A plugin that provides this feature is missing. You have two options for performing this function. You can implement your own plugin. A good place to start is probably the email ext plugin .
Alternatively, you can run the first email with the actual assembly, and then run Jenkins a separate dummy assembly that will send the second email. It would not be so elegant, but much easier, since you would not need to implement any functionality yourself. Depending on what you want the letters to be contained in, you may have to transfer some data from the first to the second assembly (for example, through a parameterized assembly).
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