end of string.\n\tconst keyBulletPattern =\n\t\t/(\"(?:[^\"\\\\]|\\\\.)*\"\\s*:\\s*)(- .+?)(,?\\s*)(?=\"(?:[^\"\\\\]|\\\\.)*\"\\s*:|[}\\]]|$)/gs;\n\n\trepaired = repaired.replace(\n\t\tkeyBulletPattern,\n\t\t(_match, keyPart: string, bulletBody: string, separator: string) => {\n\t\t\t// Split the bullet body into individual items on `- ` boundaries.\n\t\t\t// Items may contain embedded newlines for multi-line values.\n\t\t\tconst items = bulletBody\n\t\t\t\t.split(/\\n?\\s*- /)\n\t\t\t\t.filter((s) => s.trim().length > 0)\n\t\t\t\t.map((s) => s.replace(/,\\s*$/, \"\").trim());\n\n\t\t\t// JSON-encode each item as a string, then wrap in an array.\n\t\t\tconst jsonArray = \"[\" + items.map((item) => JSON.stringify(item)).join(\", \") + \"]\";\n\n\t\t\t// Re-emit the separator (comma) so the next key is properly delimited\n\t\t\tconst sep = separator.trim() ? separator : (/^\\s*\"/.test(separator + \"x\") ? \", \" : \"\");\n\t\t\treturn keyPart + jsonArray + sep;\n\t\t},\n\t);\n\n\t// Strip trailing commas before } or ] (common in repaired JSON)\n\trepaired = repaired.replace(/,(\\s*[}\\]])/g, \"$1\");\n\n\treturn repaired;\n}\n"]}

package/packages/pi-ai/dist/utils/tests/repair-tool-json.test.js

@@ -103,6 +103,32 @@ describe("repairToolJson — XML parameter tag stripping (#3403)", () => {
         assert.equal(parsed.oneLiner, "done");
         assert.ok(!parsed.narrative.includes("<parameter"), "narrative should not retain leaked XML");
     });
+    test("promotes dangling XML parameters trapped inside valid JSON string values", () => {
+        const malformed = JSON.stringify({
+            narrative: 'text.\n<parameter name="verification">all tests pass\n<parameter name="verificationEvidence">["npm test"]',
+            oneLiner: "done",
+        });
+        const repaired = repairToolJson(malformed);
+        const parsed = JSON.parse(repaired);
+        assert.equal(parsed.narrative, "text.");
+        assert.equal(parsed.verification, "all tests pass");
+        assert.deepEqual(parsed.verificationEvidence, ["npm test"]);
+        assert.equal(parsed.oneLiner, "done");
+        assert.ok(!parsed.narrative.includes("<parameter"), "narrative should not retain leaked XML");
+    });
+    test("promotes mixed dangling and closed XML parameters from valid JSON string values", () => {
+        const malformed = JSON.stringify({
+            narrative: 'text.\n<parameter name="verification">all tests pass\n<parameter name="verificationEvidence">["npm test"]</parameter>',
+            oneLiner: "done",
+        });
+        const repaired = repairToolJson(malformed);
+        const parsed = JSON.parse(repaired);
+        assert.equal(parsed.narrative, "text.");
+        assert.equal(parsed.verification, "all tests pass");
+        assert.deepEqual(parsed.verificationEvidence, ["npm test"]);
+        assert.equal(parsed.oneLiner, "done");
+        assert.ok(!parsed.narrative.includes("<parameter"), "narrative should not retain leaked XML");
+    });
 });
 // ═══════════════════════════════════════════════════════════════════════════
 // Truncated number repair (#3464)

package/packages/pi-ai/dist/utils/tests/repair-tool-json.test.js.map

@@ -1 +1 @@
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{ describe, test } from \"node:test\";\nimport assert from \"node:assert/strict\";\nimport { repairToolJson, hasYamlBulletLists, hasXmlParameterTags, hasTruncatedNumbers } from \"../repair-tool-json.js\";\n\ndescribe(\"repairToolJson — YAML bullet list repair (#2660)\", () => {\n\t// ── Detection ──────────────────────────────────────────────────────────\n\n\ttest(\"hasYamlBulletLists detects YAML-style bullets\", () => {\n\t\tassert.equal(\n\t\t\thasYamlBulletLists('\"keyDecisions\": - Used Web Notification API'),\n\t\t\ttrue,\n\t\t);\n\t});\n\n\ttest(\"hasYamlBulletLists ignores negative numbers\", () => {\n\t\tassert.equal(\n\t\t\thasYamlBulletLists('\"offset\": -1'),\n\t\t\tfalse,\n\t\t\t\"negative number should not be detected as YAML bullet\",\n\t\t);\n\t});\n\n\ttest(\"hasYamlBulletLists returns false for valid JSON\", () => {\n\t\tassert.equal(\n\t\t\thasYamlBulletLists('{\"keyDecisions\": [\"item1\", \"item2\"]}'),\n\t\t\tfalse,\n\t\t);\n\t});\n\n\t// ── Single bullet item ────────────────────────────────────────────────\n\n\ttest(\"repairs single YAML bullet to JSON array\", () => {\n\t\tconst malformed = '{\"keyDecisions\": - Used Web Notification API}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.deepEqual(parsed.keyDecisions, [\"Used Web Notification API\"]);\n\t});\n\n\t// ── Multiple bullet items (newline-separated) ─────────────────────────\n\n\ttest(\"repairs multiple YAML bullets separated by newlines\", () => {\n\t\tconst malformed =\n\t\t\t'{\"keyDecisions\": - Used Web Notification API\\n  - Chose Tauri over Electron\\n  - Adopted SQLite for storage, \"title\": \"M005\"}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.deepEqual(parsed.keyDecisions, [\n\t\t\t\"Used Web Notification API\",\n\t\t\t\"Chose Tauri over Electron\",\n\t\t\t\"Adopted SQLite for storage\",\n\t\t]);\n\t\tassert.equal(parsed.title, \"M005\");\n\t});\n\n\t// ── Multiple fields with YAML bullets ─────────────────────────────────\n\n\ttest(\"repairs multiple fields each with YAML bullet lists\", () => {\n\t\tconst malformed =\n\t\t\t'{\"keyDecisions\": - decision one\\n  - decision two, \"keyFiles\": - src/lib.rs — Extended menu\\n  - src/main.ts — Entry point, \"title\": \"done\"}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.deepEqual(parsed.keyDecisions, [\"decision one\", \"decision two\"]);\n\t\tassert.deepEqual(parsed.keyFiles, [\n\t\t\t\"src/lib.rs \\u2014 Extended menu\",\n\t\t\t\"src/main.ts \\u2014 Entry point\",\n\t\t]);\n\t\tassert.equal(parsed.title, \"done\");\n\t});\n\n\t// ── Exact reproduction from issue #2660 ───────────────────────────────\n\n\ttest(\"repairs the exact malformed JSON from issue #2660\", () => {\n\t\tconst malformed = `{\"milestoneId\": \"M005\", \"title\": \"Native Desktop Polish\", \"oneLiner\": \"summary\", \"narrative\": \"details\", \"successCriteriaResults\": \"all pass\", \"definitionOfDoneResults\": \"all done\", \"requirementOutcomes\": \"met\", \"keyDecisions\": - Used Web Notification API (new window.Notification()) instead of Tauri sendNotification wrapper, \"keyFiles\": - src-tauri/src/lib.rs \\u2014 Extended menu builder with notification toggle, \"lessonsLearned\": - Always test notification permissions before sending, \"followUps\": \"none\", \"deviations\": \"none\", \"verificationPassed\": true}`;\n\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\n\t\tassert.equal(parsed.milestoneId, \"M005\");\n\t\tassert.equal(parsed.title, \"Native Desktop Polish\");\n\t\tassert.ok(Array.isArray(parsed.keyDecisions), \"keyDecisions should be an array\");\n\t\tassert.ok(parsed.keyDecisions[0].includes(\"Web Notification API\"));\n\t\tassert.ok(Array.isArray(parsed.keyFiles), \"keyFiles should be an array\");\n\t\tassert.ok(parsed.keyFiles[0].includes(\"src-tauri/src/lib.rs\"));\n\t\tassert.ok(Array.isArray(parsed.lessonsLearned), \"lessonsLearned should be an array\");\n\t\tassert.equal(parsed.verificationPassed, true);\n\t});\n\n\t// ── Passthrough for valid JSON ────────────────────────────────────────\n\n\ttest(\"returns valid JSON unchanged\", () => {\n\t\tconst valid = '{\"keyDecisions\": [\"item1\", \"item2\"], \"count\": -5}';\n\t\tconst result = repairToolJson(valid);\n\t\tassert.equal(result, valid, \"valid JSON should be returned unchanged\");\n\t});\n\n\t// ── Negative numbers are preserved ────────────────────────────────────\n\n\ttest(\"does not mangle negative numbers\", () => {\n\t\tconst valid = '{\"offset\": -1, \"limit\": -100}';\n\t\tconst result = repairToolJson(valid);\n\t\tassert.equal(result, valid);\n\t});\n});\n\n// ═══════════════════════════════════════════════════════════════════════════\n// XML parameter tag repair (#3403)\n// ═══════════════════════════════════════════════════════════════════════════\n\ndescribe(\"repairToolJson — XML parameter tag stripping (#3403)\", () => {\n\ttest(\"hasXmlParameterTags detects opening tags\", () => {\n\t\tassert.equal(\n\t\t\thasXmlParameterTags('<parameter name=\"narrative\">some text</parameter>'),\n\t\t\ttrue,\n\t\t);\n\t});\n\n\ttest(\"hasXmlParameterTags returns false for clean JSON\", () => {\n\t\tassert.equal(\n\t\t\thasXmlParameterTags('{\"narrative\": \"some text\"}'),\n\t\t\tfalse,\n\t\t);\n\t});\n\n\ttest(\"strips XML parameter tags from JSON values\", () => {\n\t\tconst malformed = '{\"sliceId\": \"S03\", \"narrative\": <parameter name=\"narrative\">The slice work</parameter>}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\t// After stripping tags, the content should be parseable or at least tag-free\n\t\tassert.ok(!repaired.includes(\"<parameter\"), \"should not contain <parameter tags\");\n\t\tassert.ok(!repaired.includes(\"</parameter>\"), \"should not contain </parameter> tags\");\n\t});\n\n\ttest(\"handles mixed XML and JSON content\", () => {\n\t\tconst malformed = '{\"oneLiner\": \"done\", \"verification\": <parameter name=\"verification\">all tests pass</parameter>}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tassert.ok(!repaired.includes(\"<parameter\"), \"XML tags should be stripped\");\n\t\tassert.ok(repaired.includes(\"all tests pass\"), \"content should be preserved\");\n\t});\n\n\ttest(\"promotes XML parameters trapped inside valid JSON string values\", () => {\n\t\tconst malformed =\n\t\t\t'{\"narrative\":\"text.</narrative>\\\\n<parameter name=\\\\\"verification\\\\\">all tests pass</parameter>\\\\n<parameter name=\\\\\"verificationEvidence\\\\\">[\\\\\"npm test\\\\\"]</parameter>\",\"oneLiner\":\"done\"}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\n\t\tassert.equal(parsed.narrative, \"text.\");\n\t\tassert.equal(parsed.verification, \"all tests pass\");\n\t\tassert.deepEqual(parsed.verificationEvidence, [\"npm test\"]);\n\t\tassert.equal(parsed.oneLiner, \"done\");\n\t\tassert.ok(!parsed.narrative.includes(\"<parameter\"), \"narrative should not retain leaked XML\");\n\t});\n});\n\n// ═══════════════════════════════════════════════════════════════════════════\n// Truncated number repair (#3464)\n// ═══════════════════════════════════════════════════════════════════════════\n\ndescribe(\"repairToolJson — truncated number repair (#3464)\", () => {\n\ttest(\"hasTruncatedNumbers detects bare comma after colon\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": ,'), true);\n\t});\n\n\ttest(\"hasTruncatedNumbers detects bare minus before comma\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": -,'), true);\n\t});\n\n\ttest(\"hasTruncatedNumbers detects bare minus before closing brace\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"durationMs\": -}'), true);\n\t});\n\n\ttest(\"hasTruncatedNumbers returns false for valid numbers\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": 0, \"durationMs\": 1234'), false);\n\t});\n\n\ttest(\"hasTruncatedNumbers returns false for negative numbers\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": -1, \"offset\": -100'), false);\n\t});\n\n\ttest(\"repairs truncated exitCode with bare comma\", () => {\n\t\tconst malformed = '{\"command\": \"npm test\", \"exitCode\": , \"verdict\": \"pass\", \"durationMs\": 500}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.exitCode, 0);\n\t\tassert.equal(parsed.durationMs, 500);\n\t});\n\n\ttest(\"repairs truncated exitCode with bare minus\", () => {\n\t\tconst malformed = '{\"command\": \"npm test\", \"exitCode\": -, \"verdict\": \"pass\", \"durationMs\": 1234}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.exitCode, 0);\n\t\tassert.equal(parsed.verdict, \"pass\");\n\t});\n\n\ttest(\"repairs truncated durationMs at end of object\", () => {\n\t\tconst malformed = '{\"command\": \"npm test\", \"exitCode\": 0, \"verdict\": \"pass\", \"durationMs\": -}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.durationMs, 0);\n\t\tassert.equal(parsed.exitCode, 0);\n\t});\n\n\ttest(\"does not mangle valid negative numbers\", () => {\n\t\tconst valid = '{\"exitCode\": -1, \"offset\": -100}';\n\t\tconst repaired = repairToolJson(valid);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.exitCode, -1);\n\t\tassert.equal(parsed.offset, -100);\n\t});\n});\n"]}
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{ describe, test } from \"node:test\";\nimport assert from \"node:assert/strict\";\nimport { repairToolJson, hasYamlBulletLists, hasXmlParameterTags, hasTruncatedNumbers } from \"../repair-tool-json.js\";\n\ndescribe(\"repairToolJson — YAML bullet list repair (#2660)\", () => {\n\t// ── Detection ──────────────────────────────────────────────────────────\n\n\ttest(\"hasYamlBulletLists detects YAML-style bullets\", () => {\n\t\tassert.equal(\n\t\t\thasYamlBulletLists('\"keyDecisions\": - Used Web Notification API'),\n\t\t\ttrue,\n\t\t);\n\t});\n\n\ttest(\"hasYamlBulletLists ignores negative numbers\", () => {\n\t\tassert.equal(\n\t\t\thasYamlBulletLists('\"offset\": -1'),\n\t\t\tfalse,\n\t\t\t\"negative number should not be detected as YAML bullet\",\n\t\t);\n\t});\n\n\ttest(\"hasYamlBulletLists returns false for valid JSON\", () => {\n\t\tassert.equal(\n\t\t\thasYamlBulletLists('{\"keyDecisions\": [\"item1\", \"item2\"]}'),\n\t\t\tfalse,\n\t\t);\n\t});\n\n\t// ── Single bullet item ────────────────────────────────────────────────\n\n\ttest(\"repairs single YAML bullet to JSON array\", () => {\n\t\tconst malformed = '{\"keyDecisions\": - Used Web Notification API}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.deepEqual(parsed.keyDecisions, [\"Used Web Notification API\"]);\n\t});\n\n\t// ── Multiple bullet items (newline-separated) ─────────────────────────\n\n\ttest(\"repairs multiple YAML bullets separated by newlines\", () => {\n\t\tconst malformed =\n\t\t\t'{\"keyDecisions\": - Used Web Notification API\\n  - Chose Tauri over Electron\\n  - Adopted SQLite for storage, \"title\": \"M005\"}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.deepEqual(parsed.keyDecisions, [\n\t\t\t\"Used Web Notification API\",\n\t\t\t\"Chose Tauri over Electron\",\n\t\t\t\"Adopted SQLite for storage\",\n\t\t]);\n\t\tassert.equal(parsed.title, \"M005\");\n\t});\n\n\t// ── Multiple fields with YAML bullets ─────────────────────────────────\n\n\ttest(\"repairs multiple fields each with YAML bullet lists\", () => {\n\t\tconst malformed =\n\t\t\t'{\"keyDecisions\": - decision one\\n  - decision two, \"keyFiles\": - src/lib.rs — Extended menu\\n  - src/main.ts — Entry point, \"title\": \"done\"}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.deepEqual(parsed.keyDecisions, [\"decision one\", \"decision two\"]);\n\t\tassert.deepEqual(parsed.keyFiles, [\n\t\t\t\"src/lib.rs \\u2014 Extended menu\",\n\t\t\t\"src/main.ts \\u2014 Entry point\",\n\t\t]);\n\t\tassert.equal(parsed.title, \"done\");\n\t});\n\n\t// ── Exact reproduction from issue #2660 ───────────────────────────────\n\n\ttest(\"repairs the exact malformed JSON from issue #2660\", () => {\n\t\tconst malformed = `{\"milestoneId\": \"M005\", \"title\": \"Native Desktop Polish\", \"oneLiner\": \"summary\", \"narrative\": \"details\", \"successCriteriaResults\": \"all pass\", \"definitionOfDoneResults\": \"all done\", \"requirementOutcomes\": \"met\", \"keyDecisions\": - Used Web Notification API (new window.Notification()) instead of Tauri sendNotification wrapper, \"keyFiles\": - src-tauri/src/lib.rs \\u2014 Extended menu builder with notification toggle, \"lessonsLearned\": - Always test notification permissions before sending, \"followUps\": \"none\", \"deviations\": \"none\", \"verificationPassed\": true}`;\n\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\n\t\tassert.equal(parsed.milestoneId, \"M005\");\n\t\tassert.equal(parsed.title, \"Native Desktop Polish\");\n\t\tassert.ok(Array.isArray(parsed.keyDecisions), \"keyDecisions should be an array\");\n\t\tassert.ok(parsed.keyDecisions[0].includes(\"Web Notification API\"));\n\t\tassert.ok(Array.isArray(parsed.keyFiles), \"keyFiles should be an array\");\n\t\tassert.ok(parsed.keyFiles[0].includes(\"src-tauri/src/lib.rs\"));\n\t\tassert.ok(Array.isArray(parsed.lessonsLearned), \"lessonsLearned should be an array\");\n\t\tassert.equal(parsed.verificationPassed, true);\n\t});\n\n\t// ── Passthrough for valid JSON ────────────────────────────────────────\n\n\ttest(\"returns valid JSON unchanged\", () => {\n\t\tconst valid = '{\"keyDecisions\": [\"item1\", \"item2\"], \"count\": -5}';\n\t\tconst result = repairToolJson(valid);\n\t\tassert.equal(result, valid, \"valid JSON should be returned unchanged\");\n\t});\n\n\t// ── Negative numbers are preserved ────────────────────────────────────\n\n\ttest(\"does not mangle negative numbers\", () => {\n\t\tconst valid = '{\"offset\": -1, \"limit\": -100}';\n\t\tconst result = repairToolJson(valid);\n\t\tassert.equal(result, valid);\n\t});\n});\n\n// ═══════════════════════════════════════════════════════════════════════════\n// XML parameter tag repair (#3403)\n// ═══════════════════════════════════════════════════════════════════════════\n\ndescribe(\"repairToolJson — XML parameter tag stripping (#3403)\", () => {\n\ttest(\"hasXmlParameterTags detects opening tags\", () => {\n\t\tassert.equal(\n\t\t\thasXmlParameterTags('<parameter name=\"narrative\">some text</parameter>'),\n\t\t\ttrue,\n\t\t);\n\t});\n\n\ttest(\"hasXmlParameterTags returns false for clean JSON\", () => {\n\t\tassert.equal(\n\t\t\thasXmlParameterTags('{\"narrative\": \"some text\"}'),\n\t\t\tfalse,\n\t\t);\n\t});\n\n\ttest(\"strips XML parameter tags from JSON values\", () => {\n\t\tconst malformed = '{\"sliceId\": \"S03\", \"narrative\": <parameter name=\"narrative\">The slice work</parameter>}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\t// After stripping tags, the content should be parseable or at least tag-free\n\t\tassert.ok(!repaired.includes(\"<parameter\"), \"should not contain <parameter tags\");\n\t\tassert.ok(!repaired.includes(\"</parameter>\"), \"should not contain </parameter> tags\");\n\t});\n\n\ttest(\"handles mixed XML and JSON content\", () => {\n\t\tconst malformed = '{\"oneLiner\": \"done\", \"verification\": <parameter name=\"verification\">all tests pass</parameter>}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tassert.ok(!repaired.includes(\"<parameter\"), \"XML tags should be stripped\");\n\t\tassert.ok(repaired.includes(\"all tests pass\"), \"content should be preserved\");\n\t});\n\n\ttest(\"promotes XML parameters trapped inside valid JSON string values\", () => {\n\t\tconst malformed =\n\t\t\t'{\"narrative\":\"text.</narrative>\\\\n<parameter name=\\\\\"verification\\\\\">all tests pass</parameter>\\\\n<parameter name=\\\\\"verificationEvidence\\\\\">[\\\\\"npm test\\\\\"]</parameter>\",\"oneLiner\":\"done\"}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\n\t\tassert.equal(parsed.narrative, \"text.\");\n\t\tassert.equal(parsed.verification, \"all tests pass\");\n\t\tassert.deepEqual(parsed.verificationEvidence, [\"npm test\"]);\n\t\tassert.equal(parsed.oneLiner, \"done\");\n\t\tassert.ok(!parsed.narrative.includes(\"<parameter\"), \"narrative should not retain leaked XML\");\n\t});\n\n\ttest(\"promotes dangling XML parameters trapped inside valid JSON string values\", () => {\n\t\tconst malformed = JSON.stringify({\n\t\t\tnarrative:\n\t\t\t\t'text.\\n<parameter name=\"verification\">all tests pass\\n<parameter name=\"verificationEvidence\">[\"npm test\"]',\n\t\t\toneLiner: \"done\",\n\t\t});\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\n\t\tassert.equal(parsed.narrative, \"text.\");\n\t\tassert.equal(parsed.verification, \"all tests pass\");\n\t\tassert.deepEqual(parsed.verificationEvidence, [\"npm test\"]);\n\t\tassert.equal(parsed.oneLiner, \"done\");\n\t\tassert.ok(!parsed.narrative.includes(\"<parameter\"), \"narrative should not retain leaked XML\");\n\t});\n\n\ttest(\"promotes mixed dangling and closed XML parameters from valid JSON string values\", () => {\n\t\tconst malformed = JSON.stringify({\n\t\t\tnarrative:\n\t\t\t\t'text.\\n<parameter name=\"verification\">all tests pass\\n<parameter name=\"verificationEvidence\">[\"npm test\"]</parameter>',\n\t\t\toneLiner: \"done\",\n\t\t});\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\n\t\tassert.equal(parsed.narrative, \"text.\");\n\t\tassert.equal(parsed.verification, \"all tests pass\");\n\t\tassert.deepEqual(parsed.verificationEvidence, [\"npm test\"]);\n\t\tassert.equal(parsed.oneLiner, \"done\");\n\t\tassert.ok(!parsed.narrative.includes(\"<parameter\"), \"narrative should not retain leaked XML\");\n\t});\n});\n\n// ═══════════════════════════════════════════════════════════════════════════\n// Truncated number repair (#3464)\n// ═══════════════════════════════════════════════════════════════════════════\n\ndescribe(\"repairToolJson — truncated number repair (#3464)\", () => {\n\ttest(\"hasTruncatedNumbers detects bare comma after colon\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": ,'), true);\n\t});\n\n\ttest(\"hasTruncatedNumbers detects bare minus before comma\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": -,'), true);\n\t});\n\n\ttest(\"hasTruncatedNumbers detects bare minus before closing brace\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"durationMs\": -}'), true);\n\t});\n\n\ttest(\"hasTruncatedNumbers returns false for valid numbers\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": 0, \"durationMs\": 1234'), false);\n\t});\n\n\ttest(\"hasTruncatedNumbers returns false for negative numbers\", () => {\n\t\tassert.equal(hasTruncatedNumbers('\"exitCode\": -1, \"offset\": -100'), false);\n\t});\n\n\ttest(\"repairs truncated exitCode with bare comma\", () => {\n\t\tconst malformed = '{\"command\": \"npm test\", \"exitCode\": , \"verdict\": \"pass\", \"durationMs\": 500}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.exitCode, 0);\n\t\tassert.equal(parsed.durationMs, 500);\n\t});\n\n\ttest(\"repairs truncated exitCode with bare minus\", () => {\n\t\tconst malformed = '{\"command\": \"npm test\", \"exitCode\": -, \"verdict\": \"pass\", \"durationMs\": 1234}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.exitCode, 0);\n\t\tassert.equal(parsed.verdict, \"pass\");\n\t});\n\n\ttest(\"repairs truncated durationMs at end of object\", () => {\n\t\tconst malformed = '{\"command\": \"npm test\", \"exitCode\": 0, \"verdict\": \"pass\", \"durationMs\": -}';\n\t\tconst repaired = repairToolJson(malformed);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.durationMs, 0);\n\t\tassert.equal(parsed.exitCode, 0);\n\t});\n\n\ttest(\"does not mangle valid negative numbers\", () => {\n\t\tconst valid = '{\"exitCode\": -1, \"offset\": -100}';\n\t\tconst repaired = repairToolJson(valid);\n\t\tconst parsed = JSON.parse(repaired);\n\t\tassert.equal(parsed.exitCode, -1);\n\t\tassert.equal(parsed.offset, -100);\n\t});\n});\n"]}

package/packages/pi-ai/package.json

@@ -1,6 +1,6 @@
 {
   "name": "@gsd/pi-ai",
-  "version": "2.78.0",
+  "version": "2.78.1",
   "description": "Unified LLM API (vendored from pi-mono)",
   "type": "module",
   "gsd": {

package/packages/pi-ai/src/providers/anthropic-bearer-auth.test.ts

@@ -1,9 +1,15 @@
 import assert from "node:assert/strict";
 import { describe, it } from "node:test";
-import { readFileSync } from "node:fs";
+import { existsSync, readFileSync } from "node:fs";
 import { join } from "node:path";
 
-const source = readFileSync(join(import.meta.dirname, "anthropic.ts"), "utf-8");
+function resolveSourcePath(fileName: string): string {
+	const localPath = join(import.meta.dirname, fileName);
+	if (existsSync(localPath)) return localPath;
+	return join(import.meta.dirname, "..", "..", "src", "providers", fileName);
+}
+
+const source = readFileSync(resolveSourcePath("anthropic.ts"), "utf-8");
 
 describe("anthropic bearer auth for custom providers (#3874)", () => {
 	it("treats Bearer Authorization headers as authToken-capable providers", () => {

package/packages/pi-ai/src/providers/anthropic-shared.cache-breakpoint.test.ts

@@ -0,0 +1,289 @@
+// @gsd/pi-ai + anthropic-shared.cache-breakpoint.test — coverage for #5027.
+// `convertMessages` must apply Anthropic `cache_control` to:
+//   - the last message (existing volatile-suffix anchor — preserved)
+//   - the most recent message flagged with `cacheBreakpoint: true`
+//     (new compaction-boundary anchor)
+// And it must NOT exceed the 4-breakpoint limit by treating multiple
+// breakpoints as one — only the most recent earns the marker.
+
+import { describe, test } from "node:test";
+import assert from "node:assert/strict";
+
+import { buildParams, convertMessages } from "./anthropic-shared.js";
+import type { Context, Message, Model, Tool } from "../types.js";
+import type { AnthropicApi } from "./anthropic-shared.js";
+
+// Minimal model stub — convertMessages only reads `input` to decide whether to
+// drop image blocks. Returning ["image"] keeps the conversion paths exercised.
+const model = { input: ["text", "image"] } as unknown as Model<AnthropicApi>;
+const cacheControl = { type: "ephemeral" as const };
+
+function userMsg(text: string, opts: { cacheBreakpoint?: boolean } = {}): Message {
+	return {
+		role: "user",
+		content: text,
+		timestamp: 0,
+		...(opts.cacheBreakpoint ? { cacheBreakpoint: true } : {}),
+	} as Message;
+}
+
+/** Produces a UserMessage whose content is an array of text blocks —
+ * the production shape emitted by `convertToLlm()` for compaction summaries. */
+function userMsgArray(text: string, opts: { cacheBreakpoint?: boolean } = {}): Message {
+	return {
+		role: "user",
+		content: [{ type: "text", text }],
+		timestamp: 0,
+		...(opts.cacheBreakpoint ? { cacheBreakpoint: true } : {}),
+	} as Message;
+}
+
+function assistantMsg(text: string): Message {
+	return {
+		role: "assistant",
+		content: [{ type: "text", text }],
+		api: "anthropic-messages",
+		provider: "anthropic",
+		model: "claude-sonnet-4-6",
+		usage: {
+			input: 0, output: 0, cacheRead: 0, cacheWrite: 0, totalTokens: 0,
+			cost: { input: 0, output: 0, cacheRead: 0, cacheWrite: 0, total: 0 },
+		},
+		stopReason: "stop",
+		timestamp: 0,
+	} as Message;
+}
+
+/** Returns whether the message at the given index has cache_control on its last block. */
+function hasCacheControl(params: ReturnType<typeof convertMessages>, index: number): boolean {
+	const param = params[index];
+	if (!param || param.role !== "user") return false;
+	if (!Array.isArray(param.content)) return false;
+	const lastBlock = param.content[param.content.length - 1];
+	return Boolean(lastBlock && (lastBlock as any).cache_control);
+}
+
+describe("convertMessages — cache breakpoints (#5027)", () => {
+	test("with no cacheControl option: no breakpoints are placed", () => {
+		const result = convertMessages([userMsg("hello"), assistantMsg("hi"), userMsg("again")], model, false);
+		for (let i = 0; i < result.length; i++) {
+			assert.equal(hasCacheControl(result, i), false, `index ${i} should have no cache_control`);
+		}
+	});
+
+	test("no cacheBreakpoint anywhere: only the last message gets cache_control (existing behavior preserved)", () => {
+		const result = convertMessages(
+			[userMsg("first"), assistantMsg("response"), userMsg("second")],
+			model,
+			false,
+			cacheControl,
+		);
+		assert.equal(hasCacheControl(result, 0), false, "first user msg has no breakpoint");
+		assert.equal(hasCacheControl(result, result.length - 1), true, "last msg gets the volatile-suffix anchor");
+	});
+
+	test("one cacheBreakpoint message: both that message AND the last message get breakpoints", () => {
+		const result = convertMessages(
+			[
+				userMsg("ancient"),
+				assistantMsg("ancient response"),
+				userMsg("[COMPACTION SUMMARY]", { cacheBreakpoint: true }),
+				assistantMsg("post-compaction response"),
+				userMsg("new turn"),
+			],
+			model,
+			false,
+			cacheControl,
+		);
+		// Find the compaction-summary index (it's the third user-shaped param)
+		const compactionIdx = result.findIndex(
+			(p) => p.role === "user" && Array.isArray(p.content) && (p.content as any)[0]?.text?.includes("COMPACTION SUMMARY"),
+		);
+		assert.ok(compactionIdx >= 0, "compaction summary should be in the params");
+		assert.equal(hasCacheControl(result, compactionIdx), true, "compaction boundary gets a breakpoint");
+		assert.equal(hasCacheControl(result, result.length - 1), true, "last msg still gets the volatile-suffix anchor");
+	});
+
+	test("array-content cacheBreakpoint message: breakpoint is applied (production shape for compaction summary)", () => {
+		// convertToLlm() emits compaction summaries as content:[{type:"text",...}];
+		// this exercises the array-backed branch in anthropic-shared.ts.
+		const result = convertMessages(
+			[
+				userMsgArray("[COMPACTION SUMMARY]", { cacheBreakpoint: true }),
+				assistantMsg("post-compaction response"),
+				userMsg("post-compaction turn"),
+			],
+			model,
+			false,
+			cacheControl,
+		);
+		const compactionIdx = result.findIndex(
+			(p) =>
+				p.role === "user" &&
+				Array.isArray(p.content) &&
+				(p.content as any)[0]?.text?.includes("COMPACTION SUMMARY"),
+		);
+		assert.ok(compactionIdx >= 0, "compaction summary param should be present");
+		assert.equal(hasCacheControl(result, compactionIdx), true, "array-content boundary gets cache_control");
+		assert.equal(hasCacheControl(result, result.length - 1), true, "last msg still gets the volatile-suffix anchor");
+	});
+
+	test("multiple cacheBreakpoint messages: only the most recent one earns a breakpoint (4-limit safety)", () => {
+		const result = convertMessages(
+			[
+				userMsg("[OLD COMPACTION]", { cacheBreakpoint: true }),
+				assistantMsg("post-old response"),
+				userMsg("[NEW COMPACTION]", { cacheBreakpoint: true }),
+				assistantMsg("post-new response"),
+				userMsg("latest turn"),
+			],
+			model,
+			false,
+			cacheControl,
+		);
+		const oldIdx = result.findIndex(
+			(p) => p.role === "user" && Array.isArray(p.content) && (p.content as any)[0]?.text?.includes("OLD COMPACTION"),
+		);
+		const newIdx = result.findIndex(
+			(p) => p.role === "user" && Array.isArray(p.content) && (p.content as any)[0]?.text?.includes("NEW COMPACTION"),
+		);
+		assert.equal(hasCacheControl(result, oldIdx), false, "older boundary should not earn a breakpoint");
+		assert.equal(hasCacheControl(result, newIdx), true, "most recent boundary earns the breakpoint");
+		assert.equal(hasCacheControl(result, result.length - 1), true, "last msg still gets the volatile-suffix anchor");
+	});
+
+	test("cacheBreakpoint on the LAST message: only one breakpoint applied (deduplication)", () => {
+		// When the boundary message IS the last message, applying twice would be
+		// a no-op overwrite but the deduplication guard avoids the double-call.
+		const result = convertMessages(
+			[userMsg("hello"), userMsg("[BOUNDARY AS LAST]", { cacheBreakpoint: true })],
+			model,
+			false,
+			cacheControl,
+		);
+		assert.equal(hasCacheControl(result, result.length - 1), true);
+		// Only one user message besides the last, with no breakpoint
+		assert.equal(hasCacheControl(result, 0), false);
+	});
+
+	test("cacheBreakpoint flag is ignored when no cacheControl option is provided", () => {
+		const result = convertMessages(
+			[userMsg("[COMPACTION]", { cacheBreakpoint: true }), userMsg("turn")],
+			model,
+			false,
+		);
+		for (let i = 0; i < result.length; i++) {
+			assert.equal(hasCacheControl(result, i), false, `index ${i} should have no cache_control`);
+		}
+	});
+
+	test("array-content cacheBreakpoint on last message: deduplication guard prevents double application", () => {
+		// The boundary IS the last message — both anchors target the same param,
+		// so cache_control should appear exactly once.
+		const result = convertMessages(
+			[userMsg("prior turn"), userMsgArray("[BOUNDARY AS LAST]", { cacheBreakpoint: true })],
+			model,
+			false,
+			cacheControl,
+		);
+		const lastParam = result[result.length - 1];
+		assert.ok(lastParam && Array.isArray(lastParam.content), "last param has array content");
+		const cacheBlocks = (lastParam!.content as any[]).filter((b) => b.cache_control);
+		assert.equal(cacheBlocks.length, 1, "cache_control applied exactly once");
+		assert.equal(hasCacheControl(result, 0), false, "prior turn has no cache_control");
+	});
+});
+
+// ─── 4-breakpoint-limit safety at buildParams level (OAuth path) ──────────
+
+/** Count cache_control occurrences across system + tools + messages params. */
+function countBreakpoints(params: { system?: any; tools?: any[]; messages: any[] }): number {
+	let n = 0;
+	if (Array.isArray(params.system)) {
+		for (const block of params.system) if (block.cache_control) n++;
+	}
+	if (Array.isArray(params.tools)) {
+		for (const tool of params.tools) if ((tool as any).cache_control) n++;
+	}
+	for (const m of params.messages) {
+		if (m.role === "user" && Array.isArray(m.content)) {
+			for (const block of m.content) if (block.cache_control) n++;
+		}
+	}
+	return n;
+}
+
+const buildParamsModel = {
+	id: "claude-sonnet-4-6",
+	baseUrl: "https://api.anthropic.com",
+	api: "anthropic-messages",
+	input: ["text", "image"],
+	maxTokens: 64000,
+} as unknown as Model<AnthropicApi>;
+
+describe("buildParams — 4-breakpoint limit safety in OAuth + boundary scenario (#5027)", () => {
+	test("OAuth + system prompt + last user: ≤2 breakpoints (no boundary, no tools)", () => {
+		const ctx: Context = {
+			messages: [userMsg("hello")],
+			systemPrompt: "You are a helpful coding assistant.",
+		} as Context;
+		const params = buildParams(buildParamsModel, ctx, true) as any;
+		assert.ok(countBreakpoints(params) <= 4, `expected ≤4 breakpoints, got ${countBreakpoints(params)}`);
+		// One on user system block, one on last user msg.
+		assert.equal(countBreakpoints(params), 2);
+	});
+
+	test("OAuth + system prompt + boundary + last user: ≤3 breakpoints (system de-duplicated)", () => {
+		const ctx: Context = {
+			messages: [
+				userMsg("[COMPACTION SUMMARY]", { cacheBreakpoint: true }),
+				userMsg("post-compaction turn"),
+			],
+			systemPrompt: "You are a helpful coding assistant.",
+		} as Context;
+		const params = buildParams(buildParamsModel, ctx, true) as any;
+		const count = countBreakpoints(params);
+		assert.ok(count <= 4, `must stay under Anthropic's 4-breakpoint limit, got ${count}`);
+		// system(1, the user's prompt — Claude Code header skipped) + boundary(1) + last(1) = 3.
+		assert.equal(count, 3);
+	});
+
+	test("OAuth + system prompt + tools + boundary + last user: exactly 4 breakpoints (ceiling)", () => {
+		// Worst-case breakpoint budget:
+		//   system(user prompt, 1) + last tool(1) + boundary(1) + last user(1) = 4.
+		// The "You are Claude Code" header intentionally carries NO cache_control
+		// when a user systemPrompt is present (#5027), which keeps us at 4 rather than 5.
+		const tool: Tool = {
+			name: "Read",
+			description: "Read a file from disk.",
+			parameters: {
+				type: "object" as const,
+				properties: {
+					path: { type: "string" },
+				},
+				required: ["path"],
+			} as any,
+		};
+		const ctx: Context = {
+			messages: [
+				userMsg("[COMPACTION SUMMARY]", { cacheBreakpoint: true }),
+				userMsg("post-compaction turn"),
+			],
+			systemPrompt: "You are a helpful coding assistant.",
+			tools: [tool],
+		} as Context;
+		const params = buildParams(buildParamsModel, ctx, true) as any;
+		const count = countBreakpoints(params);
+		assert.ok(count <= 4, `must stay under Anthropic's 4-breakpoint limit, got ${count}`);
+		// system(1) + tool(1) + boundary(1) + last-user(1) = 4 exactly.
+		assert.equal(count, 4);
+	});
+
+	test("OAuth header WITHOUT user systemPrompt still cache-marks the header", () => {
+		// When there's no user systemPrompt, the Claude Code header IS the
+		// last system block, so it correctly carries cache_control.
+		const ctx: Context = { messages: [userMsg("hello")] } as Context;
+		const params = buildParams(buildParamsModel, ctx, true) as any;
+		assert.equal(countBreakpoints(params), 2, "header(1) + last user(1) = 2");
+	});
+});

package/packages/pi-ai/src/providers/anthropic-shared.ts

@@ -262,6 +262,11 @@ export function convertMessages(
 	cacheControl?: { type: "ephemeral"; ttl?: "1h" },
 ): MessageParam[] {
 	const params: MessageParam[] = [];
+	// Indices into `params` for messages flagged with `cacheBreakpoint: true` —
+	// e.g. compaction summaries. We apply cache_control to the most recent one
+	// (in addition to the last message) so the stable summary + kept-history
+	// block can earn cache reads on every post-compaction turn. (#5027)
+	const breakpointIndices: number[] = [];
 
 	const transformedMessages = transformMessagesWithReport(messages, model, normalizeToolCallId, "anthropic-messages");
 
@@ -275,6 +280,7 @@ export function convertMessages(
 						role: "user",
 						content: sanitizeSurrogates(msg.content),
 					});
+					if (msg.cacheBreakpoint) breakpointIndices.push(params.length - 1);
 				}
 			} else {
 				const blocks: ContentBlockParam[] = msg.content.map((item) => {
@@ -306,6 +312,7 @@ export function convertMessages(
 					role: "user",
 					content: filteredBlocks,
 				});
+				if (msg.cacheBreakpoint) breakpointIndices.push(params.length - 1);
 			}
 		} else if (msg.role === "assistant") {
 			const blocks: ContentBlockParam[] = [];
@@ -403,31 +410,50 @@ export function convertMessages(
 	}
 
 	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 (
-					lastBlock &&
-					(lastBlock.type === "text" || lastBlock.type === "image" || lastBlock.type === "tool_result")
-				) {
-					(lastBlock as any).cache_control = cacheControl;
-				}
-			} else if (typeof lastMessage.content === "string") {
-				lastMessage.content = [
-					{
-						type: "text",
-						text: lastMessage.content,
-						cache_control: cacheControl,
-					},
-				] as any;
-			}
+		// Apply to the volatile suffix anchor (last user message) — existing behavior.
+		applyCacheControlToParam(params, params.length - 1, cacheControl);
+
+		// Apply to the most recent compaction-boundary message, if any. Capping at
+		// one boundary keeps us safely under Anthropic's 4-breakpoint limit
+		// (system + tools + boundary + last user = 4). If multiple
+		// cacheBreakpoint messages are present, only the most recent one — the
+		// freshest stable boundary — earns the breakpoint. (#5027)
+		const mostRecentBreakpoint = breakpointIndices[breakpointIndices.length - 1];
+		if (mostRecentBreakpoint !== undefined && mostRecentBreakpoint !== params.length - 1) {
+			applyCacheControlToParam(params, mostRecentBreakpoint, cacheControl);
 		}
 	}
 
 	return params;
 }
 
+/** Apply `cache_control` to the last cacheable block of the user-role param at `index`. No-op for non-user roles. */
+function applyCacheControlToParam(
+	params: MessageParam[],
+	index: number,
+	cacheControl: { type: "ephemeral"; ttl?: "1h" },
+): void {
+	const param = params[index];
+	if (!param || param.role !== "user") return;
+	if (Array.isArray(param.content)) {
+		const lastBlock = param.content[param.content.length - 1];
+		if (
+			lastBlock &&
+			(lastBlock.type === "text" || lastBlock.type === "image" || lastBlock.type === "tool_result")
+		) {
+			(lastBlock as any).cache_control = cacheControl;
+		}
+	} else if (typeof param.content === "string") {
+		param.content = [
+			{
+				type: "text",
+				text: param.content,
+				cache_control: cacheControl,
+			},
+		] as any;
+	}
+}
+
 /** Convert GSD tools to Anthropic SDK tool definitions, applying cache control to the last entry. */
 export function convertTools(
 	tools: Tool[],
@@ -475,11 +501,17 @@ export function buildParams(
 	};
 
 	if (isOAuthToken) {
+		// Only the LAST system block carries `cache_control` — the boundary
+		// covers the entire system prefix up to that point. Putting cache_control
+		// on the short "You are Claude Code" header AND the user systemPrompt
+		// would consume two of Anthropic's 4 breakpoint slots for redundant
+		// coverage, leaving no room for a compaction-summary breakpoint. (#5027)
+		const hasUserSystemPrompt = Boolean(context.systemPrompt);
 		params.system = [
 			{
 				type: "text",
 				text: "You are Claude Code, Anthropic's official CLI for Claude.",
-				...(cacheControl ? { cache_control: cacheControl } : {}),
+				...(cacheControl && !hasUserSystemPrompt ? { cache_control: cacheControl } : {}),
 			},
 		];
 		if (context.systemPrompt) {