I have the free version for Outlook and it constantly logs me out. I have had our IT dept give suggestions and nothing is working. I was planning to pay for the premium version because I like the program but this is very frustrating as I have to keep logging back in every few minutes.
Do you have Internet Explorer set to remove all cookies on exit, or at a regular interval? As our plugin for Outlook uses it, and if that gets cleared you will always need to log into it.
Please try to install this new updated version of our Outlook plugin and let us know if the issue persists: https://d2dq6e731uoz0t.cloudfront.net/6cbfe87a597f69aefd816f9cdac2957a/as/OutlookTodoist.Adx.exe