Chilkat v11.3.0 Release Notes

Pinned December 16, 2025

  The main features of this release focus on Chilkat’s Ai class, enabling interactive AI response streaming directly into embedded desktop application browsers. It supports Azure, custom base URLs for OpenAI-compatible providers, and local providers like Ollama. ✨ New Features Ai Real-Time Streaming AI Responses to Embedded Browsers in Desktop Apps — Stream AI responses […]

Chilkat v11.2.0 Release Notes

Pinned November 3, 2025

Previous Version: Chilkat v11.1.0 Release Notes The main addition in v11.2.0 is the Chilkat.Ai class, and the Chilkat.StringBuilder.MarkdownToHtml method. Ai: The Chilkat AI class provides a unified API for interacting with different AI providers: OpenAI, Google, Claude, xAI, Perplexity, and DeepSeek. It provides functionality for conversation management, multimodal inputs, and streaming mode. Markdown to HTML […]

Semantic Versioning Starting with Chilkat 10.0.0

Pinned September 26, 2024

Starting with the v10.0.0 release (end of September 2024), Chilkat moves to standard semantic versioning.   Prior to this release, for various technical reasons, Chilkat was stuck with versions 9.5.0.xx, where only xx changed. For this first leap to semantic versioning, where the major version changes to 10 (from 9), there are no backward incompatible changes.  […]

Send Email from Hotmail.com, Live.com, or Outlook.com

October 1, 2024 in Microsoft Email

Question:  I want my desktop application (or script) to send email from my Hotmail.com account (or my Live.com or Outlook.com account).  My application will connect to the SMTP server for hotmail.com, authenticate using OAuth2, and send the email.  I want to use Chilkat’s MailMan class to do it.  I’m completely lost.  Where do I even […]

SMTP Server Settings for Hotmail.com, Live.com, and Outlook.com

October 1, 2024 in Uncategorized

(back to Send Email from Hotmail.com, Live.com, or Outlook.com) The SMTP settings for Hotmail.com, Live.com, and Outlook.com are the same because all these email domains are part of Microsoft’s unified Outlook email service, which uses the same mail servers. Here are the SMTP settings: SMTP Server Settings (for sending email): SMTP Server: smtp.office365.com Port: 587 […]

Office365 SMTP AUTH XOAUTH2 Fails with “535 5.7.3 Authentication unsuccessful”

April 17, 2024 in Office365

If you successfully minted an OAuth2 access token for your Azure Entra Id App, but then it fails when attempting to use it in the SMTP protocol for sending email with the error: AUTH XOAUTH2 user=xxx auth=Bearer ********************** 535 5.7.3 Authentication unsuccessful [BN9PXXXA0336.namprd03.prod.outlook.com 2024-04-16T12:11:26.548Z 08DC9999186DF999] Check your Entra Id App Registration to make sure you […]

SMTP Timeout Sending Large Email

November 20, 2023 in SMTP

Question: While trying to send an email with an attachment of size 9MB from my application, I get an error.  Interestingly, the file gets delivered to the email address still we get the error in the application. Answer: Looking at the MailMan.LastErrorText for the call to SendEmail, we can see this: ChilkatLog: SendEmail: … ReadTimeout: […]

Office365 SMTP: 535 5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant.

July 3, 2023 in Uncategorized

This blog post is about the following error encountered when trying to send email via Chilkat.MailMan.SendEmail (using the SMTP protocol). smtpAuthenticate: smtp_host: smtp.office365.com smtp_port: 587 smtp_user: **** smtpAuthenticate: login_method: XOAUTH2 auth_xoauth2: username: **** sendCmdToSmtp: SmtpCmdSent: {PasswordOrCredentials} –sendCmdToSmtp readSmtpResponse: SmtpCmdResp: 535 5.7.139 Authentication unsuccessful, SmtpClientAuthentication is disabled for the Tenant. Visit https://aka.ms/smtp_auth_disabled for more information. [****.PROD.OUTLOOK.COM […]

Office 365 IMAP, POP, SMTP OAuth2 with Client Credentials

June 19, 2023 in Uncategorized

See https://learn.microsoft.com/en-us/exchange/client-developer/legacy-protocols/how-to-authenticate-an-imap-pop-smtp-application-by-using-oauth#use-client-credentials-grant-flow In my opinion, this is still too complicated. An “easy button” is needed.

Office365 Modern Authentication for IMAP, POP3, and SMTP

August 13, 2022 in IMAP

This post documents how to implement Modern Authentication (OAuth2) for Office365 for the IMAP, POP3, and SMTP protocols.  The very first thing you’ll need to do is to create an “App Registration” in Azure Active Directory. See this Chilkat blog post for Instructions for Setting Up an App Registration in Azure for Modern Authentication for […]

Create Azure App Registration for use with IMAP, POP3, and SMTP

August 13, 2022 in Exchange Online

1) Go to https://portal.azure.com/#home and login to your Microsoft account. then go to Azure Active Directory.   2) Click On App Registrations * Copy your Tenant ID, you’ll need it later. 3) Click on “+ New registration” 4) Name your App and Click Register. Give it a name. For the Redirect URI, select “Web” and […]

smtp.office365.com – Failed to get initial SMTP Response

May 13, 2022 in Office365

If something on the client-side is blocking communications, such as a hardware or software firewall, or anti-virus, then it may be that a TLS connection is established, but then trying to read the 1st message from the server gets blocked.  When this happens, the contents of the LastErrorText look like this.   (The LastErrorText for a […]