[Bug] AI chat fails to search Microsoft/Outlook inbox

[lukoerfer]

When using the chat assistant to search emails on a Microsoft/Outlook account, the request fails with a BadRequest error:

web-1   | [chat]: Building Outlook request {
web-1   |   "maxResults": 5,
web-1   |   "hasSearchQuery": true,
web-1   |   "hasDateFilters": false,
web-1   |   "queryWasSanitized": true
web-1   | } {
web-1   |   "requestId": "d41c81fa-3b3d-4df7-8a1c-8a2fd5da40d8",
web-1   |   "url": "https://837b90b9570e:3000/api/chat",
web-1   |   "userId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "email": "xxxxx@xxxxxxx.com",
web-1   |   "provider": "microsoft"
web-1   | }
web-1   | [chat]: Using search path {
web-1   |   "rawSearchQuery": "from:\"John Doe\"",
web-1   |   "effectiveSearchQuery": "from:\"\\\"John Doe\\\"\"",
web-1   |   "queryWasSanitized": true
web-1   | } {
web-1   |   "requestId": "d41c81fa-3b3d-4df7-8a1c-8a2fd5da40d8",
web-1   |   "url": "https://837b90b9570e:3000/api/chat",
web-1   |   "userId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "email": "xxxxx@xxxxxxx.com",
web-1   |   "provider": "microsoft"
web-1   | }
web-1   | [chat]: Non-retryable error encountered {
web-1   |   "error": {
web-1   |     "error": "Syntax error: character ':' is not valid at position 4 in 'from:\"\\\"John Doe\\\"\"'.",
web-1   |     "attemptNumber": 1,
web-1   |     "retriesLeft": 5,
web-1   |     "retriesConsumed": 0,
web-1   |     "retryDelay": 1000
web-1   |   },
web-1   |   "code": "BadRequest"
web-1   | } {
web-1   |   "requestId": "d41c81fa-3b3d-4df7-8a1c-8a2fd5da40d8",
web-1   |   "url": "https://837b90b9570e:3000/api/chat",
web-1   |   "userId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "email": "xxxxx@xxxxxxx.com",
web-1   |   "provider": "microsoft"
web-1   | }
web-1   | [chat]: Failed to search inbox {
web-1   |   "error": {
web-1   |     "error": "Syntax error: character ':' is not valid at position 4 in 'from:\"\\\"John Doe\\\"\"'.",
web-1   |     "attemptNumber": 1,
web-1   |     "retriesLeft": 5,
web-1   |     "retriesConsumed": 0,
web-1   |     "retryDelay": 1000
web-1   |   }
web-1   | } {
web-1   |   "requestId": "d41c81fa-3b3d-4df7-8a1c-8a2fd5da40d8",
web-1   |   "url": "https://837b90b9570e:3000/api/chat",
web-1   |   "userId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx",
web-1   |   "email": "xxxxx@xxxxxxx.com"
web-1   | }

Steps to Reproduce

1. Connect an Outlook/Microsoft account
2. Open the chat assistant
3. Ask something like "Show me emails from johndoe@example.com" or "Show me emails from John Doe"

Possible explanation

It seems like the search functionality of Microsoft/Outlook does not support the colon in a query like from:"John Doe" and this is the reason why the BadRequest is returned. In the code of the Microsoft provider, there is even a function stripGmailPrefixes that seems to fix a similar issue for a prefix like subject:, because it is not supported by Microsoft:

// IMPORTANT: This is intentionally lossy!
// Gmail-style prefixes like "subject:" can't be translated to Microsoft Graph because:
// 1. $filter with contains(subject, ...) can't be combined with $search or date filters
//    (causes "InefficientFilter" error)
// 2. $search doesn't support field-specific syntax like "subject:term"
//
// We strip the prefixes and use plain $search which searches subject AND body.
// This is broader than intended but still finds relevant messages.
// If subject-specific search is needed in the future, add a dedicated method
// that uses only $filter without $search or date filters.
function stripGmailPrefixes(query: string): string {
  return query
    .replace(/\b(subject|from|to|label):(?:"[^"]*"|\S+)/gi, (match) => {
      // Extract the value without the prefix for searching
      const colonIndex = match.indexOf(":");
      const value = match.slice(colonIndex + 1);
      // Remove quotes if present
      return value.replace(/^"|"$/g, "");
    })
    .replace(/\s+/g, " ")
    .trim();
}

However, this function is only called in getMessagesWithPagination, not in searchMessages which also takes a query parameter.

[lukoerfer]

It seems like the same issue also effects the meeting briefs functionality:

web-1  | [sendBrief]: Building Outlook request {
web-1  |   "maxResults": 12,
web-1  |   "hasSearchQuery": true,
web-1  |   "hasDateFilters": false,
web-1  |   "queryWasSanitized": true
web-1  | } {
web-1  |   "requestId": "c47fc0d8-3e4a-41df-ad79-84b7b75ec1bb",
web-1  |   "userId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "userEmail": "xxxxx@xxxxxxx.com",
web-1  |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "provider": "microsoft",
web-1  |   "eventId": "xxxxxxxxxxxxxxxxxxxxx"
web-1  | }
web-1  | [sendBrief]: Using search path {
web-1  |   "rawSearchQuery": "participants:johndoe@example.com",
web-1  |   "effectiveSearchQuery": "participants:johndoe@example.com",
web-1  |   "queryWasSanitized": true
web-1  | } {
web-1  |   "requestId": "c47fc0d8-3e4a-41df-ad79-84b7b75ec1bb",
web-1  |   "userId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "userEmail": "xxxxx@xxxxxxx.com",
web-1  |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "provider": "microsoft",
web-1  |   "eventId": "xxxxxxxxxxxxxxxxxxxxx"
web-1  | }
web-1  | [sendBrief]: Non-retryable error encountered {
web-1  |   "error": {
web-1  |     "error": "Syntax error: character ':' is not valid at position 12 in 'participants:johndoe@example.com'.",
web-1  |     "attemptNumber": 1,
web-1  |     "retriesLeft": 5,
web-1  |     "retriesConsumed": 0,
web-1  |     "retryDelay": 1000
web-1  |   },
web-1  |   "code": "BadRequest"
web-1  | } {
web-1  |   "requestId": "c47fc0d8-3e4a-41df-ad79-84b7b75ec1bb",
web-1  |   "userId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "userEmail": "xxxxx@xxxxxxx.com",
web-1  |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "provider": "microsoft",
web-1  |   "eventId": "xxxxxxxxxxxxxxxxxxxxx"
web-1  | }
web-1  | [sendBrief]: Failed to fetch threads for participant {
web-1  |   "participantEmail": "johndoe@example.com",
web-1  |   "error": {
web-1  |     "error": "Syntax error: character ':' is not valid at position 12 in 'participants:johndoe@example.com'.",
web-1  |     "attemptNumber": 1,
web-1  |     "retriesLeft": 5,
web-1  |     "retriesConsumed": 0,
web-1  |     "retryDelay": 1000
web-1  |   }
web-1  | } {
web-1  |   "requestId": "c47fc0d8-3e4a-41df-ad79-84b7b75ec1bb",
web-1  |   "userId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "userEmail": "xxxxx@xxxxxxx.com",
web-1  |   "emailAccountId": "xxxxxxxxxxxxxxxxxxxxx",
web-1  |   "provider": "microsoft",
web-1  |   "eventId": "xxxxxxxxxxxxxxxxxxxxx"
web-1  | }

[elie222]

Making a big update to chat today. Will take a look at this afterwards

[lukoerfer]

I think we updated a week ago and it seems like the errors in chat are mostly fixed, but the issue with the meeting briefs still persists as no information from the last mails is included yet. Hopefully, the pull request linked above might fix this as well.