diff --git a/.gitignore b/.gitignore
index b542341..2ab2bc9 100644
--- a/.gitignore
+++ b/.gitignore
@@ -25,4 +25,5 @@ dist/
 /findings/
 /recon/
 /.pentesterflow/
+/.agentpond/
 bughunter-report-*.md
diff --git a/README.md b/README.md
index c1e836f..5dd2ace 100644
--- a/README.md
+++ b/README.md
@@ -479,6 +479,27 @@ Reports include:
 | `~/.pentesterflow/logs/pentesterflow.log` | Structured JSON-lines logs. |
 | `~/.pentesterflow/debug/session-*.jsonl` | Opt-in full session debug logs. |
 
+### Optional AgentPond traces
+
+OpenAI-compatible provider calls can be traced to storage you control. Tracing
+is off unless `AGENTPOND_ENABLED=true`; the spans contain only the provider,
+model, streaming flag, message/tool counts, finish reason, and output sizes.
+Prompts, responses, target data, and credentials are not recorded.
+
+For a local filesystem store:
+
+```sh
+npx agentpond env init local --provider fs \
+  --root "$PWD/.agentpond/envs/local/objects"
+npx agentpond env use local
+eval "$(npx agentpond env get local)"
+AGENTPOND_ENABLED=true npm run dev
+```
+
+After an AI request, run `npx agentpond sync` and
+`npx agentpond traces list` to inspect the trace. Configure another Files SDK
+provider for persistent or shared storage.
+
 Enable complete debug logs when reproducing usage issues:
 
 ```sh
diff --git a/package-lock.json b/package-lock.json
index aa9d4cc..6e3f169 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -9,11 +9,17 @@
       "version": "0.1.0-dev",
       "license": "Apache-2.0",
       "dependencies": {
+        "@agentpond/files-sdk": "^0.1.0",
+        "@agentpond/otel": "^0.1.4",
         "@modelcontextprotocol/sdk": "^1.0.0",
+        "@opentelemetry/api": "^1.9.1",
+        "@opentelemetry/sdk-node": "^0.221.0",
+        "@opentelemetry/sdk-trace-base": "^2.10.0",
         "chalk": "^5.6.2",
         "cli-highlight": "^2.1.11",
         "execa": "^9.5.1",
         "fast-glob": "^3.3.2",
+        "files-sdk": "^2.2.1",
         "gray-matter": "^4.0.3",
         "ink": "^5.0.1",
         "ink-spinner": "^5.0.0",
@@ -47,6 +53,58 @@
         "node": ">=20.0.0"
       }
     },
+    "node_modules/@agentpond/core": {
+      "version": "0.6.0",
+      "resolved": "https://registry.npmjs.org/@agentpond/core/-/core-0.6.0.tgz",
+      "integrity": "sha512-6CazVyUU80AU54U/jwJ3H/IUho0fFDpW2oo0oESQdn8T3qiW8ed/dyaC1YnSb0lVJn6v5Z7x4aoaxbYHR195OA==",
+      "license": "MIT",
+      "dependencies": {
+        "protobufjs": "^7.6.5",
+        "zod": "^4.3.6"
+      }
+    },
+    "node_modules/@agentpond/core/node_modules/zod": {
+      "version": "4.4.3",
+      "resolved": "https://registry.npmjs.org/zod/-/zod-4.4.3.tgz",
+      "integrity": "sha512-ytENFjIJFl2UwYglde2jchW2Hwm4GJFLDiSXWdTrJQBIN9Fcyp7n4DhxJEiWNAJMV1/BqWfW/kkg71UDcHJyTQ==",
+      "license": "MIT",
+      "funding": {
+        "url": "https://github.com/sponsors/colinhacks"
+      }
+    },
+    "node_modules/@agentpond/files-sdk": {
+      "version": "0.1.0",
+      "resolved": "https://registry.npmjs.org/@agentpond/files-sdk/-/files-sdk-0.1.0.tgz",
+      "integrity": "sha512-BzT9/gUbQE/uglhdbAQWHlIAt76OJXQvF0pQG4OY8cDoBemLEFjpHLVfqWU9yqEzsKJisSe84fnC2BJdG8w5TA==",
+      "license": "MIT",
+      "dependencies": {
+        "@agentpond/core": "0.6.0"
+      },
+      "peerDependencies": {
+        "@agentpond/otel": "0.1.4",
+        "files-sdk": "^2.2.1"
+      },
+      "peerDependenciesMeta": {
+        "@agentpond/otel": {
+          "optional": true
+        }
+      }
+    },
+    "node_modules/@agentpond/otel": {
+      "version": "0.1.4",
+      "resolved": "https://registry.npmjs.org/@agentpond/otel/-/otel-0.1.4.tgz",
+      "integrity": "sha512-KvuhpCvxnpDC7Y0HK/uDrMG9t5A8COagt7ktExSZ50Yh8UqOZkJaiQP0VBMEa16U2SbiP0JDxBnA7QgaKfW5Hg==",
+      "license": "MIT",
+      "dependencies": {
+        "@agentpond/core": "0.6.0",
+        "@opentelemetry/core": "^2.9.0",
+        "@opentelemetry/otlp-transformer": "^0.220.0",
+        "@opentelemetry/sdk-trace-base": "^2.9.0"
+      },
+      "peerDependencies": {
+        "@opentelemetry/api": ">=1.3.0 <1.10.0"
+      }
+    },
     "node_modules/@alcalzone/ansi-tokenize": {
       "version": "0.1.3",
       "resolved": "https://registry.npmjs.org/@alcalzone/ansi-tokenize/-/ansi-tokenize-0.1.3.tgz",
@@ -688,6 +746,160 @@
         "node": ">=18"
       }
     },
+    "node_modules/@grpc/grpc-js": {
+      "version": "1.14.4",
+      "resolved": "https://registry.npmjs.org/@grpc/grpc-js/-/grpc-js-1.14.4.tgz",
+      "integrity": "sha512-k9Dj3DV/itK9D06Y8f190Qgop7/Ui+D0njFV3LHMPwPT75DpXLQohE9Wmz0QElrJnzsjB7KPWiKJbOl7IPDArQ==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@grpc/proto-loader": "^0.8.0",
+        "@js-sdsl/ordered-map": "^4.4.2"
+      },
+      "engines": {
+        "node": ">=12.10.0"
+      }
+    },
+    "node_modules/@grpc/proto-loader": {
+      "version": "0.8.1",
+      "resolved": "https://registry.npmjs.org/@grpc/proto-loader/-/proto-loader-0.8.1.tgz",
+      "integrity": "sha512-wtF6h+DY6M3YaDBPAmvuuA6jV8Sif9MjtOI5euKFWRgCDl5PeDpPsHR9u2l6St5ceY8AZgoNDww5+HvEsXFsGg==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "lodash.camelcase": "^4.3.0",
+        "long": "^5.0.0",
+        "protobufjs": "^7.5.5",
+        "yargs": "^17.7.2"
+      },
+      "bin": {
+        "proto-loader-gen-types": "build/bin/proto-loader-gen-types.js"
+      },
+      "engines": {
+        "node": ">=6"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/ansi-regex": {
+      "version": "5.0.1",
+      "resolved": "https://registry.npmjs.org/ansi-regex/-/ansi-regex-5.0.1.tgz",
+      "integrity": "sha512-quJQXlTSUGL2LH9SUXo8VwsY4soanhgo6LNSm84E1LBcE8s3O0wpdiRzyR9z/ZZJMlMWv37qOOb9pdJlMUEKFQ==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/ansi-styles": {
+      "version": "4.3.0",
+      "resolved": "https://registry.npmjs.org/ansi-styles/-/ansi-styles-4.3.0.tgz",
+      "integrity": "sha512-zbB9rCJAT1rbjiVDb2hqKFHNYLxgtk8NURxZ3IZwD3F6NtxbXZQCnnSi1Lkx+IDohdPlFp222wVALIheZJQSEg==",
+      "license": "MIT",
+      "dependencies": {
+        "color-convert": "^2.0.1"
+      },
+      "engines": {
+        "node": ">=8"
+      },
+      "funding": {
+        "url": "https://github.com/chalk/ansi-styles?sponsor=1"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/cliui": {
+      "version": "8.0.1",
+      "resolved": "https://registry.npmjs.org/cliui/-/cliui-8.0.1.tgz",
+      "integrity": "sha512-BSeNnyus75C4//NQ9gQt1/csTXyo/8Sb+afLAkzAptFuMsod9HFokGNudZpi/oQV73hnVK+sR+5PVRMd+Dr7YQ==",
+      "license": "ISC",
+      "dependencies": {
+        "string-width": "^4.2.0",
+        "strip-ansi": "^6.0.1",
+        "wrap-ansi": "^7.0.0"
+      },
+      "engines": {
+        "node": ">=12"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/emoji-regex": {
+      "version": "8.0.0",
+      "resolved": "https://registry.npmjs.org/emoji-regex/-/emoji-regex-8.0.0.tgz",
+      "integrity": "sha512-MSjYzcWNOA0ewAHpz0MxpYFvwg6yjy1NG3xteoqz644VCo/RPgnr1/GGt+ic3iJTzQ8Eu3TdM14SawnVUmGE6A==",
+      "license": "MIT"
+    },
+    "node_modules/@grpc/proto-loader/node_modules/is-fullwidth-code-point": {
+      "version": "3.0.0",
+      "resolved": "https://registry.npmjs.org/is-fullwidth-code-point/-/is-fullwidth-code-point-3.0.0.tgz",
+      "integrity": "sha512-zymm5+u+sCsSWyD9qNaejV3DFvhCKclKdizYaJUuHA83RLjb7nSuGnddCHGv0hk+KY7BMAlsWeK4Ueg6EV6XQg==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/string-width": {
+      "version": "4.2.3",
+      "resolved": "https://registry.npmjs.org/string-width/-/string-width-4.2.3.tgz",
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+      "license": "MIT",
+      "dependencies": {
+        "emoji-regex": "^8.0.0",
+        "is-fullwidth-code-point": "^3.0.0",
+        "strip-ansi": "^6.0.1"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/strip-ansi": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/strip-ansi/-/strip-ansi-6.0.1.tgz",
+      "integrity": "sha512-Y38VPSHcqkFrCpFnQ9vuSXmquuv5oXOKpGeT6aGrr3o3Gc9AlVa6JBfUSOCnbxGGZF+/0ooI7KrPuUSztUdU5A==",
+      "license": "MIT",
+      "dependencies": {
+        "ansi-regex": "^5.0.1"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/wrap-ansi": {
+      "version": "7.0.0",
+      "resolved": "https://registry.npmjs.org/wrap-ansi/-/wrap-ansi-7.0.0.tgz",
+      "integrity": "sha512-YVGIj2kamLSTxw6NsZjoBxfSwsn0ycdesmc4p+Q21c5zPuZ1pl+NfxVdxPtdHvmNVOQ6XSYG4AUtyt/Fi7D16Q==",
+      "license": "MIT",
+      "dependencies": {
+        "ansi-styles": "^4.0.0",
+        "string-width": "^4.1.0",
+        "strip-ansi": "^6.0.0"
+      },
+      "engines": {
+        "node": ">=10"
+      },
+      "funding": {
+        "url": "https://github.com/chalk/wrap-ansi?sponsor=1"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/yargs": {
+      "version": "17.7.3",
+      "resolved": "https://registry.npmjs.org/yargs/-/yargs-17.7.3.tgz",
+      "integrity": "sha512-GZtjxm/J/4TSxuL3FNYjCmLktBTnIw/rVmKSIyKeYAZpmJB2ig9VauCC5xsa82GNKVKDAqpOn3KVzNt0zmrU0g==",
+      "license": "MIT",
+      "dependencies": {
+        "cliui": "^8.0.1",
+        "escalade": "^3.1.1",
+        "get-caller-file": "^2.0.5",
+        "require-directory": "^2.1.1",
+        "string-width": "^4.2.3",
+        "y18n": "^5.0.5",
+        "yargs-parser": "^21.1.1"
+      },
+      "engines": {
+        "node": ">=12"
+      }
+    },
+    "node_modules/@grpc/proto-loader/node_modules/yargs-parser": {
+      "version": "21.1.1",
+      "resolved": "https://registry.npmjs.org/yargs-parser/-/yargs-parser-21.1.1.tgz",
+      "integrity": "sha512-tVpsJW7DdjecAiFpbIB1e3qxIQsE6NoPc5/eTdrbbIC4h0LVsWhnoa3g+m2HclBIujHzsxZ4VJVA+GUuc2/LBw==",
+      "license": "ISC",
+      "engines": {
+        "node": ">=12"
+      }
+    },
     "node_modules/@hono/node-server": {
       "version": "1.19.14",
       "resolved": "https://registry.npmjs.org/@hono/node-server/-/node-server-1.19.14.tgz",
@@ -739,6 +951,16 @@
         "@jridgewell/sourcemap-codec": "^1.4.14"
       }
     },
+    "node_modules/@js-sdsl/ordered-map": {
+      "version": "4.4.2",
+      "resolved": "https://registry.npmjs.org/@js-sdsl/ordered-map/-/ordered-map-4.4.2.tgz",
+      "integrity": "sha512-iUKgm52T8HOE/makSxjqoWhe95ZJA1/G1sYsGev2JDKUSS14KAgg1LHb+Ba+IPow0xflbnSkOsZcO08C7w1gYw==",
+      "license": "MIT",
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/js-sdsl"
+      }
+    },
     "node_modules/@modelcontextprotocol/sdk": {
       "version": "1.29.0",
       "resolved": "https://registry.npmjs.org/@modelcontextprotocol/sdk/-/sdk-1.29.0.tgz",
@@ -789,29 +1011,1892 @@
         "run-parallel": "^1.1.9"
       },
       "engines": {
-        "node": ">= 8"
+        "node": ">= 8"
+      }
+    },
+    "node_modules/@nodelib/fs.stat": {
+      "version": "2.0.5",
+      "resolved": "https://registry.npmjs.org/@nodelib/fs.stat/-/fs.stat-2.0.5.tgz",
+      "integrity": "sha512-RkhPPp2zrqDAQA/2jNhnztcPAlv64XdhIp7a7454A5ovI7Bukxgt7MX7udwAu3zg1DcpPU0rz3VV1SeaqvY4+A==",
+      "license": "MIT",
+      "engines": {
+        "node": ">= 8"
+      }
+    },
+    "node_modules/@nodelib/fs.walk": {
+      "version": "1.2.8",
+      "resolved": "https://registry.npmjs.org/@nodelib/fs.walk/-/fs.walk-1.2.8.tgz",
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+      "license": "MIT",
+      "dependencies": {
+        "@nodelib/fs.scandir": "2.1.5",
+        "fastq": "^1.6.0"
+      },
+      "engines": {
+        "node": ">= 8"
+      }
+    },
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+      },
+      "funding": {
+        "url": "https://github.com/sponsors/jonschlinkert"
+      }
+    },
     "node_modules/fill-range": {
       "version": "7.1.1",
       "resolved": "https://registry.npmjs.org/fill-range/-/fill-range-7.1.1.tgz",
@@ -2899,6 +5279,26 @@
         "url": "https://opencollective.com/express"
       }
     },
+    "node_modules/import-in-the-middle": {
+      "version": "3.3.2",
+      "resolved": "https://registry.npmjs.org/import-in-the-middle/-/import-in-the-middle-3.3.2.tgz",
+      "integrity": "sha512-jTd2FfOgOWOdgjkHuk/1Ms8VKFXkPs15ymYBETw1sAOrO/dY3XeGVRWir9qBbw7pXr0T2eTFwfCZ+N02HmiNGA==",
+      "license": "Apache-2.0",
+      "dependencies": {
+        "cjs-module-lexer": "^2.2.0",
+        "es-module-lexer": "^2.2.0",
+        "module-details-from-path": "^1.0.4"
+      },
+      "engines": {
+        "node": ">=18"
+      }
+    },
+    "node_modules/import-in-the-middle/node_modules/es-module-lexer": {
+      "version": "2.3.1",
+      "resolved": "https://registry.npmjs.org/es-module-lexer/-/es-module-lexer-2.3.1.tgz",
+      "integrity": "sha512-shc1dbU90Yl/xq1QrC7QRtfcwURZuVRfPhZbDoldJ1cn1gzDvBaBWlv0eFolj5+0znnPJz5TXLxsN77X/12KTA==",
+      "license": "MIT"
+    },
     "node_modules/imurmurhash": {
       "version": "0.1.4",
       "resolved": "https://registry.npmjs.org/imurmurhash/-/imurmurhash-0.1.4.tgz",
@@ -3235,6 +5635,18 @@
         "node": "^12.20.0 || ^14.13.1 || >=16.0.0"
       }
     },
+    "node_modules/lodash.camelcase": {
+      "version": "4.3.0",
+      "resolved": "https://registry.npmjs.org/lodash.camelcase/-/lodash.camelcase-4.3.0.tgz",
+      "integrity": "sha512-TwuEnCnxbc3rAvhf/LbG7tJUDzhqXyFnv3dtzLOPgCG/hODL7WFnsbwktkD7yUV0RrreP/l1PALq/YSg6VvjlA==",
+      "license": "MIT"
+    },
+    "node_modules/long": {
+      "version": "5.3.2",
+      "resolved": "https://registry.npmjs.org/long/-/long-5.3.2.tgz",
+      "integrity": "sha512-mNAgZ1GmyNhD7AuqnTG3/VQ26o760+ZYBPKjPvugO8+nLbYfX6TVpJPseBvopbdY+qpZ/lKUnmEc1LeZYS3QAA==",
+      "license": "Apache-2.0"
+    },
     "node_modules/loose-envify": {
       "version": "1.4.0",
       "resolved": "https://registry.npmjs.org/loose-envify/-/loose-envify-1.4.0.tgz",
@@ -3396,6 +5808,12 @@
         "ufo": "^1.6.3"
       }
     },
+    "node_modules/module-details-from-path": {
+      "version": "1.0.4",
+      "resolved": "https://registry.npmjs.org/module-details-from-path/-/module-details-from-path-1.0.4.tgz",
+      "integrity": "sha512-EGWKgxALGMgzvxYF1UyGTy0HXX/2vHLkw6+NvDKW2jypWbHpjQuj4UMcqQWXHERJhVGKikolT06G3bcKe4fi7w==",
+      "license": "MIT"
+    },
     "node_modules/ms": {
       "version": "2.1.3",
       "resolved": "https://registry.npmjs.org/ms/-/ms-2.1.3.tgz",
@@ -3827,6 +6245,29 @@
       ],
       "license": "MIT"
     },
+    "node_modules/protobufjs": {
+      "version": "7.6.5",
+      "resolved": "https://registry.npmjs.org/protobufjs/-/protobufjs-7.6.5.tgz",
+      "integrity": "sha512-/FPD0nUc9jH6rfFjji9IBqOz4pcSE3CsT1m7Ep6Mdb0LxSUMj8hgl6GomOvZzpNpAqqGaXA0P3VSrZLFzIhQrw==",
+      "hasInstallScript": true,
+      "license": "BSD-3-Clause",
+      "dependencies": {
+        "@protobufjs/aspromise": "^1.1.2",
+        "@protobufjs/base64": "^1.1.2",
+        "@protobufjs/codegen": "^2.0.5",
+        "@protobufjs/eventemitter": "^1.1.1",
+        "@protobufjs/fetch": "^1.1.1",
+        "@protobufjs/float": "^1.0.2",
+        "@protobufjs/path": "^1.1.2",
+        "@protobufjs/pool": "^1.1.0",
+        "@protobufjs/utf8": "^1.1.1",
+        "@types/node": ">=13.7.0",
+        "long": "^5.3.2"
+      },
+      "engines": {
+        "node": ">=12.0.0"
+      }
+    },
     "node_modules/proxy-addr": {
       "version": "2.0.7",
       "resolved": "https://registry.npmjs.org/proxy-addr/-/proxy-addr-2.0.7.tgz",
@@ -3921,7 +6362,7 @@
       "version": "4.28.5",
       "resolved": "https://registry.npmjs.org/react-devtools-core/-/react-devtools-core-4.28.5.tgz",
       "integrity": "sha512-cq/o30z9W2Wb4rzBefjv5fBalHU0rJGZCHAkf/RHSBWSSYwh8PlQTqqOJmgIIbBtpj27T6FIPXeomIjZtCNVqA==",
-      "devOptional": true,
+      "dev": true,
       "license": "MIT",
       "dependencies": {
         "shell-quote": "^1.6.1",
@@ -3932,7 +6373,7 @@
       "version": "7.5.11",
       "resolved": "https://registry.npmjs.org/ws/-/ws-7.5.11.tgz",
       "integrity": "sha512-zS54Oen9bITtp7kp2XM3AydrCIq1D+HwJOuH+c+e4LfpL/lotP5osijd+UoMnxwAam1GN8R4KtLAyIrIcBNpiA==",
-      "devOptional": true,
+      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">=8.3.0"
@@ -4007,6 +6448,19 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/require-in-the-middle": {
+      "version": "8.0.1",
+      "resolved": "https://registry.npmjs.org/require-in-the-middle/-/require-in-the-middle-8.0.1.tgz",
+      "integrity": "sha512-QT7FVMXfWOYFbeRBF6nu+I6tr2Tf3u0q8RIEjNob/heKY/nh7drD/k7eeMFmSQgnTtCzLDcCu/XEnpW2wk4xCQ==",
+      "license": "MIT",
+      "dependencies": {
+        "debug": "^4.3.5",
+        "module-details-from-path": "^1.0.3"
+      },
+      "engines": {
+        "node": ">=9.3.0 || >=8.10.0 <9.0.0"
+      }
+    },
     "node_modules/resolve-from": {
       "version": "5.0.0",
       "resolved": "https://registry.npmjs.org/resolve-from/-/resolve-from-5.0.0.tgz",
@@ -4039,6 +6493,15 @@
       "integrity": "sha512-wnD2ZE+l+SPC/uoS0vXeE9L1+0wuaMqKlfz9AMUo38JsyLSBWSFcHR1Rri62LZc12vLr1gb3jl7iwQhgwpAbGQ==",
       "license": "ISC"
     },
+    "node_modules/ret": {
+      "version": "0.5.0",
+      "resolved": "https://registry.npmjs.org/ret/-/ret-0.5.0.tgz",
+      "integrity": "sha512-I1XxrZSQ+oErkRR4jYbAyEEu2I0avBvvMM5JN+6EBprOGRCs63ENqZ3vjavq8fBw2+62G5LF5XelKwuJpcvcxw==",
+      "license": "MIT",
+      "engines": {
+        "node": ">=10"
+      }
+    },
     "node_modules/reusify": {
       "version": "1.1.0",
       "resolved": "https://registry.npmjs.org/reusify/-/reusify-1.1.0.tgz",
@@ -4133,6 +6596,28 @@
         "queue-microtask": "^1.2.2"
       }
     },
+    "node_modules/safe-regex2": {
+      "version": "5.1.1",
+      "resolved": "https://registry.npmjs.org/safe-regex2/-/safe-regex2-5.1.1.tgz",
+      "integrity": "sha512-mOSBvHGDZMuIEZMdOz/aCEYDCv0E7nfcNsIhUF+/P+xC7Hyf3FkvymqgPbg9D1EdSGu+uKbJgy09K/RKKc7kJA==",
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/fastify"
+        },
+        {
+          "type": "opencollective",
+          "url": "https://opencollective.com/fastify"
+        }
+      ],
+      "license": "MIT",
+      "dependencies": {
+        "ret": "~0.5.0"
+      },
+      "bin": {
+        "safe-regex2": "bin/safe-regex2.js"
+      }
+    },
     "node_modules/safe-stable-stringify": {
       "version": "2.5.0",
       "resolved": "https://registry.npmjs.org/safe-stable-stringify/-/safe-stable-stringify-2.5.0.tgz",
@@ -4246,7 +6731,7 @@
       "version": "1.8.4",
       "resolved": "https://registry.npmjs.org/shell-quote/-/shell-quote-1.8.4.tgz",
       "integrity": "sha512-VsC6n6vz1ihYYyZZwX7YZSF5l5x36ca17OC+a69h94YqB7X6XLwf+5MOgynYir2SLFUbl8gIYvBo8K8RoNQ6bQ==",
-      "devOptional": true,
+      "dev": true,
       "license": "MIT",
       "engines": {
         "node": ">= 0.4"
@@ -5365,7 +7850,6 @@
       "version": "6.21.0",
       "resolved": "https://registry.npmjs.org/undici-types/-/undici-types-6.21.0.tgz",
       "integrity": "sha512-iwDZqg0QAGrg9Rav5H4n0M64c3mkR59cJ6wQp+7C4nI0gsmExaedaYLNO44eT4AtBBwjbTiGPMlt2Md0T9H9JQ==",
-      "dev": true,
       "license": "MIT"
     },
     "node_modules/unicode-emoji-modifier-base": {
@@ -6113,6 +8597,21 @@
         "node": ">=10"
       }
     },
+    "node_modules/yaml": {
+      "version": "2.9.0",
+      "resolved": "https://registry.npmjs.org/yaml/-/yaml-2.9.0.tgz",
+      "integrity": "sha512-2AvhNX3mb8zd6Zy7INTtSpl1F15HW6Wnqj0srWlkKLcpYl/gMIMJiyuGq2KeI2YFxUPjdlB+3Lc10seMLtL4cA==",
+      "license": "ISC",
+      "bin": {
+        "yaml": "bin.mjs"
+      },
+      "engines": {
+        "node": ">= 14.6"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/eemeli"
+      }
+    },
     "node_modules/yargs": {
       "version": "16.2.0",
       "resolved": "https://registry.npmjs.org/yargs/-/yargs-16.2.0.tgz",
diff --git a/package.json b/package.json
index 78c8750..657b30c 100644
--- a/package.json
+++ b/package.json
@@ -46,11 +46,17 @@
     "node": ">=20.0.0"
   },
   "dependencies": {
+    "@agentpond/files-sdk": "^0.1.0",
+    "@agentpond/otel": "^0.1.4",
     "@modelcontextprotocol/sdk": "^1.0.0",
+    "@opentelemetry/api": "^1.9.1",
+    "@opentelemetry/sdk-node": "^0.221.0",
+    "@opentelemetry/sdk-trace-base": "^2.10.0",
     "chalk": "^5.6.2",
     "cli-highlight": "^2.1.11",
     "execa": "^9.5.1",
     "fast-glob": "^3.3.2",
+    "files-sdk": "^2.2.1",
     "gray-matter": "^4.0.3",
     "ink": "^5.0.1",
     "ink-spinner": "^5.0.0",
diff --git a/src/llm/openai.ts b/src/llm/openai.ts
index f640b62..2e1386c 100644
--- a/src/llm/openai.ts
+++ b/src/llm/openai.ts
@@ -6,6 +6,7 @@
 // position; we accumulate them per-index and assign a fallback ID if the
 // server omits one.
 
+import { traceModelRequest } from '../telemetry/agentpond.js';
 import type { Client, Pinger, StreamingClient } from './client.js';
 import { type BackendError, classifyBackend, parseRetryAfter } from './errors.js';
 import { newCallID } from './ids.js';
@@ -150,7 +151,16 @@ export class OpenAIClient implements Client, StreamingClient, Pinger {
     // Retry rate limits / transient 5xx with backoff (E7). The non-streaming
     // call has no observable side effects before it returns, so it's safe to
     // re-run wholesale.
-    return withRetry(() => this.chatOnce(req, signal), { signal });
+    return traceModelRequest(
+      {
+        messageCount: req.messages.length,
+        model: this.modelID,
+        provider: this.label,
+        streaming: false,
+        toolCount: req.tools?.length ?? 0,
+      },
+      () => withRetry(() => this.chatOnce(req, signal), { signal }),
+    );
   }
 
   private async chatOnce(req: ChatRequest, signal?: AbortSignal): Promise<ChatResponse> {
@@ -219,6 +229,23 @@ export class OpenAIClient implements Client, StreamingClient, Pinger {
     req: ChatRequest,
     onDelta: (delta: string) => void,
     signal?: AbortSignal,
+  ): Promise<ChatResponse> {
+    return traceModelRequest(
+      {
+        messageCount: req.messages.length,
+        model: this.modelID,
+        provider: this.label,
+        streaming: true,
+        toolCount: req.tools?.length ?? 0,
+      },
+      () => this.chatStreamOnce(req, onDelta, signal),
+    );
+  }
+
+  private async chatStreamOnce(
+    req: ChatRequest,
+    onDelta: (delta: string) => void,
+    signal?: AbortSignal,
   ): Promise<ChatResponse> {
     // Retry only the connection setup (E7): a transient 429/5xx surfaces before
     // any delta is emitted, so re-running openStream can't double-emit tokens.
diff --git a/src/telemetry/agentpond.ts b/src/telemetry/agentpond.ts
new file mode 100644
index 0000000..ac35660
--- /dev/null
+++ b/src/telemetry/agentpond.ts
@@ -0,0 +1,120 @@
+type ModelResult = {
+  finishReason: string;
+  message: {
+    content: string;
+    toolCalls?: unknown[];
+  };
+};
+
+type ModelSpanOptions = {
+  messageCount: number;
+  model: string;
+  provider: string;
+  streaming: boolean;
+  toolCount: number;
+};
+
+type AgentPondRuntime = {
+  forceFlush: () => Promise<void>;
+  spanStatusCode: {
+    ERROR: number;
+    OK: number;
+  };
+  tracer: {
+    startActiveSpan<T>(
+      name: string,
+      options: { attributes: Record<string, boolean | number | string> },
+      callback: (span: {
+        end(): void;
+        recordException(error: Error): void;
+        setAttribute(name: string, value: string): void;
+        setStatus(status: { code: number; message?: string }): void;
+      }) => Promise<T>,
+    ): Promise<T>;
+  };
+};
+
+let runtimePromise: Promise<AgentPondRuntime> | undefined;
+
+async function startRuntime(): Promise<AgentPondRuntime> {
+  const [
+    { createFilesSpanExporterFromRuntimeEnv },
+    { trace, SpanStatusCode },
+    { NodeSDK },
+    { BatchSpanProcessor },
+  ] = await Promise.all([
+    import('@agentpond/files-sdk/otel'),
+    import('@opentelemetry/api'),
+    import('@opentelemetry/sdk-node'),
+    import('@opentelemetry/sdk-trace-base'),
+  ]);
+
+  const processor = new BatchSpanProcessor(createFilesSpanExporterFromRuntimeEnv());
+  const sdk = new NodeSDK({ spanProcessors: [processor] });
+  sdk.start();
+
+  return {
+    forceFlush: () => processor.forceFlush(),
+    spanStatusCode: SpanStatusCode,
+    tracer: trace.getTracer('pentesterflow'),
+  };
+}
+
+function getRuntime(): Promise<AgentPondRuntime> {
+  runtimePromise ??= startRuntime();
+  return runtimePromise;
+}
+
+/**
+ * Trace one provider request when the operator explicitly enables AgentPond.
+ * Only structural metadata is recorded so prompts, responses, targets, and
+ * credentials remain out of the trace.
+ */
+export async function traceModelRequest<T extends ModelResult>(
+  options: ModelSpanOptions,
+  operation: () => Promise<T>,
+): Promise<T> {
+  if (process.env.AGENTPOND_ENABLED !== 'true') return operation();
+
+  const runtime = await getRuntime();
+  return runtime.tracer.startActiveSpan(
+    `${options.provider}.chat`,
+    {
+      attributes: {
+        'input.mime_type': 'application/json',
+        'input.value': JSON.stringify({
+          messageCount: options.messageCount,
+          streaming: options.streaming,
+          toolCount: options.toolCount,
+        }),
+        'llm.model_name': options.model,
+        'llm.provider': options.provider,
+        'openinference.span.kind': 'LLM',
+      },
+    },
+    async (span) => {
+      try {
+        const result = await operation();
+        span.setAttribute('output.mime_type', 'application/json');
+        span.setAttribute(
+          'output.value',
+          JSON.stringify({
+            contentCharacters: result.message.content.length,
+            finishReason: result.finishReason,
+            toolCallCount: result.message.toolCalls?.length ?? 0,
+          }),
+        );
+        span.setStatus({ code: runtime.spanStatusCode.OK });
+        return result;
+      } catch (error) {
+        const normalized = error instanceof Error ? error : new Error(String(error));
+        span.recordException(normalized);
+        span.setStatus({ code: runtime.spanStatusCode.ERROR, message: normalized.message });
+        throw error;
+      } finally {
+        span.end();
+        await runtime.forceFlush();
+      }
+    },
+  );
+}