esxi 7.0 upd 3, OmniOS v11 r151042, Napp-IT 21.06a8 with TLS email alerts

[minimaster]

Since I couldn't find any recent and working information on the web how to get TLS emails to work with the latest versions of ESXi, OmniOS and Napp-It in a home lab environment I like to share my experience on what worked eventually after a few failed approaches.
Hardware and general network description:
Homelab server with INTEL S1200BTL, Xeon E3 1220L, 16GB ECC RAM with 120GB SSD as boot drive and Dell H310 HBA FW p20
Internetrouter Fritzbox 7530 firmware v7.29 50 Mbit VDSL connection without any extra open ports, other than the factory settings for VOIP.
Step by step guide until email sending works:
1. Downloaded latest ESXi iso from VMware site:
VMware-VMvisor-Installer-7.0U3d-19482537.x86_64.iso and writing with Rufus onto a USB stick
Then edited the file boot.cfg and changed the line
"kernelopt=runweasel cdromBoot"
to
"kernelopt=runweasel cdromBoot systemMediaSize=min"
With this edit you get a small datastore on the SSD, otherwise no datastore gets created on a 120GB SSD.
2. Installed ESXi on SSD
3. Downloaded OmniOS iso: https://downloads.omnios.org/media/stable/omnios-r151042.iso
4. Added new VM in ESXi type Oracle Solaris 11
5. Starting / installing /configuring/reboot the new OmniOS VM
6. Log in as root and install Napp-it with
wget -O - www.napp-it.org/nappit | perl
7. Reboot VM, login as root and install TLS as per TLS email. Doing this before the napp-it installation does not work !!
8. Opened an account with a SMTP relay service. I used sendgrid.com
Before I tried SMTP servers directly from a gmail account and from another acoount with web.de and with both accounts I couldn't get napp-it email and TLS email to work. Tried smtp.gmail.com, aspmx.l.google.com, smtp.web.de, all without success. Only the approach with the sendgrid smtp relay service did work.
9. In Napp-IT entered in Settings
SMTP Mailserver: smtp.sendgrid.net
SMTP user: apikey
SMTP password: xxxxxxxx (apikey created in Sendgrid)
Mailto: my email adress for the email notifications
Mail from: the same email as registerd in sendgrid
10. In Napp-IT click Jobs/TLS email/Enable TLS email
11. Added Jobs for status and alert emails and tested successfully.

If anyone can tell me why the email sending with the smtp servers from my email accounts don't work I'd be grateful.

 

[gea]

You need to run the napp-it installer first as you require a compiler that is installed during setup.

When you run the Cpan commands:
- did you just confirm questions just with enter?
- at the end of an install, did you get ok?
- For Gmail you must allow less secure apps in Gmail security settings

 

[minimaster]

When you run the Cpan commands:
- did you just confirm questions just with enter? yes
- at the end of an install, did you get ok? yes
- For Gmail you must allow less secure apps in Gmail security settings. Not possible anymore

from Google account settings:
Zugriff auf Ihr Google-Konto durch weniger sichere Apps
Zum besseren Schutz Ihres Kontos unterstützt Google ab dem 30. Mai 2022 keine Drittanbieter-Apps oder ‑Geräte mehr, bei denen Ihr Nutzername und Passwort ausreichen, um sich in Ihrem Google-Konto anzumelden.

 

[gea]

Current settings with Gmail:
(2FA must be enabled in Google settings)

1. Generate an app pw in Google security settings ex "napp-it"
2. napp-it settings

smtp server: smtp.gmail.com
smtp username: yourname@gmail.com
smtp pw: app pw (16 char)
mailto: receiver of alerts

Check functionality in Jobs > Tls > Test

 

[minimaster]

Confirmed. 2FA + app specific password works with a gmail account. Many thx gea.