email-reply-00 Challenge

The email-reply-00 challenge permits to get end-user S/MIME certificates, as specified in RFC 8823.

The CA must support issuance of S/MIME certificates. Let's Encrypt does not currently support it.


The support of this challenge is experimental. The implementation is only unit tested for compliance with the RFC, but is not integration tested yet. There may be breaking changes in this part of the API in future releases.

Setup and Requirements

To use the S/MIME support, you need to:

  • add the acme4j-smime module to your list of dependencies
  • make sure that BouncyCastleProvider is added as security provider
  • add a javax.mail implementation to your classpath (e.g. the JavaMail Reference Implementation)

RFC 8823 requires that the DKIM or S/MIME signature of incoming mails must be checked. Outgoing mails must have a valid DKIM or S/MIME signature. This is out of the scope of acme4j-smime, but is usually performed by a MTA.


The certificate ordering process is similar to a standard domain certificate order.

However, if Identifier objects are needed, use to generate an identifier for the email address you want an S/MIME certificate for.

To generate a CSR, the module provides a SMIMECSRBuilder that works similar to the standard CSRBuilder, but accepts EmailIdentifier objects.

With the SMIMECSRBuilder.setKeyUsageType(), the desired usage type of the S/MIME certificate can be selected. By default the certificate can be used both for encryption and signing. However this is just a proposal, and the CA is free to ignore it or return an error if the desired usage type is not supported.

Challenge and Response

The CA validates ownership of the email address by two components.

Firstly, the CA sends a challenge email to the email address that requested the S/MIME certificate. The subject of this email always starts with an ACME: prefix, so it can be filtered by the inbound MTA for automatic processing. After the prefix, the mail subject contains the first part of the challenge token (called "Token 1").

Secondly, the CA provides a new EmailReply00Challenge challenge that needs to be verified by the client. The challenge contains the second part of the challenge token (called "Token 2"). Both token parts are concatenated to give the full token that is required for generating the key authorization. The EmailReply00Challenge class offers methods like getToken(String part1), getTokenPart2(), and getAuthorization(String part1) for that.

The client now needs to generate a response to the request email. This is a standard mail response to the sender's address. The subject line must be kept, except of an optional Re: or a similar prefix. The mail body must contain a text/plain part that contains the wrapped key authorization string. For example:


This response is sent back to the CA.

After that, the EmailReply00Challenge is triggered. The CA now has a proof of ownership of the email address, and can issue the S/MIME certificate.

Response Helper

The response process can be executed programatically, or even manually. To help with the process, acme4j-smime provides an EmailProcessor that helps you parsing the challenge email, and generate a matching response mail.

It is basically invoked like this:

Message               challengeMessage = // incoming challenge message from the CA
EmailReply00Challenge challenge        = // challenge that is requested by the CA
EmailIdentifier       identifier       = // email address to get the S/MIME cert for
javax.mail.Session    mailSession      = // javax.mail session

Message response = new EmailProcessor(challengeMessage)

Transport.send(response);   // send response to the CA
challenge.trigger();        // trigger the challenge

The EmailProcessor and the related ResponseGenerator offer more methods for validating and for customizing the response email.