diff --git a/openadapt/cli.py b/openadapt/cli.py
index cfc69dbb9..2232edecf 100644
--- a/openadapt/cli.py
+++ b/openadapt/cli.py
@@ -38,7 +38,11 @@ def main():
         openadapt train --capture my-task        # Train a model
         openadapt eval --checkpoint model.pt     # Evaluate the model
     """
-    pass
+    # Initialize crash reporting before dispatching to any subcommand. Lazy
+    # import keeps CLI startup fast and import-safe; the call never raises.
+    from openadapt.error_reporting import configure_error_reporting
+
+    configure_error_reporting()
 
 
 # =============================================================================
diff --git a/openadapt/config.py b/openadapt/config.py
index 3580e8f28..69841bcfa 100644
--- a/openadapt/config.py
+++ b/openadapt/config.py
@@ -49,6 +49,20 @@ class OpenAdaptSettings(BaseSettings):
     google_api_key: Optional[str] = None
     lambda_api_key: Optional[str] = None
 
+    # =========================================================================
+    # Crash reporting (see openadapt/error_reporting.py)
+    # =========================================================================
+    # Master switch (OPENADAPT_ERROR_REPORTING_ENABLED).
+    error_reporting_enabled: bool = True
+    # Report from a source run too (default: only packaged/frozen builds report).
+    error_reporting_force: bool = False
+    # Sentry-compatible DSN; defaults to the GlitchTip openadaptai/openadapt (3798)
+    # project. The DSN public key is an ingestion key, not a secret.
+    error_reporting_dsn: Optional[str] = (
+        "https://dcf5d7889a3b4b47ae12a3af9ffcbeb7@app.glitchtip.com/3798"
+    )
+    error_reporting_environment: str = "production"
+
     # =========================================================================
     # Paths
     # =========================================================================
diff --git a/openadapt/error_reporting.py b/openadapt/error_reporting.py
new file mode 100644
index 000000000..02e94e5e4
--- /dev/null
+++ b/openadapt/error_reporting.py
@@ -0,0 +1,95 @@
+"""Optional crash reporting for the OpenAdapt CLI.
+
+Reports unhandled errors to a Sentry-compatible backend (GlitchTip). Designed to
+be safe and quiet:
+
+- **Off unless it's a packaged build.** By default reporting is active only in a
+  frozen/packaged build (the released app). Source / dev / CI / headless runs do
+  NOT report -- that source-run flooding is what previously buried real issues.
+  Set ``OPENADAPT_ERROR_REPORTING_FORCE=1`` to report from a source run (e.g. to
+  test it). This replaces the old, fragile ``active_branch == "main"`` gate.
+- **Master switch:** ``OPENADAPT_ERROR_REPORTING_ENABLED=0`` disables entirely.
+- **Filtered:** unactionable unsupported-environment errors (no display, wrong
+  platform, broken native deps) are dropped in ``before_send``.
+- **Never raises:** if ``sentry-sdk`` is missing or init fails, it is a silent
+  no-op -- telemetry must never break the app.
+
+Config lives on ``openadapt.config.settings`` (``OPENADAPT_ERROR_REPORTING_*``).
+"""
+
+from __future__ import annotations
+
+import sys
+from typing import Optional
+
+from openadapt.config import settings
+from openadapt.version import __version__
+
+try:
+    import sentry_sdk
+except ImportError:  # optional dependency -> reporting becomes a no-op
+    sentry_sdk = None  # type: ignore[assignment]
+
+
+# Unactionable: errors from environments where OpenAdapt cannot run -- headless /
+# no display, wrong platform, or a broken/partial native dependency set. These
+# flood the dashboard from CI and automated/headless environments and bury real
+# issues. Drop them.
+_UNSUPPORTED_ENV_SUBSTRINGS = (
+    "failed to acquire X connection",
+    "Bad display name",
+    "DISPLAY not set",
+    "this platform is not supported",
+    "No module named 'pywinauto'",
+    "module 'pywinauto' has no attribute",
+    "_ARRAY_API not found",
+)
+
+
+def is_unsupported_environment_error(event: dict, hint: dict) -> bool:
+    """Return True if the event is an unactionable unsupported-environment error."""
+    texts = []
+    exc_info = hint.get("exc_info") if hint else None
+    if exc_info and exc_info[1] is not None:
+        texts.append(f"{type(exc_info[1]).__name__}: {exc_info[1]}")
+    for value in (event.get("exception", {}) or {}).get("values", []) or []:
+        texts.append(f"{value.get('type')}: {value.get('value')}")
+    blob = " ".join(texts)
+    return any(sub in blob for sub in _UNSUPPORTED_ENV_SUBSTRINGS)
+
+
+def before_send_event(event: dict, hint: dict) -> Optional[dict]:
+    """Drop unactionable unsupported-environment events; keep the rest."""
+    if is_unsupported_environment_error(event, hint):
+        return None
+    return event
+
+
+def _reporting_enabled() -> bool:
+    """Report only from a packaged build by default (never source/dev/CI/headless)."""
+    if not settings.error_reporting_enabled:
+        return False
+    if getattr(sys, "frozen", False):
+        return True
+    return settings.error_reporting_force
+
+
+def configure_error_reporting() -> None:
+    """Initialize crash reporting if enabled. Safe to call always; never raises."""
+    if (
+        sentry_sdk is None
+        or not _reporting_enabled()
+        or not settings.error_reporting_dsn
+    ):
+        return
+    try:
+        sentry_sdk.init(
+            dsn=settings.error_reporting_dsn,
+            release=f"openadapt@{__version__}",
+            environment=settings.error_reporting_environment,
+            before_send=before_send_event,
+            ignore_errors=[KeyboardInterrupt],
+        )
+    except Exception:
+        # Telemetry must never break the app.
+        pass
diff --git a/pyproject.toml b/pyproject.toml
index aad41fe52..48970d83a 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -25,6 +25,12 @@ classifiers = [
 # Minimal base - just the CLI
 dependencies = [
     "click>=8.0.0",
+    # Backs openadapt.config (BaseSettings) -- was a latent missing base dep:
+    # a clean install could not `import openadapt.config` without it.
+    "pydantic-settings>=2.0.0",
+    # Optional crash reporting (see openadapt/error_reporting.py). Lightweight,
+    # pure-Python; reporting is off unless running a packaged build.
+    "sentry-sdk>=2.0.0",
 ]
 
 [project.optional-dependencies]
diff --git a/tests/test_error_reporting.py b/tests/test_error_reporting.py
new file mode 100644
index 000000000..228ba2e92
--- /dev/null
+++ b/tests/test_error_reporting.py
@@ -0,0 +1,65 @@
+"""Tests for openadapt.error_reporting: filtering + gating (no network)."""
+
+from openadapt import error_reporting as er
+from openadapt.config import settings
+
+
+def _hint(exc: Exception) -> dict:
+    return {"exc_info": (type(exc), exc, None)}
+
+
+def test_drops_unsupported_environment_errors() -> None:
+    for msg in [
+        "this platform is not supported: failed to acquire X connection",
+        "ScreenShotError: $DISPLAY not set.",
+        "No module named 'pywinauto'",
+        "module 'pywinauto' has no attribute 'application'",
+        "_ARRAY_API not found",
+    ]:
+        assert er.before_send_event({}, _hint(RuntimeError(msg))) is None
+
+
+def test_keeps_real_errors() -> None:
+    event = {"id": "real"}
+    result = er.before_send_event(event, _hint(ValueError("real extraction bug")))
+    assert result is event
+
+
+def test_filter_reads_event_exception_values_too() -> None:
+    event = {
+        "exception": {
+            "values": [{"type": "ImportError", "value": "No module named 'pywinauto'"}]
+        }
+    }
+    assert er.before_send_event(event, {}) is None
+
+
+def test_disabled_by_default_from_source(monkeypatch) -> None:
+    monkeypatch.setattr(er.sys, "frozen", False, raising=False)
+    monkeypatch.setattr(settings, "error_reporting_enabled", True)
+    monkeypatch.setattr(settings, "error_reporting_force", False)
+    assert er._reporting_enabled() is False
+
+
+def test_enabled_when_frozen(monkeypatch) -> None:
+    monkeypatch.setattr(er.sys, "frozen", True, raising=False)
+    monkeypatch.setattr(settings, "error_reporting_enabled", True)
+    assert er._reporting_enabled() is True
+
+
+def test_master_switch_off(monkeypatch) -> None:
+    monkeypatch.setattr(er.sys, "frozen", True, raising=False)
+    monkeypatch.setattr(settings, "error_reporting_enabled", False)
+    assert er._reporting_enabled() is False
+
+
+def test_force_enables_from_source(monkeypatch) -> None:
+    monkeypatch.setattr(er.sys, "frozen", False, raising=False)
+    monkeypatch.setattr(settings, "error_reporting_enabled", True)
+    monkeypatch.setattr(settings, "error_reporting_force", True)
+    assert er._reporting_enabled() is True
+
+
+def test_configure_never_raises_when_disabled(monkeypatch) -> None:
+    monkeypatch.setattr(settings, "error_reporting_enabled", False)
+    er.configure_error_reporting()  # no-op, must not raise