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“Queued” usually does not mean that core msmtp has an internal spool. In its default sendmail mode, msmtp reads the message from standard input and submits it to an SMTP server immediately. A queue message normally means that your mail user agent or script is calling a wrapper such as msmtpq, which stores the message and retries delivery later. Find which executable is being called, inspect the queue and its log, then test the SMTP account directly; the exact server response—not the word “queued”—determines the fix.
What “queued” means in an msmtp setup
msmtp is an SMTP client with a sendmail-compatible interface. The Debian manual describes its default behavior precisely: it reads a mail from standard input and sends it to an SMTP server for delivery. Core msmtp does not normally keep a persistent queue waiting for a scheduler.
Queueing is generally added by msmtpq (sometimes seen in older documentation as msmtpQ). The wrapper manages outgoing messages, chooses when to attempt delivery, records queue events, and invokes msmtp for the actual SMTP transaction. A mail application configured to call /path/to/msmtpq can therefore report success from the hand-off while the message remains on disk awaiting a connection or a successful SMTP response.
This distinction determines the troubleshooting path:
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- If the application calls
msmtpdirectly, investigate the immediate exit status and SMTP error. - If it calls
msmtpq, inspect the queue, queue log, connection-test settings, permissions, and retry operation before investigating the SMTP account.
The project’s newer naming uses msmtpq and the msmtp-queue management command. Seeing an old msmtpQ reference in a script is a clue to check whether that script still points to the installed executable.
1. Identify the program that actually receives the message
Start with the mail user agent (MUA), application, cron job, or shell script that sends the mail. Look for its “sendmail path,” “sendmail command,” or transport setting. Also inspect wrapper scripts and service-unit files. The important question is whether the command is msmtp or msmtpq.
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/usr/bin/msmtp -a accountattempts the SMTP submission during that invocation. - Queued path: a command such as
/usr/local/bin/msmtpqstores the message in the queue and returns control before final delivery.
Do not infer the path from a desktop notification alone. Confirm the executable in the MUA’s configuration and, if necessary, trace the launch command in the application or script. A queue wrapper can be selected globally while a test command in your shell calls plain msmtp, producing apparently contradictory results.
2. Inspect, flush, or selectively retry the queue
Use the documented queue utility rather than deleting files by hand. The core operations are:
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| Command | Purpose | Use it when |
|---|---|---|
msmtp-queue -d |
Display queued messages | You need to confirm that a message is present and review its queue metadata. |
msmtp-queue -r |
Run the queue, attempting all queued messages | You have corrected connectivity or configuration and want a full flush. |
msmtp-queue -R |
Send selected queued messages | You want to retry particular entries instead of the whole queue. |
Run the display command first and preserve any message needed for diagnosis. Purge operations exist, but purging before recording the queue entry, SMTP error, and original message removes the evidence needed to distinguish a transient outage from a permanent rejection.
A flush is not a guarantee of delivery. It merely starts another attempt. If the wrapper’s connection test fails, if the SMTP server rejects the envelope, or if the account cannot authenticate, the message can remain queued after msmtp-queue -r.
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3. Verify queue and log locations
msmtpq uses environment settings for its queue and queue log:
MSMTPQ_Qselects the queue directory.MSMTPQ_LOGselects the queue-operation log.
Make sure the same values are available to the process that enqueues mail and to the process that flushes it. A common failure is running the MUA under one account or service environment while manually running msmtp-queue under another, so each process sees a different default directory.
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Create the queue directory before first use and restrict it to mode 0700, as the msmtpq documentation recommends. The directory must be writable by the account that sends mail and readable by the account that performs retries. Check ownership, parent-directory traversal permissions, filesystem space, and whether a service sandbox prevents access. A queue can appear “stuck” simply because the retry process cannot read or rename its files.
Keep the queue log separate from the logfile configured in .msmtprc. The msmtp logfile records client activity; the queue log records enqueueing and queue-operation events. Comparing both timelines shows whether a queued item was ever handed to msmtp.
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msmtpq can test network connectivity before attempting delivery. That test is useful when a machine is often offline, but it can also be the reason a message waits: a conservative or failing test prevents the SMTP attempt even when the endpoint would have accepted a connection.
Review the wrapper’s documented environment settings and startup options for three behaviors:
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- Whether a connection test runs before delivery.
- Whether all messages are forced into the queue, even when a network appears available.
- Whether queue status chatter is suppressed, which can hide a useful reason from the terminal.
After changing a test or forced-queue setting, enqueue one small diagnostic message and run the queue manually. Record the queue log and the msmtp result. Do not assume that a successful ping proves SMTP is reachable: DNS, TCP policy, TLS negotiation, and authenticated submission are separate checks.
5. Test the SMTP endpoint without the queue
Use msmtp’s --serverinfo mode with the same account selection and configuration that the queue wrapper uses. This asks the server what it advertises, including supported authentication mechanisms, TLS capability, certificate information, DSN support, and message-size limits.
A practical test sequence is:
- Identify the account name passed by the MUA or wrapper.
- Run
msmtp --serverinfo -a account(replaceaccountwith the configured account name). - Compare the reported hostname, port, TLS state, certificate, and authentication mechanisms with the provider’s submission requirements.
- Save the exit status and the non-secret diagnostic output.
If --serverinfo cannot resolve the host or establish TLS, flushing the queue will not help; fix name resolution, routing, firewall policy, certificate trust, or the endpoint settings first. If the server is reachable but advertises no method compatible with your account configuration, change the authentication or TLS settings as required by that provider.
6. Validate the account as one consistent set of values
SMTP failures often come from a mismatched combination rather than one isolated field. Check these values together:
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| Setting | What to verify | Typical consequence of a mismatch |
|---|---|---|
| SMTP hostname | The provider’s authenticated submission host, not an unrelated web or IMAP host. | DNS or connection failure, or a server that does not accept submission. |
| Port | The port required for submission; the documented example uses 587. | Connection refusal, timeout, or an unexpected protocol. |
| TLS mode | Whether TLS is enabled and whether the server expects a negotiated or implicit TLS session. | TLS negotiation errors or a server greeting that cannot be parsed. |
| Trusted CA file | A CA bundle that can validate the server certificate. | Certificate verification failure, especially on minimal systems. |
| Authentication method | A mechanism advertised by --serverinfo and permitted by the provider. |
Authentication failure despite a correct password. |
| Username | The exact identity required by the provider, often a full address. | 535-style authentication rejection or policy failure. |
| Password source | The password, token, or password-file reference available to the sending process. | Missing-secret errors or repeated authentication failures. |
Port 587 with TLS enabled and a trusted CA file is a documented example, not a universal rule. The provider’s current requirements control the valid combination. Ensure that the queue worker has the same .msmtprc, password source, environment, and file permissions as the interactive test; a service account may not inherit your shell’s home directory or secret variables.
7. Capture the real failure with a controlled debug retry
Once you have one diagnostic message, retry it directly with msmtp’s --debug option, or run the equivalent controlled invocation used by the wrapper. Capture the complete transcript and the process exit status. The transcript shows DNS and connection progress, the server greeting, TLS negotiation, authentication exchange, envelope commands, and the final response.
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Debug output is sensitive. The msmtp manual warns that it includes the entire SMTP conversation and may expose password material. Store it with restrictive permissions, remove or redact credentials before sharing it, and delete temporary copies when the investigation is complete. Never paste an unredacted transcript into a public issue or chat.
Repeat the test with one message and one recipient. This avoids mixing several queue entries and makes the server response unambiguous. If direct msmtp succeeds while the queue remains unchanged, compare the wrapper’s executable path, account selection, environment variables, and configuration file with the successful command.
8. Match the SMTP response to the correct fix
| Observed evidence | Likely class of problem | Next action |
|---|---|---|
| Host cannot be resolved, connection timeout, or connection refused | DNS, routing, firewall, offline link, wrong hostname, or wrong port | Correct the endpoint or network path, then rerun --serverinfo. |
| TLS certificate is untrusted, expired, or for another name | CA trust or endpoint identity problem | Use the correct hostname and trusted CA bundle; do not disable verification merely to make delivery proceed. |
| Authentication mechanism rejected or credentials refused | Wrong username, password/token, mechanism, or provider policy | Use an allowed mechanism and the secret source available to the queue worker. |
| Envelope sender or recipient rejected | Address policy, unverified sender, relay restriction, or invalid recipient | Correct the envelope addresses or provider policy; retrying unchanged will not fix a permanent rejection. |
| Message exceeds the advertised limit | Server size policy | Reduce the message or use an endpoint with a sufficient limit. |
| Successful SMTP transaction but no expected mailbox delivery | Post-acceptance filtering or recipient-side processing | Use the server’s accepted response and provider-side delivery records; the local queue is no longer the cause. |
The queue label alone cannot distinguish these cases. Use the exact SMTP response together with the queue and msmtp logs. A temporary network error calls for a later retry; a permanent address or policy rejection calls for correcting the message or account first.
Direct msmtp or a queued wrapper?
| Characteristic | Direct msmtp | msmtpq-style queue |
|---|---|---|
| Delivery timing | Attempts submission during the sending command. | Stores the message and retries during a queue run. |
| Offline behavior | The command fails unless the caller supplies its own retry logic. | Messages persist until a later flush, subject to queue settings. |
| Operational commands | Inspect the command’s exit status and logfile. | Use msmtp-queue -d, -r, and -R plus the queue log. |
| Failure visibility | Immediate SMTP response in the caller’s context. | Failure may be deferred to the queue log or next retry. |
| Main risk | Transient outages can lose the send attempt unless the application retries. | Misconfigured paths, permissions, or connection tests can leave mail waiting unnoticed. |
Choose the model deliberately. Direct submission is easier to reason about for a continuously connected host and a caller that handles errors. A queue is useful for laptops, intermittent links, or applications that must accept mail locally and retry later. In either model, reliable operation depends on a correct authenticated SMTP endpoint, certificate trust, and protected credentials.
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- Record the MUA’s sendmail command and determine whether it invokes
msmtpormsmtpq. - Run
msmtp-queue -dif a queue wrapper is involved; preserve the message and its identifier. - Check
MSMTPQ_Q,MSMTPQ_LOG, directory mode0700, ownership, disk space, and service access. - Review connection-test, forced-queue, and suppressed-output settings.
- Run
msmtp --serverinfo -a accountusing the worker’s actual account and configuration. - Correct hostname, port, TLS mode, CA file, authentication method, username, or password source as indicated by the result.
- Retry one message with
--debug; protect and redact the transcript. - Classify the exact SMTP response, then run
msmtp-queue -Rfor selected entries ormsmtp-queue -rfor the full queue. - Confirm that the queue entry disappears only after a successful SMTP hand-off, and retain the final response in the operational log.
Preventing silent queues
- Document whether each application uses direct msmtp or msmtpq, including the absolute executable path.
- Keep queue and msmtp logs in known, writable locations and rotate them without deleting recent failure evidence.
- Monitor queue depth and age rather than treating a successful local enqueue as successful delivery.
- Test the configured account with
--serverinfoafter changing the provider, certificate bundle, port, or authentication policy. - Run a scheduled queue flush appropriate to the host’s connectivity, and alert when retries continue to fail.
- Restrict queue and password files to the sending account; debug transcripts require the same protection.
With those checks in place, “queued” becomes a useful state: it tells you where the message is waiting, while the queue log and SMTP transcript tell you why it has not advanced.
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