Hi everyone,
Outlook does not pull data from SmarterMail when connected with SharePoint. You must use the Send/Receive option within Outlook to get updates from the server. That said, in Outlook's Send/Receive Groups settings, I found: "Schedule an automatic send/receive every X minutes" and "Perform an automatic send/receive when exiting." With both of those enabled, I find that GAL entries are updated around every 15-30 minutes or so and each time I reopen Outlook.
Regarding the issue with using the Add to Outlook option again, I'm afraid I can't replicate this problem. I'd recommend upgrading to the latest version and reviewing this issue with the Support Department if it persists.
Andrea Free
SmarterTools Inc.
877-357-6278
www.smartertools.com