Having managed Mailman installations since its 2.x days, I've hit several pain points that motivated my search for alternatives:

# Typical Mailman configuration pain points
1. Python 2.x dependency hell
2. Archaic web interface (circa early 2000s)
3. Limited REST API capabilities
4. No native modern authentication (OAuth/SAML)
5. Difficult moderation workflow

For our mixed Windows/Linux environment, we needed:

• Web-based administration with granular permissions
• Discussion list functionality (not just announcements)
• DKIM/DMARC support out of the box
• Modern subscriber management
• API-first architecture

After testing several options, here are the most promising alternatives:

1. Sympa

The most mature Mailman alternative with excellent enterprise features:

# Sympa quick setup on Ubuntu
sudo apt install sympa
sudo sympa_newaliases.pl
sudo service sympa start

Key advantages:
- Perl-based (no Python 2 dependency)
- Modern web interface
- LDAP/AD integration
- Granular list owner permissions

2. Mailtrain

Node.js-based alternative with excellent API support:

// Sample API call to create list
fetch('https://yourdomain/api/lists', {
  method: 'POST',
  headers: { 'Authorization': 'Bearer YOUR_TOKEN' },
  body: JSON.stringify({
    name: 'dev-discuss',
    description: 'Engineering discussions'
  })
})

3. Listmonk

Golang implementation with impressive performance:

# Docker compose example
version: '3'
services:
  listmonk:
    image: listmonk/listmonk:latest
    ports:
      - "9000:9000"
    environment:
      - TZ=UTC

When migrating from Mailman, pay attention to:

# Mailman export command
sudo /usr/lib/mailman/bin/list_lists -b > lists.txt
sudo /usr/lib/mailman/bin/config_list -o listname.cfg listname

For large lists, consider gradual migration with parallel operation during transition period.

Modern solutions support OAuth out of the box. Here's a sample Keycloak configuration for Sympa:

<oauth>
  client_id = sympa-web
  client_secret = YOUR_SECRET
  auth_url = https://auth.yourdomain.com/auth/realms/master/protocol/openid-connect/auth
  token_url = https://auth.yourdomain.com/auth/realms/master/protocol/openid-connect/token
  userinfo_url = https://auth.yourdomain.com/auth/realms/master/protocol/openid-connect/userinfo
  scope = openid email profile
</oauth>