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What version of FM are you using 32bit or 64bit? Are you using the same version with Outlook? You need to use 32bit version of FM with 32bit version of Outlook or 64bit FM with 64bit Outlook.
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Actually the problems started when software companies started to build softare in both 32 and 64-bit. Everyone know that 64-bit is much faster then 32-bit, but for some reason people stick to old 32-bit for different reasons. Microsoft Outlock is a part of the Office Package and FileMaker still needs to be installed bit same bit (32/64) as Office Package to be able to send email out through Outlock.
Outlock 2016 would most probably just come as 64-bit version and if you install that you have to install your FileMaker Pro with 64-bit too, that is the only way for you to make it work
Here is a little explanation from FileMaker Inc.
Maybe better send email with SMTP.
And BCC to yourself to get a copy.
This copy can be ruled to go into Sent folder in Outlook.