diff --git a/core/cli/main.py b/core/cli/main.py
index 3ae9b224..169c7ac0 100644
--- a/core/cli/main.py
+++ b/core/cli/main.py
@@ -5,9 +5,12 @@ import sys
 from argparse import Namespace
 from asyncio import run
 
+import sentry_sdk
+
 from core.agents.orchestrator import Orchestrator
 from core.cli.helpers import delete_project, init, list_projects, list_projects_json, load_project, show_config
 from core.config import LLMProvider, get_config
+from core.config.version import get_version
 from core.db.session import SessionManager
 from core.db.v0importer import LegacyDatabaseImporter
 from core.llm.anthropic_client import CustomAssertionError
@@ -277,6 +280,16 @@ async def async_main(
         return success
 
     telemetry.set("user_contact", args.email)
+    sentry_sdk.set_user({"email": args.email or "CLI only"})
+    sentry_sdk.set_context(
+        "pythagora-data",
+        {
+            "extension-version": args.extension_version or "CLI only",
+            "core-version": get_version(),
+            # TODO get environment from the extension
+            # "environment": args.environment,
+        },
+    )
     if args.extension_version:
         telemetry.set("is_extension", True)
         telemetry.set("extension_version", args.extension_version)
diff --git a/main.py b/main.py
index db271215..79e36e88 100644
--- a/main.py
+++ b/main.py
@@ -1,9 +1,17 @@
 #!/usr/bin/env python
-
-
 import os.path
 import sys
 
+import sentry_sdk
+
+sentry_sdk.init(
+    dsn="https://4101633bc5560bae67d6eab013ba9686@o4508731634221056.ingest.us.sentry.io/4508732401909760",
+    send_default_pii=True,
+    traces_sample_rate=1.0,
+)
+
+sentry_sdk.profiler.start_profiler()
+
 try:
     from core.cli.main import run_pythagora
 except ImportError as err:
diff --git a/requirements.txt b/requirements.txt
index 03095f9a..11270f9f 100644
--- a/requirements.txt
+++ b/requirements.txt
@@ -34,3 +34,4 @@ tqdm==4.67.1
 typing-extensions==4.12.2
 urllib3==2.2.3
 wcwidth==0.2.13
+sentry-sdk==2.20.0