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Email Setup.md

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Note on the note

I used to run Ubuntu on my VMs before switching to Debian. I found that Debian already had some packages installed and the steps were slightly different even though Ubuntu is based on Debian. If you're using Ubuntu I would suggest trying the Debian walkthrough and if it doesn't work then check out what is different and make those changes.

Debian Based

Email Alerts Setup (Gmail)

  1. Make sure you have mailutils and postfix installed

  1. Enable 2FA for the gmail account that will be used by going to security settings

  2. Create app password for the account.

    1. Go to App Passwords
    2. Select app: Mail
    3. Select device: Other
    4. Type in: Proxmox

==[[Default Debian VM (SeaBIOS)]] part 1==

  • The next few steps have already been done in an attempt to save time so skip to the next section with a highlighted header below

Create the main postfix config:

sudo nano /etc/postfix/main.cf

Paste the following into the file:

# See /usr/share/postfix/main.cf.dist for a commented, more complete version

myhostname=Crow.local

# Debian specific:  Specifying a file name will cause the first
# line of that file to be used as the name.  The Debian default
# is /etc/mailname.
#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# See http://www.postfix.org/COMPATIBILITY_README.html -- default to 3.6 on
# fresh installs.
compatibility_level = 3.6

# TLS parameters
smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
smtpd_tls_security_level=may
smtp_tls_CApath=/etc/ssl/certs
smtp_tls_security_level=may
# smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

# this has to do with changing the from name... somehow
sender_canonical_maps = static:[email protected]

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
# myhostname = websites.tailf3fc5.ts.net
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases

mydestination = $myhostname, asd, websites, localhost.localdomain, localhost
# relayhost =
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = all

relayhost = smtp.gmail.com:587
smtp_use_tls = yes
smtp_sasl_auth_enable = yes
smtp_sasl_security_options =
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_tls_CAfile = /etc/ssl/certs/Entrust_Root_Certification_Authority.pem
smtp_tls_session_cache_database = btree:/var/lib/postfix/smtp_tls_session_cache
smtp_tls_session_cache_timeout = 3600s
smtp_header_checks = regexp:/etc/postfix/header_checks

Write Gmail credentials to file and hash it. Again, make sure you are root.

sudo nano /etc/postfix/sasl_passwd

Add this, replacing with your password

smtp.gmail.com [email protected]:your-password
  • Password is in 1P
sudo chmod 600 /etc/postfix/sasl_passwd

==[[Default Debian VM (SeaBIOS)]] part 2==

Create a file where you can edit who the email is from:

cd /etc/postfix

sudo nano /etc/postfix/header_checks

Add this:

/^From:[[:space:]]+(.*)/ REPLACE From: "VM or Machine Name" <[email protected]>

sudo postmap header_checks

sudo postmap hash:/etc/postfix/sasl_passwd

sudo systemctl enable postfix

sudo systemctl start postfix

Test to make sure everything is hunky-dory.

echo "sample message" | mail -s "sample subject" [email protected]

Reload with this if you need to:

sudo postfix reload

Ubuntu Based

Email Alerts Setup (Gmail)

  1. SSH into proxmox node and become root user. Run the following commands to download extra software dependencies we'll need.
sudo apt update

sudo apt install libsasl2-modules mailutils postfix -y
  • When the postfix install dialogue comes up, enter 1 for No configuration

Reboot to get all of the new services working

sudo reboot
  1. Setup Gmail 2FA (if you haven't already)

  • Enable 2FA for the gmail account that will be used (if you haven't already) by going to Gmails's security settings

  • Create app password for the account (if you haven't already).

    • Go to App Passwords
    • Select app: Mail
    • Select device: Other
    • Type in: VMs or whatever describes your needs
  1. Configure Postfix

Create the Postfix configuration file:

sudo vim /etc/postfix/main.cf

Append the following to the end of the file:

# See /usr/share/postfix/main.cf.dist for a commented, more complete version

# Debian specific:  Specifying a file name will cause the first
# line of that file to be used as the name.  The Debian default
# is /etc/mailname.
#myorigin = /etc/mailname

smtpd_banner = $myhostname ESMTP $mail_name (Ubuntu)
biff = no

# appending .domain is the MUA's job.
append_dot_mydomain = no

# Uncomment the next line to generate "delayed mail" warnings
#delay_warning_time = 4h

readme_directory = no

# See http://www.postfix.org/COMPATIBILITY_README.html -- default to 3.6 on
# fresh installs.
compatibility_level = 3.6

# TLS parameters
smtpd_tls_cert_file=/etc/ssl/certs/ssl-cert-snakeoil.pem
smtpd_tls_key_file=/etc/ssl/private/ssl-cert-snakeoil.key
smtpd_tls_security_level=may
smtp_tls_CApath=/etc/ssl/certs
smtp_tls_security_level=may
# smtp_tls_session_cache_database = btree:${data_directory}/smtp_scache

smtpd_relay_restrictions = permit_mynetworks permit_sasl_authenticated defer_unauth_destination
myhostname = websites.tailf3fc5.ts.net
alias_maps = hash:/etc/aliases
alias_database = hash:/etc/aliases
mydestination = $myhostname, asd, websites, localhost.localdomain, localhost
# relayhost =
mynetworks = 127.0.0.0/8 [::ffff:127.0.0.0]/104 [::1]/128
mailbox_size_limit = 0
recipient_delimiter = +
inet_interfaces = all
inet_protocols = all

relayhost = smtp.gmail.com:587
smtp_use_tls = yes
smtp_sasl_auth_enable = yes
smtp_sasl_security_options =
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_tls_CAfile = /etc/ssl/certs/Entrust_Root_Certification_Authority.pem
smtp_tls_session_cache_database = btree:/var/lib/postfix/smtp_tls_session_cache
smtp_tls_session_cache_timeout = 3600s
  • Save
sudo vim /etc/postfix/sasl_passwd

Add the following line making sure to set the correct email and 2FA secure password from the step above:

smtp.gmail.com [email protected]:yourpassword

sudo chmod 600 /etc/postfix/sasl_passwd

sudo postmap hash:/etc/postfix/sasl_passwd
  • That last line will generate /etc/postfix/sasl_passwd.db so that sasl_passwd is secure
sudo systemctl enable postfix

sudo systemctl start postfix

Reload if needed

sudo postfix reload
  1. Test to make sure everything is working
sudo echo "sample message" | mail -s "sample subject" [email protected]

IMPORTANT With updates to Postfix and SMTP and the rest, this configuration will likely need to be updated in the future