diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 9a8c83bee..df3af27b5 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -64,3 +64,10 @@ jobs:
 
       - name: Run Flake8
         run: poetry run flake8 --exclude=alembic,.venv,venv,contrib,.cache,.git
+
+      # Guard against import-time breakage (missing/renamed imports, bad lazy
+      # imports) -- the class of error that dominates GlitchTip. See
+      # GLITCHTIP_FIX_PLAN.md. TODO: extend to a Windows matrix to cover the
+      # pywinauto import path.
+      - name: Import-smoke (core modules must import cleanly)
+        run: poetry run python -c "import openadapt, openadapt.config, openadapt.utils, openadapt.models, openadapt.db.db, openadapt.window, openadapt.error_reporting; print('imports ok')"
diff --git a/.gitignore b/.gitignore
index 9e7beb0dc..0150674cb 100644
--- a/.gitignore
+++ b/.gitignore
@@ -41,3 +41,6 @@ build/
 
 OpenAdapt.spec
 build_scripts/OpenAdapt.iss
+
+# Private keys (never commit)
+*.pem
diff --git a/openadapt/config.py b/openadapt/config.py
index ca3c01801..d8b700aac 100644
--- a/openadapt/config.py
+++ b/openadapt/config.py
@@ -124,9 +124,11 @@ class SegmentationAdapter(str, Enum):
 
     # Error reporting
     ERROR_REPORTING_ENABLED: bool = True
+    # Reports to the live GlitchTip project openadaptai/openadapt (id 3798).
+    # (Project 8771, previously set here, is not in the org and is unreachable,
+    # so its events were never visible in the dashboard.)
     ERROR_REPORTING_DSN: ClassVar = (
-        # "https://dcf5d7889a3b4b47ae12a3af9ffcbeb7@app.glitchtip.com/3798"
-        "https://5d24fc5a2e674ea6b42275e5702499ce@app.glitchtip.com/8771"
+        "https://dcf5d7889a3b4b47ae12a3af9ffcbeb7@app.glitchtip.com/3798"
     )
     ERROR_REPORTING_BRANCH: ClassVar = "main"
 
diff --git a/openadapt/error_reporting.py b/openadapt/error_reporting.py
index 2dee6a616..0527a6228 100644
--- a/openadapt/error_reporting.py
+++ b/openadapt/error_reporting.py
@@ -60,10 +60,50 @@ def show_alert() -> None:
     msg.exec()
 
 
+# Errors from environments where OpenAdapt cannot run -- headless / no display,
+# unsupported platform, or a broken/partial native dependency set -- are not
+# actionable bugs. They otherwise flood the dashboard from CI and automated
+# headless environments and bury real issues. Drop them. See GLITCHTIP_FIX_PLAN.md.
+_UNSUPPORTED_ENV_SUBSTRINGS = (
+    "failed to acquire X connection",
+    "Bad display name",
+    "DISPLAY not set",
+    "this platform is not supported",  # pynput import on headless Linux
+    "No module named 'pywinauto'",  # non-Windows / old releases (guarded on main)
+    "module 'pywinauto' has no attribute",
+    "_ARRAY_API not found",  # numpy 1.x/2.x ABI mismatch in a broken env
+    "crop_active_window should return an image",  # headless screenshot returned None
+)
+
+
+def is_unsupported_environment_error(event: Any, hint: Any) -> 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(substring in blob for substring in _UNSUPPORTED_ENV_SUBSTRINGS)
+
+
 def before_send_event(event: Any, hint: Any) -> Any:
-    """Handle the event before sending it to Sentry."""
+    """Filter events before sending to GlitchTip.
+
+    Drops unactionable unsupported-environment errors (headless, wrong platform,
+    broken native deps) that otherwise flood the dashboard from CI/automated
+    environments. For genuine errors, surfaces a user alert -- but only when a GUI
+    is actually running, never headless, and never for filtered noise.
+    """
+    if is_unsupported_environment_error(event, hint):
+        return None  # drop -- not an actionable bug
+
     try:
-        show_alert()
+        from PySide6.QtWidgets import QApplication
+
+        if QApplication.instance() is not None:
+            show_alert()
     except Exception:
         pass
     return event