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Version 2.7.4 had a breaking change, MAILER_SECURE was renamed to MAILER_SECURITY and contains a string now with possible values: none, tls, or starttls https://joplinapp.org/changelog_server/#server-v2-7-4-https-github-com-laurent22-joplin-releases-tag-server-v2-7-4-2022-02-02t19-23-34z https://discourse.joplinapp.org/t/breaking-change-on-mailer-configuration-in-joplin-server-2-7/23464