I've had similar problems over the last year or two with Gmail and with Outlook/Live Mail.
Our 2 person small time company sends a few hundred mails a month at most. We replay to someone on Gmail and get spam-binned. They whitelist us, we reply again and get spam binned. We send the mail via a major provider and it gets through.
On Outlook a website mail form sending emails to a hotmail.co.uk address was getting blocked - the server has the same IP it's had for years, the form has been used for years, the recipient has whitelisted the email address. I forget what eventually fixed it, think it was addition of a reply-to address; quite ridiculous.
In both cases they are long term domains with real ID info that hasn't changed, the domains have been on the same IP held by the same ISP for at least 3 years and owned by the same owner used for the same businesses for at least 10 years. Both domains are long-term registered in (Google|Microsoft) analytics.
Yes I can see that such domains could be purchased by spammers and the prior owners may not change their ID info and the new holders may be able to purchase space on the old server and so keep the IP address (despite the established ISP having strong anti-spam policies) and may be able to then send out spam emails, but who would whitelist those emails???
IMO on either Outlook or Gmail if you whitelist something, even if it were spam from a known spammer, then they should let it through (sanitised if needs be). If they wanted to they could add a "99.999996% of others blocked this but you have whitelisted it, do you want to block emails from YourBestFriendWhoSendsSpam@theirISP.com in the future?".
Our 2 person small time company sends a few hundred mails a month at most. We replay to someone on Gmail and get spam-binned. They whitelist us, we reply again and get spam binned. We send the mail via a major provider and it gets through.
On Outlook a website mail form sending emails to a hotmail.co.uk address was getting blocked - the server has the same IP it's had for years, the form has been used for years, the recipient has whitelisted the email address. I forget what eventually fixed it, think it was addition of a reply-to address; quite ridiculous.
In both cases they are long term domains with real ID info that hasn't changed, the domains have been on the same IP held by the same ISP for at least 3 years and owned by the same owner used for the same businesses for at least 10 years. Both domains are long-term registered in (Google|Microsoft) analytics.
Yes I can see that such domains could be purchased by spammers and the prior owners may not change their ID info and the new holders may be able to purchase space on the old server and so keep the IP address (despite the established ISP having strong anti-spam policies) and may be able to then send out spam emails, but who would whitelist those emails???
IMO on either Outlook or Gmail if you whitelist something, even if it were spam from a known spammer, then they should let it through (sanitised if needs be). If they wanted to they could add a "99.999996% of others blocked this but you have whitelisted it, do you want to block emails from YourBestFriendWhoSendsSpam@theirISP.com in the future?".
/rant