Comment by mrweasel

What I'd be concerned with is that if you have never sent anything to these users, they might have forgotten where and when they gave you their email address and simply mark your message as spam.

We've trained users to not use "unsubscribe" because some spammers once used that to verify addresses, or they may simply click "Spam" because they forgot who you are and think you got their address illegitimately. Gmail also doesn't make unsubscribe as visible as "Spam", making flagging the easier option. So now Gmail will see some percentage of users manually flagging you as a spammer, tainting your sender. This is why I'd switch the newsletter to a new domain or at least a new sender address. That does mean preparing that new sender, give it a bit of time to mature and send a few emails to Gmail accounts you control and ensure that they are not flagged as spam.

Probably also test with a list of Gmail account you control and check if you're tagged as spam and fix that, before doing the big push.

As a gmail user who may or may not have had to enter an email address to do something on the web, and who gets annoyed by spam, let me describe my decision points (anecdote is not the plural of data, of course, but here I am) when it comes to "unsubscribe" vs marking something "spam."

If your email reminds me (upfront!) how and when and why I specifically gave you (and not some other third party) my email address, and promises that you are advertising this newsletter one time, and it is opt-in, and you keep your promise, I am highly unlikely to mark it spam.

Now, this presupposes that it was really me who gave you my email address. I have a fairly generic email address because I got on gmail early. There are many variants of it, but sometimes people forget to add the trailing numbers or letters, so I get misdirected email all the time.

If the misdirected email is personal, I usually respond letting them know of the issue.

If the misdirected email shows a clear understanding that I might not have been the one who really signed up then I give them a pass.

If the misdirected email blithely assumes that I am the one who signed up, then I blithely assume that its senders are too fucking stupid to use the internet and it goes straight into the spam bucket. (And this is usually an easy call because they use the name of the person with the similar email address, which is not my name. My email address is firstinitiallastname@gmail.com and there are many different first names that start with the same initial.)

Any failure on any of those other points starts to increase the likelihood of it being marked spam, and...

> The unsubscribe links must work without even opening the email, according to gmail rules.

So here's where I'm a hard-ass and maybe even worse than google's rules.

If I see the RFC8058 unsubscribe link, it is too late. I only notice that link after I've decided to mark your email as "spam" and google asks if I'm sure, or if I merely want to unsubscribe.

Why did I decide to mark your email as spam? One possible reason is that I read through it, decided that the sender legitimately had my email address and was acting honorably, and then clicked the unsubscribe link embedded in the email.

When I do that, one of two things happens. Either I get some form of "thank you, you've been unsubscribed" or nothing happens because the sender assumes that I am OK with them executing javascript on my computer.

This is a privilege I jealously guard and only reluctantly offer to as few websites as possible.

Even if I previously gave you my email address, that did not come with an open invitation to use my computing resources for your own purposes.