Outlook connector for Simpplr Enterprise Search

• Introduction
• Capabilities at a glance
• Objects and content supported
• Versions and editions supported
• Prerequisites
• Authentication and security
• Setup and configuration
• Crawling and sync behavior
• Field mapping and search experience
• Monitoring and troubleshooting
• Frequently asked questions (FAQ)

Introduction

The Outlook connector allows Simpplr Enterprise Search to index Microsoft Outlook Mails, making your critical communications easily discoverable and searchable directly within the intranet.

With this connector, you can:

• Bring Outlook content into Simpplr Enterprise Search so users can find important emails alongside intranet content in one place.
• Search across your Microsoft mailbox including email subject lines, message bodies, without leaving Simpplr.
• Use advanced features like autocomplete, hybrid ranking, and Smart Answers on top of your Outlook data to quickly surface relevant threads or upcoming events.

Indexed content from Simpplr Enterprise Search is available in:

• In main search listing
• Smart answers

Capabilities at a glance

Objects and content supported

1. Objects - List the object types that are indexed, for example:

• Mails

2. Metadata - For each indexed item, Outlook captures:

• title
• url
• message
• to_recipients
• cc_recipients
• sender
• Permissions (users)

3. Permissions model - Permissions are read from Outlook and enforced in Simpplr Enterprise Search. Include:

• How user permissions are synchronized
  • Outlook users are fetched and stored in the ACL index.
  • The ACL index is updated the next time the ACL sync runs (by default, every hour) to ensure search permissions remain synchronized with outlook.
• How public or link-shared content is handled
  • Content that is only available via anonymous or public shared links is not indexed in the current version
• What happens when access is removed in Outlook
  • When a user’s access to their mailbox is revoked (for example, if an account is disabled or a license is removed in Microsoft 365), the updated status is applied during the next ACL sync.
  • The user's emails will no longer appear in Simpplr search results after the ACL sync completes.

Versions and editions supported

• Supported Outlook editions: All
• Not supported: N/A

Prerequisites

Before you begin, ensure the following:

1. Source system permissions

• Admin Center Access: You need access to the Microsoft Entra admin center (formerly Azure AD) or the Azure Portal to create and configure your application registration.
• Required Role: Your user account must have at least the Application Developer or Cloud Application Administrator role to register applications and manage their identities within your tenant.

2. Application / service account

• Ability to register a new Application Registration: You must be able to create a new registration in Microsoft Entra ID. This generates the unique Application (client) ID and Directory (tenant) ID required for your Outlook integration.
• Ability to generate Client Credentials (Client Id, Client secret).
• Ability to Authorize the application (Admin Consent and Custom App Upload)
• You must have the authority to grant Admin Consent for the following Microsoft Graph permissions required to index mail:
  • full_access_as_app
  • User.Read.All (to map users to their mailboxes for ACL security).

Authentication and security

1. Authentication mechanism
   Describe how  Simpplr Enterprise Search connects to Outlook:

• Auth type: Server Authentication (Client credentials)
• Scopes or permissions required (examples):
  • full_access_as_app
  • User.Read.All

2. Data security

• Data storage and residency: Indexed content  from Outlook are stored within your Simpplr Enterprise Search environment, in the same region as your Simpplr tenant.
• Encryption in transit: Server-side encryption with Amazon S3 managed keys (SSE-S3), TLS encryption in Kafka.
• Encryption at rest: SSL (TLS 1.2 or higher), Auth: OAuth 2.0 Bearer tokens (client-credential).
• Permission enforcement: Outlook access controls (User-based) are stored in the ACL index and applied at query time. Search results are always filtered by the signed-in user’s primary identity, ensuring that users can only search for and view emails from their own authorized mailbox.

Setup and configuration

Step 1 - Set Up Azure API Credentials for Outlook

To connect to Outlook you need to create an Azure Active Directory application and service principal that can access resources. Follow these steps:

1. Go to the Azure portal and sign in with your Azure account.
2. Navigate to the Azure Active Directory service.
3. Search and Navigate to the “App Registration” service.
   
4. Click on the New registration button to register a new application.
   
5. Provide a name for your app, and optionally select the supported account types (e.g., single tenant, multi-tenant).
   
6. Click on the Register button to create the app registration.
7. After the registration is complete, you will be redirected to the app’s overview page. Take note of the Application (client) ID  and Directory (Tenant) ID  value, as you’ll need it later.
   
   
    
8. Navigate to Manage →  API permissions section and click on the Add a permission button.
   
   
    
9. Choose "APIs my organization uses".
10. Search for and select "Office 365 Exchange Online".
11. Add the full_access_as_app application permission.
    
12. Search for and select "Microsoft Graph"
13. Add the User.Read.All application permission.
    
14. Click on the Add permissions button to add the selected permissions to your app.
15. Click on the Grant admin consent button to grant the required permissions to the app. This step requires administrative privileges. If you are not an admin, you need to request the admin to grant consent via their Azure Portal.
    
16. Under the "Certificates & Secrets" tab, go to Client Secrets. Generate a new client secret and keep a note of the string under the Value column.
    
    
    

Step 2 - Create the connector in Simpplr

1. In Simpplr, go to: Enterprise Search → Connectors → Add connector.
   
   
    
2. Select “Outlook”.
   
3. Enter basic information:
   • Name: (ConnectorName for this instance)
4. Provide authentication details:
   • Tenant ID
   • Client ID
   • Secret value
     
     
5. Save the configuration.

Step 3 - Define sync scope

1. Configure inclusion rules:
   • Not configurable in the current version
2. Configure exclusion rules:
   • Not configurable in the current version

3. Configure Audience based filtering.
   • Include audiences
   • Exclude audiences

Step 4 - Configure sync schedule

• Default schedule: Full crawl at first setup and once in a week, incremental sync every hour.
• Configuration options:
  • No option to configure the sync schedule, however sync can be paused and resumed.

Step 5 - Run Initial Sync and Monitor the sync

1. Run the initial sync by clicking the start sync button.
2. Monitor the latest sync status in the connector dashboard. This page shows the status of first full sync completed with latest full/incremental completed/failed status here.

Crawling and sync behavior

Describe how the connector works over time:

1.  Initial full crawl

• The connector performs a comprehensive scan of the user's mailbox. Every existing email (within the configured scope/history) is fetched and indexed for the first time.
• How long it may take: Depends on the size of the content.

2. Incremental updates

• Mechanism: Based on Timestamp of previous sync
• What changes trigger reindexing:
  • New items created (Any new emails received or sent since the last sync)
  • Existing items updated
  • Permissions changed
  • Items moved or renamed
  • Items deleted or archived (When an email is moved to the "Deleted Items”)

3. Deletion and permission changes

• Deleted items (mails) are removed from index at next sync.
• Permission changes are updated at the next sync cycle.

4. Expected latency

• With the default schedule (incremental sync every hour), changes made to Microsoft Outlook content are generally reflected in Simpplr search results within an hour of the update. Similarly, the permission lag in the system is typically up to one hour, as the ACL sync also runs hourly. On top of that, there can be certain cases, where the permission sync can take up-to 7days (When the full sync is run), subject to content volume and system load.

Field mapping and search experience

1. Default field mapping

Source field (Outlook) → Index field Simpplr

2.  Search experience - how content from this connector appears in search:

• Result layout: (Icon, Connector name, title as link, body(excerpt), Updated Date/ Created Date, object type)

• Available filters and facets:
  • Source = Outlook
  • Created Date
• Participation in advanced features:
  • Smart Answers / Q&A: Yes
  • Autocomplete: Yes
  • Recommendations / “Suggested for you”: N/A
  • Trending / popular results: N/A
  • Semantic / hybrid ranking: Yes

3. Limits and known limitations

Monitoring and troubleshooting

1. Connector health and monitoring - Describe where admins can see status information:

• Enterprise Search -> Connector name
• Available metrics:
  • Last sync status (Success / Warning / Failed)
  • Last sync time
  • Next scheduled sync
  • Sync Type
  • Total items indexed count

2. Common issues and resolutions. Example pattern:
   • Issue: Authentication failed (invalid credentials or missing scopes)
     Possible causes:
     1. Incorrect client ID or secret
     2. App not granted the required permissions
     3. Consent not approved by an admin
   • Resolution:
     1. Verify and re-enter credentials
     2. Confirm required scopes are granted
     3. Re-run admin consent flow
3. When to contact support
   • Authentication error persists even after trying the above-mentioned resolutions
   • Sync is stuck in the Pending state.
   • Sync is in progress but no documents are getting ingested.
   • Sync failure with cancelled error (when not cancelled manually)
   • Incomplete or Partial sync. 
4. When contacting, Support, include:

• Connector name and instance ID (if available)
• Organization URL
• Approximate time and date of the issue
• Error messages or screenshots
• Steps you already tried

Frequently asked questions (FAQ)

Q1. Can I connect multiple Outlook tenants or domains?
A. Multiple Outlook connections can be configured in the Simpplr environment. But functionality to connect multiple tenants or domains in a single connector is not implemented yet.

Q2. How often does Outlook sync data?
A. The connector runs a full crawl on first setup and then once per week. Incremental sync runs every hour and ACL (permission) sync runs every hour by default.

Q3. Are comments, revisions, or version history indexed?
A. Comments and individual versions are not indexed as separate items. The connector indexes the latest file metadata, including the last updated time and updated-by user.

Q4. Does the connector index content from external guests or shared links?
A. Not implemented yet.

Q5. What happens when a user loses access to an item in Outlook?
A. The updated access permissions will be indexed during the next sync.

Q6. Can I exclude certain sites/teams/folders from being indexed?
A. Documents can be included or excluded based on audiences.

Q7. How are deletions handled?
A. Objects deleted from the source are permanently deleted from the index.

Q8. Are image files searchable ?

A. No, images are not searchable.