How to send emails from an Outlook/Microsoft 365 account using Automation Anywhere Community Edition?

Hi ​@williamreyes ,

I have tried this in past with Outlook,Office365, & Email package in community edition.

Before proceeding with the configuration, could you please confirm the following prerequisites?

1. Do you have access to the Microsoft 365 / Microsoft Entra ID (Azure) admin portal for the Outlook account? If yes, do you have permission to register an application and grant the required Microsoft Graph API permissions?

2. If you do not have Entra ID/admin access, is the Microsoft Outlook desktop application installed on the machine where the Automation Anywhere bot will run?

3. Is the Microsoft 365/Outlook account active and already signed in to the Outlook application on that machine?

4. Could you also confirm the type of Outlook/Microsoft 365 license associated with the account (for example, Microsoft 365 Business, Enterprise, Personal, etc.)? Identifying the license/account type will help determine which authentication and email-sending approach is appropriate.

5. If Microsoft 365/Outlook is not available, you could also try testing the email functionality using a Gmail account. This would help determine whether the issue is specific to the Microsoft 365/Outlook configuration or related to the Automation Anywhere Email package/configuration.

Once these prerequisites are confirmed, we can determine the appropriate configuration path for your Community Edition environment and provide the relevant step-by-step instructions.

Hi ​@williamreyes 
 

Welcome to the community! You have several options depending on whether you have the classic Outlook desktop app installed locally or want to connect directly to Microsoft 365 in the cloud.
 

Quick Answers to Your Questions

• Should I use the Microsoft 365 Outlook package or the Email package?

  • For a quick local test (Easiest): Use the Email package (Send action) and choose Outlook instead of Email server. It sends through your local classic Outlook desktop app with zero OAuth or SMTP setup required.

  • For direct cloud integration (Recommended): Use the Microsoft 365 Outlook package (Connect + Send actions), which communicates with Microsoft 365 via the Microsoft Graph API using OAuth 2.0.

• Why don't I see Control Room managed OAuth connections in Community Edition?

  • In Enterprise editions, an administrator sets up reusable OAuth connections under Manage → OAuth connections. Community Edition does not include the Control Room Administration / Manage OAuth Connections tab. Because of this limitation, you cannot use the Control Room managed option in Community Edition—you must select Authorization Code with PKCE or Client Credentials directly inside the action and provide your own Azure App details (Client ID, Tenant ID, etc.).

• Why does smtp.office365.com:587 with Basic Authentication fail in Email package 3.33.7?

  • This is not a bug with Email package version 3.33.7. The error "There was an error in sending the email message. Please check your connection details provided and try again" happens because Microsoft has disabled Basic Authentication across Exchange Online / Outlook.com and disables Authenticated SMTP (SMTP AUTH) on mailboxes by default.
     

Option 1: The Easiest Way for a Simple Test (Local Classic Outlook App)

If you have the classic Microsoft Outlook desktop application installed and signed into your Microsoft 365 account on the same machine where your Bot Agent is running, you can bypass Azure Entra ID and SMTP completely:

1. In your bot, drag in the Email: Send action.

2. Enter the To address, Subject, and Message.

3. Under Send email via, select Outlook (do not select Email server or EWS).

4. Save and Run the bot.

(Note: Make sure you are using classic Outlook for Windows—not the "New Outlook" web-based app—and only have one account configured in that Outlook profile.)
 

Option 2: Recommended Cloud Setup (Microsoft 365 Outlook Package with OAuth 2.0)

If you want to connect directly to Microsoft 365 without using the local Outlook desktop app, use the Microsoft 365 Outlook package with Authorization Code with PKCE (best for attended testing in Community Edition).

Step 1: Register an App in Microsoft Entra ID (Azure Portal)

1. Sign in to the Microsoft Entra admin center ([https://entra.microsoft.com](https://entra.microsoft.com)) or Azure Portal ([https://portal.azure.com](https://portal.azure.com)) with your Microsoft 365 / Outlook account.

2. Go to Identity (or Microsoft Entra ID) → Applications → App registrations and click + New registration.

3. Name: Enter a name (e.g., AA-Community-Outlook-Bot).

4. Supported account types:

   • Select Accounts in this organizational directory only (Single tenant) for a work/school M365 account, or

   • Select Accounts in any organizational directory and personal Microsoft accounts if you are using a personal @outlook.com / @hotmail.com account.

5. Redirect URI:

   • In the platform dropdown, select Public client/native (mobile & desktop) (Important: Do not select "Web" for PKCE).

   • Enter http://localhost:9999/Callback (Ensure port 9999 is open, or use another open port like 8899).

6. Click Register.

7. On the app's Overview page, copy and save two values:

   • Application (client) ID (This is your Client ID)

   • Directory (tenant) ID (This is your Tenant ID)

Step 2: Configure API Permissions in Entra ID

1. In your registered app, go to Manage → API permissions on the left menu.

2. Click + Add a permission → Microsoft APIs → Microsoft Graph.

3. Select Delegated permissions.

4. Search for and check the following 7 permissions:

   • OpenId permissions: email, offline_access, openid, profile

   • User: User.Read

   • Mail: Mail.ReadWrite, Mail.Send

5. Click Add permissions.

6. (Work/School accounts) If you have admin rights in your M365 tenant, click Grant admin consent for [Your Organization] and click Yes.

(Note: If you want to run the bot unattended using the Client Credentials mode instead of PKCE, you must select Application permissions instead of Delegated permissions, add Mail.ReadWrite, Mail.Send, and User.Read.All, grant Admin Consent, and generate a Client secret under Certificates & secrets.)
 

Step 3: Configure Microsoft 365 Outlook: Connect in Community Edition

1. In your bot, drag in the Microsoft 365 Outlook: Connect action.

2. Configure the fields as follows:

   • Azure cloud: Azure Global

   • OAuth2 Authentication mode: Authorization Code with PKCE

   • Client ID: Paste your Application (client) ID (via Credential Vault, Variable, or Insecure string).

   • Tenant ID: Paste your Directory (tenant) ID (Tip: If using a personal @outlook.com account and your Tenant ID throws an authority error, try entering consumers as the Tenant ID).

   • Redirect URI: http://localhost:9999/Callback (Must match your Azure Redirect URI exactly, including the capital C).

   • Username: Enter your full Microsoft 365 / Outlook email address.

   • Session name: Leave as Default.

Step 4: Add Microsoft 365 Outlook: Send and Run

1. Drag the Microsoft 365 Outlook: Send action below Connect.

2. Keep the Session name as Default and fill in To, Subject, and Body.

3. Add Microsoft 365 Outlook: Disconnect at the end.

4. Run the bot:

   • On your first run with Authorization Code with PKCE, a browser window will pop up asking you to sign into your Microsoft account and accept permissions.

   • Once authenticated, close the browser window—this signals the Bot Agent to continue to the Send action.
     
      

Option 3: Why smtp.office365.com:587 Failed (and When SMTP Works)

If you still prefer to use the Email: Send action via Email server (smtp.office365.com, Port 587):

1. Why Basic Authentication failed:

   • Personal Outlook.com accounts: Microsoft permanently removed Basic Authentication for SMTP/IMAP on personal accounts. Basic auth (and even App Passwords) will no longer work on smtp.office365.com.

   • Work/School Microsoft 365 accounts: Even though Microsoft still supports SMTP AUTH at the protocol level for Exchange Online, two things block it by default:

     1. Authenticated SMTP is disabled on the mailbox: A Microsoft 365 Admin must go to Microsoft 365 Admin Center → Users → Active users → [Your User] → Mail → Manage email apps and check Authenticated SMTP.

     2. Security Defaults / Conditional Access: Microsoft Entra's Security Defaults (enabled by default on all modern tenants) block all Basic Authentication requests regardless of mailbox settings.

2. How to use OAuth2 with the Email package:

   • In the Email: Send action (under Send email via: Email server), change Authentication mode from Basic to OAuth2 – Authorization code with PKCE, select Outlook/Office365 as the Email provider, and provide the Azure App Registration details (Client ID, Tenant ID, Redirect URI). However, Authenticated SMTP must still be enabled on the mailbox—which is why Option 2 (Microsoft 365 Outlook package) is strongly preferred.
      

Helpful Documentation Links

• Using Connect action in Microsoft 365 Outlook package: 
  https://docs.automationanywhere.com/r/automation-360/ms-365-outlook-connect-action

• Set up OAuth 2.0 using authorization code with PKCE: 
  https://docs.automationanywhere.com/r/automation-360/setting-up-oauth-2-authorization-code-with-pkce

• Set up OAuth 2.0 using client credentials: 
  https://docs.automationanywhere.com/r/automation-360/setting-up-oauth-2-client-credentials

• Using Send action in Email package:
  https://docs.automationanywhere.com/r/automation-360/cloud-using-send-action
   

Hope this helps you get your test bot up and running! Let me know if you run into any specific error messages while testing.

Hi ​@williamreyes

Welcome to the community! You have several options depending on whether you have the classic Outlook desktop app installed locally or want to connect directly to Microsoft 365 in the cloud.

Here are the direct answers to your questions, followed by a step-by-step guide for Automation Anywhere Community Edition.

Quick Answers to Your Questions

• Should I use the Microsoft 365 Outlook package or the Email package?

  • For a quick local test (Easiest): Use the Email package (Send action) and choose Outlook instead of Email server. It sends through your local classic Outlook desktop app with zero OAuth or SMTP setup required.

  • For direct cloud integration (Recommended): Use the Microsoft 365 Outlook package (Connect + Send actions), which communicates with Microsoft 365 via the Microsoft Graph API using OAuth 2.0.

• Why don't I see Control Room managed OAuth connections in Community Edition?

  • In Enterprise editions, an administrator sets up reusable OAuth connections under Manage → OAuth connections. Community Edition does not include the Control Room Administration / Manage OAuth Connections tab. Because of this limitation, you cannot use the Control Room managed option in Community Edition—you must select Authorization Code with PKCE or Client Credentials directly inside the action and provide your own Azure App details (Client ID, Tenant ID, etc.).

• Why does smtp.office365.com:587 with Basic Authentication fail in Email package 3.33.7?

  • This is not a bug with Email package version 3.33.7. The error "There was an error in sending the email message. Please check your connection details provided and try again" happens because Microsoft has disabled Basic Authentication across Exchange Online / Outlook.com and disables Authenticated SMTP (SMTP AUTH) on mailboxes by default.

Option 1: The Easiest Way for a Simple Test (Local Classic Outlook App)

If you have the classic Microsoft Outlook desktop application installed and signed into your Microsoft 365 account on the same machine where your Bot Agent is running, you can bypass Azure Entra ID and SMTP completely:

1. In your bot, drag in the Email: Send action.

2. Enter the To address, Subject, and Message.

3. Under Send email via, select Outlook (do not select Email server or EWS).

4. Save and Run the bot.

(Note: Make sure you are using classic Outlook for Windows—not the "New Outlook" web-based app—and only have one account configured in that Outlook profile.)

Option 2: Recommended Cloud Setup (Microsoft 365 Outlook Package with OAuth 2.0)

If you want to connect directly to Microsoft 365 without using the local Outlook desktop app, use the Microsoft 365 Outlook package with Authorization Code with PKCE (best for attended testing in Community Edition).

Step 1: Register an App in Microsoft Entra ID (Azure Portal)

1. Sign in to the Microsoft Entra admin center ([https://entra.microsoft.com](https://entra.microsoft.com)) or Azure Portal ([https://portal.azure.com](https://portal.azure.com)) with your Microsoft 365 / Outlook account.

2. Go to Identity (or Microsoft Entra ID) → Applications → App registrations and click + New registration.

3. Name: Enter a name (e.g., AA-Community-Outlook-Bot).

4. Supported account types:

   • Select Accounts in this organizational directory only (Single tenant) for a work/school M365 account, or

   • Select Accounts in any organizational directory and personal Microsoft accounts if you are using a personal @outlook.com / @hotmail.com account.

5. Redirect URI:

   • In the platform dropdown, select Public client/native (mobile & desktop) (Important: Do not select "Web" for PKCE).

   • Enter http://localhost:9999/Callback (Ensure port 9999 is open, or use another open port like 8899).

6. Click Register.

7. On the app's Overview page, copy and save two values:

   • Application (client) ID (This is your Client ID)

   • Directory (tenant) ID (This is your Tenant ID)

Step 2: Configure API Permissions in Entra ID

1. In your registered app, go to Manage → API permissions on the left menu.

2. Click + Add a permission → Microsoft APIs → Microsoft Graph.

3. Select Delegated permissions.

4. Search for and check the following 7 permissions:

   • OpenId permissions: email, offline_access, openid, profile

   • User: User.Read

   • Mail: Mail.ReadWrite, Mail.Send

5. Click Add permissions.

6. (Work/School accounts) If you have admin rights in your M365 tenant, click Grant admin consent for [Your Organization] and click Yes.

(Note: If you want to run the bot unattended using the Client Credentials mode instead of PKCE, you must select Application permissions instead of Delegated permissions, add Mail.ReadWrite, Mail.Send, and User.Read.All, grant Admin Consent, and generate a Client secret under Certificates & secrets.)

Step 3: Configure Microsoft 365 Outlook: Connect in Community Edition

1. In your bot, drag in the Microsoft 365 Outlook: Connect action.

2. Configure the fields as follows:

   • Azure cloud: Azure Global

   • OAuth2 Authentication mode: Authorization Code with PKCE

   • Client ID: Paste your Application (client) ID (via Credential Vault, Variable, or Insecure string).

   • Tenant ID: Paste your Directory (tenant) ID (Tip: If using a personal @outlook.com account and your Tenant ID throws an authority error, try entering consumers as the Tenant ID).

   • Redirect URI: http://localhost:9999/Callback (Must match your Azure Redirect URI exactly, including the capital C).

   • Username: Enter your full Microsoft 365 / Outlook email address.

   • Session name: Leave as Default.

Step 4: Add Microsoft 365 Outlook: Send and Run

1. Drag the Microsoft 365 Outlook: Send action below Connect.

2. Keep the Session name as Default and fill in To, Subject, and Body.

3. Add Microsoft 365 Outlook: Disconnect at the end.

4. Run the bot:

   • On your first run with Authorization Code with PKCE, a browser window will pop up asking you to sign into your Microsoft account and accept permissions.

   • Once authenticated, close the browser window—this signals the Bot Agent to continue to the Send action.

Option 3: Why smtp.office365.com:587 Failed (and When SMTP Works)

If you still prefer to use the Email: Send action via Email server (smtp.office365.com, Port 587):

1. Why Basic Authentication failed:

   • Personal Outlook.com accounts: Microsoft permanently removed Basic Authentication for SMTP/IMAP on personal accounts. Basic auth (and even App Passwords) will no longer work on smtp.office365.com.

   • Work/School Microsoft 365 accounts: Even though Microsoft still supports SMTP AUTH at the protocol level for Exchange Online, two things block it by default:

     1. Authenticated SMTP is disabled on the mailbox: A Microsoft 365 Admin must go to Microsoft 365 Admin Center → Users → Active users → [Your User] → Mail → Manage email apps and check Authenticated SMTP.

     2. Security Defaults / Conditional Access: Microsoft Entra's Security Defaults (enabled by default on all modern tenants) block all Basic Authentication requests regardless of mailbox settings.

2. How to use OAuth2 with the Email package:

   • In the Email: Send action (under Send email via: Email server), change Authentication mode from Basic to OAuth2 – Authorization code with PKCE, select Outlook/Office365 as the Email provider, and provide the Azure App Registration details (Client ID, Tenant ID, Redirect URI). However, Authenticated SMTP must still be enabled on the mailbox—which is why Option 2 (Microsoft 365 Outlook package) is strongly preferred.

Helpful Documentation Links

• Using Connect action in Microsoft 365 Outlook package: 
  https://docs.automationanywhere.com/r/automation-360/ms-365-outlook-connect-action

• Set up OAuth 2.0 using authorization code with PKCE: 
  https://docs.automationanywhere.com/r/automation-360/setting-up-oauth-2-authorization-code-with-pkce

• Set up OAuth 2.0 using client credentials: 
  https://docs.automationanywhere.com/r/automation-360/setting-up-oauth-2-client-credentials

• Using Send action in Email package: 
  https://docs.automationanywhere.com/r/automation-360/cloud-using-send-action

Hope this helps you get your test bot up and running! Let me know if you run into any specific error messages while testing.

Hi ​@KhaledMostafaMe 

Thank you very much for your detailed guidance. I first tried the Option 1 you suggested (using the Email package → Send action with the classic Outlook desktop app). However, I had to discard this approach because the classic Outlook client is no longer the recommended version, and for future RPA development I need a solution that works with the new Outlook experience. 

After that, I moved on to Option 2 and attempted to configure the Microsoft 365 Outlook package using OAuth2, following the steps you described. When I opened the Azure Portal and clicked on Microsoft Entra ID, I inmediately received a pop-up warning indicating that the portal could not retrieve access tokens.

I then clicked “Sign in again” and tried authenticating with my Outlook.com account, but I received another error stating “Selected user account does not exist in tenant 'Microsoft Services' and cannot access the application '74658136-14ec-4630-ad9b-26e160ff0fc6' in that tenant. The account needs to be added as an external user in the tenant first.”

This made it clear that personal Outlook accounts do not have a tenant and therefore cannot register applications or use OAuth2 with Automation Anywhere.

Given this limitation, I wanted to ask if you see any alternative approach or if you would recommend a specific path forward for cases where only a personal Outlook account is available.

Hi ​@shubhamThakare8055 

Thank you for your message and for outlining the prerequisites. I can confirm the details based on what I have tested so far. I attempted to access the Microsoft Entra ID (Azure) admin portal using my Outlook.com account, but I do not have admin access or the ability to register applications. When I opened the Azure Portal and clicked on Microsoft Entra ID, I immediately received an “Interaction required” pop‑up indicating that access tokens could not be retrieved.

After selecting “Sign in again,” I tried authenticating with my Microsoft 365 Personal account (william.ra.002@outlook.com), but I received the following error: “Selected user account does not exist in tenant 'Microsoft Services' and cannot access the application '74658136-14ec-4630-ad9b-26e160ff0fc6' in that tenant.” This confirmed that Microsoft 365 Personal accounts do not have a tenant and therefore cannot register applications or grant Microsoft Graph API permissions.

Regarding the Outlook desktop application, I am using the new Outlook experience, not the classic Outlook client. Since Automation Anywhere only integrates with the classic version, this path is not viable for my RPA development. As an additional test, I tried sending emails using a Gmail account with the Email package, and this worked successfully, which suggests the issue is specific to the Microsoft 365 Personal account limitations rather than the Email package itself.

Given these constraints, I would appreciate your recommendation on whether there is any alternative approach for Community Edition when only a Microsoft 365 Personal account is available, or if using a Microsoft 365 Business/Developer tenant is the only viable path forward.

Hi ​@williamreyes ,

You can use the email package to connect outlook 

Select Outlook in Connect to option after that you can able to see the your mail box name in Outlook mailbox list option at the end you have select the respective mail box and try to send the email.