Outlook 2013 VBA rule random failures

Question

My goal is no make Outlook delete all mail from a specified address keeping maximum 3 latest (it really helps with some daily subscriptions like coupons, etc.).

I have lots of rules sorting mail into different folders and marking them with a special category (let's call it "Amount: 3"). I also have the last rule in the list that runs my VBA script: it counts mail from the same sender in a folder (having this "Amount: 3" category) and deletes old leaving no more than the amount requested.
The whole thing works fine when Outlook is running and receives new mail. But when I start Outlook for the first time and there's new mail on the server - it randomly tells that the script rule failed to execute and turns it off...
My script does logging so I'm quite sure it's not an incorrect script issue. Moreover it seems like when I turn on debug logging in Outlook - the problem disappears. And there's nothing suspicious in the system journal too...

So the question is how can I find out what's wrong with it?? If negative - is there a way to acheive what I want in Outlook 2013?
And yes I know that MS suggests not using VBA rule together with other kinds of rules no matter the order and so on, but still can't believe they've made it so unpredictable...

ps: the same solution worked more or less stable at Outlook 2007 back in the days...

Answer 1

If instead of trying to do everything in one go, you were to mark anything you want deleted with a Category. You could then create a virtual search folder for that category. This has the advantage of working across all actual folders.

You could then write some simple VBA that is executed at startup and shutdown of Outlook that deletes the contents of that virtual search folder.

Then you are not dependent on the mail transport events firing in the right order.

Answer 2

Man! It looks like I've finally fixed it (facepalm) So the way it works all the times is:

• Same rule-based VBA sub doing major stuff
• Application_Startup/Application_Quit event handlers to turn on/off corresponding rule to avoid random errors on Outlook start (see my comments to question/answers here)
• Autolaunch shortcut copypasted from Microsoft Office 2013 folder of Start -> All Programs (it was shortcut to OUTLOOK.EXE originally and it appears that it doesn't fire event handlers at all when you launch Outlook that way O_o)