If msmtp reports that a message is “queued,” the queue is usually being created by msmtpq (or another sendmail wrapper), not by the core msmtp SMTP client. In its default mode, msmtp reads a message from standard input and submits it to an SMTP server immediately. Find which executable your mail program calls, inspect the queue with msmtp-queue, then test the SMTP account and capture one redacted debug transcript. The word “queued” by itself does not tell you whether the problem is a connection test, TLS, authentication, recipient policy, or message size.
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What “queued” means in msmtp
msmtp is an SMTP client with a sendmail-compatible interface. The Debian msmtp manual describes its default sendmail mode this way: it reads a mail from standard input and sends it to an SMTP server for delivery. Core msmtp does not normally maintain a persistent spool that waits for a later retry.
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1Fix the driver behind crashes, sound loss and screen glitches2Clear out junk files and repair common Windows errors3Scan for outdated or missing drivers - takes under a minuteA queued message generally means that your mail user agent, script, or system sendmail setting invokes msmtpq, a queue wrapper around msmtp. The msmtpq documentation says it manages and routes outgoing mail, stores messages in a queue directory, records queue events in a queue log, and can be configured to force every message into the queue. A message can therefore be safely stored while delivery is deferred, even though the final SMTP failure has not yet been fixed.
The older project name msmtpQ was changed to msmtpq; queue administration is performed with the msmtp-queue command. Do not troubleshoot the queue as if it were an SMTP response. First determine which layer produced the status.
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The quickest diagnostic path
- Find the executable. Inspect the mail program’s sendmail command, a wrapper script, and any service or cron configuration. If it points to
/path/to/msmtpq, queueing is intentional. If it points directly tomsmtp, look for another wrapper that intercepts the call. - List queued messages. Run
msmtp-queue -das the same user that submitted the mail. Record message identifiers, recipients, timestamps, and any displayed error text before changing files. - Attempt a full flush. Run
msmtp-queue -r. This is the documented operation for running or flushing all queued messages. Keep the terminal output and check the queue again afterward. - Retry selected messages. Use
msmtp-queue -Rwhen you need to send selected queued messages rather than everything. Confirm the command’s selection prompt or syntax on your installed version before acting on a large queue. - Verify paths and permissions. Check the queue directory and queue log configured by
MSMTPQ_QandMSMTPQ_LOG. The msmtpq README recommends creating the queue directory before use with mode0700. - Test the SMTP endpoint. Run msmtp’s
--serverinfomode with the intended account. It reports advertised authentication and TLS capabilities, certificate information, and the server’s message-size limit. - Check the account as one set of values. Verify hostname, port, TLS mode, trusted CA file, authentication method, username, and password source together. A correct password cannot compensate for a wrong port or certificate policy.
- Capture one controlled retry. Use
--debugfor a single test message, save the exit status and SMTP transcript, then redact credentials and message content before sharing the log.
Identify whether msmtpq is in the delivery path
Inspect the mail user agent and scripts
Applications often expose a “sendmail path” setting. Check that setting, shell scripts that call sendmail, system service definitions, and scheduled jobs. Search for both msmtp and msmtpq; a script may call one while a symlink or alternate path resolves to the other. Also check which Unix account owns the process, because queue directories and configuration files are commonly user-specific.
If the command includes msmtpq, the message may be queued before any network connection is attempted. If it includes only msmtp, a “queued” notice likely comes from the calling application or a different local spool. The distinction determines where to look for logs and retry controls.
Separate queue logs from msmtp’s SMTP logfile
MSMTPQ_LOG selects the queue-operation log. That log records events such as enqueueing and retry attempts. The logfile setting in .msmtprc is separate and records msmtp delivery activity. Read both when diagnosing a deferred message; an empty SMTP logfile can simply mean that msmtp has not yet been called by the queue runner.
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Inspect, flush, and preserve the queue
Display the queue before deleting anything
Start with msmtp-queue -d. Save its output, including any error text and timestamps. Purge commands exist, but deleting a message removes useful evidence and may destroy the only copy of an unsent mail. Export or copy any message needed for diagnosis before purging.
Run a controlled flush
msmtp-queue -r asks the queue manager to process all queued messages. Watch whether the queue count decreases, whether new SMTP errors appear, and whether the process exits successfully. A flush that immediately returns without attempting delivery points toward queue configuration, permissions, or a connection-test decision rather than recipient rejection.
Retry only selected mail
Use msmtp-queue -R for selected messages when one recipient or one malformed message should not block unrelated mail. Preserve the original queue and log output first. If selected retries work while a full flush does not, inspect the remaining messages for address, size, or content-specific failures.
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Queue settings that can prevent a retry
Queue directory and mode
The directory named by MSMTPQ_Q must exist and be writable by the submitting account. Follow the project’s recommendation of mode 0700 so queued messages and credentials are not readable by other users. A missing directory, incorrect owner, read-only filesystem, or overly restrictive parent directory can make enqueueing or dequeueing fail.
Queue log path
The path in MSMTPQ_LOG must also be writable. If the log cannot be opened, you may see little more than a generic queue status. Fix the path and permissions, then run a single flush while monitoring the resulting log.
Connection-test policy
msmtpq can run a network connection test before attempting delivery. The test may defer mail when DNS, routing, or the selected port is unavailable. Environment settings can also force queueing or suppress queue chatter. Review those settings for the account and execution environment, especially when an interactive flush behaves differently from a cron or service job. A conservative or failed test can leave mail queued until a later run even though the SMTP server itself would have accepted the message.
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Check what the SMTP server actually supports
Use msmtp’s server-information mode with the same account configuration used by the queue:
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msmtp --serverinfo --account=ACCOUNTThe output is a capability check, not a delivery attempt. It can show the server’s advertised authentication mechanisms, TLS support, certificate details, DSN support, and maximum message size. Compare those values with the account settings and your provider’s documented requirements. If the command cannot resolve or connect to the host, fix DNS, firewall, proxy, routing, hostname, or port problems before changing passwords.
Validate the complete account configuration
- SMTP hostname: use the provider’s submission host, not an unrelated web or IMAP hostname.
- Port: submission commonly uses port 587, but the provider determines the valid port and encryption policy.
- TLS mode: ensure the setting matches whether TLS is required immediately, negotiated with STARTTLS, or not offered on that endpoint.
- Trusted CA file: point msmtp to a certificate trust source that contains the issuer for the server certificate. A hostname mismatch or expired certificate is not repaired by disabling authentication.
- Authentication method: select a mechanism the server advertises. If the provider requires an application-specific password or a token, a normal account password may be rejected.
- Username and password source: confirm the account name, permissions on the password file, and the environment available to the queue runner.
The example configuration in the msmtp documentation uses submission port 587, TLS enabled, and a trusted CA file. Treat that as an example, not a universal recipe; providers differ in ports, TLS requirements, and permitted authentication methods.
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Run one debug delivery safely
After preserving the queue, send a harmless test message through the same account. For example:
printf 'Subject: msmtp testnnQueue diagnosticn' | msmtp --debug --account=ACCOUNT [email protected]Add the recipient only in a controlled environment and check the command’s exit status. The --debug option prints the SMTP conversation, including server greetings, TLS negotiation, authentication exchanges, envelope commands, and final responses. The manual warns that debug output can expose password material. Store it with restricted permissions, remove credentials and private message content, and do not paste an unredacted transcript into a ticket or public forum.
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Match the exact failure to the fix
| Observed response or symptom | Likely layer | Next action |
|---|---|---|
| No SMTP attempt appears; message remains queued | msmtpq policy, connection test, queue path, or permissions | Check MSMTPQ_Q, MSMTPQ_LOG, directory mode, and connection-test settings; then run msmtp-queue -r. |
| DNS failure, timeout, or connection refused | Network, hostname, firewall, proxy, or wrong port | Correct the endpoint or network path and rerun --serverinfo. |
| TLS certificate or verification error | Certificate trust or hostname validation | Use the correct trusted CA file and server hostname. Do not treat disabling verification as a routine fix. |
| Authentication rejected | Username, password, token, or mechanism | Confirm the credential source and choose an authentication method advertised by --serverinfo. |
| Envelope sender or recipient rejected | Provider policy or address syntax | Correct the envelope addresses and review the provider’s sender and relay rules. |
| Message exceeds the advertised limit | Server size policy | Reduce the message or attachment size, or use an endpoint with a documented larger limit. |
| One message fails while others deliver | Message-specific address, size, or policy issue | Use msmtp-queue -R for unaffected messages and preserve the failing message for analysis. |
Do not infer the cause from the word “queued.” The SMTP response, queue log, msmtp logfile, and exit status provide the evidence needed to choose a fix.
Direct msmtp versus a queued wrapper
| Characteristic | Direct msmtp | msmtpq |
|---|---|---|
| Delivery model | Submits the message to an SMTP server during the call. | Stores and routes mail, then invokes msmtp during a queue run. |
| Retry control | The calling application must retry after a failure. | Queue operations such as msmtp-queue -r and -R provide deferred retries. |
| Persistence | No msmtp-managed persistent spool in default sendmail mode. | Messages persist in the configured queue directory. |
| Primary diagnostics | Exit status, SMTP transcript, and msmtp logfile. | Queue log and status first, then msmtp’s SMTP diagnostics. |
| Typical trade-off | Simpler path and immediate error visibility, but no offline buffer. | Offline resilience and retry control, but an extra policy, directory, and scheduler layer can defer delivery. |
Prevent the same queue from growing again
- Document the exact executable path, account name, queue directory, queue log, and service user.
- Keep the queue directory at mode
0700and verify ownership after system migrations or home-directory changes. - Test the SMTP account with
--serverinfoafter changing the provider, port, TLS policy, certificate bundle, or authentication method. - Give the queue runner a stable, writable password source and certificate path; do not assume it inherits your interactive shell environment.
- Monitor queue age and log growth. A queue that grows after every connection-test run needs a network or configuration fix, not repeated blind flushes.
- Redact debug transcripts and restrict access to queue files, because queued messages and authentication diagnostics can contain sensitive data.
When to bypass the queue temporarily
For a single controlled diagnostic, call msmtp directly with the intended account and capture its exit status. This isolates SMTP behavior from msmtpq’s connection test and scheduling logic. Do not permanently bypass a queue merely because one direct test succeeds: doing so removes offline persistence and automatic retry behavior. Restore the normal path after identifying whether the failure belongs to the wrapper, the network, or the SMTP account.
The practical diagnosis
“Queued” is a state, not a root cause. In most installations it means msmtpq accepted the message for later processing. Identify the executable, preserve and inspect the queue, verify queue paths and connection-test settings, flush with the documented commands, and then test the same SMTP account with --serverinfo and one carefully redacted --debug retry. The exact server response tells you whether to repair networking, TLS trust, authentication, envelope policy, or message size.
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