If the issue is intermittent, then it may be worth checking the logs on your SMTP server to see if it is encountering any errors at those times.
You could also inspect the network logs for any devices between the Octopus Server and the SMTP server to check for any errors there.
I checked the SMTP logs and the issue is when the mail step takes more time to send an email the deployment fails and the mail is sent. Is it possible to increase timeout so that send a mail step doesn’t fail in the process .
Just jumping in for Paul who is currently on PTO, we have been discussing this in our daily support meeting and we don’t think there are any specific places you can increase the timeout for the SMTP email step in Octopus. I have asked our engineers if they know a way to do this but I do not think this is possible in Octopus itself, there may be a script you can run to increase that timeout but if there is one the engineers would know so I will get back to you if they know of any workarounds for you regarding this.
Sorry for the double post here but I am wondering if you had seen the SMTP timeout settings in the UI at all? (This may be under Configuration on your instance if you are not on 2023.2 yet, for me its under the configuration cog on the right)
We are seeing a similar issue. We failed to get some certificate expiry messages (these had always worked previously) and the Test SMTP email fails in the same manner as described above. I have tried changing the timeout from 12secs to 30secs with no effect.
In the issue above, the test email was working, and the timeout was only occurring intermittently.
As your test email is failing outright, the problem may be different.
It would be worth reviewing your SMTP server logs to see if they provide additional detail.