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Configure Postfix as a local mail-transfer agent and set Mailgun as its authenticated smarthost. The dependable baseline is Mailgun on smtp.mailgun.org:587, SASL credentials in a root-only password map, STARTTLS certificate validation, and relay restrictions that reject unauthorized destinations. Validate the configuration, send a real message, and confirm both the queue and logs before putting the host into service.
What this setup does
Postfix normally can deliver mail directly to each recipient domain’s MX server. In a relay arrangement, it does not perform that final handoff itself. The relayhost setting sends remote messages to Mailgun’s SMTP service, where Mailgun authenticates the Ubuntu host and performs onward delivery.
The path is therefore:
- A local application submits a message to Postfix on the Ubuntu server.
- Postfix places the message in its queue and opens an SMTP connection to the configured Mailgun endpoint.
- Postfix authenticates with the SMTP username and password belonging to the Mailgun sending domain.
- Postfix negotiates TLS (STARTTLS on port 587) and transfers the message.
- Mailgun accepts the message for delivery and reports acceptance or a rejection that Postfix records in its logs.
This design avoids exposing application code to Internet delivery details, while still requiring you to protect credentials and prevent the server from becoming an open relay.
Prerequisites and decisions
Ubuntu host
- An Ubuntu server with
sudoaccess. - A resolvable hostname for the server. Set the system hostname and make sure local name resolution agrees with it before testing mail.
- Outbound TCP access from the server to the Mailgun submission port you choose.
Mailgun sending domain and credentials
Create or select the Mailgun sending domain that will appear in your messages. SMTP credentials are managed per domain. The password for the Mailgun control panel is not the password Postfix should use; retrieve the SMTP username and SMTP password shown for the sending domain instead.
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Choose a submission port
| Port | Encryption behavior | When it fits | Important qualification |
|---|---|---|---|
| 587 | Plain SMTP connection upgraded with STARTTLS | Default choice for a Postfix smarthost | Mailgun recommends it when port 25 is blocked or throttled. |
| 2525 | Plain SMTP connection upgraded with STARTTLS | Alternative when firewall policy prevents 587 | Use the same authenticated-relay and certificate-validation safeguards. |
| 25 | Plain SMTP connection upgraded with STARTTLS | Only when your network permits normal outbound SMTP | More likely than submission ports to be blocked or throttled. |
| 465 | TLS starts immediately when the connection opens (implicit TLS) | Networks or applications that specifically require implicit TLS | Postfix must be configured for TLS wrapper mode; it is not the STARTTLS flow used on 587. |
Use port 587 in the commands below. If your firewall requires another endpoint, change the port consistently in both relayhost and the password-map key, then apply the matching TLS mode.
Install Postfix and select a smarthost configuration
- Update the package index and install Postfix:
sudo apt update
sudo apt install postfix
Ubuntu’s package configuration asks how this machine should send mail. Select the option described as an Internet smarthost, satellite system, or equivalent smarthost-oriented choice, depending on the Ubuntu release. The wording can differ, but the intent is the same: remote mail is handed to a specified SMTP server rather than delivered directly to recipient MX servers.
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Ubuntu enables Postfix as a service. Do not assume that a successful package installation proves relay configuration is complete; the service can run while every remote message is deferred because authentication, TLS, or the relay endpoint is wrong.
Configure Postfix to use Mailgun
1. Set the relay and SMTP client security options
Edit /etc/postfix/main.cf and add or update the following parameters:
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relayhost = [smtp.mailgun.org]:587
smtp_sasl_auth_enable = yes
smtp_sasl_password_maps = hash:/etc/postfix/sasl_passwd
smtp_sasl_security_options = noanonymous
smtp_tls_security_level = may
smtp_tls_note_starttls_offer = yes
smtp_tls_CAfile = /etc/ssl/certs/ca-certificates.crt
The square brackets in [smtp.mailgun.org]:587 are intentional. They tell Postfix to use that exact host and port instead of looking up the destination domain’s MX records. The same bracketed host and port must be used as the key in the password map.
smtp_sasl_auth_enable turns on authenticated SMTP. noanonymous prevents anonymous SASL mechanisms. The may TLS setting allows Postfix to attempt STARTTLS without making encryption mandatory; the stricter option is discussed below. Keep the CA-file setting pointed at the Ubuntu CA bundle installed on your release. If that path does not exist, install or repair the system CA certificates and use the bundle path provided by that Ubuntu installation.
Do not put a password directly in main.cf. Keeping credentials in a separate hash map limits accidental disclosure and is the format expected by the smtp_sasl_password_maps setting.
2. Create the SMTP password map
Create /etc/postfix/sasl_passwd as root. Its one-line entry must exactly match the relay host and port:
[smtp.mailgun.org]:587 SMTP_USERNAME:SMTP_PASSWORD
Replace SMTP_USERNAME and SMTP_PASSWORD with the credentials for the Mailgun sending domain. Do not substitute the control-panel login. If you selected port 2525 or 25, use that port in both places; a mismatch causes authentication to fail even when the credentials themselves are correct.
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Build the indexed database and lock down both files:
sudo postmap /etc/postfix/sasl_passwd
sudo chown root:root /etc/postfix/sasl_passwd /etc/postfix/sasl_passwd.db
sudo chmod 600 /etc/postfix/sasl_passwd
The plaintext map contains a reusable secret. Keep it readable only by root, remove accidental copies from shell history and temporary directories, and check that backups do not make it world-readable. After changing the password, edit the plaintext map, run postmap again, and restart or reload Postfix so the new database is used.
Keep the server from becoming an open relay
A relayhost controls where Postfix sends mail; it does not, by itself, authorize arbitrary Internet users to submit mail through your server. The SMTP daemon must still reject destinations that are neither local nor authorized. Preserve your existing restrictions and ensure the effective recipient restrictions include the following pattern:
smtpd_recipient_restrictions =
permit_sasl_authenticated,
permit_mynetworks,
reject_unauth_destination
permit_sasl_authenticated allows a client that has authenticated, and permit_mynetworks allows trusted local networks defined by Postfix. The final reject_unauth_destination is the critical guard: it rejects unauthenticated attempts to relay to arbitrary external domains. Do not replace it with a blanket permit rule. If your Ubuntu/Postfix version uses smtpd_relay_restrictions for this policy, apply the same allow-authenticated/allow-trusted/reject-unauthorized logic there and verify which parameter is active.
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Choose an appropriate TLS policy
Optional TLS: smtp_tls_security_level = may
The Mailgun example uses may. Postfix offers STARTTLS and authenticates when the server advertises it, but delivery can fall back if TLS negotiation fails. This can keep mail moving during a temporary TLS problem, but a fallback can expose SMTP credentials or message content on a hostile or misconfigured path. Treat this as a compatibility setting, not a guarantee that every hop from your server is encrypted.
Required TLS: smtp_tls_security_level = encrypt
After confirming the endpoint, CA bundle, system clock, and certificate validation, you can change the setting to encrypt. With required TLS, Postfix will not deliver when it cannot establish an encrypted session. Mailgun’s TLS policy documentation describes this as a deliberate fail-closed behavior: an unavailable or invalid TLS upgrade produces a delivery failure rather than plaintext fallback.
Port 465 and implicit TLS
Port 465 begins TLS immediately and therefore is not interchangeable with STARTTLS on 587, 25, or 2525. If you use it, configure Postfix’s SMTP client wrapper mode and an encryption-required policy, then validate the certificate before sending production mail. Do not merely change :587 to :465 while leaving the STARTTLS configuration unchanged.
Validate and restart Postfix
Run a syntax and file-permission check before restarting:
sudo postfix check
sudo systemctl restart postfix
sudo systemctl --no-pager --full status postfix
postfix check catches many malformed settings and missing files. A running service is not proof of a working relay, so continue with an authenticated message test and log inspection.
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Send a real test message
Test through the local submission path
Use the same local interface your application will use. For a simple command-line test, provide a recipient mailbox you control and a sender address authorized for the Mailgun sending domain:
printf 'Subject: Postfix Mailgun testnnThis is a relay test.n' | sendmail -v recipient@example.net
Replace the example recipient with a real test address. The -v option prints the local submission and queueing result; Postfix then performs the remote SMTP transaction asynchronously.
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Test Mailgun authentication directly with Swaks
A direct SMTP test separates Mailgun credentials and network reachability from local application behavior. Supply the SMTP username and password for the sending domain, not the control-panel password:
export SMTP_USERNAME='your-domain-smtp-username'
read -rsp 'Mailgun SMTP password: ' SMTP_PASSWORD; printf 'n'
swaks --server smtp.mailgun.org --port 587 --tls
--auth LOGIN
--auth-user "$SMTP_USERNAME"
--auth-password "$SMTP_PASSWORD"
--from 'sender@your-sending-domain.example'
--to 'recipient@example.net'
--header 'Subject: Mailgun SMTP test'
--body 'Authenticated STARTTLS test from Ubuntu.'
Entering the password interactively avoids placing it literally in the command line. Clear the variables after the test and remember that shell history, process inspection, and diagnostic output can still disclose secrets if you paste them into commands.
Prove delivery with queue and log evidence
Immediately after submitting the message, inspect the queue:
mailq
An empty queue after a short interval usually means Postfix handed the message off; a persistent entry means delivery is deferred or failed. Review both the systemd journal and the traditional mail log because Ubuntu installations can use either or both:
sudo journalctl -u postfix -n 100 --no-pager
sudo tail -n 100 /var/log/mail.log
For a successful relay, look for SASL authentication followed by an accepted SMTP response from Mailgun. Also verify that the test message arrived at the recipient and that the sender address belongs to the configured sending domain. A local “queued” response alone does not prove remote acceptance.
Troubleshoot by symptom
| Symptom or log clue | Likely cause | What to check |
|---|---|---|
| Authentication failure or “SASL authentication failed” | Wrong per-domain credential, control-panel password, or map-key mismatch | Confirm the Mailgun SMTP username/password; verify the password-map key is exactly [smtp.mailgun.org]:587; rerun postmap after edits. |
| “No SASL mechanisms” or anonymous-authentication errors | SASL client support is missing or anonymous mechanisms are allowed | Check smtp_sasl_auth_enable = yes, smtp_sasl_security_options = noanonymous, and the installed Postfix package capabilities. |
| TLS handshake, certificate, or “cannot verify” errors | Missing CA bundle, incorrect hostname, wrong system clock, or a policy that requires TLS | Check the CA-file path, DNS resolution of smtp.mailgun.org, the server clock, and whether encrypt is being enforced before the endpoint is validated. |
| Connection timeout or “connection refused” | Outbound firewall filtering, blocked port, or a transient provider/network issue | Test the selected TCP port from the Ubuntu host, review egress firewall rules, and try 587 or 2525 when policy permits. Do not switch ports without changing the password-map key. |
| Message remains queued with repeated deferrals | DNS failure, blocked egress, provider limit, or a remote SMTP response | Read the exact status line in journalctl and /var/log/mail.log; investigate the named DNS, firewall, Mailgun-limit, or SMTP-response condition rather than deleting the queue blindly. |
| Unauthenticated external client can relay | Overly broad mynetworks or a permissive recipient restriction |
Restore reject_unauth_destination, narrow trusted networks, reload Postfix, and test from an unauthorized host. |
Operational safeguards after the first successful message
- Protect and rotate credentials. Treat
/etc/postfix/sasl_passwdand its database as secrets. When Mailgun credentials change, update the map, runpostmap, and reload or restart Postfix. - Monitor the queue. A growing queue can indicate an outage, an authentication regression, a blocked port, or a provider limit. Keep the original SMTP response when escalating the issue.
- Keep TLS validation enabled. Do not disable certificate checks simply to make a handshake succeed. Repair the CA bundle, hostname resolution, or clock instead.
- Restrict submission access. Allow local applications and only the networks that need to submit. Authentication and trusted-network rules should both be explicit.
- Protect configuration backups. Backups of
main.cfmay be harmless, but backups containingsasl_passwdare credential stores and require root-only access. - Retest after network changes. Firewall, DNS, hostname, and time-service changes can break SMTP even when no Postfix file changed.
Deployment checklist
- Ubuntu hostname resolves correctly and the server has sudo access.
- Mailgun sending domain is active and its SMTP credentials are available.
- Outbound access to the selected Mailgun port is allowed.
relayhostuses the bracketed host and the selected port.- SASL is enabled, anonymous mechanisms are disabled, and credentials are in
hash:/etc/postfix/sasl_passwd. - The password map is rebuilt with
postmapand readable only by root. - The Ubuntu CA bundle is present and its path is configured.
- TLS mode matches the selected port: STARTTLS for 587, 25, or 2525; implicit TLS for 465.
- Relay restrictions include authenticated/trusted permits followed by
reject_unauth_destination. postfix checkpasses, the service restarts cleanly, and status output is healthy.- A real test message is accepted by Mailgun and reaches the test mailbox.
- Queue and log output show no continuing deferrals or authentication errors.
Why this configuration is a sound default
Using Mailgun as the smarthost keeps Postfix’s role deliberately small: accept mail locally, authenticate to one provider endpoint, negotiate the required transport security, and report delivery status. Port 587 offers the broadest practical compatibility for this pattern because it uses STARTTLS and is less likely than port 25 to be blocked. The protected SASL map prevents credentials from being mixed into general configuration, while an explicit unauthorized-destination rejection prevents the Ubuntu host from relaying for strangers. Finally, a successful authenticated test plus queue and log evidence distinguishes a genuinely working relay from a service that merely starts without errors.
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