Smart Task not working with MS O365

[AmitS]

Hi Team,

We have a use case of change management approval with Smart task. Once the session is published & Approve then there needs to be a mail. Also once the policy is installed a mail needs to be sent.

We have configure MSO365 in SMTP server setting in CMS & configured Smart task to send mail after session publish & after policy install, but its not working we are facing multiple errors. Pls assist.

Error after session Publish:

Task: Execution of SmartTask "After Session Publish"
Initiator: System
Start Time: 25-03-2025 13:28
Completed: 25-03-2025 13:28
Status: Failed
--------------------------------------------------------------------------------
SmartTask execution ended in failure status.
Execution output:
Failed to send mail: Could not convert socket to TLS
--------------------------------------------------------------------------------

Error After Policy install:

Task: Execution of SmartTask "After Install Policy"
Initiator: System
Start Time: 25-03-2025 13:29
Completed: 25-03-2025 13:29
Status: Failed
--------------------------------------------------------------------------------
send mail to test@domain.com failed
--------------------------------------------------------------------------------

SMTP server setting in CMS:

Server: smtp.office365.com

port:587

Require Authentication: Yes

Encryption: TLS

[PhoneBoy]

I'm fairly certain that you can only use a local SMTP server that doesn't require authentication for this feature.

[AmitS]

Is there any relevant Sk or document which clearly states this. I will then have to convey this ahead accordingly.

[PhoneBoy]

I assume these alerts are sent with the internal_sendmail command, which clearly states these limitations: https://support.checkpoint.com/results/sk/sk25941 

[AmitS]

Referring to the sk, does it means O365 is not supported for smart task?

[PhoneBoy]

As per your own instructions, the M365 SMTP Server requires TLS and Authentication.
As per the SK I provided, these options are not supported by internal_sendmail.
That would suggest Office 365 is not supported.

However, I see that you can configure an SMTP Server with both an arbitrary port, TLS encryption, and authentication.
This is from R81.20:

Which means, if you have configured everything correctly, it should work with Office 365.
If it's not, I suggest engaging TAC.

[AmitS]

You mean to say we configure new smtp server with port 25 with TLS and authentication?

currently we have configured the same just port is 587, as i have mentioned previously.

[PhoneBoy]

You have to configure an outbound SMTP server to use this feature.
Further, it looks like you can configure it as per Office 365 requirements with server, port, TLS encryption, and authentication credentials necessary to send SMTP mail (usually the O365 credentials for a specific user).
If you've done this correctly and it's still not working, please engage with the TAC.

[AmitS]

Hi @PhoneBoy 

Pls refer to the attached SMTP server config we have done.

[PhoneBoy]

Right, and TAC will be required for further troubleshooting here.

[AmitS]

TAC is already opened but no fruitful update.😥

[the_rock]

Please let us know how it gets solved.

Andy

[the_rock]

What version? I can try test this in the lab, eiother R81.20 or R82

Andy

[AmitS]

Version is R81.20

[the_rock]

Will test it later and update you.

Andy

[the_rock]

@AmitS 

Same result here, even in R82. I have a feeling what @PhoneBoy gave you is actually needed.

Andy

[AmitS]

You mean local smtp server right?

this wont work with O365?

[the_rock]

right

[AmitS]

Any Checkpoint document which clearly states this? 

[the_rock]

Maybe @PhoneBoy can confirm for sure.

Andy

[Itai_Minuhin · Accepted solution]

Hi,

My name is Itai and I'm a group manager in Check Point R&D. My team is responsible for SmartTasks.
I'd like to update that we are aware to this issue, a hotfix is ready, it will be released as part of the next jumbo hotfix to all relevant versions. In addition, we will prepare a private hotfix suitable to R81.20 and the installed jumbo, according to the ticket. This way you'll have a solution for the issue in few days instead of waiting to the jumbo release. 

Regards, 
Itai