From a32072f454a766f7e0f988f4a0fbeff938565d9b Mon Sep 17 00:00:00 2001
From: Sara Burke <115188+saralilyb@users.noreply.github.com>
Date: Wed, 3 Jun 2026 15:55:34 -0400
Subject: [PATCH] fix(gateway): deliver ics files as attachments

---
 gateway/platforms/base.py              |  3 ++-
 tests/gateway/test_media_extraction.py | 30 ++++++++++++++++++++++++++
 2 files changed, 32 insertions(+), 1 deletion(-)

diff --git a/gateway/platforms/base.py b/gateway/platforms/base.py
index d7654ff6c147..54a09e9f8b5e 100644
--- a/gateway/platforms/base.py
+++ b/gateway/platforms/base.py
@@ -1539,6 +1539,7 @@ def _log_safe_path(path: str) -> str:
 
 SUPPORTED_DOCUMENT_TYPES = {
     ".pdf": "application/pdf",
+    ".ics": "text/calendar",
     ".md": "text/markdown",
     ".txt": "text/plain",
     ".csv": "text/csv",
@@ -1644,7 +1645,7 @@ def _log_safe_path(path: str) -> str:
     # Audio (delivered as voice/audio where supported)
     ".mp3", ".m2a", ".wav", ".ogg", ".opus", ".m4a", ".flac",
     # Documents (uploaded as file attachments)
-    ".pdf", ".docx", ".doc", ".odt", ".rtf", ".txt", ".md", ".epub",
+    ".pdf", ".ics", ".docx", ".doc", ".odt", ".rtf", ".txt", ".md", ".epub",
     # Spreadsheets / data
     ".xlsx", ".xls", ".ods", ".csv", ".tsv", ".json", ".xml", ".yaml", ".yml",
     # Geospatial / GIS (#24032)
diff --git a/tests/gateway/test_media_extraction.py b/tests/gateway/test_media_extraction.py
index 65f64e6650bc..4a790550f339 100644
--- a/tests/gateway/test_media_extraction.py
+++ b/tests/gateway/test_media_extraction.py
@@ -102,6 +102,36 @@ def extract_media_tags_broken(result_messages):
     return media_tags, has_voice_directive
 
 
+class TestMediaDeliveryExtensions:
+    """Tests for the shared outbound media-delivery allowlist."""
+
+    def test_ics_media_tag_is_extracted_for_document_delivery(self):
+        """Calendar invites should upload instead of rendering MEDIA: text."""
+        from gateway.platforms.base import BasePlatformAdapter
+
+        media, cleaned = BasePlatformAdapter.extract_media(
+            "Here is the calendar invite.\nMEDIA:/tmp/event.ics"
+        )
+
+        assert media == [("/tmp/event.ics", False)]
+        assert "MEDIA:" not in cleaned
+        assert "event.ics" not in cleaned
+
+    def test_ics_bare_path_is_allowed_for_document_delivery(self, tmp_path):
+        """Bare local .ics paths should use the same delivery allowlist."""
+        from gateway.platforms.base import BasePlatformAdapter
+
+        invite_path = tmp_path / "event.ics"
+        invite_path.write_text("BEGIN:VCALENDAR\nEND:VCALENDAR\n")
+
+        files, cleaned = BasePlatformAdapter.extract_local_files(
+            f"The invite is at {invite_path}"
+        )
+
+        assert files == [str(invite_path)]
+        assert "event.ics" not in cleaned
+
+
 class TestMediaExtraction:
     """Tests for MEDIA tag extraction from tool results."""