Outlook Clients Unable to Connect After Upgrading to SmarterMail Build 9777
Question asked by Martin Ouellet - 10/16/2026 at 8:25 AM
Answered
Hello,

After upgrading our SmarterMail server to Build 9777, our Outlook clients can no longer connect. Outlook displays this error: “Your server does not support the connection encryption type you have specified. Try changing encryption method. Contact your mail server administrator or Internet service provider (ISP)."

I noticed the Build 9777 release notes mention a fix for secure connections serving an incomplete SSL/TLS certificate chain. Could this be related to the issue?

Could you advise what to check on the SmarterMail server and in Outlook? I can provide more details about our configuration, including the protocol, ports, and certificate, if needed.

Thank you.
Brian Replied
Marked As Answer
What server version and have you tried running iiscrypto.exe on the server and chose best practises?
Martin Ouellet Replied
Hi Brian,

Thank you for your reply. 

The server is running Windows Server 2022. 
I haven’t applied the IIS Crypto Best Practices settings yet. 

The output below shows the current configuration:

.\IISCryptoCli.exe /view

IIS Crypto CLI 4.0

Created by Nartac Software  
Copyright (c) 2011-2025 Nartac Software Inc.


Viewing current settings
Server protocol Multi-Protocol Unified Hello: <null>
Server protocol PCT 1.0: <null>
Server protocol SSL 2.0: <null>
Server protocol SSL 3.0: <null>
Server protocol TLS 1.0: Enabled
Server protocol TLS 1.1: Enabled
Server protocol TLS 1.2: <null>
Server protocol TLS 1.3: <null>
Client protocol Multi-Protocol Unified Hello: <null>
Client protocol PCT 1.0: <null>
Client protocol SSL 2.0: <null>
Client protocol SSL 3.0: <null>
Client protocol TLS 1.0: Enabled
Client protocol TLS 1.1: Enabled
Client protocol TLS 1.2: <null>
Client protocol TLS 1.3: <null>
Cipher NULL: <null>
Cipher DES 56/56: <null>
Cipher RC2 40/128: <null>
Cipher RC2 56/128: <null>
Cipher RC2 128/128: <null>
Cipher RC4 40/128: <null>
Cipher RC4 56/128: <null>
Cipher RC4 64/128: <null>
Cipher RC4 128/128: <null>
Cipher Triple DES 168: <null>
Cipher AES 128/128: <null>
Cipher AES 256/256: <null>
Hash MD5: <null>
Hash SHA: <null>
Hash SHA 256: <null>
Hash SHA 384: <null>
Hash SHA 512: <null>
Key Exchange Diffie-Hellman: <null>
Key Exchange PKCS: <null>
Key Exchange ECDH: <null>
DHE Minimum Key Length: <null>
FIPS Algorithm Policy: Disabled
Enable HTTP3: <null>
Enable AltSvc: <null>
Configured Cipher Suites: <null>
Martin Ouellet Replied
Hi Rian,

Thank you for your help. 
I fixed the configuration on the Windows Server 2022 server. 
All is fine now

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