On EmailConnectSMTP for both Gmail and iCloud, I get this error when trying to use TLS. Is my syntax wrong, or is there a bigger issue here?

EmailConnectSMTP( "smtp.mail.me.com:587" ; "[email protected]" ; "XXX" ; "tls=true" ; "timeout=10" )

Without logs there isn't much we can do. You can find them using these instructions:

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http://docs.360works.com/index.php/Plugin_log_files
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Although, I'm not quite sure if "tls=true" resolves to true. Try "tls=1". If I recall correctly, we try to convert string booleans the same way FileMaker does. if you do:

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If ( "true" ; "true" ; "false" )
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In a script / dataviewer it will return false. If you do "1" it'll return true. There was a big talk on how exactly to make them function though, I may just be going based off of old information. Give the "1" a try, if it doesn't help go ahead and send your logs to support - at - 360works.com