One reason, Outlook IntegrateR1 doesn’t record history to Outlook is the address book connection doesn’t activate. In Outlook 2013, it’s doesn’t wait long for any plugins. If Outlook senses a delay, it will turn it off so the inbox appears no matter what.

One trick is force the add-ins to always start.

Click "File" in Outlook
Click “File” in Outlook
enable act step 02
Click Manage Addins
Enable Outlook Integrate R1
Click “Always Enable this addin”
Enable Redemption Helper Outlook Extension
Sometimes, (Not Always). This plugin needs to be enabled as well.