Hi

When using WIndows 8 Pro, using Local Group Policy Editor (gpedit.msc)

"System cryptography: Use FIPS compliant algorithms for encryption, hashing, and signing"

is set to enabled, Outlook cannot send E-Mails if an Outlook.com account is used.

More of the issue:

"System cryptography: Use FIPS compliant algorithms for encryption, hashing, and signing"

is found in

Computer Configuration\Windows Settings\Security Settings\Local Policies\Security Options

or, by looking at the registry: FIPSAlgorithmPolicy

HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion\SecEdit\Reg Values\MACHINE/System/CurrentControlSet/Control/Lsa/FIPSAlgorithmPolicy/Enabled

which as per description does

This policy setting determines whether the Transport Layer Security/Secure Sockets Layer (TLS/SSL) Security Provider supports only the TLS_RSA_WITH_3DES_EDE_CBC_SHA cipher suite.

Settings:

SMTP Server: smtp.live.com
Port 587
Type of encrypted connection: TLS

In Outlook when testing the account settings, I get:

Send test e-mail message: The connection to the server was interrupted. If this problem continues ´, contact your server administrator or internet service provider (ISP).

In Outlook when sending, I get:

Task '...(at)hotmail.com - Sending reported error (0x800CCC0F) : The connection to the server was interrupted. If this problem continues, contact your server administrator or Internet service provider (ISP).'

Software

Windows 8 Pro x64
Outlook 2013 x64

Which raises the question

Why is it that Outlook.com/Hotmail does NOT have FIPS compliance whereas my other free email provider does?!