It's possible that your login issue is related to Outloook's autodiscover behavior. If you haven't yet, it may be worth reviewing the KB article Autodiscover and Registry Edits for Outlook and MAPI. It covers information Microsoft has put out about when Outlook does autodiscover checks, what steps it takes during the autodiscover process, and some registry keys you can try modifying to adjust that behavior.

As for Outlook rules, it could be a functional limitation. In spite of the "client-side rule" terminology, those rules aren't actually evaluated by Outlook. Since client-side and server-side rules can be mixed together, with any of those rules having an indicator that additional rules should not be processed, all rule are evaluated by the server to determine which apply to the message. The server then executes any applicable server-side rules and then tells Outlook which of the client-side rules should be applied. Since SmarterMail doesn't currently support server-side rules, there could be issues if your rule set includes a mix of server-side and client-side rules. If your setup only has client-side rules, please open a ticket and provide us with the details of those rules. It may help us determine what the problem is and improve SmarterMail's support for client-side rules.

I think the reason your rule isn't automatically running in Outlook is because Outlook considers it a server-side rule. Outlook identifies rules as client-side or server-side based on the conditions and actions configured in the rule. Even the presence of one client-side condition or action will lead to the entire rule being marked client-side.

The closest feature SmarterMail has to the rules in Outlook is content filtering. While there is some overlap in functionality, there are enough differences between rules and content filtering to prevent us from trying to make them interoperable in MAPI.

With that in mind, it is possible to create the rule you described as a content filter in SmarterMail. Just log into webmail and got to Settings > Content Filtering and create it there.