Sometimes you can get that insider by becoming a customer of a different part of the company from the one that is giving you trouble.
We had an email problem with a major free email provider that also ran an advertising network (no, it was NOT Google or Microsoft...).
Our problem was that they kept deciding all the mail we sent to their users was spam. None of it was actually spam. The only things we were sending were:
• receipts for purchases
• installation instructions and license keys for whatever the user had just purchased
• if the user was on a subscription plan with a term longer than a month, a notice a few days before subscription billing that they were going to be billed
• responses to support tickets the user initiated
We'd complain to the louts running the email service, and they would fix it...and a month later it would happen again. Each time it took them longer and longer to fix it.
Then we realized we were spending a large amount buying ads on their ad network. Our guy in charge of ad buying called up our account rep at their advertising sales department, and asked why the heck we should keep paying them a large amount to drive customers to us, if they were going to make it so we could not communicate with those customers if those customers used their email service? It doesn't take a young Einstein to figure we shouldn't.
The account rep put our guy on hold a few minutes, then came back and had conference called in someone high up in their IT department, explained the problem. The IT department head conferenced in the person in charge of mail filtering and told him to put in a white list entry for us, and he wanted it done right away. About ten minutes later we were told it was done, and we never had another problem that I know of with email being misclassified as spam.
This disturbed me quite a bit. None of our mail was spam, so no one was harmed by that white list entry. But they had plenty of people using their ad network who were pushing sleazy products and who I greatly doubt only sent non-spam mail. Would they also be able to get white listed just be calling an ad rep and complaining?
We never had any spam classification problems with customers who used Google or Microsoft free email services, so have no idea if similar things work there, or if they keep a stronger separation between the ad network and the mail services.
In my more cynical moments I wonder if this sort of the thing might be the reason advertising companies run free email services. If they can amass a large number of email users, and they grant exceptions in the spam filters for their bigger advertisers, that provides an incentive to use their ad network over one with a smaller email service or without an email server, so you'll get more customers that you email market to at will.