Setting up OSSEC alerts

OSSEC is an open source host-based intrusion detection system (IDS) that we use to perform log analysis, file integrity checking, policy monitoring, rootkit detection and real-time alerting. It is installed on the Monitor Server and constitutes that machine’s main function. OSSEC works in a server-agent scheme, that is, the OSSEC server extends its existing functions to the Application Server through an agent installed on that server, covering monitoring for both machines.

In order to receive email alerts from OSSEC, you need to supply several settings to Ansible in the playbook for your environment. If you don’t already have a working mail server or don’t know what to do, then see the section below about using Gmail as a fallback option. We assume that you’re working out of the ‘securedrop’ directory you cloned the code into, and editing install_files/ansible-base/group_vars/all/site-specific prior to installing SecureDrop.

What you need:

  • The GPG key that OSSEC will encrypt alerts to
  • The email address that will receive alerts from OSSEC
  • Information for your SMTP server or relay (hostname, port)
  • Credentials for the email address that OSSEC will send alerts from

Receiving email alerts from OSSEC requires that you have an SMTP relay to route the emails. You can use an SMTP relay hosted internally, if one is available to you, or you can use a third-party SMTP relay such as Gmail. The SMTP relay does not have to be on the same domain as the destination email address, i.e. smtp.gmail.com can be the SMTP relay and the destination address can be securedrop@freedom.press.

While there are risks involved with receiving these alerts, such as information leakage through metadata, we feel the benefit of knowing how the SecureDrop servers are functioning is worth it. If a third-party SMTP relay is used, that relay will be able to learn information such as the IP address the alerts were sent from, the subject of the alerts, and the destination email address the alerts were sent to. Only the body of an alert email is encrypted with the recipient’s GPG key. A third-party SMTP relay could also prevent you from receiving any or specific alerts.

The SMTP relay that you use should support SASL authentication and SMTP TLS protocols TLSv1.2, TLSv1.1, and TLSv1. Most enterprise email solutions should be able to meet those requirements.

Below are the values you must specify in to configure OSSEC correctly. For first-time installs, you can use the configuration playbook, or edit install_files/ansible-base/group_vars/all/site-specific manually.

  • GPG public key used to encrypt OSSEC alerts: ossec_alert_gpg_public_key
  • Fingerprint of key used when encrypting OSSEC alerts: ossec_gpg_fpr
  • The email address that will receive alerts from OSSEC: ossec_alert_email
  • The reachable hostname of your SMTP relay: smtp_relay
  • The secure SMTP port of your SMTP relay: smtp_relay_port (typically 25, 587, or 465. must support TLS encryption)
  • Email username to authenticate to the SMTP relay: sasl_username
  • Domain name of the email used to send OSSEC alerts: sasl_domain
  • Password of the email used to send OSSEC alerts: sasl_password

If you don’t know what value to enter for one of these, please ask your organization’s email administrator for the full configuration before proceeding. It is better to get these right the first time rather than changing them after SecureDrop is installed. If you’re not sure of the correct smtp_relay_port number, you can use a simple mail client such as Thunderbird to test different settings or a port scanning tool such as nmap to see what’s open. You could also use telnet to make sure you can connect to an SMTP server, which will always transmit a reply code of 220 meaning “Service ready” upon a successful connection.

The smtp_relay mail server hostname is often, but not always, different from the sasl_domain, e.g. smtp.gmail.com and gmail.com.

In some cases, authentication or transport encryption mechanisms will vary and you may require later edits to the Postfix configuration (mainly /etc/postfix/main.cf) on the Monitor Server in order to get alerts to work. You can consult Postfix’s official documentation for help, although we’ve described some common scenarios in the troubleshooting section.

If you have your GPG public key handy, copy it to install_files/ansible-base and then specify the filename, e.g. ossec.pub, in the ossec_alert_gpg_public_key line of group_vars/all/site-specific.

If you don’t have your GPG key ready, you can run GnuPG on the command line in order to find, import, and export your public key. It’s best to copy the key from a trusted and verified source, but you can also request it from keyservers using the known fingerprint. Looking it up by email address or a shorter key ID format could cause you to obtain a wrong, malicious, or expired key. Instead, we recommend you type out your fingerprint in groups of four (just like GPG prints it) enclosed by double quotes. The reason we suggest this formatting for the fingerprint is simply because it’s easiest to type and verify correctly. In the code below simply replace <fingerprint> with your full, space-separated fingerprint:

Download your key and import it into the local keyring:

gpg --recv-key "<fingerprint>"


It is important you type this out correctly. If you are not copy-pasting this command, we recommend you double-check you have entered it correctly before pressing enter.

Again, when passing the full public key fingerprint to the --recv-key command, GPG will implicitly verify that the fingerprint of the key received matches the argument passed.


If GPG warns you that the fingerprint of the key received does not match the one requested do not proceed with the installation. If this happens, please email us at securedrop@freedom.press.

Next we export the key to a local file.

gpg --export -a "<fingerprint>" > ossec.pub

Copy the key to a directory where it’s accessible by the SecureDrop installation:

cp ossec.pub install_files/ansible-base/

The fingerprint is a unique identifier for an encryption (public) key. The short and long key ids correspond to the last 8 and 16 hexadecimal digits of the fingerprint, respectively, and are thus a subset of the fingerprint. The value for ossec_gpg_fpr must be the full 40 hexadecimal digit GPG fingerprint for this same key, with all capital letters and no spaces. The following command will retrieve and format the fingerprint per our requirements:

gpg --with-colons --fingerprint "<fingerprint>" | grep "^fpr" | cut -d: -f10

Next you specify the e-mail that you’ll be sending alerts to, as ossec_alert_email. This could be your work email, or an alias for a group of IT administrators at your organization. It helps for your mail client to have the ability to filter the numerous messages from OSSEC into a separate folder.

Now you can move on to the SMTP and SASL settings, which are straightforward. These correspond to the outgoing e-mail address used to send the alerts instead of where you’re receiving them. If that e-mail is ossec@news-org.com, the sasl_username would be ossec and sasl_domain would be news-org.com.

The Postfix configuration enforces certificate verification, and requires both a valid certificate and STARTTLS support on the SMTP relay. By default the system CAs will be used for validating the relay certificate. If you need to provide a custom CA to perform the validation, copy the cert file to install_files/ansible-base add a new variable to group_vars/all/site-specific:

smtp_relay_cert_override_file: MyOrg.crt

where MyOrg.crt is the filename. The file will be copied to the server in /etc/ssl/certs_local and the system CAs will be ignored when validating the SMTP relay TLS certificate.

Save group_vars/all/site-specific, exit the editor and proceed with the installation by running the playbooks.

Using Gmail for OSSEC alerts

It’s easy to get SecureDrop to use Google’s servers to deliver the alerts, but it’s not ideal from a security perspective. This option should be regarded as a backup plan. Keep in mind that you’re leaking metadata about the timing of alerts to a third party — the alerts are encrypted and only readable to you, however that timing may prove useful to an attacker.

First you should sign up for a new account. While it’s technically possible to use an existing Gmail account, it’s best to compartmentalize these alerts from any of your other activities. Choose a strong and random passphrase for the new account. Skip the creation of a Google+ profile and continue straight to Gmail. Next, enable Google’s 2-Step Verification. With 2-Step Verification enabled, you won’t use the normal account password in this configuration — it will not work; instead you must navigate (using the settings in the top right) to Account > Signing in > App passwords, and generate a new App password which you will use as the sasl_passwd.

Once the account is created you can log out and provide the values for sasl_username as your new Gmail username (without the domain), sasl_domain, which is typically gmail.com (or your custom Google Apps domain), and sasl_passwd. Remember to use the App password generated from the 2-step config for sasl_passwd, as the primary account password won’t work. The smtp_relay is smtp.gmail.com and the smtp_relay_port is 587.

Configuring fingerprint verification

If you run your own mail server, you may wish to increase the security level used by Postfix for sending mail to fingerprint, rather than secure. Doing so will require an exact match for the fingerprint of TLS certificate on the SMTP relay. The advantage to fingerprint verification is additional security, but the disadvantage is potential maintenance cost if the fingerprint changes often. If you manage the mail server and handle the certificate rotation, you should update the SecureDrop configuration whenever the certificate changes, so that OSSEC alerts continue to send. Using fingerprint verification does not work well for popular mail relays such as smtp.gmail.com, as those fingerprints can change frequently, due to load balancing or other factors.

You can retrieve the fingerprint of your SMTP relay by running the command below (all on one line). Please note that you will need to replace smtp.gmail.com and 587 with the correct domain and port for your SMTP relay.

openssl s_client -connect smtp.gmail.com:587 -starttls smtp < /dev/null 2>/dev/null |
    openssl x509 -fingerprint -noout -in /dev/stdin | cut -d'=' -f2

If you are using Tails, you will not be able to connect directly with openssl s_client due to the default firewall rules. To get around this, proxy the requests over Tor by adding torify at the beginning of the command. The output of the command above should look like the following:


Finally, add a new variable to group_vars/all/site-specific as smtp_relay_fingerprint, like so:

smtp_relay_fingerprint: "6D:87:EE:CB:D0:37:2F:88:B8:29:06:FB:35:F4:65:00:7F:FD:84:29"

Specifying the fingerprint will configure Postfix to use it for verification on the next playbook run. (To disable fingerprint verification, simply delete the variable line you added, and rerun the playbooks.) Save group_vars/all/site-specific, exit the editor and proceed with the installation by running the playbooks.


Some OSSEC alerts should begin to arrive as soon as the installation has finished.

The easiest way to test that OSSEC is working is to SSH to the Monitor Server and run service ossec restart. This will trigger an Alert level 3 saying: “Ossec server started.”

So you’ve finished installing SecureDrop, but you haven’t received any OSSEC alerts. First, check your spam/junk folder. If they’re not in there, then most likely there is a problem with the email configuration. In order to find out what’s wrong, you’ll have to SSH to the Monitor Server and take a look at the logs. To examine the mail log created by Postfix, run the following command:

tail /var/log/mail.log

The output will show you attempts to send the alerts and provide hints as to what went wrong. Here’s a few possibilities and how to fix them:

Problem Solution
Connection timed out
Check that the hostname and port is correct in the relayhost line of
Server certificate not verified
Check that the relay certificate is valid (for more detailed help, see Troubleshooting SMTP TLS). Consider adding smtp_relay_cert_override_file
to prod_specific.yml as described above.
Authentication failure
Edit /etc/postfix/sasl_passwd and make sure the username, domain and password are correct. Run postmap /etc/postfix/sasl_passwd
to update when finished.

After making changes to the Postfix configuration, you should run service postfix reload and test the new settings by restarting the OSSEC service.


If you change the SMTP relay port after installation for any reason, you must update the smtp_relay_port variable in the group_vars/all/site-specific file, then rerun the Ansible playbook. As a general best practice, we recommend modifying and rerunning the Ansible playbook instead of manually editing the files live on the servers, since values like smtp_relay_port are used in several locations throughout the config.

Useful log files for OSSEC

Other log files that may contain useful information:

Includes lines for sending mail containing OSSEC alerts.
Messages related to grsecurity, AppArmor and iptables.
OSSEC’s general operation is covered here.
Contains details of every recent OSSEC alert.


Remember to encrypt any log files before sending via email, for example to securedrop@freedom.press, in order to protect security-related information about your organization’s SecureDrop instance.

Not receiving emails

Some mail servers require that the sending email address match the account that authenticated to send mail. By default the Monitor Server will use ossec@ossec.server for the from line, but your mail provider may not support the mismatch between the domain of that value and your real mail host. If the Admin email address (configured as ossec_alert_email in group_vars/all/site-specific) does not start receiving OSSEC alerts updates shortly after the first playbook run, try setting ossec_from_address in group_vars/all/site-specific to the full email address used for sending the alerts, then run the playbook again.

Message failed to encrypt

If OSSEC cannot encrypt the alert to the GPG public key for the Admin email address (configured as ossec_alert_email in group_vars/all/site-specific), the system will send a static message instead of the scheduled alert:

Failed to encrypt OSSEC alert. Investigate the mailing configuration on the Monitor Server.

Check the GPG configuration vars in group_vars/all/site-specific. In particular, make sure the GPG fingerprint matches that of the public key file you exported.

Troubleshooting SMTP TLS

Your choice of SMTP relay server must support STARTTLS and have a valid server certificate. By default, the Monitor Server‘s Postfix configuration will try to validate the server certificate using the default root store (in Ubuntu, this is maintained in the ca-certificates package). You can override this by setting smtp_relay_cert_override_file as described earlier in this document.

In either situation, it can be helpful to use the openssl command line tool to verify that you can successfully connect to your chosen SMTP relay securely. We recommend doing this before running the playbook, but it can also be useful as part of troubleshooting OSSEC email send failures.

In either case, start by attempting to make a STARTTLS connection to your chosen smtp_relay:smtp_relay_port (get the values from your group_vars/all/site-specific file). On a machine running Ubuntu, run the following openssl command, replacing smtp_relay and smtp_relay_port with your specific values:

openssl s_client -showcerts -starttls smtp -connect smtp_relay:smtp_relay_port < /dev/null 2> /dev/null

Note that you will not be able to run this command on the Application Server because of the firewall rules. You can run it on the Monitor Server, but you will need to run it as the Postfix user (again, due to the firewall rules):

sudo -u postfix openssl s_client -showcerts -starttls smtp -connect smtp.gmail.com:587 < /dev/null 2> /dev/null

If the command fails with “Could not connect” or a similar message, then this mail server does not support STARTTLS. Verify that the values you are using for smtp_relay and smtp_relay_port are correct. If they are, you should contact the admin of that relay and talk to them about supporting STARTTLS, or consider using another relay that already has support.

If the command succeeds, the first line of the output should be “CONNECTED” followed by a lot of diagnostic information about the connection. You should look for the line that starts with “Verify return code”, which is usually one of the last lines of the output. Since we did not give openssl any information about how to verify certificates in the previous command, it should be a non-zero value (indicating verification failed). In my case, it is Verify return code: 20 (unable to get local issuer certificate), which indicates that openssl does not know how to build the certificate chain to a trusted root.

If you are using the default verification setup, you can check whether your cert is verifiable by the default root store with -CApath:

openssl s_client -CApath /etc/ssl/certs -showcerts -starttls smtp -connect smtp_relay:smtp_relay_port < /dev/null 2> /dev/null

For example, if I’m testing Gmail as my SMTP relay (smtp.gmail.com:587), running the openssl with the default root store results in Verify return code: 0 (ok) because their certificate is valid and signed by one of the roots in the default store. This indicates that can be successfully used to securely relay email in the default configuration of the Monitor Server.

If your SMTP relay server does not successfully verify, you should use the return code and its text description to help you diagnose the cause. Your cert may be expired, in which case you should renew it. It may not be signed by a trusted CA, in which case you should obtain a signature from a trusted CA and install it on the mail server. It may not have the right hostnames in the Common Name or Subject Alternative Names, in which case you will need to generate a new CSR with the correct hostnames and then obtain a new certificate and install it. Etc., etc.

If you are not using the the default verification setup, and intentionally do not want to use a certificate signed by one of the default CA’s in Ubuntu, you can still use openssl to test whether you can successfully negotiate a secure connection. Begin by copying your certificate file (smtp_relay_cert_override_file from group_vars/all/site-specific) to the computer you are using for testing. You can use -CAfile to test if your connection will succeed using your custom root certificate:

openssl s_client -CAfile /path/to/smtp_relay_cert_override_file -showcerts -starttls smtp -connect smtp_relay:smtp_relay_port < /dev/null 2> /dev/null

Finally, if you have a specific server in mind but are not sure what certificate you need to verify the connection, you can use the output of openssl s_client to figure it out. Since we have -showcerts turned on, openssl prints the entire certificate chain it receives from the server. A properly configured server will provide all of the certificates in the chain up to the root cert, which needs to be identified as “trusted” for the verification to succeed. To see the chain, find the part of the output that start with Certificate chain. It will look something like this (example from smtp.gmail.com, with certificate contents snipped for brevity):

Certificate chain
0 s:/C=US/ST=California/L=Mountain View/O=Google Inc/CN=smtp.gmail.com
i:/C=US/O=Google Inc/CN=Google Internet Authority G2
1 s:/C=US/O=Google Inc/CN=Google Internet Authority G2
i:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
2 s:/C=US/O=GeoTrust Inc./CN=GeoTrust Global CA
i:/C=US/O=Equifax/OU=Equifax Secure Certificate Authority

The certificates are in reverse order from leaf to root. openssl handily prints the Subject (s:) and Issuer (i:) information for each cert. In order to find the root certificate, look at the Issuer of the last certificate. In this case, that’s Equifax Secure Certificate Authority. This is the root certificate that issued the first certificate in the chain, and it is what you need to tell Postfix to use in order to trust the whole connection.

Actually obtaining this certificate and establishing trust in it is beyond the scope of this document. Typically, if you are using your own SMTP relay with a custom CA, you will be able to obtain this certificate from an intranet portal or someone on your IT staff. For a well-known global CA, you can obtain it from the CA’s website. For example, a quick search for “Equifax Secure Certificate Authority” finds the web page of GeoTrust’s Root Certificates, which have accompanying background information and are available for download.

Once you have the root certificate file, you can use -CAfile to test that it will successfully verify the connection.

Analyzing the Alerts

Understanding the contents of the OSSEC alerts requires a background and knowledge in Linux systems administration. They may be confusing, and at first it will be hard to tell between a genuine problem and a fluke. You should examine these alerts regularly to ensure that the SecureDrop environment has not been compromised in any way, and follow up on any particularly concerning messages with direct investigation.

Common OSSEC Alerts

The SecureDrop Application and Monitor Servers reboot every night, as part of the unattended upgrades process. When the servers come back up, OSSEC will start again and report the change in status. Therefore you should receive an email alert every morning containing text similar to:

Received From: mon->ossec-monitord
Rule: 502 fired (level 3) -> "Ossec server started."
Portion of the log(s):

ossec: Ossec started.

This is a normal alert, and informs you that the system is working as expected.

Similarly, your SecureDrop Application and Monitoring Servers will check for application updates on your servers. Should your servers require updates, OSSEC will alarm because the packages binaries will have changed Below is a sample alert, but you may see any number of these records in the logs. This will happen in batches so these emails might be longer than the below alert. You should also see them in an email named Daily Report: File Changes. To verify this activity matches the package history, you can review the logs in /var/log/apt/history.log.

Received From: (app)
Rule: 2902 fired (level 7) -> "New (Debian Package) installed."
Portion of the log(s):

status installed <package name> <version>

This is a normal alert, it tells you your system is up-to-date and patched.

Occasionally your SecureDrop Servers will send an alert for failing to connect to Tor relays. Since SecureDrop runs as a Tor Onion Service, it is possible for Tor connections to timeout or become overloaded.

Received From: (app)
Rule: 1002 fired (level 2) -> "Unknown problem somewhere in the system."
Portion of the log(s):

[warn] Your Guard <name> ($fingerprint) is failing a very large amount of
circuits. Most likely this means the Tor network is overloaded, but it
could also mean an attack against you or potentially the guard itself.

This alert is common but if you see them for sustained periods of time (several times a day), please contact us at the SecureDrop Support Portal or at securedrop@freedom.press for help.

Uncommon OSSEC Alerts

If you believe that the system is behaving abnormally, you should contact us at the SecureDrop Support Portal or securedrop@freedom.press for help.