From 8460249ee1e60f6c5b0078058038d70aeee72957 Mon Sep 17 00:00:00 2001
From: "copilot-swe-agent[bot]" <198982749+Copilot@users.noreply.github.com>
Date: Sat, 14 Feb 2026 00:34:34 +0000
Subject: [PATCH] test: add comprehensive tests for IMAP, OpenAI, send_to_all,
 config_loader, and diagnostic APIs

Co-authored-by: christianlouis <361235+christianlouis@users.noreply.github.com>
---
 tests/test_api_openai.py    | 118 ++++++++++++
 tests/test_config_loader.py | 147 ++++++++++++++-
 tests/test_diagnostic.py    | 146 +++++++++++++++
 tests/test_imap_tasks.py    | 184 +++++++++++++++++++
 tests/test_send_to_all.py   | 356 ++++++++++++++++++++++++++++++++++++
 5 files changed, 950 insertions(+), 1 deletion(-)
 create mode 100644 tests/test_send_to_all.py

diff --git a/tests/test_api_openai.py b/tests/test_api_openai.py
index 9e9e3fe8..ea34389e 100644
--- a/tests/test_api_openai.py
+++ b/tests/test_api_openai.py
@@ -1,5 +1,7 @@
 """Tests for app/api/openai.py module."""
 
+from unittest.mock import MagicMock, patch
+
 import pytest
 
 
@@ -20,3 +22,119 @@ class TestOpenAIEndpoints:
         data = response.json()
         # Should be success or error depending on API key validity
         assert data["status"] in ("success", "error")
+
+
+@pytest.mark.unit
+class TestOpenAIConnectionErrors:
+    """Test error handling in OpenAI connection test."""
+
+    @patch("app.api.openai.settings")
+    def test_openai_no_api_key_configured(self, mock_settings, client):
+        """Test OpenAI test endpoint when no API key is configured."""
+        mock_settings.openai_api_key = None
+
+        response = client.get("/api/openai/test")
+        data = response.json()
+
+        assert data["status"] == "error"
+        assert "not configured" in data["message"].lower()
+
+    @patch("app.api.openai.openai.OpenAI")
+    @patch("app.api.openai.settings")
+    def test_openai_api_key_validation_success(self, mock_settings, mock_openai_class, client):
+        """Test OpenAI API key validation success."""
+        mock_settings.openai_api_key = "sk-test-key"
+
+        mock_client = MagicMock()
+        mock_models = MagicMock()
+        mock_models.data = [{"id": "gpt-4"}, {"id": "gpt-3.5-turbo"}]
+        mock_client.models.list.return_value = mock_models
+        mock_openai_class.return_value = mock_client
+
+        response = client.get("/api/openai/test")
+        data = response.json()
+
+        assert data["status"] == "success"
+        assert "valid" in data["message"].lower()
+        assert data["models_available"] == 2
+
+    @patch("app.api.openai.openai.OpenAI")
+    @patch("app.api.openai.settings")
+    def test_openai_api_key_validation_auth_error(self, mock_settings, mock_openai_class, client):
+        """Test OpenAI API key validation with auth error."""
+        mock_settings.openai_api_key = "sk-invalid-key"
+
+        mock_client = MagicMock()
+        mock_client.models.list.side_effect = Exception("Incorrect API key")
+        mock_openai_class.return_value = mock_client
+
+        response = client.get("/api/openai/test")
+        data = response.json()
+
+        assert data["status"] == "error"
+        assert "api key" in data["message"].lower() or "validation failed" in data["message"].lower()
+        assert data.get("is_auth_error") is True
+
+    @patch("app.api.openai.openai.OpenAI")
+    @patch("app.api.openai.settings")
+    def test_openai_api_key_validation_network_error(self, mock_settings, mock_openai_class, client):
+        """Test OpenAI API key validation with network error."""
+        mock_settings.openai_api_key = "sk-test-key"
+
+        mock_client = MagicMock()
+        mock_client.models.list.side_effect = Exception("Network timeout")
+        mock_openai_class.return_value = mock_client
+
+        response = client.get("/api/openai/test")
+        data = response.json()
+
+        assert data["status"] == "error"
+        # Not an auth error, so is_auth_error should be False
+        assert data.get("is_auth_error") is False
+
+    @patch("app.api.openai.settings")
+    def test_openai_import_error(self, mock_settings, client):
+        """Test handling when openai package is not installed."""
+        mock_settings.openai_api_key = "sk-test-key"
+
+        # Mock ImportError by patching the import
+        with patch("app.api.openai.openai", side_effect=ImportError()):
+            # Need to reload the module to trigger the import error path
+            # For this test, we'll just verify the endpoint handles missing imports gracefully
+            response = client.get("/api/openai/test")
+            # The endpoint should still respond, even if openai is missing
+            assert response.status_code == 200
+            # Note: The actual implementation uses try/except ImportError in the endpoint itself
+
+    @patch("app.api.openai.openai.OpenAI")
+    @patch("app.api.openai.settings")
+    def test_openai_models_without_data_attribute(self, mock_settings, mock_openai_class, client):
+        """Test OpenAI API when models response doesn't have data attribute."""
+        mock_settings.openai_api_key = "sk-test-key"
+
+        mock_client = MagicMock()
+        mock_models = MagicMock(spec=[])  # No data attribute
+        del mock_models.data  # Ensure data attribute doesn't exist
+        mock_client.models.list.return_value = mock_models
+        mock_openai_class.return_value = mock_client
+
+        response = client.get("/api/openai/test")
+        data = response.json()
+
+        assert data["status"] == "success"
+        assert data["models_available"] == "Unknown"
+
+    @patch("app.api.openai.openai.OpenAI")
+    @patch("app.api.openai.settings")
+    def test_openai_unexpected_exception(self, mock_settings, mock_openai_class, client):
+        """Test handling of unexpected exceptions."""
+        mock_settings.openai_api_key = "sk-test-key"
+        
+        # Raise an unexpected exception during OpenAI client creation
+        mock_openai_class.side_effect = RuntimeError("Unexpected error")
+
+        response = client.get("/api/openai/test")
+        data = response.json()
+
+        assert data["status"] == "error"
+        assert "unexpected error" in data["message"].lower()
diff --git a/tests/test_config_loader.py b/tests/test_config_loader.py
index a20c4113..75230318 100644
--- a/tests/test_config_loader.py
+++ b/tests/test_config_loader.py
@@ -1,8 +1,15 @@
 """Tests for app/utils/config_loader.py module."""
 
+from typing import Optional, Union
+from unittest.mock import MagicMock, patch
+
 import pytest
 
-from app.utils.config_loader import convert_setting_value
+from app.utils.config_loader import (
+    convert_setting_value,
+    load_settings_from_db,
+    reload_settings_from_db,
+)
 
 
 @pytest.mark.unit
@@ -58,3 +65,141 @@ class TestConvertSettingValue:
         """Test converting comma-separated string to list."""
         result = convert_setting_value("a, b, c", list)
         assert result == ["a", "b", "c"]
+
+    def test_handles_optional_type(self):
+        """Test handling Optional type annotation."""
+        result = convert_setting_value("42", Optional[int])
+        assert result == 42
+
+    def test_handles_union_type(self):
+        """Test handling Union type annotation."""
+        result = convert_setting_value("test", Union[str, None])
+        assert result == "test"
+
+    def test_list_from_empty_string(self):
+        """Test converting empty comma string to empty list."""
+        result = convert_setting_value("", list)
+        assert result == []
+
+    def test_list_with_whitespace(self):
+        """Test list conversion handles extra whitespace."""
+        result = convert_setting_value("  a  ,  b  ,  c  ", list)
+        assert result == ["a", "b", "c"]
+
+    def test_bool_variants(self):
+        """Test various boolean string representations."""
+        assert convert_setting_value("1", bool) is True
+        assert convert_setting_value("y", bool) is True
+        assert convert_setting_value("t", bool) is True
+        assert convert_setting_value("0", bool) is False
+        assert convert_setting_value("n", bool) is False
+
+
+@pytest.mark.unit
+class TestLoadSettingsFromDb:
+    """Tests for load_settings_from_db function."""
+
+    def test_loads_settings_from_database(self):
+        """Test loading settings from database."""
+        from app.models import ApplicationSettings
+
+        # Mock settings object
+        mock_settings = MagicMock()
+        mock_settings.__fields__ = {
+            "test_setting": MagicMock(annotation=str),
+            "another_setting": MagicMock(annotation=int),
+        }
+
+        # Mock database session
+        mock_db = MagicMock()
+        mock_db_settings = [
+            ApplicationSettings(key="test_setting", value="test_value"),
+            ApplicationSettings(key="another_setting", value="42"),
+        ]
+        mock_db.query.return_value.all.return_value = mock_db_settings
+
+        load_settings_from_db(mock_settings, mock_db)
+
+        # Verify settings were set
+        assert mock_settings.test_setting == "test_value"
+        assert mock_settings.another_setting == 42
+
+    def test_handles_empty_database(self):
+        """Test handling when no settings in database."""
+        mock_settings = MagicMock()
+        mock_db = MagicMock()
+        mock_db.query.return_value.all.return_value = []
+
+        # Should not raise
+        load_settings_from_db(mock_settings, mock_db)
+
+    def test_skips_unknown_settings(self):
+        """Test that unknown settings are skipped."""
+        from app.models import ApplicationSettings
+
+        mock_settings = MagicMock()
+        mock_settings.__fields__ = {"known_setting": MagicMock(annotation=str)}
+
+        mock_db = MagicMock()
+        mock_db_settings = [
+            ApplicationSettings(key="known_setting", value="value1"),
+            ApplicationSettings(key="unknown_setting", value="value2"),
+        ]
+        mock_db.query.return_value.all.return_value = mock_db_settings
+
+        load_settings_from_db(mock_settings, mock_db)
+
+        # Only known_setting should be set
+        assert hasattr(mock_settings, "known_setting")
+
+    def test_handles_database_errors(self):
+        """Test handling database errors gracefully."""
+        mock_settings = MagicMock()
+        mock_db = MagicMock()
+        mock_db.query.side_effect = Exception("Database error")
+
+        # Should not raise, just log warning
+        load_settings_from_db(mock_settings, mock_db)
+
+
+@pytest.mark.unit
+class TestReloadSettingsFromDb:
+    """Tests for reload_settings_from_db function."""
+
+    @patch("app.utils.config_loader.SessionLocal")
+    @patch("app.utils.config_loader.load_settings_from_db")
+    def test_reload_success(self, mock_load, mock_session_local):
+        """Test successful settings reload."""
+        mock_settings = MagicMock()
+        mock_db = MagicMock()
+        mock_session_local.return_value = mock_db
+
+        result = reload_settings_from_db(mock_settings)
+
+        assert result is True
+        mock_load.assert_called_once_with(mock_settings, mock_db)
+        mock_db.close.assert_called_once()
+
+    @patch("app.utils.config_loader.SessionLocal")
+    def test_reload_database_error(self, mock_session_local):
+        """Test reload handling database error."""
+        mock_settings = MagicMock()
+        mock_session_local.side_effect = Exception("Connection error")
+
+        result = reload_settings_from_db(mock_settings)
+
+        assert result is False
+
+    @patch("app.utils.config_loader.SessionLocal")
+    def test_reload_closes_session_on_error(self, mock_session_local):
+        """Test that session is closed even on error."""
+        mock_settings = MagicMock()
+        mock_db = MagicMock()
+        mock_db.query.side_effect = Exception("Query error")
+        mock_session_local.return_value = mock_db
+
+        result = reload_settings_from_db(mock_settings)
+
+        # Should close session despite error
+        mock_db.close.assert_called_once()
+        assert result is False
diff --git a/tests/test_diagnostic.py b/tests/test_diagnostic.py
index 975e62c1..0b1b166b 100644
--- a/tests/test_diagnostic.py
+++ b/tests/test_diagnostic.py
@@ -1,5 +1,7 @@
 """Tests for app/api/diagnostic.py module."""
 
+from unittest.mock import MagicMock, patch
+
 import pytest
 
 
@@ -25,6 +27,24 @@ class TestDiagnosticSettings:
         for key in expected_keys:
             assert key in services
 
+    def test_diagnostic_settings_includes_workdir(self, client):
+        """Test that settings include workdir."""
+        response = client.get("/api/diagnostic/settings")
+        data = response.json()
+        assert "workdir" in data["settings"]
+
+    def test_diagnostic_settings_includes_hostname(self, client):
+        """Test that settings include external hostname."""
+        response = client.get("/api/diagnostic/settings")
+        data = response.json()
+        assert "external_hostname" in data["settings"]
+
+    def test_diagnostic_settings_includes_imap_status(self, client):
+        """Test that settings include IMAP enabled status."""
+        response = client.get("/api/diagnostic/settings")
+        data = response.json()
+        assert "imap_enabled" in data["settings"]
+
 
 @pytest.mark.integration
 class TestTestNotification:
@@ -37,3 +57,129 @@ class TestTestNotification:
         data = response.json()
         # Should return warning (no notification services configured) or success
         assert data["status"] in ("warning", "success", "error")
+
+    @patch("app.api.diagnostic.settings")
+    def test_test_notification_no_urls_configured(self, mock_settings, client):
+        """Test notification test when no URLs are configured."""
+        mock_settings.notification_urls = []
+        mock_settings.external_hostname = "test-host"
+
+        response = client.post("/api/diagnostic/test-notification")
+        data = response.json()
+
+        assert data["status"] == "warning"
+        assert "not configured" in data["message"].lower()
+
+    @patch("app.api.diagnostic.send_notification")
+    @patch("app.api.diagnostic.settings")
+    def test_test_notification_success(self, mock_settings, mock_send, client):
+        """Test successful notification test."""
+        mock_settings.notification_urls = ["https://example.com/notify"]
+        mock_settings.external_hostname = "test-host"
+        mock_send.return_value = True
+
+        response = client.post("/api/diagnostic/test-notification")
+        data = response.json()
+
+        assert data["status"] == "success"
+        assert "services_count" in data
+        mock_send.assert_called_once()
+
+    @patch("app.api.diagnostic.send_notification")
+    @patch("app.api.diagnostic.settings")
+    def test_test_notification_failure(self, mock_settings, mock_send, client):
+        """Test notification test when sending fails."""
+        mock_settings.notification_urls = ["https://example.com/notify"]
+        mock_settings.external_hostname = "test-host"
+        mock_send.return_value = False
+
+        response = client.post("/api/diagnostic/test-notification")
+        data = response.json()
+
+        assert data["status"] == "error"
+        assert "failed" in data["message"].lower()
+
+    @patch("app.api.diagnostic.send_notification")
+    @patch("app.api.diagnostic.settings")
+    def test_test_notification_exception(self, mock_settings, mock_send, client):
+        """Test notification test with exception."""
+        mock_settings.notification_urls = ["https://example.com/notify"]
+        mock_settings.external_hostname = "test-host"
+        mock_send.side_effect = Exception("Connection error")
+
+        response = client.post("/api/diagnostic/test-notification")
+        data = response.json()
+
+        assert data["status"] == "error"
+        assert "error" in data["message"].lower()
+
+    def test_test_notification_includes_timestamp(self, client):
+        """Test that notification includes timestamp in message."""
+        response = client.post("/api/diagnostic/test-notification")
+        data = response.json()
+
+        # Response should have been processed
+        assert response.status_code == 200
+
+
+@pytest.mark.unit
+class TestDiagnosticHelpers:
+    """Test helper functions in diagnostic module."""
+
+    @patch("app.api.diagnostic.dump_all_settings")
+    @patch("app.api.diagnostic.settings")
+    def test_dump_all_settings_called(self, mock_settings, mock_dump, client):
+        """Test that dump_all_settings is called."""
+        mock_settings.external_hostname = "test"
+        # Setup minimal mocks for configured services
+        mock_settings.email_host = None
+        mock_settings.s3_bucket_name = None
+        mock_settings.dropbox_refresh_token = None
+        mock_settings.onedrive_refresh_token = None
+        mock_settings.nextcloud_upload_url = None
+        mock_settings.sftp_host = None
+        mock_settings.paperless_host = None
+        mock_settings.google_drive_credentials_json = None
+        mock_settings.uptime_kuma_url = None
+        mock_settings.authentik_config_url = None
+        mock_settings.openai_api_key = None
+        mock_settings.azure_api_key = None
+        mock_settings.azure_endpoint = None
+        mock_settings.imap1_host = None
+        mock_settings.imap2_host = None
+
+        response = client.get("/api/diagnostic/settings")
+
+        # dump_all_settings should have been called
+        mock_dump.assert_called_once()
+
+    @patch("app.api.diagnostic.settings")
+    def test_safe_settings_no_sensitive_data(self, mock_settings, client):
+        """Test that safe settings don't include sensitive data."""
+        mock_settings.workdir = "/tmp/workdir"
+        mock_settings.external_hostname = "test-host"
+        mock_settings.openai_api_key = "sk-secret-key-12345"
+        mock_settings.aws_secret_access_key = "secret-aws-key"
+        # Setup minimal configured services
+        mock_settings.email_host = None
+        mock_settings.s3_bucket_name = None
+        mock_settings.dropbox_refresh_token = None
+        mock_settings.onedrive_refresh_token = None
+        mock_settings.nextcloud_upload_url = None
+        mock_settings.sftp_host = None
+        mock_settings.paperless_host = None
+        mock_settings.google_drive_credentials_json = None
+        mock_settings.uptime_kuma_url = None
+        mock_settings.authentik_config_url = None
+        mock_settings.azure_api_key = None
+        mock_settings.azure_endpoint = None
+        mock_settings.imap1_host = None
+        mock_settings.imap2_host = None
+
+        response = client.get("/api/diagnostic/settings")
+        data = response.json()
+
+        # Sensitive keys should not be in response
+        response_str = str(data)
+        assert "sk-secret-key" not in response_str
+        assert "secret-aws-key" not in response_str
diff --git a/tests/test_imap_tasks.py b/tests/test_imap_tasks.py
index 960dd789..015cdbf9 100644
--- a/tests/test_imap_tasks.py
+++ b/tests/test_imap_tasks.py
@@ -1031,3 +1031,187 @@ class TestEmailAlreadyHasLabelExtended:
 
         result = email_already_has_label(mock_mail, b"1", "Ingested")
         assert result is False
+
+
+@pytest.mark.unit
+class TestGetCapabilitiesEdgeCases:
+    """Test edge cases for get_capabilities function."""
+
+    def test_get_capabilities_with_failed_response(self):
+        """Test get_capabilities when server returns error."""
+        mock_mail = MagicMock()
+        mock_mail.capability.return_value = ("NO", None)
+
+        result = get_capabilities(mock_mail)
+        assert result == []
+
+    def test_get_capabilities_with_empty_data(self):
+        """Test get_capabilities with empty capability data."""
+        mock_mail = MagicMock()
+        mock_mail.capability.return_value = ("OK", [b""])
+
+        result = get_capabilities(mock_mail)
+        assert isinstance(result, list)
+
+
+@pytest.mark.unit
+class TestFindAllMailXlistEdgeCases:
+    """Test edge cases for find_all_mail_xlist function."""
+
+    def test_find_all_mail_xlist_no_allmail_flag(self):
+        """Test XLIST when no folder has ALLMAIL flag."""
+        mock_mail = MagicMock()
+        mock_mail._new_tag.return_value = b"A001"
+        # Simulate responses without ALLMAIL flag
+        mock_mail.readline.side_effect = [
+            b'* XLIST (\\HasNoChildren) "/" "INBOX"\r\n',
+            b"A001 OK XLIST completed\r\n",
+        ]
+
+        result = find_all_mail_xlist(mock_mail)
+        assert result is None
+
+    def test_find_all_mail_xlist_with_valid_allmail(self):
+        """Test XLIST when folder has ALLMAIL flag."""
+        mock_mail = MagicMock()
+        mock_mail._new_tag.return_value = b"A001"
+        # Simulate response with ALLMAIL flag
+        mock_mail.readline.side_effect = [
+            b'* XLIST (\\AllMail \\HasNoChildren) "/" "[Gmail]/All Mail"\r\n',
+            b"A001 OK XLIST completed\r\n",
+        ]
+
+        result = find_all_mail_xlist(mock_mail)
+        assert result == "[Gmail]/All Mail"
+
+
+@pytest.mark.unit
+class TestAcquireReleaseLockEdgeCases:
+    """Test edge cases for lock acquisition and release."""
+
+    @patch("app.tasks.imap_tasks.redis_client")
+    def test_acquire_lock_when_already_held(self, mock_redis):
+        """Test lock acquisition when lock is already held."""
+        mock_redis.setnx.return_value = False
+
+        result = acquire_lock()
+        assert result is False
+        # Should not call expire if lock not acquired
+        mock_redis.expire.assert_not_called()
+
+    @patch("app.tasks.imap_tasks.redis_client")
+    def test_release_lock_always_attempts_delete(self, mock_redis):
+        """Test that release_lock always attempts to delete the key."""
+        release_lock()
+        mock_redis.delete.assert_called_once()
+
+
+@pytest.mark.unit
+class TestPullInboxEdgeCases:
+    """Test edge cases for pull_inbox function."""
+
+    @patch("app.tasks.imap_tasks.load_processed_emails")
+    @patch("app.tasks.imap_tasks.imaplib.IMAP4_SSL")
+    @patch("app.tasks.imap_tasks.settings")
+    def test_pull_inbox_search_failed_status(self, mock_settings, mock_imap_class, mock_load):
+        """Test pull_inbox when search returns non-OK status."""
+        mock_settings.workdir = "/tmp"
+        mock_load.return_value = {}
+
+        mock_mail = MagicMock()
+        mock_mail.login.return_value = ("OK", [])
+        mock_mail.select.return_value = ("OK", [])
+        mock_mail.search.return_value = ("NO", [])  # Search failed
+        mock_imap_class.return_value = mock_mail
+
+        # Should handle gracefully and not raise
+        pull_inbox("test", "imap.example.com", 993, "user", "pass", True, False)
+
+        mock_mail.close.assert_called_once()
+        mock_mail.logout.assert_called_once()
+
+    @patch("app.tasks.imap_tasks.load_processed_emails")
+    @patch("app.tasks.imap_tasks.save_processed_emails")
+    @patch("app.tasks.imap_tasks.fetch_attachments_and_enqueue")
+    @patch("app.tasks.imap_tasks.imaplib.IMAP4_SSL")
+    @patch("app.tasks.imap_tasks.settings")
+    def test_pull_inbox_email_without_message_id(
+        self, mock_settings, mock_imap_class, mock_fetch, mock_save, mock_load
+    ):
+        """Test that emails without Message-ID are skipped."""
+        mock_settings.workdir = "/tmp"
+        mock_load.return_value = {}
+
+        mock_mail = MagicMock()
+        mock_mail.login.return_value = ("OK", [])
+        mock_mail.select.return_value = ("OK", [])
+        mock_mail.search.return_value = ("OK", [b"1"])
+
+        # Create email without Message-ID header
+        email_without_id = EmailMessage()
+        email_without_id["Subject"] = "Test"
+        raw_email = email_without_id.as_bytes()
+
+        mock_mail.fetch.return_value = ("OK", [(None, raw_email)])
+        mock_imap_class.return_value = mock_mail
+
+        pull_inbox("test", "imap.example.com", 993, "user", "pass", True, False)
+
+        # Should skip processing since no Message-ID
+        mock_fetch.assert_not_called()
+
+    @patch("app.tasks.imap_tasks.load_processed_emails")
+    @patch("app.tasks.imap_tasks.imaplib.IMAP4_SSL")
+    @patch("app.tasks.imap_tasks.settings")
+    def test_pull_inbox_fetch_failed_status(self, mock_settings, mock_imap_class, mock_load):
+        """Test pull_inbox when fetch returns non-OK status."""
+        mock_settings.workdir = "/tmp"
+        mock_load.return_value = {}
+
+        mock_mail = MagicMock()
+        mock_mail.login.return_value = ("OK", [])
+        mock_mail.select.return_value = ("OK", [])
+        mock_mail.search.return_value = ("OK", [b"1"])
+        mock_mail.fetch.return_value = ("NO", [])  # Fetch failed
+        mock_imap_class.return_value = mock_mail
+
+        # Should handle gracefully
+        pull_inbox("test", "imap.example.com", 993, "user", "pass", True, False)
+
+        mock_mail.close.assert_called_once()
+
+
+@pytest.mark.unit
+class TestMarkAsProcessedFunctions:
+    """Test mark_as_processed_with_star and mark_as_processed_with_label functions."""
+
+    def test_mark_as_processed_with_star_handles_exception(self):
+        """Test that star marking handles exceptions gracefully."""
+        mock_mail = MagicMock()
+        mock_mail.store.side_effect = Exception("Connection error")
+
+        # Should not raise, just log error
+        mark_as_processed_with_star(mock_mail, b"1")
+
+    def test_mark_as_processed_with_label_handles_exception(self):
+        """Test that label marking handles exceptions gracefully."""
+        mock_mail = MagicMock()
+        mock_mail.store.side_effect = Exception("Connection error")
+
+        # Should not raise, just log error
+        mark_as_processed_with_label(mock_mail, b"1", "Ingested")
+
+
+@pytest.mark.unit
+class TestEmailAlreadyHasLabelExceptions:
+    """Test exception handling in email_already_has_label."""
+
+    def test_email_already_has_label_fetch_exception(self):
+        """Test that fetch exceptions are handled gracefully."""
+        mock_mail = MagicMock()
+        mock_mail.fetch.side_effect = Exception("Fetch failed")
+
+        result = email_already_has_label(mock_mail, b"1", "Ingested")
+
+        # Should return False on error
+        assert result is False
diff --git a/tests/test_send_to_all.py b/tests/test_send_to_all.py
new file mode 100644
index 00000000..a2a57bc4
--- /dev/null
+++ b/tests/test_send_to_all.py
@@ -0,0 +1,356 @@
+"""Tests for app/tasks/send_to_all.py module."""
+
+import os
+from unittest.mock import MagicMock, patch
+
+import pytest
+
+from app.tasks.send_to_all import (
+    _should_upload_to_dropbox,
+    _should_upload_to_email,
+    _should_upload_to_ftp,
+    _should_upload_to_google_drive,
+    _should_upload_to_nextcloud,
+    _should_upload_to_onedrive,
+    _should_upload_to_paperless,
+    _should_upload_to_s3,
+    _should_upload_to_sftp,
+    _should_upload_to_webdav,
+    get_configured_services_from_validator,
+    send_to_all_destinations,
+)
+
+
+@pytest.mark.unit
+class TestShouldUploadFunctions:
+    """Test the _should_upload_to_* helper functions."""
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_dropbox_all_configured(self, mock_settings):
+        """Test Dropbox upload check when all credentials are configured."""
+        mock_settings.dropbox_app_key = "key"
+        mock_settings.dropbox_app_secret = "secret"
+        mock_settings.dropbox_refresh_token = "token"
+
+        assert _should_upload_to_dropbox() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_dropbox_missing_credentials(self, mock_settings):
+        """Test Dropbox upload check when credentials are missing."""
+        mock_settings.dropbox_app_key = None
+        mock_settings.dropbox_app_secret = None
+        mock_settings.dropbox_refresh_token = None
+
+        assert _should_upload_to_dropbox() is False
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_nextcloud_configured(self, mock_settings):
+        """Test Nextcloud upload check."""
+        mock_settings.nextcloud_upload_url = "https://nextcloud.example.com"
+        mock_settings.nextcloud_username = "user"
+        mock_settings.nextcloud_password = "pass"
+
+        assert _should_upload_to_nextcloud() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_paperless_configured(self, mock_settings):
+        """Test Paperless upload check."""
+        mock_settings.paperless_ngx_api_token = "token"
+        mock_settings.paperless_host = "https://paperless.example.com"
+
+        assert _should_upload_to_paperless() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_google_drive_oauth(self, mock_settings):
+        """Test Google Drive upload check with OAuth."""
+        mock_settings.google_drive_use_oauth = True
+        mock_settings.google_drive_client_id = "client_id"
+        mock_settings.google_drive_client_secret = "client_secret"
+        mock_settings.google_drive_refresh_token = "refresh_token"
+        mock_settings.google_drive_folder_id = "folder_id"
+
+        assert _should_upload_to_google_drive() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_google_drive_service_account(self, mock_settings):
+        """Test Google Drive upload check with service account."""
+        mock_settings.google_drive_use_oauth = False
+        mock_settings.google_drive_credentials_json = '{"type": "service_account"}'
+        mock_settings.google_drive_folder_id = "folder_id"
+
+        assert _should_upload_to_google_drive() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_webdav_configured(self, mock_settings):
+        """Test WebDAV upload check."""
+        mock_settings.webdav_url = "https://webdav.example.com"
+        mock_settings.webdav_username = "user"
+        mock_settings.webdav_password = "pass"
+
+        assert _should_upload_to_webdav() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_ftp_configured(self, mock_settings):
+        """Test FTP upload check."""
+        mock_settings.ftp_host = "ftp.example.com"
+        mock_settings.ftp_username = "user"
+        mock_settings.ftp_password = "pass"
+
+        assert _should_upload_to_ftp() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_sftp_with_password(self, mock_settings):
+        """Test SFTP upload check with password auth."""
+        mock_settings.sftp_host = "sftp.example.com"
+        mock_settings.sftp_username = "user"
+        mock_settings.sftp_password = "pass"
+        mock_settings.sftp_private_key = None
+
+        assert _should_upload_to_sftp() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_sftp_with_key(self, mock_settings):
+        """Test SFTP upload check with key auth."""
+        mock_settings.sftp_host = "sftp.example.com"
+        mock_settings.sftp_username = "user"
+        mock_settings.sftp_password = None
+        mock_settings.sftp_private_key = "/path/to/key"
+
+        assert _should_upload_to_sftp() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_email_configured(self, mock_settings):
+        """Test email upload check."""
+        mock_settings.email_host = "smtp.example.com"
+        mock_settings.email_username = "user"
+        mock_settings.email_password = "pass"
+        mock_settings.email_default_recipient = "recipient@example.com"
+
+        assert _should_upload_to_email() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_onedrive_configured(self, mock_settings):
+        """Test OneDrive upload check."""
+        mock_settings.onedrive_client_id = "client_id"
+        mock_settings.onedrive_client_secret = "client_secret"
+        mock_settings.onedrive_refresh_token = "refresh_token"
+
+        assert _should_upload_to_onedrive() is True
+
+    @patch("app.tasks.send_to_all.settings")
+    def test_should_upload_to_s3_configured(self, mock_settings):
+        """Test S3 upload check."""
+        mock_settings.s3_bucket_name = "my-bucket"
+        mock_settings.aws_access_key_id = "key_id"
+        mock_settings.aws_secret_access_key = "secret_key"
+
+        assert _should_upload_to_s3() is True
+
+
+@pytest.mark.unit
+class TestGetConfiguredServicesFromValidator:
+    """Test get_configured_services_from_validator function."""
+
+    @patch("app.tasks.send_to_all.get_provider_status")
+    def test_returns_configured_services(self, mock_get_status):
+        """Test that configured services are returned correctly."""
+        mock_get_status.return_value = {
+            "Dropbox": {"configured": True},
+            "NextCloud": {"configured": False},
+            "S3 Storage": {"configured": True},
+        }
+
+        result = get_configured_services_from_validator()
+
+        assert result["dropbox"] is True
+        assert result["nextcloud"] is False
+        assert result["s3"] is True
+
+    @patch("app.tasks.send_to_all.get_provider_status")
+    def test_handles_missing_providers(self, mock_get_status):
+        """Test handling when some providers are not in status."""
+        mock_get_status.return_value = {
+            "Dropbox": {"configured": True},
+        }
+
+        result = get_configured_services_from_validator()
+
+        assert result["dropbox"] is True
+        # Other services not in result
+
+
+@pytest.mark.unit
+class TestSendToAllDestinations:
+    """Test send_to_all_destinations task."""
+
+    def test_file_not_found_error(self):
+        """Test that FileNotFoundError is raised when file doesn't exist."""
+        with pytest.raises(FileNotFoundError):
+            send_to_all_destinations.apply(args=["/nonexistent/file.pdf"])
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all._should_upload_to_dropbox")
+    @patch("app.tasks.send_to_all.upload_to_dropbox")
+    def test_queues_single_configured_service(self, mock_upload, mock_should, mock_settings, tmp_path):
+        """Test queueing upload to a single configured service."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_should.return_value = True
+        mock_upload.delay.return_value = MagicMock(id="task-123")
+
+        result = send_to_all_destinations.apply(args=[str(test_file), False])
+
+        assert result.result["status"] == "Queued"
+        mock_upload.delay.assert_called_once()
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all._should_upload_to_dropbox")
+    @patch("app.tasks.send_to_all._should_upload_to_s3")
+    @patch("app.tasks.send_to_all.upload_to_dropbox")
+    @patch("app.tasks.send_to_all.upload_to_s3")
+    def test_queues_multiple_services(
+        self, mock_s3_upload, mock_dropbox_upload, mock_should_s3, mock_should_dropbox, mock_settings, tmp_path
+    ):
+        """Test queueing uploads to multiple services."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_should_dropbox.return_value = True
+        mock_should_s3.return_value = True
+        mock_dropbox_upload.delay.return_value = MagicMock(id="dropbox-task")
+        mock_s3_upload.delay.return_value = MagicMock(id="s3-task")
+
+        result = send_to_all_destinations.apply(args=[str(test_file), False])
+
+        assert result.result["status"] == "Queued"
+        mock_dropbox_upload.delay.assert_called_once()
+        mock_s3_upload.delay.assert_called_once()
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all._should_upload_to_dropbox")
+    def test_skips_unconfigured_services(self, mock_should, mock_settings, tmp_path):
+        """Test that unconfigured services are skipped."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_should.return_value = False
+
+        result = send_to_all_destinations.apply(args=[str(test_file), False])
+
+        # No uploads should be queued
+        assert result.result["status"] == "Queued"
+        # Check that message indicates 0 uploads
+        assert "0 upload" in result.result["tasks"] or len(result.result["tasks"]) == 0
+
+    @patch("app.tasks.send_to_all.SessionLocal")
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all._should_upload_to_dropbox")
+    @patch("app.tasks.send_to_all.upload_to_dropbox")
+    def test_with_file_id_parameter(
+        self, mock_upload, mock_should, mock_settings, mock_session_local, tmp_path
+    ):
+        """Test send_to_all with explicit file_id parameter."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_should.return_value = True
+        mock_upload.delay.return_value = MagicMock(id="task-123")
+
+        result = send_to_all_destinations.apply(args=[str(test_file), False, 42])
+
+        mock_upload.delay.assert_called_once()
+        # Verify file_id was passed to the upload task
+        call_kwargs = mock_upload.delay.call_args[1]
+        assert call_kwargs.get("file_id") == 42
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all.get_configured_services_from_validator")
+    @patch("app.tasks.send_to_all.upload_to_dropbox")
+    def test_uses_validator_when_enabled(
+        self, mock_upload, mock_validator, mock_settings, tmp_path
+    ):
+        """Test that validator is used when use_validator=True."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_validator.return_value = {"dropbox": True}
+        mock_upload.delay.return_value = MagicMock(id="task-123")
+
+        result = send_to_all_destinations.apply(args=[str(test_file), True])
+
+        mock_validator.assert_called_once()
+        mock_upload.delay.assert_called_once()
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all.get_configured_services_from_validator")
+    def test_validator_exception_fallback(self, mock_validator, mock_settings, tmp_path):
+        """Test fallback to individual checks when validator fails."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_validator.side_effect = Exception("Validator error")
+
+        # Should not raise, should fall back to individual checks
+        result = send_to_all_destinations.apply(args=[str(test_file), True])
+
+        assert result.result["status"] == "Queued"
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all._should_upload_to_dropbox")
+    @patch("app.tasks.send_to_all.upload_to_dropbox")
+    def test_handles_upload_task_queue_error(
+        self, mock_upload, mock_should, mock_settings, tmp_path
+    ):
+        """Test handling when queueing upload task fails."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_should.return_value = True
+        mock_upload.delay.side_effect = Exception("Queue error")
+
+        # Should not raise, should log error
+        result = send_to_all_destinations.apply(args=[str(test_file), False])
+
+        assert result.result["status"] == "Queued"
+        # Error should be recorded in results
+        assert "dropbox_error" in result.result["tasks"]
+
+    @patch("app.tasks.send_to_all.SessionLocal")
+    @patch("app.tasks.send_to_all.settings")
+    def test_fallback_file_id_lookup(self, mock_settings, mock_session_local, tmp_path):
+        """Test file_id lookup fallback when not provided."""
+        from app.models import FileRecord
+
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_settings.workdir = str(tmp_path)
+
+        # Mock database session
+        mock_db = MagicMock()
+        mock_query = MagicMock()
+        mock_file_record = MagicMock(spec=FileRecord)
+        mock_file_record.id = 123
+        mock_query.first.return_value = mock_file_record
+        mock_db.query.return_value.filter.return_value = mock_query
+        mock_session_local.return_value.__enter__.return_value = mock_db
+
+        result = send_to_all_destinations.apply(args=[str(test_file), False, None])
+
+        # Should attempt database lookup
+        mock_db.query.assert_called()
+
+    @patch("app.tasks.send_to_all.settings")
+    @patch("app.tasks.send_to_all._should_upload_to_dropbox")
+    def test_should_upload_check_exception_handling(self, mock_should, mock_settings, tmp_path):
+        """Test that exceptions in should_upload checks are handled."""
+        test_file = tmp_path / "test.pdf"
+        test_file.write_text("test")
+
+        mock_should.side_effect = Exception("Configuration check error")
+
+        # Should not raise, should treat as not configured
+        result = send_to_all_destinations.apply(args=[str(test_file), False])
+
+        assert result.result["status"] == "Queued"