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I will be more to the point than the others. You should continue to use Outlook to send/receive emails. Emails that need to be saved, you can TM Save them and a copy will be saved into Time Matters. You can save more than one email at a time by highlighting them before pressing TM Connect.
So in short:
1. TM Connect works in any folder2. As you are using Outlook your signatures are created there3. When you send an email, you can have Outlook prompt you to save to TM. In Outlook - Tools -options - Time Matters Tab.
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This is a topic that many of us could write on for a while.... having been involved in all of the email options for many years (including training Time Matters tech support), if you are going to attempt to use the internal email options in Time Matters, someone has to completely understand all of the options and each user must be fully trained and monitored to ensure everyone understands. When compared to the TM Connect (and a properly set up Documents list to make attachments easier) the Outlook option rises to the top and you will have quicker adoption and better data in Time Matters .
In summary though, no one recommended using MAPI here. In years past I have implemented it, but we had to worry about issues including (as Tom has stated) sending attachment issues and there used to be an Exchange setting (or some other server setting) to increase the number of allowed connections so it worked better.... I still do not recommend it. There is no option to have MAPI see the sent items folder.
To answer your question directly, each user can configure their settings in Outlook. Tools-Options-Time Matters tab. Here you will find the prompt to save when sending an email.