Reckon Accounts Accounting Small Business Edition 2024. Email configuration for outlook.com.

Question

Hi all,

Does Reckon Accounts Accounting Small Business Edition 2024 support sending emails via an outlook.com address?

I’ve tried the following settings:

server name: smtp-mail.outlook.com

port: 587

App password

…but no luck so far. My Gmail account works without any issues.

Any guidance on how to get an Outlook.com  address working would be greatly appreciated.

Thanks:-)

nele2 · Answer

Thanks, @Rav

The error message I’m getting is the generic one (“email or password is incorrect”).

I’m 100% certain the email and app password are correct, so this looks more like a protocol level issue rather than credentials.

From what I can tell, Microsoft has tightened their SMTP security requirements and Reckon 2024 doesn’t support the specific STARTTLS handshake that Outlook.com now enforces.

Here’s a quick summary of what I’ve tested:

Service

Port

Encryption

Reckon Result

Why

Gmail

587

STARTTLS

Works

Gmail allows “auto‑upgrade” without explicit STARTTLS

Outlook.com

587

STARTTLS

Fails

Requires explicit STARTTLS command, which Reckon cannot send

SMTP2Go

465

SSL

Works

Reckon fully supports SSL‑465

Given this, it seems Reckon 2024 cannot perform a proper STARTTLS negotiation, which Outlook.com now requires.

I was wondering if anyone has found a workaround to force Reckon 2024 to use STARTTLS explicitly or otherwise make Outlook.com SMTP work.

Thanks!

Rav · Answer

Hi @nele2

Welcome to the Reckon Community 🙂

Can you let us know what's happening specifically when you try to send an email out with your outlook email address?

Are you encountering a specific error message? If so, what is it? A screenshot would be helpful as well if possible