Hi @Stacey Levine, 

Using oAuth2 we can do it. 

1. Configuring Office 365 (Microsoft Exchange) with OAuth2

Step 1: Register Your Application in Azure Active Directory (Azure AD)

1. Go to Azure Portal and log in.
2. Navigate to Azure Active Directory > App registrations.
3. Click on New registration:
   • Give your app a name (e.g., OutSystems Email).
   • Select Accounts in this organizational directory only if you are working within your organization.
   • Set the redirect URI (you can update this later if required).
4. After registering, note down the Application (Client) ID and Directory (Tenant) ID.

Step 2: Add API Permissions

1. Navigate to API Permissions in the left-hand menu.
2. Click Add a permission > Microsoft Graph > Delegated permissions.
3. Search for and add the following permissions:
   • Mail.Send
   • Mail.ReadWrite
   • offline_access (optional, for refresh tokens).
4. Grant admin consent for your application to make sure these permissions are applied.

Step 3: Create a Client Secret

1. Go to Certificates & secrets.
2. Click New client secret, and give it a description (e.g., OutSystems Email Secret).
3. Set the expiration period and click Add.
4. Copy and save the Client Secret, as it will be used in OutSystems.

Step 4: Acquire OAuth2 Token Programmatically in OutSystems

1. Implement the OAuth2 flow in OutSystems to acquire the Access Token using the Authorization Code grant type.

   • You can use the HTTP Request component in OutSystems to call Azure’s token endpoint and get an OAuth2 token.
   • The URL for token acquisition is:
   bashCopy codehttps://login.microsoftonline.com/{tenant}/oauth2/v2.0/token

   Where {tenant} is your Azure AD tenant ID.

2. You’ll need to send the following parameters in the request body:

   • client_id: Your Azure AD App’s Client ID.
   • client_secret: The secret you created.
   • scope: https://graph.microsoft.com/.default.
   • grant_type: client_credentials.
   • resource: https://graph.microsoft.com/.

Step 5: Configure SMTP in OutSystems

Once you have the OAuth2 token, configure OutSystems email sending using the following details:

• SMTP Server: smtp.office365.com
• Port: 587 (for TLS) or 465 (for SSL)
• Authentication Type: OAuth2
• Token: Use the OAuth2 token acquired.

2. Configuring Gmail with OAuth2

Step 1: Create a Google Cloud Project

1. Go to Google Cloud Console.
2. Create a new project (or select an existing one).
3. Navigate to APIs & Services > Credentials.
4. Click Create Credentials > OAuth 2.0 Client IDs.
5. Set the application type to Web application and configure the redirect URIs if needed.

Step 2: Enable Gmail API

1. In the Google Cloud Console, navigate to Library.
2. Search for and enable the Gmail API.

Step 3: Generate OAuth2 Credentials

1. After enabling the API, go to Credentials > Create Credentials > OAuth2 Client ID.
2. Set up your OAuth2 credentials (you will get a Client ID and Client Secret).
3. Make sure the OAuth consent screen is set up correctly.

Step 4: OAuth2 Flow in OutSystems

1. Use OutSystems to call Google’s OAuth2 token endpoint:

   bashCopy codehttps://oauth2.googleapis.com/token

   The request body should include:

   • client_id: Your Google app’s Client ID.
   • client_secret: The secret you created.
   • grant_type: authorization_code.
   • code: The authorization code received after user authentication.
   • redirect_uri: The URI registered in Google Cloud Console.

2. Handle the token acquisition and use the Access Token for subsequent requests.

Step 5: Configure SMTP in OutSystems

Once you acquire the OAuth2 token, configure the SMTP settings in OutSystems:

• SMTP Server: smtp.gmail.com
• Port: 587 (TLS) or 465 (SSL)
• Authentication Type: OAuth2
• Token: Use the OAuth2 token acquired.