> Source: [sk179628](https://support.checkpoint.com/results/sk/sk179628)

# sk179628 - Unable to send alert email from SmartEndpoint

| Property | Value |
|----------|-------|
| Solution ID | sk179628 |
| Date Created | 2022-07-03 |
| Last Modified | 2024-01-08 |
| Technical Level | General |
| Products | Endpoint Security |
| Versions | R81.10 (EOS), R81 (EOS) |
| OS | Gaia |

## Symptoms

- * Could not configure Email Service Settings. This error shows "Error "SMTP Error: Could not connect to SMTP host: smtp.office365.com, port 587. Unrecognized SSL message, plaintext connection?"
* The Server_Messages.log shows this error: "\[2022-06-27T17:57:01,775\] ERROR http-nio2-127.0.0.1-8080-exec-255 - 421 4.7.66 TLS 1.0 and 1.1 are not supported". Please upgrade/update your client to support TLS 1.2. Visit https://aka.ms/smtp_auth_tls. \[DXXP273CA0009.AREP273.PROD.OUTLOOK.COM\] Caused by: com.checkpoint.util.mail.MailMessageFailedException: javax.mail.AuthenticationFailedException: 421 4.7.66 TLS 1.0 and 1.1 are not supported. Please upgrade/update your client to support TLS 1.2. Visit https://aka.ms/smtp_auth_tls. \[DXXP273CA0009.AREP273.PROD.OUTLOOK.COM\]".

## Cause

TLS 1.0 and 1.1 are not supported.  
When the "TLS" checkbox is not selected as part of the configuration, it uses TLS1.2+ (which includes earlier versions), but TLS1.2+ was not used.

## Solution

**Do these Solution steps:**

1. Check Point recommends that you make sure connectivity to the Email Server and all O365 settings are correct with no 2FA or special authorizations.
2. Upgrade your client to support TLS 1.2.
3. If you continue to get the error message, [Contact Check Point Support](https://www.checkpoint.com/support-services/contact-support/) to get a Hotfix for this issue. A Support Engineer will make sure the Hotfix is compatible with your environment before providing the Hotfix.  
   For faster resolution and verification, collect [EPCPinfo](https://supportcenter.us.checkpoint.com/supportcenter/portal?eventSubmit_doGoviewsolutiondetails=&solutionid=sk158572)file from the Endpoint Management Server.

**Hotfix installation instructions:**   
Refer to [sk168597 - How to install a Hotfix](https://supportcenter.checkpoint.com/supportcenter/portal?eventSubmit_doGoviewsolutiondetails=&solutionid=sk168597).

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